Light-emitting elements and amine compounds for light-emitting elements

Abstract

To provide: a light-emitting element exhibiting excellent emission efficiency and long service life characteristics; and an amine compound which is a material for a light-emitting element having high efficiency and long service life characteristics.SOLUTION: A light-emitting element includes a first electrode, a second electrode, and at least one functional layer disposed between the first electrode and the second electrode and including, e.g., an amine compound 1 obtained by the reaction formula in the figure, thereby exhibiting high emission efficiency characteristics and improved service life characteristics.SELECTED DRAWING: Figure 3

Description

[Technical Field]

[0001] The present invention relates to a light-emitting element and an amine compound used therein, and more particularly to an amine compound used in a hole transport region and a light-emitting element containing the same. [Background technology]

[0002] Recently, there has been a lot of development going on in the field of video display devices, such as organic electroluminescence display devices. Organic electroluminescence display devices are display devices that include so-called self-emissive light-emitting elements that emit light from the light-emitting material of the light-emitting layer by recombining holes and electrons injected from the first and second electrodes in the light-emitting layer.

[0003] When applying light-emitting elements to display devices, there is a demand for lower driving voltage, higher luminous efficiency, and longer lifespan. Therefore, there is a continuous need for the development of light-emitting element materials that can stably achieve these requirements.

[0004] Furthermore, in order to realize highly efficient light-emitting elements, research is underway on materials for the hole transport region to suppress the diffusion of exciton energy in the light-emitting layer. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] U.S. Patent Application Publication No. 2011 / 0198581 [Patent Document 2] Korean Published Patent Publication No. 2019-0063368 [Patent Document 3] Korean Published Patent No. 2012-0096097 [Overview of the project] [Problems that the invention aims to solve]

[0006] The objective of the present invention is to provide a light-emitting element that exhibits excellent luminous efficiency and long lifespan characteristics.

[0007] Another object of the present invention is to provide an amine compound that is a material for light-emitting devices having high efficiency and long lifespan characteristics. [Means for solving the problem]

[0008] One embodiment provides an amine compound represented by the following chemical formula 1. [ka] ...(chemical formula 1) In Chemical Formula 1, R1 is an adamantyl group, a cyclohexyl group, or a bicycloheptyl group, and Ar1 and Ar2 are each independently substituted or unsubstituted arylene groups with 6 to 30 ring-forming carbon atoms. L is a single bond (direct linkage), a substituted or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 30 ring-forming carbon atoms, and FR is represented by the following Chemical Formula 2. [ka] ...(chemical formula 2) In chemical formula 2, X is CR a R b , N, NR c , O, or S, R a ~R c Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, and can bond with adjacent groups to form a ring. d and e are each independently integers between 0 and 4, and R d and R eEach is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and adjacent groups can be bonded to each other to form a ring. FR is bonded to the L in Chemical Formula 1 or the N atom of the amine compound at the position of X in Chemical Formula 2 or at any one of the ring-forming atoms of the benzene ring.

[0009] Chemical Formula 1 may be represented by the following Chemical Formula 1-1 or Chemical Formula 1-2.

Chem.

Chem.

[0010] Chemical Formula 1-2 may be represented by the following Chemical Formula 1-2A.

Chem.

[0011] In Chemical Formula 1, Ar1 and Ar2 may be a substituted or unsubstituted phenylene group.

[0012] Chemical formula 1 may also be represented by the following chemical formula 1A. [ka] ...(chemical formula 1A) In chemical formula 1A, R1, L, and FR are as defined in chemical formula 1.

[0013] Chemistry 1A may also be represented by the following chemical formula 1A-1. [ka] ...(chemical formula 1A-1) In chemical formula 1A-1, R1, L, and FR are as defined in chemical formula 1.

[0014] Another embodiment provides a light-emitting element comprising a first electrode, a second electrode disposed on the first electrode, and at least one functional layer disposed between the first electrode and the second electrode, the functional layer containing the ami compound according to the above embodiment.

[0015] 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, wherein the hole transport region may contain the amine compound.

[0016] 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, wherein the hole transport layer may contain the amine compound.

[0017] The at least one functional layer includes a light-emitting layer, a first hole transport layer disposed between the first electrode and the light-emitting layer, a second hole transport layer disposed between the first hole transport layer and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode, wherein the first hole transport layer may contain the amine compound.

[0018] The second hole transport layer may contain an amine derivative compound represented by the following chemical formula 3. [ka] ...(chemical formula 3) In chemical formula 3, L 11 R is a single bond, a substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group with 2 to 30 carbon atoms. 11 ~R 14 Each of these groups is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, and can bond with adjacent groups to form a ring.

[0019] Chemical formula 3 may also be represented by chemical formula 3-1 or chemical formula 3-2 below. [ka] ...(Chemical formula 3-1) [ka] ...(chemical formula 3-2) In chemical formulas 3-1 and 3-2, L 11 , and R 11 ~R 14 This is defined as shown in chemical formula 3. [Effects of the Invention]

[0020] A light-emitting element according to one embodiment exhibits high efficiency and long lifespan characteristics by including an amine compound according to one embodiment in the hole transport region.

[0021] An amine compound according to one embodiment improves the luminescence efficiency and device lifespan of a light-emitting element. [Brief explanation of the drawing]

[0022] [Figure 1] This is a plan view showing a display device according to one embodiment. [Figure 2] This is a cross-sectional view of a display device according to one embodiment. [Figure 3] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment. [Figure 4] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment. [Figure 5] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment. [Figure 6] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment. [Figure 7] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment. [Figure 8] This is a cross-sectional view of a display device according to one embodiment. [Figure 9] This is a cross-sectional view of a display device according to one embodiment. [Modes for carrying out the invention]

[0023] Because the present invention can be modified in various ways and take on various forms, specific embodiments are illustrated in the drawings and described in detail in the text. However, this should be understood not as an attempt to limit the present invention to any particular disclosure, but rather as including all modifications, equivalents, or substitutions that fall within the spirit and technical scope of the present invention.

[0024] In each drawing, similar reference numerals are used for similar components. In the attached drawings, the dimensions of structures may be enlarged for clarity of the invention. Terms such as "first," "second," etc., are used to describe a variety of components, but the components are not limited to these terms. These terms are used solely for the purpose of distinguishing one component from another. For example, as long as it does not exceed the scope of the invention, the first component may be called the second component, and similarly, the second component may be called the first component. A singular expression includes plural expressions unless the context clearly indicates otherwise.

[0025] In this application, terms such as “includes” or “having” should be understood to mean that the features, figures, steps, actions, components, parts, or combinations thereof described in the specification exist, and not to presuppose the existence or possibility of adding one or more other features, figures, steps, actions, components, parts, or combinations thereof.

[0026] In this application, when a part such as a layer, film, region, or plate is said to be "above" or "above" another part, this includes not only when it is "directly above" the other part, but also when there is another part in between. Similarly, when a part such as a layer, film, region, or plate is said to be "below" or "below" another part, this includes not only when it is "directly below" the other part, but also when there is another part in between. Furthermore, in this application, "positioned above" includes not only when it is positioned above, but also when it is positioned below.

[0027] In this specification, "substituted or unsubstituted" means that a molecule is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, nitro groups, amino groups, silyl groups, oxy groups, thio groups, sulfinyl groups, sulfonyl groups, carbonyl groups, boryl groups, phosphine oxide groups, phosphine sulfide groups, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, hydrocarbon ring groups, aryl groups, and heterocyclic groups. Furthermore, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenylyl group may be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.

[0028] In this specification, "bonding with adjacent groups to form a ring" means bonding with adjacent groups to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles can be monocyclic or polycyclic. Furthermore, rings formed by bonding with each other may bond with other rings to form a spirostructure.

[0029] In this specification, “adjacent group” means a substituent substituted on an atom directly bonded to the atom to which the substituent is substituted, another substituent substituted on the atom to which the substituent is substituted, or the substituent that is most stereostructically adjacent to the substituent. For example, the two methyl groups in 1,2-dimethylbenzene are interpreted as “adjacent groups,” and the two ethyl groups in 1,1-diethylcyclopentane are interpreted as “adjacent groups.” Similarly, the two methyl groups in 4,5-dimethylphenanthrene are interpreted as “adjacent groups.”

[0030] In this specification, examples of halogen atoms include fluorine, chlorine, bromine, or iodine.

[0031] In this specification, alkyl groups are linear, branched, or cyclic. The number of carbon atoms in an alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, and 2-ethyl Hexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1-methylpeptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, Adamantine Ntyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldecyl 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 Examples include, but are not limited to, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-icosyl group, 2-ethylicosyl group, 2-butylicosyl group, 2-hexylicosyl group, 2-octylicosyl group, n-henicosyl group, n-docosyl group, n-tricosyl group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, and n-triacontyl group.

[0032] In this specification, a hydrocarbon ring group means any active group or substituent derived from an aliphatic hydrocarbon ring. For example, a hydrocarbon ring group is a saturated hydrocarbon ring group having 5 to 20 carbon atoms.

[0033] In this specification, an aryl group means any active group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms in the aryl group may be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenylyl, terphenylyl, quarterphenylyl, quinkphenylyl, sexiphenylyl, triphenylenyl, pyrenyl, benzofluoranteyl, and crisenyl groups.

[0034] In this specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of substitutions of the fluorenyl group are as follows, but are not limited to these. [ka]

[0035] In this specification, a heterocyclic group means any active group or substituent derived from a ring containing one or more heteroatoms from B, O, N, P, Si, and S. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups are heteroaryl groups.

[0036] In this specification, when a heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different. A heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept that includes a heteroaryl group. The number of ring-forming carbon atoms in a heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.

[0037] In this specification, the number of ring-forming carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups include, but are not limited to, oxyranyl, thyranyl, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, thianyl, tetrahydropyranyl, and 1,4-dioxanyl groups.

[0038] In this specification, the heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring-forming carbon atoms of the heteroaryl group is, for example, 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, triazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, triazinyl group, triazolyl group, acridinyl group, pyridadinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phenoxadinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyradinyl group, pyrazinopyradinyl group, isoquinolinyl group, indolyl group, carbazolyl group, N-arylcarbazolyl group, N Examples include, but are not limited to, heteroarylcarbazolyl groups, N-alkylcarbazolyl groups, benzoxazolyl groups, benzimidazolyl groups, benzothiazolyl groups, benzocarbazolyl groups, benzothiophenyl groups, dibenzothiophenyl groups, thienothiophenyl groups, benzofuranyl groups, phenanthrolinyl groups, thiazolyl groups, isoxazolyl groups, oxazolyl groups, oxadiazolyl groups, thiadiazolyl groups, phenothiazinyl groups, dibenzosilolyl groups, and dibenzofuranyl groups.

[0039] In this specification, the above-described description of aryl groups applies to arylene groups, except that they are divalent. The above-described description of heteroaryl groups applies to heteroarylene groups, except that they are divalent.

[0040] In this specification, the silyl group includes alkylsilyl groups and arylsilyl groups. Examples of silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0041] In this specification, the number of carbon atoms in an amino group is not particularly limited, but for example, it is between 1 and 30. The amino group includes alkylamino groups, arylamino groups, or heteroarylamino groups. Specific examples of amino groups include, but are not limited to, methylamino groups, dimethylamino groups, phenylamino groups, diphenylamino groups, naphthylamino groups, 9-methyl-anthracenylamino groups, and triphenylamino groups.

[0042] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but for example, it may have 1 to 40 carbon atoms, 1 to 30 carbon atoms, or 1 to 20 carbon atoms. The carbonyl group may have, for example, the following structures, but is not limited to these. [ka]

[0043] In this specification, the number of carbon atoms in the sulfinyl group and sulfonyl group is not particularly limited, but may be, for example, 1 to 30. The sulfinyl group includes alkylsulfinyl groups and arylsulfinyl groups. The sulfonyl group includes alkylsulfonyl groups and arylsulfonyl groups.

[0044] In this specification, the term "thio group" includes alkylthio groups and arylthio groups. A thio group means a group to which a sulfur atom is bonded, in the alkyl or aryl group as defined above. Examples of thio groups include, but are not limited to, methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, and naphthylthio groups.

[0045] In this specification, an oxy group means a group in which an oxygen atom is bonded to an alkyl group or aryl group as defined above. Oxy groups include alkoxy groups and aryloxy groups. Alkoxy groups may be linear, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, and benzyloxy.

[0046] In this specification, a boryl group means a group in which a boron atom is bonded to an alkyl or aryl group as defined above. Boryl groups include alkylboryl groups and arylboryl groups. Examples of boryl groups include, but are not limited to, trimethylboryl, triethylboryl, t-butyldimethylboryl, triphenylboryl, diphenylboryl, and phenylboryl groups.

[0047] In this specification, the alkenyl group may be linear or branched. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienylaryl, styrenyl, and styrylvinyl groups.

[0048] In this specification, among alkylthio groups, alkylsulfoxy groups, alkylaryl groups, alkylamino groups, alkylboryl groups, alkylsilyl groups, and alkylamino groups, alkyl refers to, for example, the alkyl groups described above.

[0049] In this specification, among the aryloxy group, arylthio group, arylsulfoxy group, arylamino group, arylboron group, arylsilyl group, and arylamine group, the aryl group is, for example, the aryl group described above.

[0050] In this specification, direct bond means single bond.

[0051] JPEG0007881317000013.jpg24149

[0052] One embodiment of the present invention will be described below with reference to the drawings.

[0053] Figure 1 is a plan view showing an example of a display device DD according to one embodiment. Figure 2 is a cross-sectional view of the display device DD according to one embodiment. Figure 2 is a cross-sectional view showing the portion corresponding to the line I-I' in Figure 1.

[0054] The display device DD includes a display panel DP and an optical layer PP disposed on top of the display panel DP. The display panel PP includes light-emitting elements ED-1, ED-2, and ED-3. The display device DD includes multiple light-emitting elements ED-1, ED-2, and ED-3. The optical layer PP is disposed on top of the display panel DP and controls the reflected light on the display panel DP from external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. On the other hand, the optical layer PP may be omitted from the display device DD, contrary to the illustration.

[0055] A base substrate BL is placed on top of the optical layer PP. The base substrate BL is a component that provides the base surface on which the optical layer PP is placed. The base substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, it is not limited to these, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, contrary to the figures, in one embodiment the base substrate BL may be omitted.

[0056] The display device DD according to one embodiment may further include a charging layer (not shown). The packing layer (not shown) is disposed between the display element layer DP-ED and the base substrate BL. The packing layer (not shown) is an organic material layer. The packing layer (not shown) includes at least one of an acrylic resin, a silicone resin, and an epoxy resin.

[0057] 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. The display element layer DP-ED includes a pixel definition film PDL, light-emitting elements ED-1, ED-2, and ED-3 arranged between the pixel definition films PDL, and a sealing layer TFE provided on the light-emitting elements ED-1, ED-2, and ED-3.

[0058] The base layer BS is a component that provides the base surface on which the display element layer EP-ED is placed. The base layer BS can be a glass substrate, a metal substrate, a plastic substrate, etc. However, it is not limited to these, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.

[0059] The circuit layer DP-CL is located on the base layer BS. The circuit layer DP-CL includes a plurality of transistors (not shown). Each transistor (not shown) includes a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-ED may include switching transistors and drive transistors for driving organic electroluminescent elements ED-1, ED-2, and ED-3.

[0060] Each of the light-emitting elements ED-1, ED-2, and ED-3 has the structure of a light-emitting element ED according to one embodiment, as shown in Figures 3 to 7, 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, light-emitting layers EML-R, EML-G, EML-B, an electron transport region ETR, and a second electrode EL2.

[0061] Figure 2 shows an example in which the light-emitting layers EML-R, EML-G, and 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 film PDL, and the hole transport region HTR, electron transport region ETR, and second electrode EL2 are provided as a common layer for all light-emitting elements ED-1, ED-2, and ED-3. However, this is not limited to this, and in one embodiment, contrary to the illustration in Figure 2, the hole transport region HTR and electron transport region ETR may be patterned and provided inside the opening OH defined in the pixel-defining film PDL. For example, in one embodiment, the hole transport region HTR, light-emitting layers EML-R, EML-G, EML-B, and electron transport region ETR of the light-emitting elements ED-1, ED-2, and ED-3 may be patterned and provided by an inkjet printing method.

[0062] The sealing layer TFE covers the organic electroluminescent elements ED-1, ED-2, and ED-3. The sealing layer TFE seals the display element layer DP-ED. The sealing layer TFE may be a thin film sealing layer. The sealing layer TFE consists of one or more layers laminated together. The sealing layer TFE includes at least one insulating layer. The sealing layer TFE according to one embodiment includes at least one inorganic film (hereinafter referred to as the sealing inorganic film). The sealing layer TFE according to one embodiment also includes at least one organic film (hereinafter referred to as the sealing organic film) and at least one sealing inorganic film.

[0063] The encapsulating inorganic film protects the display element layer DP-ED from moisture / oxygen, and the encapsulating organic film protects the display element layer DP-ED from foreign matter such as dust particles. The encapsulating inorganic film may contain, but is not limited to, silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide. The encapsulating organic film may contain, but is not limited to, acrylic compounds or epoxy compounds. The encapsulating organic film may contain, but is not limited to, photopolymerizable organic materials.

[0064] The sealing layer TFE is placed on the second electrode EL2 and filled with the opening OH.

[0065] Referring to Figures 1 and 2, the display device DD includes a non-emitting region NPXA and emitting regions PXA-R, PXA-G, and PXA-B. Each of the emitting regions PXA-R, PXA-G, and PXA-B is a region from which light generated by the light-emitting elements ED-1, ED-2, and ED-3, respectively, is emitted. The emitting regions PXA-R, PXA-G, and PXA-B are spaced apart from each other on a plane.

[0066] The light-emitting regions PXA-R, PXA-G, and PXA-B are regions separated by the pixel definition film PPL. The non-light-emitting region NPXA is the region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and corresponds to the pixel definition film PDL. In this specification, the light-emitting regions PXA-R, PXA-G, and PXA-B each correspond to a pixel. The pixel definition film PDL separates the light-emitting elements ED-1, ED-2, and ED-3. The light-emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 are located and separated by the aperture OH defined in the pixel definition film PDL.

[0067] The light-emitting regions PXA-R, PXA-G, and PXA-B are divided into multiple groups according to the color of the light generated from the light-emitting elements ED-1, ED-2, and ED-3. The display device DD of one embodiment shown in Figures 1 and 2 exemplifies three light-emitting regions PXA-R, PXA-G, and PXA-B that emit red light, green light, and blue light, respectively. For example, the display device DD may include a red light-emitting region PXA-R, a green light-emitting region PXA-G, and a blue light-emitting region PXA-B that are separated from each other.

[0068] In the display device DD, multiple light-emitting elements ED-1, ED-2, and ED-3 emit light of different wavelengths from each other. For example, the display device DD may include a light-emitting element ED-1 that emits red light, a second light-emitting element ED-3 that emits green light, and a third light-emitting element ED-3 that emits blue light. In other words, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B of the display device DD may correspond to the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, respectively.

[0069] However, the embodiments are not limited to these, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light in the same wavelength region, or at least one of them may emit light in a different wavelength region. Furthermore, all of the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit blue light.

[0070] In one embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B in the display device DD are arranged in a striped pattern. Referring to Figure 1, multiple red light-emitting regions PXA-R, multiple green light-emitting regions PXA-G, and multiple blue light-emitting regions PXA-B are aligned along the second directional axis DR2. In addition, the red light-emitting regions PXA-R, green light-emitting regions PXA-G, and blue light-emitting regions PXA-B are arranged alternately along the first directional axis DR1.

[0071] In Figures 1 and 2, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B are shown to be approximately the same. However, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may differ from each other depending on the wavelength range of the emitted light. The areas of the light-emitting regions PXA-R, PXA-G, and PXA-B refer to the area as viewed from the plane defined by the first directional axis DR1 and the second directional axis DR2.

[0072] The arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B is not limited to that shown in Figure 1. The order in which the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B are arranged can be combined in various ways depending on the display quality characteristics required by the display device DD. For example, the arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B may be a pentile arrangement or a diamond arrangement.

[0073] Furthermore, the areas of the light-emitting regions 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 region PXA-G may be smaller than the area of ​​the blue light-emitting region PXA-B, but this is not limited to this.

[0074] Figures 3 to 7 below are schematic cross-sectional views of a light-emitting element according to one embodiment. The light-emitting element ED according to one embodiment includes a first electrode EL1, a second electrode EL2 facing the first electrode EL1, and at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The at least one functional layer includes sequentially stacked hole transport region HTR, light-emitting layer EML, and electron transport region ETR. In other words, the light-emitting element ED according to one embodiment includes sequentially stacked first electrode EL1, hole transport region HTR, light-emitting layer EML, electron transport region ETR, and second electrode EL2.

[0075] Unlike Figure 3, Figure 4 shows a cross-sectional view of an embodiment of a light-emitting element ED in which 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. Also, unlike Figure 3, Figure 5 shows a cross-sectional view of an embodiment of a light-emitting element ED in which the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Unlike Figure 4, Figure 6 shows a cross-sectional view of an embodiment of a light-emitting element ED in which a capping layer CPL is placed on the second electrode EL2. Unlike Figure 4, Figure 7 shows a cross-sectional view of an embodiment of a light-emitting element ED in which the hole transport region HTR includes multiple hole transport layers HTL1 and HTL2.

[0076] One embodiment of the light-emitting element ED includes an amine compound according to one embodiment of the present disclosure, described later, in at least one functional layer such as a hole transport region (HTR), an emissive layer (EML), and an electron transport region (ETR).

[0077] In one embodiment of a light-emitting element ED, the first electrode EL1 is conductive. The first electrode EL1 is made of a metallic material, a metal alloy, or a conductive compound. The first electrode EL1 is either an anode or a cathode. However, the embodiment is not limited to this. The first electrode EL1 is also a pixel electrode. The first electrode EL1 is a transmissive electrode, a semitransmissive electrode, or a reflective electrode. If the first electrode EL1 is a transmissive electrode, it includes transparent metal oxides, such as ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. If the first electrode EL1 is a semi-transparent or reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, W, or compounds or mixtures thereof (e.g., an alloy of Ag and Mg). Alternatively, the first electrode EL1 may have a multi-layer structure including a reflective or semi-transparent film made of the aforementioned materials, and a transparent conductive film made of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited to this. Furthermore, the embodiments are not limited to these, and the first electrode EL1 may include the above-mentioned metallic materials, a combination of two or more metallic materials selected from the above-mentioned metallic materials, or oxides of the above-mentioned metallic materials. The thickness of the first electrode EL1 may be approximately 70 nm to approximately 1000 nm. For example, the thickness of the first electrode EL1 may be approximately 100 nm to approximately 300 nm.

[0078] The hole transport region (HTR) is provided on the first electrode EL1. The hole transport region (HTR) includes at least one of a hole injection layer (HIL), a hole transport layer (HTL), a hole buffer layer or luminescence auxiliary layer (not shown), and an electron blocking layer (EBL). The thickness of the hole transport region (HTR) may be, for example, about 5 nm to about 1,500 nm.

[0079] The hole transport region (HTR) has a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0080] For example, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or it may have a single-layer structure consisting of a hole injection material and a hole transport material. Alternatively, the hole transport region HTR may have a single-layer structure consisting of multiple different materials, or it may have a structure of a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / buffer layer (not shown), a hole injection layer HIL / buffer layer (not shown), a hole transport layer HTL / buffer layer (not shown), or a hole injection layer HIL / hole transport layer HTL / hole blocking layer EBL stacked in order from the first electrode EL1. However, the embodiments are not limited to these.

[0081] Furthermore, in one embodiment, the hole transport region HTR may have a structure in which multiple hole transport layers are stacked. For example, it may have a structure of hole injection layer HIL / first hole transport layer HTL1 / second hole transport layer HTL2. However, the embodiments are not limited thereto.

[0082] Hole transport regions (HTRs) are formed using a variety of methods, including vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0083] In one embodiment of the light-emitting element ED, the hole transport region HTR contains an amine compound represented by the following chemical formula 1. In one embodiment of the light-emitting element ED, the hole transport layer HTL contains an amine compound represented by the following chemical formula 1, and in one embodiment of the light-emitting element ED, the first hole transport layer HTL1 may also contain an amine compound represented by the following chemical formula 1. [ka] ...(chemical formula 1)

[0084] In chemical formula 1, R1 is an adamantyl group, a cyclohexyl group, or a bicycloheptyl group, and FR is represented by the following chemical formula 2. [ka] ...(chemical formula 2)

[0085] In other words, the amine compound according to one embodiment includes a first substituent of a bicycloheptyl group bonded to the N atom via Ar2, a second substituent selected from an adamantyl group, a cyclohexyl group, or a bicycloheptyl group bonded to the N atom via Ar1, and a third substituent selected from a fluorenyl group or a dibenzoheterol group bonded to the N atom (via L). For example, in the amine compound of one embodiment, the bicycloheptyl group used as a substituent may be an unsubstituted bicyclo[2,2,1]heptyl group. In the amine compound of one embodiment, R1 may be an unsubstituted adamantyl group, an unsubstituted cyclohexyl group, or an unsubstituted bicyclo[2,2,1]heptyl group.

[0086] JPEG0007881317000016.jpg32147 [ka] ...(chemical formula 2A) [ka] ...(chemical formula 2B)

[0087] In chemical formula 1, Ar1 and Ar2 are each independently substituted or unsubstituted arylene groups having 6 to 30 ring-forming carbon atoms. For example, Ar1 and Ar2 may each independently be substituted or unsubstituted phenylene groups. Specifically, in one embodiment, Ar1 and Ar2 may be unsubstituted phenylene groups.

[0088] In chemical formula 1, L is a single-bonded, substituted, or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 30 ring-forming carbon atoms. If L is a single bond, the nitrogen atom (N) of the amine and the "FR" group are directly bonded by a single bond in chemical formula 1. L may also be a substituted or unsubstituted phenylene.

[0089] In chemical formula 2, X is CR a R b , N, NR c It is either O or S. In other words, the "FR" group represented by chemical formula 2 is a substituted or unsubstituted fluorene derivative, a substituted or unsubstituted carbazole derivative, a substituted or unsubstituted dibenzofuran derivative, or a substituted or unsubstituted dibenzothiophene derivative.

[0090] In chemical formula 2, R a ~R c Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. a ~R c Each of these groups can bond with an adjacent group to form a ring.

[0091] In chemical formula 2, d and e are independent integers between 0 and 4. Also, in chemical formula 2, R d and R eEach of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. d and R e Each of these groups can bond with an adjacent group to form a ring.

[0092] In chemical formula 2, if d is 0, then R is in chemical formula 2. d This means that it is not substituted, and if e is 0, then R is in chemical formula 2. e This means that it is not substituted. For example, in chemical formula 2, if both d and e are 0, the benzene ring in chemical formula 2 is unsubstituted. In chemical formula 2, if d is an integer of 2 or more, multiple R d All of them may be the same, or at least one may be different from the rest. Also, if e is an integer greater than or equal to 2, multiple R e All of them may be the same, or at least one may be different from the others.

[0093] In chemical formula 2, X in "FR" is CR a R b When expressed as R d and R b Each of these is independently a linear alkyl group, a cyclic alkyl group, or an aryl group. Also, R a and R b They may be joined to each other to form a ring. a and R b It may be bonded to a fluorene group, in which case the "FR" represented by chemical formula 2 has a spiro structure.

[0094] Also, the X in "FR" is CR a R b In the case of R a or R b It either directly binds with L, or R a or R bIt directly bonds to the nitrogen atom (N) of the amine.

[0095] In one embodiment, chemical formula 1 is represented by chemical formula 1-1 or chemical formula 1-2. In chemical formulas 1-1 and 1-2, the same provisions as described above for chemical formula 1 apply to R1, L, Ar1, and Ar2, and X, R d , R e The same explanation as described above for chemical formula 2 applies to d and e. [ka] ...(chemical formula 1-1) [ka] ...(chemical formula 1-2)

[0096] Furthermore, chemical formula 1-2 may also be represented by the following chemical formula 1-2A. In chemical formula 1-2A, the same explanation as for chemical formula 1 above applies to R1, L, Ar1, and Ar2, and R a , R d , R e The same explanation as described above for chemical formula 2 applies to d and e. [ka] ...(chemical formula 1-2A)

[0097] Chemical formula 1 may also be represented by the following chemical formula 1A. That is, in the amine compound according to one embodiment represented by chemical formula 1, Ar1 and Ar2 may both be unsubstituted phenylene groups. [ka] ...(chemical formula 1A)

[0098] Furthermore, chemical formula 1A may also be represented by the following chemical formula 1A-1. That is, in the amine compound according to one embodiment represented by chemical formula 1, the bicycloheptyl group and the substituent represented by R1 may be bonded to the para position of the phenylene group, which is a linker, relative to the nitrogen atom (N) of the amine. However, the embodiments are not limited thereto. [ka] ...(chemical formula 1A-1)

[0099] In the above chemical formulas 1A and 1A-1, the same principles as those described for chemical formula 1 apply to R1, L, and FR.

[0100] The amine compound of one embodiment represented by chemical formula 1 may be one of the following first group of compounds. In the light-emitting element ED according to one embodiment, the hole transport region HTR includes at least one of the amine compounds disclosed in the following first group of compounds. [First compound group] [ka] [ka] [ka] [ka]

[0101] The amine compound according to one embodiment, represented by chemical formula 1, contains one bicycloheptyl group as an essential component, and also has a structure containing one of the following as essential components: a bicycloheptyl group, a cyclohexyl group, or an adamantyl group, thereby exhibiting high glass transition temperature characteristics. Due to these high glass transition temperature characteristics, it exhibits excellent heat resistance and durability. Furthermore, the amine compound according to one embodiment, having the above structure, allows for a reduction in temperature when forming a film in the vapor deposition process, thereby increasing the productivity of the film formation process.

[0102] When the amine compound according to one embodiment is used in the hole transport region, the refractive index changes between the first and second electrodes, increasing the external quantum efficiency. As a result, using the amine compound according to one embodiment in the hole transport region increases the luminous efficiency of the light-emitting element and improves its lifespan. Furthermore, by including the amine compound according to one embodiment, which has excellent heat resistance and durability as described above, as a material for the light-emitting element, both the lifespan and luminous efficiency of the light-emitting element are improved.

[0103] On the other hand, if the light-emitting element ED includes multiple hole transport layers HTL1 and HTL2, the first hole transport layer HTL2 adjacent to the first electrode EL1 may contain the amine compound represented by the chemical formula 1 described above according to one embodiment. Furthermore, the second hole transport layer HTL2, which is placed on the first hole transport layer HTL1 and adjacent to the light-emitting layer EML, may contain the amine derivative compound represented by the chemical formula 3 below. [ka] ...(chemical formula 3)

[0104] In chemical formula 3, L 11 R is a single-bonded, substituted, or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group with 2 to 30 carbon atoms. Also, in chemical formula 3, 11 ~R 14Each of these groups is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, and can bond with adjacent groups to form a ring.

[0105] For example, L 11 R may be a single bond, or a substituted or unsubstituted phenylene group. 11 This may be a substituted or unsubstituted phenyl group. However, the embodiments are not limited to these.

[0106] In the amine derivative represented by chemical formula 3, R 12 R may be an aryl group or a heteroaryl group. For example, R 12 This may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0107] Chemical formula 3 may also be represented by the following chemical formula 3-1 or chemical formula 3-2. In chemical formulas 3-1 and 3-2, L 11 , and R 11 ~R 14 The same principles as those explained above for chemical formula 3 apply to this. [ka] ...(Chemical formula 3-1) [ka] ...(chemical formula 3-2)

[0108] In one embodiment, the light-emitting element ED contains the amine compound described above in the first hole transport layer HTL1, and the second hole transport layer HTL2 may contain the amine derivative compound represented by chemical formula 3-1 or the amine derivative compound represented by chemical formula 3-2.

[0109] The amine derivative compound represented by chemical formula 3-1 may be any one of the compounds shown in the compound group 2-1 below. For example, the second hole transport layer HTL2 may contain at least one of the compounds shown in the compound group 2-1 below. [2nd-1 compound group] [ka]

[0110] The amine derivative compound represented by chemical formula 3-2 may be any one of the compounds shown in the compound group 2-2 below. For example, the second hole transport layer HTL2 may contain at least one of the compounds shown in the compound group 2-2 below. [2nd-2nd compound group] [ka]

[0111] Furthermore, the light-emitting element ED according to one embodiment may further include, in the hole transport region HTR, a hole transport region material other than the amine compound and the amine derivative compound represented by chemical formula 3 described above.

[0112] For example, the hole transport region (HTR) may include a compound represented by the following chemical formula H-1. [ka] ...(chemical formula H-1)

[0113] In chemical formula H-1, L1 and L2 are each independently single-bonded, substituted, or unsubstituted arylene groups with 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroarylene groups with 2 to 30 ring-forming carbon atoms. a and b are each independently integers between 0 and 10. If a or b is an integer of 2 or more, then multiple L1 and L2 are each independently substituted or unsubstituted arylene groups with 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroarylene groups with 2 to 30 ring-forming carbon atoms.

[0114] In chemical formula H-1, Ar1 and Ar2 are independently substituted or unsubstituted aryl groups with 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl groups with 2 to 30 ring-forming carbon atoms. Furthermore, in chemical formula H-1, Ar3 is a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms.

[0115] The compound represented by chemical formula H-1 may be a monoamine compound. Alternatively, the compound represented by chemical formula H-1 may be a diamine compound in which at least one of Ar1 to Ar3 has an amino group as a substituent. Furthermore, the compound represented by chemical formula H-1 may be a carbazole compound in which at least one of Ar1 and Ar2 has a substituted or unsubstituted carbazolyl group, or a fluorene compound in which at least one of Ar1 and Ar2 has a substituted or unsubstituted fluorenyl group.

[0116] The compound represented by the chemical formula H-1 may be any one of the compounds in compound group H below. However, the compounds listed in compound group H below are illustrative examples, and the compound represented by the chemical formula H-1 is not limited to those shown in compound group H below. [Compound group H] [ka] [ka] [ka] [ka]

[0117] The hole transport region HTR is used for phthalocyanine compounds such as copper phthalocyanine, DNTPD (N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine)), m-MTDATA (4,4',4”-[tris(3-methylphenyl)phenylamino)triphenylamino], TDATA (4,4',4”-tris(N,N-diphenylamino)triphenylamine), 2-TNATA (4,4',4”-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrene) It may also contain ((polyaniline) / (poly(4-styrene sulfonate)), PANI / DBSA (polyaniline / dodecylbenzenesulfonic acid), PANI / CSA (polyaniline / camphor sulfonic acid), PANI / PSS ((polyaniline) / poly(4-styrene sulfonate)), NPB (N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine), polyether ketone containing triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl) borate, HATCN (dipyradino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitride), etc.

[0118] The hole transport region HTR may include, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine) and TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine), TAPC (4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzeneamine]), and HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl).

[0119] Furthermore, the hole transport region HTR may also include CzSi(9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-(carbazole), CCP(9-phenyl-9H-3,9'-bicarbazole), mCP(1,3-bis(N-carbazolyl)benzene), or mDCP(1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene).

[0120] The hole transport region (HTR) may contain at least one of the hole transport region compounds described above, including the hole injection layer (HIL), the hole transport layer (HTL), and the electron blocking layer (EBL).

[0121] The thickness of the hole transport region (HTR) may be approximately 10 nm to 1000 nm, for example, approximately 10 nm to 500 nm. If the hole transport region (HTR) includes a hole injection layer (HIL), the thickness of the hole injection layer (HIL) is, for example, approximately 3 nm to 100 nm. If the hole transport region (HTR) includes a hole transport layer (HTL), the thickness of the hole transport layer (HTL) is, for example, approximately 3 nm to 100 nm. If the hole transport region (HTR) includes a hole blocking layer (EBL), the thickness of the hole blocking layer (EBL) is, for example, approximately 1 nm to 100 nm. When the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) satisfy the above-described ranges, sufficient hole transport characteristics can be obtained without a substantial increase in the driving voltage.

[0122] The hole transport region (HTR) may further contain charge-generating materials in addition to the materials described above to improve conductivity. The charge-generating materials are uniformly or non-uniformly dispersed within the hole transport region (HTR). The charge-generating materials are, for example, p-dopant. The p-dopant may contain, but is not limited to, at least one of metal halide compounds, quinone derivatives, metal oxides, and cyano group-containing compounds. Examples of p-dopants include, but are not limited to, metal halide 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, and cyano group-containing compounds such as HATCN (dipyradino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonnitrile) and NDP9 (4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile).

[0123] As described above, the hole transport region (HTR) may further include at least one of a buffer layer (not shown) and an electron blocking layer (EBL) in addition to the hole transport layer (HTL) and the hole injection layer (HIL). The buffer layer (not shown) compensates for the resonance distance due to the wavelength of light emitted from the light emission layer (EML) and increases the light emission efficiency. The material included in the buffer layer (not shown) is a material that can be included in the hole transport region (HTR). The electron blocking layer (EBL) is a layer that prevents electron injection from the electron transport region (ETR) to the hole transport region (HTR).

[0124] The emissive layer (EML) is provided on top of the hole transport region (HTR). The emissive layer (EML) has a thickness of, for example, about 10 nm to about 100 nm, or about 10 nm to about 30 nm. The emissive layer (EML) has a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0125] In one embodiment of the light-emitting element ED, the light-emitting layer EML contains an anthracene derivative, a pyrene derivative, a fluorantene derivative, a chrysene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. More specifically, the light-emitting layer EML may contain an anthracene derivative or a pyrene derivative.

[0126] In one embodiment of the light-emitting element ED shown in Figures 3 to 7, the light-emitting layer EML contains a host and a dopant, and the light-emitting layer EML contains a compound represented by the following chemical formula E-1. The compound represented by the following chemical formula E-1 is used as a fluorescent host material. [ka] ...(chemical formula E-1)

[0127] In chemical formula E-1, R 31 ~R 40 Each of these groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, and can bond with adjacent groups to form a ring. 31 ~R 40 These groups may bond with adjacent groups to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocycle, or an unsaturated heterocycle.

[0128] In chemical formula E-1, c and d are each independent integers between 0 and 5 (inclusive).

[0129] The compound represented by chemical formula E-1 may be any one of the following compounds E1 to E19. [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0130] In one embodiment, the light-emitting layer EML may contain a compound represented by the following chemical formula E-2a or the chemical formula E-2b described later. The compounds represented by the following chemical formulas E-2a and E-2b are used as phosphorescent host materials. [ka] ...(chemical formula E-2a)

[0131] In chemical formula E-2a, a is an integer between 0 and 10, and L ais a single bond, a substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group with 2 to 30 carbon atoms. If a is an integer of 2 or more, L a Each of these is independently a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0132] In chemical formula E-2a, A1 to A5 are each independently either N or CR. i That is. R a ~R i Each of these groups is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, and can bond with adjacent groups to form a ring. a ~R i These groups may bond with adjacent groups to form a hydrocarbon ring or a heterocycle containing N, O, S, etc., as ring-forming atoms.

[0133] In chemical formula E-2a, two or three of A1 to A5 are N and the rest are CR. i That's fine.

[0134] Chemical formula E-2b is shown below. [ka] ...(chemical formula E-2b)

[0135] In chemical formula E-2b, Cbz1 and Cbz2 are independently either a carbazole group or an aryl group with 6 to 30 carbon atoms substituted with a carbazole group. bis a single bond, substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group with 2 to 30 carbon atoms. b is an integer between 0 and 10, and if b is an integer of 2 or more, multiple L b Each of these is independently a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0136] The compound represented by chemical formula E-2a or chemical formula E-2b may be any one of the compounds in compound group E-2 below. However, the compounds listed in compound group E-2 below are illustrative examples, and the compound represented by chemical formula E-2a or chemical formula E-2b is not limited to those shown in compound group E-2 below. [Compound group E-2] [ka] [ka] [ka] [ka] [ka]

[0137] The luminescent layer EML may further contain common materials known in the relevant art as a host material. For example, the luminescent layer EML may contain at least one of the following as a host material: DPEPO (bis[2-(diphenylphosphino)phenyl] ether oxide), CBP (4,4-bis(carbazole-9-yl)biphenyl), mCP (1,3-bis(carbazole-9-yl)benzene), PPF (2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan), TCTA (4,4',4”-tris(carbazole-9-yl)-triphenylamine), and TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene). However, it is not limited to these, for example, Alq3 (tris(8-hydroxyquinoli) The following can also be used as host materials: (aluminum), ADN (9,10-di(naphthalene-2-yl)anthracene), TBADN (3-tert-butyl-9,10-di(naphtho-2-yl)anthracene), DSA (distylyl arylene), CDBP (4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl), MADN (2-methyl-9,10-bis(naphthalene-2-yl)anthracene), CP1 (hexaphenylcyclotriphosphazene), UGH2 (1,4-bis(triphenylsilyl)benzene), DPSiO3 (hexaphenylcyclotrisiloxane), DPSiO4 (octaphenylcyclotetrasiloxane), etc.

[0138] In one embodiment, the light-emitting layer EML may contain a compound represented by the following chemical formula Ma or the chemical formula Mb described later. The compounds represented by the following chemical formulas Ma and Mb are used as phosphorescent dopant materials. [ka] ...(Chemical formula Ma)

[0139] In Chemical Formula M-a, Y1 to Y4 and Z1 to Z4 are each independently CR1 or N, and R1 to R4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and adjacent groups can combine with each other to form a ring. In Chemical Formula M-a, m is 0 or 1, and n is 2 or 3. In Chemical Formula M-a, if m is 0, then n is 3, and if m is 1, then n is 2.

[0140] The compound represented by Chemical Formula M-a may be any one of the compounds in the following compound groups M-a1 to M-a25. However, the following compounds M-a1 to M-a25 are illustrative, and the compound represented by Chemical Formula M-a is not limited to the following compounds M-a1 to M-a25.

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Chem.

Chem.

[0141] Compound M-a1 and compound M-a2 are used as red dopant materials, and compounds M-a3 to M-a7 are used as green dopant materials.

[0142] Chemical formula M-b is shown below.

Chemical formula

[0143] TIFF0007881317000062.tif139170

[0144] The compound represented by chemical formula M-b is used as a blue phosphorescent dopant or a green phosphorescent dopant.

[0145] The compound represented by chemical formula M-b may be any one of the following compounds. However, the following compounds are exemplary, and the compound represented by chemical formula M-b is not limited to the following compounds.

Chemical formula

Chemical formula

[0146] 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 amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0147] The light-emitting layer EML contains a compound represented by any one of the following chemical formulas F-a to F-c. The compounds represented by the following chemical formulas F-a to F-c are used as fluorescent dopant materials.

[0148] The chemical formula Fa is shown below. [ka] ...(Chemical formula Fa)

[0149] TIFF0007881317000066.tif87170

[0150] The chemical formula Fb is shown below. [ka] ...(Chemical formula Fb)

[0151] In the chemical formula Fb, R a and R b Each of these groups is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, and can bond with adjacent groups to form a ring.

[0152] In the chemical formula Fb, U and V are independently substituted or unsubstituted hydrocarbon rings with 5 to 30 ring-forming carbon atoms, or substituted or unsubstituted heterocycles with 2 to 30 ring-forming carbon atoms.

[0153] In Chemical Formula F-b, the number of rings represented by U and V are each independently 0 or 1. For example, in Chemical Formula F-b, if the number of U or V is 1, one ring in the part described by U or V forms a fused ring, and if the number of U or V is 0, it means that the ring described by U or V does not exist. Specifically, if the number of U is 0 and the number of V is 1, or if the number of U is 1 and the number of V is 0, the fused ring having the fluorene core of Chemical Formula F-b is a 4-ring cyclic compound. Also, if the numbers of both U and V are 0, the fused ring of Chemical Formula F-b is a 3-ring cyclic compound. Further, if the numbers of both U and V are 1, the fused ring having the fluorene core of Chemical Formula F-b is a 5-ring cyclic compound.

[0154] Chemical Formula F-c is shown below.

Chemical Structure

[0155] In Chemical Formula F-c, A1 and A2 are each independently O, S, Se, or NR m where R m is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. R1 to R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and adjacent groups can combine with each other to form a ring.

[0156] In the chemical formula Fc, A1 and A2 may each independently bond to a substituent on an adjacent ring to form a fused ring. For example, A1 and A2 may each independently form NR m Therefore, A1 can bond with R4 or R5 to form a ring. Also, A2 can bond with R7 or R8 to form a ring.

[0157] In one embodiment, the luminescent layer EML is a known dopant material, and is a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazol)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)- This may include N-phenylbenzeneamine (N-BDAVBi), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1-dipylene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene, etc.).

[0158] The luminescent layer EML may contain known phosphorescent dopant materials. For example, metal complexes containing iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) may be used as phosphorescent dopants. Specifically, Flrpic (iridium(III)bis(4,6-difluorophenylpyridinate-N,C2')picolinate), Fir6 (bis(2,4-difluorophenylpyridinate)-tetrakis(1-pyrazolyl)borate-iridium(III)) or PtOEP (platinum-octaethylporphyrin) may be used as phosphorescent dopants. However, the embodiments are not limited to these.

[0159] The luminescent layer EML may contain quantum dot material. The core of the quantum dot can be selected from group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0160] Group II-VI compounds are binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof, including CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgT e, a ternary compound selected from the group consisting of HgZnS, HeZnSe, HeZnTe, MgZnSe, MgZnS, and mixtures thereof, and a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof.

[0161] Group III-VI compounds may include binary compounds such as In2S3 and In2Se3, ternary compounds such as InGaS3 and InGaSe3, or any combination thereof.

[0162] The group I-III-VI compounds may be selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2, and mixtures thereof, or from quaternary compounds such as AgInGaS2 and CuInGaS2.

[0163] The group III-V compounds may be selected from the group consisting of binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. On the other hand, the group III-V compounds may further contain group II metals. For example, InZnP may be selected as a III-II-V group compound.

[0164] Group IV-VI compounds may be selected from the group consisting of binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0165] Binary, ternary, or quaternary compounds may exist within a particle at a uniform concentration, or they may be separated into states with partially different concentration distributions within the same particle. Furthermore, a core-shell structure may exist in which one quantum dot surrounds another. In a core-shell structure, there may be a concentration gradient where the concentration of elements in the shell decreases towards the core.

[0166] In some embodiments, the quantum dot has a core-shell structure comprising a core containing the nanocrystals described above, and a shell surrounding the core. The shell of the quantum dot acts as a protective layer to prevent chemical degradation of the core and maintain its semiconductor properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. Examples of quantum dot shells include metallic or nonmetallic oxides, semiconductor compounds, or combinations thereof.

[0167] For example, examples of metal or nonmetal oxides used in shells include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and NiO, or ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and CoMn2O4, but the present invention is not limited to these.

[0168] Furthermore, while semiconductor compounds used in shells include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, and AlSb, the present invention is not limited to these.

[0169] Quantum dots have an emission wavelength spectrum with a full width at half maximum (FWHM) of approximately 45 nm or less, preferably approximately 40 nm or less, and more preferably approximately 30 nm or less, and can improve color purity and color reproducibility within this range. Furthermore, since the light emitted through such quantum dots is emitted in all directions, the optical viewing angle is improved.

[0170] Furthermore, the form of the quantum dots is not limited to those commonly used in this field, but more specifically, spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate-like particles may be used.

[0171] Quantum dots can adjust the hue of the light they emit depending on the size of the particle, and as a result, quantum dots have a variety of emission hues, such as blue, red, and green.

[0172] In one embodiment of the light-emitting element ED shown in Figures 3 to 7, the electron transport region ETR is provided on the light-emitting layer EML. The electron transport region ETR includes at least one of the hole blocking layer HBL, the electron transport layer ETL, and the electron injection layer EIL, but the embodiment is not limited to this.

[0173] The electron transport region (ETR) has a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0174] For example, the electron transport region (ETR) may have a single-layer structure of an electron injection layer (EIL) or electron transport layer (ETL), or a single-layer structure consisting of an electron injection material and an electron transport material. Furthermore, the electron transport region (ETR) may have a single-layer structure consisting of multiple different materials, and may have structures such as an electron transport layer (ETL) / electron injection layer (EIL) or a hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) stacked sequentially from the light-emitting layer (EML), but is not limited to these. The thickness of the electron transport region (ETR) may be, for example, about 100 nm to about 150 nm.

[0175] The electron transport region (ETR) is formed using a variety of methods, including vacuum deposition, spin coating, casting, LB (Laser-Blocked) method, inkjet printing, laser printing, and laser thermal transfer.

[0176] The electron transport region (ETR) may include the compound represented by the following chemical formula ET-1. [ka] ...(Chemical formula ET-1)

[0177] In the chemical formula ET-1, at least one of X1 to X3 is N and the rest are CR. a That is. R a Each of the following is 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-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and Ar1 to Ar3 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-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0178] In chemical formula ET-1, a to c are each independent integers between 0 and 10. In chemical formula ET-1, L1 to L3 are each independent arylene groups with single bonds, substituted or unsubstituted ring-forming carbon atoms between 6 and 30, or substituted or unsubstituted heteroarylene groups with 2 to 30 ring-forming carbon atoms. If a to c are integers of 2 or more, then multiple L1 to L3 are each independently substituted or unsubstituted arylene groups with 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroarylene groups with 2 to 30 ring-forming carbon atoms.

[0179] The electron transport region (ETR) may include anthracene compounds. However, it is not limited to these; the electron transport region (ETR) may include, for example, Alq3 (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-phenylbenzimidazole-1-yl)phenyl)-9,10-dinaphthylanthracene, TPBi (1,3,5-tri(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene), BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), TAZ (3-(4-biphenyl The following may be included: (4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), NTAZ (4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD (2-(4-biphenylyl)-5-(4-tertobutylphenyl)-1,3,4-oxadiazole), BAlq (bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-orato)aluminum), Bebq2 (beryllium bis(benzoquinoline-10-orato), ADN (9,10-di(naphthalene-2-yl)anthracene), BmPyPhB (1,3-bis[3,5-di(pyridine-3-yl)phenyl]benzene), and mixtures thereof.

[0180] Furthermore, the electron transport region (ETR) may include metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI, lanthanide metals such as Yb, or co-deposited materials of metal halides and lanthanide metals. For example, the electron transport region (ETR) may include KI:Yb, RbI:Yb, etc., as co-deposited materials. In addition, metal oxides such as Li2O and BaO, or Liq(8-hydroxylithium quinolate) may be used in the electron transport region (ETR), but are not limited to these. The electron transport region (ETR) may also include a substance which is a mixture of an electron transport material and an insulating organometallic salt. The organometallic salt is a substance which has an energy band gap of about 4 eV or more. For more details, organometallic salts include, for example, metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.

[0181] The electron transport region (ETR) may, but is not limited to, further contain at least one of the following materials: BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) and Bphen (4,7-diphenyl-1,10-phenanthroline).

[0182] The electron transport region ETR includes the aforementioned electron transport region compound in at least one of the electron injection layer EIL, electron transport layer ETL, and hole blocking layer HBL.

[0183] If the electron transport region (ETR) includes an electron transport layer (ETL), the thickness of the electron transport layer (ETL) may be approximately 10 nm to 100 nm, for example, approximately 15 nm to 50 nm. If the thickness of the electron transport layer (HTL) satisfies the above-mentioned range, sufficient electron transport characteristics can be obtained without a substantial increase in driving voltage. If the electron transport region (ETR) includes an electron injection layer (EIL), the thickness of the electron injection layer (EIL) may be approximately 0.1 nm to 10 nm, or approximately 0.3 nm to 9 nm. If the thickness of the electron injection layer (EIL) satisfies the above-mentioned range, sufficient electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0184] The second electrode EL2 is located on the electron transport region ETR. The second electrode EL2 is a common electrode. The second electrode EL2 may be a cathode or an anode, but is not limited to these two. For example, if the first electrode EL1 is an anode, the second electrode may be a cathode, and if the first electrode EL1 is a cathode, the second electrode may be an anode.

[0185] The second electrode EL2 is a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode, it is made of a transparent metal oxide, such as ITO, IZO, ZnO, ITZO, etc.

[0186] If the second electrode EL2 is a semi-transparent or reflective electrode, the second electrode EL2 may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, Yb, W, or compounds or mixtures containing these (e.g., AgMg, AgYb, or MgAg). The second electrode EL2 may also have a multilayer structure including a reflective or semi-transparent film made of the material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may contain the above-mentioned metallic materials, a combination of two or more metallic materials selected from the above-mentioned metallic materials, or oxides of the above-mentioned metallic materials.

[0187] Although not shown in the diagram, the second electrode EL2 may be connected to an auxiliary electrode. Connecting the second electrode EL2 to an auxiliary electrode can reduce the resistance of the second electrode EL2.

[0188] On the other hand, a capping layer CPL may be further disposed on the second electrode EL2 of the light-emitting element ED in one embodiment. The capping layer CPL may be multilayer or monolayer. In one embodiment, the capping layer CPL may contain the amine compound according to the embodiment described above.

[0189] In one embodiment, the capping layer (CPL) is an organic or inorganic layer. For example, if the capping layer (CPL) contains an inorganic substance, the inorganic substance may include alkali metal compounds such as LiF, alkaline earth compounds such as MgF2, SiON, SiNx, SiOy, etc.

[0190] If the capping layer CPL contains organic matter, it may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, TPD15 (N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine), TCTA (4,4',4”-tris(carbazolesol-9-yl)triphenylamine), and may also contain epoxy resin or acrylates such as methacrylate. However, the embodiments are not limited to these, and the capping layer CPL may contain at least one of the compounds P1 to P5 described below. [ka]

[0191] In one embodiment, the refractive index of the capping layer CPL is 1.6 or higher. Specifically, for light in the wavelength range of 550 nm to 660 nm, the refractive index of the capping layer CPL is 1.6 or higher.

[0192] Figures 8 and 9 are cross-sectional views of a display device according to one embodiment. In the following description of the display device according to one embodiment, with reference to Figures 8 and 9, we will not repeat the content described in Figures 1 to 7 above, but will focus on the differences.

[0193] Referring to Figure 8, a display device DD according to one embodiment includes a display panel DP including a display element layer DP-ED, an optical control layer CCL disposed on the display panel DP, and a color filter layer CFL.

[0194] In one embodiment shown in Figure 8, 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, the display element layer DP-ED including a light-emitting element ED.

[0195] The light-emitting element ED includes a first electrode EL1, a hole transport region HTR placed on the first electrode EL1, an emissive layer EML placed on the hole transport region HTR, an electron transport region ETR placed on the emissive layer EML, and a second electrode EL2 placed on the electron transport region ETR. On the other hand, the structure of the light-emitting element ED shown in Figure 8 is also to which the structures of the light-emitting elements shown in Figures 3 to 7 described above apply.

[0196] Referring to Figure 8, the light-emitting layer EML is positioned within the aperture OH defined in the pixel definition film DPL. For example, light-emitting layers EML provided in each light-emitting region PXA-R, PXA-G, and PXA-B, separated by the pixel definition film PDL, emit light in the same wavelength range. In one embodiment of the display device DD, the light-emitting layer EML emits blue light. On the other hand, contrary to the illustration, the light-emitting layer EML in one embodiment may be provided in common across the entire light-emitting regions PXA-R, PXA-G, and PXA-B.

[0197] The optical control layer (CCL) is positioned above the display panel (DP). The CCL contains photoconverters, such as quantum dots or phosphors. These photoconverters convert the wavelength of incident light and emit it. Therefore, the CCL is either a layer containing quantum dots or a layer containing phosphors.

[0198] The optical control layer (CCL) includes multiple optical control units CCP1, CCP2, and CCP3. The optical control units CCP1, CCP2, and CCP3 are spaced apart from each other.

[0199] Referring to Figure 8, a division pattern BMP is provided between the optical control units CCP1, CCP2, and CCP3, which are separated from each other, but the embodiment is not limited to this. In Figure 8, the division pattern BMP is shown without overlapping with the optical control units CCP1, CCP2, and CCP3, but the edges of the optical control units CCP1, CCP2, and CCP3 may overlap with the division pattern BMP in at least part.

[0200] The optical control layer CCL includes a first optical control unit CCP1 which includes a first quantum dot QD1 that converts the first color light emitted from the light-emitting element ED into second color light, a second optical control unit CCP2 which includes a second quantum dot QD2 that converts the first color light into third color light, and a third optical control unit CCP3 which transmits the first color light.

[0201] In one embodiment, the first light control unit CCP1 emits red light, which is the second color, and the second light control unit CCP2 emits green light, which is the third color. The third light control unit CCP3 transmits blue light, which is the first color, emitted from the light-emitting element ED. For example, the first quantum dot QD1 may be a red quantum dot, and the second quantum dot QD2 may be a green quantum dot. The same provisions as described above apply to quantum dots QD1 and QD2.

[0202] Furthermore, the optical control layer CCL further includes a scatterer SP. The first optical control unit CCP1 includes a first quantum dot QD1 and a scatterer SP, the second optical control unit CCP2 includes a second quantum dot QD2 and a scatterer SP, and the third optical control unit CCP3 includes a scatterer SP but does not include a quantum dot.

[0203] The scatterer SP is an inorganic particle. For example, the scatterer SP may contain at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer SP contains at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or it is a mixture of two or more substances selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.

[0204] The first optical control unit CCP1, the second optical control unit CCP2, and the third optical control unit CCP3 each include base resins BR1, BR2, and BR3 for dispersing quantum dots QD1 and QD2 and scatterers SP. In one embodiment, the first optical control unit CCP1 includes first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second optical control unit CCP2 includes second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third optical control unit CCP1 includes scatterers SP dispersed in the third base resin BR3. The base resins BR1, BR2, and BR3 are media in which the quantum dots QD1 and QD2 and scatterers SP are dispersed, and consist of various resin compositions generally referred to as binders. For example, the base resins BR1, BR2, and BR3 are acrylic resins, urethane resins, silicone resins, epoxy resins, etc. The base resins BR1, BR2, and BR3 are transparent resins. In one embodiment, the first base resin BR1, the second base resin BR2, and the third base resin BR3 may be the same as or different from each other.

[0205] The light control layer CCL includes a barrier layer BFL1. The barrier layer BFL1 prevents the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 is placed on top of the light control units CCP1, CCP2, and CCP3, blocking them from being exposed to moisture / oxygen. The barrier layer BFL1 covers the light control units CCP1, CCP2, and CCP3. In addition, a barrier layer BLF2 may be provided between the light control units CCP1, CCP2, and CCP3 and the color filter layer CFL.

[0206] The barrier layers BFL1 and BFL2 each contain at least one inorganic layer. In other words, the barrier layers BFL1 and BFL2 are formed by including inorganic materials. For example, the barrier layers BFL1 and BFL2 are formed by including 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 a thin metal film with sufficient light transmittance. The barrier layers BFL1 and BFL2 may also further contain an organic film. The barrier layers BFL1 and BFL2 consist of a single layer or multiple layers.

[0207] In one embodiment of the display device DD, the color filter layer CFL is placed on top of the color control layer CCL. For example, the color filter layer CFL may be placed directly on top of the color control layer CCL. In this case, the barrier layer BFL2 may be omitted.

[0208] The color filter layer CFL includes a light-shielding section BM and filters CF1, CF2, and CF3. The color filter layer CFL includes a first filter CF1 that transmits a second color of light, a second filter CF2 that transmits a third color of light, and a third filter CF3 that transmits a first color of light. For example, the first filter CF1 may be a red filter, the second filter CF2 a green filter, and the third filter CF3 a blue filter. Each of the filters CF1, CF2, and CF3 contains a polymer photosensitive resin and a pigment or dye. The first filter CF1 contains a red pigment or dye, the second filter CF2 contains a green pigment or dye, and the third filter CF3 contains a blue pigment or dye. On the other hand, the embodiment is not limited to this, and the third filter CF3 does not have to contain a pigment or dye. For example, the third filter CF3 contains a polymer photosensitive resin and does not contain a pigment or dye. In this case, the third filter CF3 is transparent and made of a transparent photosensitive resin.

[0209] 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 be provided as a single unit without being separated from each other.

[0210] The light-shielding portion BM is a black matrix. The light-shielding portion BM is formed by comprising an organic or inorganic light-shielding material containing a black pigment or black dye. The light-shielding portion BM prevents light leakage and demarcates the boundaries between adjacent filters CF1, CF2, and CF3. In one embodiment, the light-shielding portion BM may also be formed of a blue filter.

[0211] The first to third filters CF1, CF2, and CF3 are positioned to correspond to the red emission region PXA-R, the green emission region PXA-G, and the blue emission region PXA-B, respectively.

[0212] A base substrate BL is placed on top of the color filter layer CFL. The base substrate BL is a component that provides a base surface on which the color filter layer CFL and the light control layer CCL are placed. The base substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited to these, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, contrary to the figures, in one embodiment the base substrate BL may be omitted.

[0213] Figure 9 is a cross-sectional view showing a part of a display device according to one embodiment. Figure 9 shows a cross-sectional view of a part corresponding to the display panel DP in Figure 8. In the display device DD-TD according to one embodiment, the light-emitting element ED-BT includes a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The light-emitting element ED-BT includes a first electrode EL1 and a second electrode EL2 facing each other, and a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 that are sequentially stacked in the thickness direction between the first electrode EL1 and the second electrode EL2. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 includes a light-emitting layer EML (Figure 7) and a hole transport region HTR and an electron transport region ETR arranged with the light-emitting layer EML (Figure 7) in between.

[0214] In other words, the light-emitting element ED-BT included in the display device DD-TD of one embodiment is a light-emitting element with a tandem structure that includes multiple light-emitting layers.

[0215] In one embodiment shown in Figure 9, the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 is blue light. However, the embodiment is not limited to this, and the wavelength ranges of the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may be different from each other. For example, an ED-BT light-emitting element that includes multiple light-emitting structures OL-B1, OL-B2, and OL-B3 that emit light in different wavelength ranges may emit white light.

[0216] A charge generation layer CGL is positioned between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layer CGL includes a p-type charge generation layer and / or an n-type charge generation layer.

[0217] 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 contains the amine compound described above according to one embodiment.

[0218] A light-emitting element ED according to one embodiment of the present invention exhibits improved luminescence efficiency and improved long-life characteristics by including the amine compound according to the above embodiment in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. In one embodiment of the light-emitting element ED, the amine compound according to the above embodiment may be included in at least one of the hole transport region HTR, the light-emitting layer EML, and the electron transport region ETR disposed between the first electrode EL1 and the second electrode EL2, or it may be included in the capping layer CPL.

[0219] For example, the amine compound according to one embodiment may be included in the hole transport region HTR of the light-emitting element ED of one embodiment, and the light-emitting element according to one embodiment containing the amine compound exhibits excellent luminous efficiency and long lifetime characteristics.

[0220] The amine compound according to the above embodiment contains a bicycloheptyl group as an essential component and has a molecular structure further containing one of an adamantyl group, a cyclohexyl group, or a bicycloheptyl group, thereby exhibiting excellent durability and heat resistance, and improved lifetime characteristics. Furthermore, the amine compound according to the above embodiment has improved material stability and hole transport capability, contributing to the long lifetime and high efficiency characteristics of the light-emitting element. [Examples]

[0221] The following describes in detail an amine compound according to one embodiment of the present invention and a light-emitting element according to one embodiment, with reference to examples and comparative examples. Furthermore, the following examples are illustrative examples to aid in understanding the present invention, and the scope of the present invention is not limited thereto.

[0222] 1. Synthesis of amine compounds First, the synthesis method of the compounds according to this embodiment will be explained in detail, with examples of the synthesis methods for compounds 1, 2, 30, 41, 50, and 65 of the first compound group. Furthermore, the synthesis methods of the amine compounds described below are examples only, and the synthesis methods of the amine compounds according to the embodiments of the present invention are not limited to the examples below.

[0223] (1) Synthesis of compound 1 Amine compound 1 according to one embodiment can be synthesized, for example, by the following reaction steps. <Synthesis of Intermediate A> [ka]

[0224] 12.9 g (100 mmol) of 1-bromo-4-iodobenzene, 23.3 g of bicyclo[2,2,1]hept-2-ene, 19.5 g (100 mmol) of CuI, and 25.8 g (200 mmol) of K2CO3 were added to 200 ml of DMF solution and stirred at 150°C for 96 hours. After the reaction was complete, the temperature was lowered to room temperature and the mixture was extracted three times with ethyl acetate / H2O. The mixture was dried over anhydrous magnesium sulfate and purified by column chromatography in a mixed solvent of dichloromethane (MC):hexane (HEX) = 1:10 to obtain 18.8 g of intermediate A (yield 80%).

[0225] <Synthesis of Intermediate B> [ka]

[0226] (Synthesis of intermediate B-1) 21.4 g (100 mmol) of 1-bromoadamantane was added to 100 ml of phenol, and the mixture was stirred at 110°C for 24 hours. After the reaction was complete, the resulting solid was washed three times with H2O at 60°C. After dissolving in MC, it was dried over anhydrous magnesium sulfate to obtain 22 g of intermediate B-1 (100% yield).

[0227] (Synthesis of intermediate B) After dissolving 22g of intermediate B-1 and 10g of Et3N in MC, the solution temperature was lowered to 0°C. 50g of trifluoromethanesulfonic acid anhydride was added for 1 hour. Next, the temperature was raised to room temperature and stirred for 4 hours. After the reaction was complete, the resulting solid was extracted three times with Et2O / H2O at 60°C. After drying with anhydrous magnesium sulfate, the mixture was separated and purified by column chromatography to obtain 33g of intermediate B (90% yield).

[0228] <Synthesis of Compound 1> [ka]

[0229] (Synthesis of intermediate 1-1) 4.2 g (20 mmol) of 9,9-dimethyl-9H-fluorene-2-amine, 5 g (20 mmol) of Intermediate A, 0.915 g (1 mmol) of Pd2(dba)3, 0.410 g (1 ml) of Sphos, and 3.6 g (40 mmol) of NaO t Bu were dissolved in toluene (200 ml), and then stirred at 90 °C for 2 hours. Extracted three times with Et2O / H2O. After drying over anhydrous magnesium sulfate, separated and purified by column chromatography to obtain 6.8 g (18 mmol) of Intermediate 1-1 with a yield of 90%.

[0230] (Synthesis of Compound 1) Compound 1 (5.3 g, 9 mmol) was obtained with a yield of 90% using the same method as the synthesis of Intermediate 1-1, except that Intermediate 1-1 was used instead of 9,9-dimethyl-9H-fluorene-2-amine and Intermediate B was used instead of Intermediate A.

[0231] The molecular weight and NMR results were confirmed as follows, and it was confirmed that it was Compound 1. [C 44 H 47 N M+1: 590.45, 1 1H NMR (500 MHz, CDCl3) δ = 7.80 (m, 2H), 7.60 (d, 1H), 7.55 - 7.10 (m, 12H), 2.5 - 0.9 (m, 32H)]

[0232] (2) Synthesis of Compound 2 According to one embodiment, the amine compound 2 is synthesized, for example, by the following reaction steps.

Chemical formula

[0233] <Synthesis of Intermediate 2-1> 9 g (18 mmol) of Intermediate 2-1 was obtained with a yield of 90% using the same method as the synthesis of Intermediate 1-1, except that 9,9-diphenyl-9H-fluorene-2-amine was used instead of 9,9-dimethyl-9H-fluorene-2-amine.

[0234] <Synthesis of Compound 2> Compound 2 was obtained in 6.4 g (9 mmol) in 90% yield using the same method as the synthesis of intermediate 1, except that intermediate 2-1 was used instead of intermediate 1-1.

[0235] The molecular weight and NMR results were confirmed as follows, and it was confirmed to be compound 2. [C 54 H 51 N M+1:714.55, 1 H NMR (500MHz, CDCl3)δ=7.80(m, 2H), 7.60(d, 1H), 7.55-7.10(m, 22H), 2.5-1.5(m, 26H)]

[0236] (3) Synthesis of compound 30 The amine compound 30 according to one embodiment can be synthesized, for example, by the following reaction steps. [ka]

[0237] <Synthesis of Intermediate 30-1> Intermediate 30-1 was obtained in 7.7 g (18 mmol) in 90% yield using the same method as the synthesis of intermediate 1-1, except that 9-phenyl-9H-carbazole-3-amine was used instead of 9,9-dimethyl-9H-fluoren-2-amine.

[0238] <Synthesis of Compound 30> Compound 30 was obtained in 5.2 g (9 mmol) in 90% yield using the same method as the synthesis of intermediate 1, except that intermediate 30-1 was used instead of intermediate 1-1, and 1-bromo-4-cyclohexylbenzene was used instead of intermediate A.

[0239] The molecular weight and NMR results were confirmed as follows, and it was confirmed that it was compound 30. [C 43 H 42 N2M+1: 587.33 11H NMR (500 MHz, CDCl3) δ = 7.80 (m, 2H), 7.60 (d, 1H), 7.55 - 7.10 (m, 17H), 2.5 - 1.5 (m, 22H)

[0240] (4) Synthesis of Compound 41 The amine compound 41 according to one embodiment is synthesized, for example, by the following reaction steps. [Chemical formula]

[0241] Compound 41 (5.2 g, 9 mmol) was obtained in a yield of 90% by using the same method as the synthesis of Intermediate 1-1 except for using 2.1 g (10 mmol) of 9,9-dimethyl-9H-fluorene-2-amine.

[0242] The molecular weight and NMR results were confirmed as follows, and it was confirmed that it was Compound 41. [C 41 H 43 1H NMR + 1: 550.52, 1 1H NMR (500 MHz, CDCl3) δ = 7.80 (m, 2H), 7.60 (d, 1H), 7.55 - 7.10 (m, 12H), 2.5 - 1.5 (m, 22H), 1.3 (d, 6H)

[0243] (5) Synthesis of Compound 50 The amine compound 50 according to one embodiment is synthesized, for example, by the following reaction steps. [Chemical formula]

[0244] Compound 50 (5.38 g, 9 mmol) was obtained in a yield of 90% by using the same method as the synthesis of Compound 41 except for using 2.6 g (10 mmol) of 9-phenyl-9H-carbazole-2-amine instead of 9,9-dimethyl-9H-fluorene-2-amine.

[0245] The molecular weight and NMR results were confirmed as follows, and it was confirmed that the compound was 50. [C 44 H 42 N2M+1:599,22, 1 H NMR (500MHz, CDCl3)δ=7.80(m, 2H), 7.60(d, 1H), 7.55-7.10(m, 17H), 2.5-1.5(m, 22H)]

[0246] (6) Synthesis of compound 65 According to one embodiment, the amine compound 65 is synthesized, for example, by the following reaction steps. [ka]

[0247] <Synthesis of Intermediate 65-1> Intermediate 65-1 was obtained in 8.19 g (18 mmol) in 90% yield using the same method as the synthesis of intermediate 1-1, except that 4-(9,9-dimethyl-9H-fluoren-2-yl)aniline was used instead of 9,9-dimethyl-9H-fluoren-2-amine.

[0248] <Synthesis of Compound 65> Compound 65 was obtained in 5.5 g (9 mmol) in 90% yield using the same method as the synthesis of intermediate 1, except that intermediate 65-1 was used instead of intermediate 1-1, and 1-bromo-4-cyclohexylbenzene was used instead of intermediate A.

[0249] The molecular weight and NMR results were confirmed as follows, and it was confirmed that the compound was 65. [C 46 H 47 N M+1:614.44, 1 H NMR (500MHz, CDCl3)δ=7.80(m, 2H), 7.60(d, 1H), 7.55-7.10(m, 16H), 2.5-1.5(m, 22H), 1.3(d, 6H)]

[0250] 2. Fabrication and evaluation of light-emitting devices (Fabrication of light-emitting elements) A light-emitting device of one embodiment, containing an amine compound of one embodiment in the hole transport layer, was fabricated by the following method. Examples 1 to 6, Comparative Examples 1 and 2 fabricated light-emitting devices containing one hole transport layer, while Examples 7 and 8 fabricated light-emitting devices containing two hole transport layers.

[0251] The light-emitting devices of Examples 1 to 6 were fabricated using compounds 1, 2, 30, 41, 50, and 65 as materials for the hole transport layer. In addition, light-emitting devices of Examples 7 and 8 were fabricated using compound 1 as the material for the first hole transport layer and amine derivative compounds of compounds 85 and 97 as materials for the second hole transport layer, respectively.

[0252] Comparative Example 1 was fabricated using comparative compound C1 as the material for the hole transport layer. Comparative Example 2 was fabricated using comparative compound C2 as the material for the hole transport layer.

[0253] The example compounds and comparative example compounds used in the fabrication of the light-emitting element are shown below.

[0254] (Example Compounds) [ka]

[0255] (Comparative Compounds) [ka]

[0256] (Other compounds used in the fabrication of light-emitting devices) [ka]

[0257] A glass substrate patterned with 120 nm thick ITO was ultrasonically cleaned for 5 minutes each using isopropyl alcohol and pure water. After ultrasonic cleaning, it was irradiated with UV light for 30 minutes and then ozone-treated. Subsequently, 2-TNATA was deposited to form a 60 nm thick hole injection layer. Next, in Examples 1 to 6 and the Comparative Example, a 30 nm thick hole transport layer was formed by depositing the example compound or the comparative example compound. On the other hand, in Examples 7 and 8, a first hole transport layer was formed by depositing compound 1, and then a second hole transport layer was formed by depositing compounds 85 and 97. In Examples 7 and 8, the first hole transport layer and the second hole transport layer were each 15 nm thick.

[0258] Next, ADN and the blue fluorescent dopant DPAVBi were simultaneously deposited in a weight ratio of 98:2 to form a 30 nm thick luminescent layer. Then, Alq3 was deposited to form a 30 nm thick electron transport layer, and LiF was deposited to form a 1 nm thick electron injection layer.

[0259] Next, a second electrode with a thickness of 300 nm was formed using Al.

[0260] In the examples, the hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, and second electrode were formed using a vacuum deposition apparatus.

[0261] (Evaluation of light-emitting element characteristics) Table 1 shows the evaluation results of the light-emitting elements for Examples 1 to 8, and Comparative Examples 1 and 2. Table 1 compares the driving voltage, brightness, luminous efficiency, and half-life of the fabricated light-emitting elements. In the characteristic evaluation results for the examples and comparative examples shown in Table 1, the luminous efficiency was 50 mA / cm². 2 The efficiency value at the current density is shown, and the half-life is 100 mA / cm². 2 This shows the luminance half-life in [location]. On the other hand, it was confirmed that all the fabricated light-emitting elements had a blue emission color.

[0262] The current density, voltage, and luminous efficiency of the light-emitting elements in the examples and comparative examples were measured in a darkroom using a Keithley Instruments 2400 series source meter, a Konica Minolta CS-200 colorimeter, and the National Instruments Japan LabVIEW 2.0 measurement PC program. [Table 1]

[0263] Referring to the results in Table 1, it can be seen that in the case of an example of a light-emitting device using an amine compound according to one embodiment of the present invention as a material for the hole transport layer, it exhibits a low driving voltage, high brightness characteristics, excellent device efficiency, and improved device lifetime characteristics.

[0264] In other words, referring to Table 1, it can be seen that Examples 1 to 8 exhibit characteristics of lower voltage, higher brightness, longer lifespan, and higher efficiency compared to the elements of Comparative Examples 1 and 2.

[0265] Thus, Examples 1 to 8 show that both luminous efficiency and luminous lifetime are improved simultaneously compared to Comparative Examples 1 and 2. In other words, by using the amine compound of one embodiment having a compound structure containing at least one bicycloheptyl group, it is possible to simultaneously improve the device efficiency and device lifetime of a light-emitting element.

[0266] The amine compound according to one embodiment has a compound structure containing one bicycloheptyl group and one of adamantyl group, cyclohexyl group, or bicycloheptyl group, which contributes to the low voltage, long lifespan, and high efficiency characteristics of the light-emitting element. Furthermore, the light-emitting element according to one embodiment exhibits both long lifespan and high efficiency characteristics simultaneously by containing the amine compound according to one embodiment.

[0267] Although embodiments of the present invention have been described so far with reference, a person skilled in the art or a person with ordinary knowledge in the art will understand that the present invention can be modified and altered in various ways without departing from the spirit and technical domain of the invention as described in the claims below.

[0268] Therefore, the technical scope of the present invention is not limited to what is described in the detailed description of the specification, but should be determined by the claims. [Explanation of symbols]

[0269] DD, DD-TD: Display device ED: Light-emitting element EL1: First electrode EL2: Second electrode HTR: Hole transport region EML: Emitting layer ETR: Electron transport region

Claims

1. An amine compound represented by the following chemical formula 1. 【Chemistry 1】 ...(chemical formula 1) (In the above chemical formula 1, R １ This is an adamantyl group or a cyclohexyl group. Ar １ and Ar ２ Each of these is independently a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms. L is a single-bonded, substituted, or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group with 2 to 30 carbon atoms. FR is represented by compound 2 below, 【Chemistry 2】 ...(chemical formula 2) In the aforementioned chemical formula 2, X is CR ａ R ｂ , N, NR ｃ , O, or S, R ａ ~R ｃ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. If X is CR a R b, then optionally, Ra a and R b can bond to each other so that the chemical formula 2 has the following structure: 【change】 Form a ring so that it becomes one of the following: d and e are independent integers between 0 and 4, R ｄ and R ｅ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, The FR is bonded to either the L in chemical formula 1 or the N atom of the amine compound at either the position of X in chemical formula 2 or at one of the ring-forming atoms of the benzene ring.

2. The amine compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1 or 1-2. 【Transformation 3】 ...(Chemical formula 1-1) 【Chemistry 4】 ...(Chemical formula 1-2)

3. The amine compound according to claim 2, wherein the aforementioned chemical formula 1-2 is represented by the following chemical formula 1-2A. 【Transformation 5】 ...(Chemical formula 1-2A)

4. In the above chemical formula 1, Ar １ and Ar ２ The amine compound according to claim 1, wherein is a substituted or unsubstituted phenylene group.

5. The amine compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1A. 【Transformation 6】 ...(Chemical formula 1A)

6. The chemical compound 1A is the amine compound according to claim 5, represented by the following chemical formula 1A-1. 【Transformation 7】 ...(Chemical formula 1A-1)

7. The amine compound according to claim 1, wherein the chemical formula 1 is one of the compounds from the following first group of compounds. [First compound group] 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】

8. First electrode and, A second electrode is placed on the first electrode, A light-emitting element comprising at least one functional layer disposed between the first electrode and the second electrode, the functional layer containing any one amine compound from claims 1 to 7.

9. 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 light-emitting element according to claim 8, wherein the hole transport region comprises the amine compound.

10. The at least one functional layer includes a light-emitting layer, a first hole transport layer disposed between the first electrode and the light-emitting layer, a second hole transport layer disposed between the first hole transport layer and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode. The first hole transport layer contains the amine compound, The light-emitting element according to claim 8, wherein the second hole transport layer comprises an amine derivative compound represented by the following chemical formula 3. 【Chemistry 12】 ...(chemical formula 3) (In the above chemical formula 3, L １１ This is an arylene group with 6 to 30 ring-forming carbon atoms, which is a single bond, substituted or unsubstituted ring-forming carbon group, or a heteroarylene group with 2 to 30 ring-forming carbon atoms, R １１ ~R １４ Each of these is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

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