Light emitting element
Patent Information
- Application Number
- CN202111395405.6
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-12-02
- Filing Date
- 2021-11-23
- Publication Date
- 2026-10-27
- Estimated Expiration
- 2041-11-23
Smart Images

Figure CN114583073B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to a light-emitting element, and more specifically, to a light-emitting element comprising a dopant and a plurality of bodies in a light-emitting layer. Background Technology
[0002] Recently, as an image display device, there has been a great deal of development on organic electroluminescence display devices and the like. Organic electroluminescence display devices are display devices that include so-called self-emissive light-emitting elements that achieve display by causing the light-emitting material of the light-emitting layer to emit light through the recombination of holes and electrons injected from the first electrode and the second electrode in the light-emitting layer.
[0003] When applying light-emitting elements to display devices, there is a need for low driving voltage, high luminous efficiency, and long lifespan, and there is a continuous need to develop materials for light-emitting elements that can reliably achieve these goals.
[0004] Furthermore, in order to achieve high-efficiency and long-life light-emitting elements, research is underway on the combination of various materials used for light-emitting layers and the improvement of the stability of each material. Summary of the Invention
[0005] The purpose of this invention is to provide a light-emitting element that exhibits both good luminous efficiency and long lifespan.
[0006] One embodiment provides a light-emitting element, comprising: a first electrode; a second electrode disposed on the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode, comprising a first body represented by the following chemical formula 1, a second body different from the first body, and a dopant comprising an organometallic complex.
[0007] [Chemical Formula 1]
[0008]
[0009] In the chemical formula 1, Ar1 to Ar3 are each independently an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted), and at least one of Ar1 to Ar3 is an aryl group with 6 to 30 cyclic carbon atoms (including a halogen atom or a cyano group as a substituent) or a six-membered heterocyclic group (including a nitrogen atom as a cyclic atom).
[0010] At least one of Ar1 to Ar3 can be represented by any one of EW-1 to EW-5 below.
[0011]
[0012] The second entity can be represented by the following chemical formula 2.
[0013] [Chemical Formula 2]
[0014]
[0015] In the chemical formula 2, X is NR. a O or CR b R c ,
[0016] R1 to R8, R a R b and R c R is independently composed of a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, an alkyl group with 1 to 20 carbon atoms (substituted or unsubstituted), an aryl group with 6 to 60 cyclic carbon atoms (substituted or unsubstituted), or a heterocyclic group with 2 to 60 cyclic carbon atoms (substituted or unsubstituted). a R b and R c At least one of them is represented by the following chemical formula A.
[0017] [Chemical Formula A]
[0018]
[0019] In the chemical formula A, m can be an integer between 0 and 2, and Ar4 can be a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group with 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group with 2 to 60 cyclic carbon atoms.
[0020] The dopant can be represented by the following chemical formula 3.
[0021] [Chemical Formula 3]
[0022]
[0023] In the chemical formula 3, Q1 to Q4 are each independently C or N, and the rings of C1 to C4 are each independently a hydrocarbon ring with 5 to 30 substituted or unsubstituted carbon atoms, or a heterocycle with 2 to 30 substituted or unsubstituted carbon atoms. Y is O or S, d1 to d4 are each independently an integer between 0 and 4, and R... 31 To R 34Each group is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 1 to 30 substituted or unsubstituted cyclic carbon atoms, and may optionally be combined with adjacent groups to form a ring.
[0024] The chemical formula 3 can be represented by the following chemical formula 3-1.
[0025] [Chemical Formula 3-1]
[0026]
[0027] In the chemical formula 3-1, Q 11 Q 31 Q 32 And Q 33 N and NR are independent of each other. 11 CR 12 CR 12 R 13 BR 14 Or BR 14 R 15 R 11 To R 15 Each group is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 1 to 30 substituted or unsubstituted cyclic carbon atoms, and may optionally be linked to adjacent groups to form a ring. Y, C4 ring, R 31 R 32 R 34 d1, d2, and d4 are defined in the same way as in the chemical formula 3.
[0028] The weight ratio of the first body to the second body can be 3:7 to 7:3.
[0029] The light-emitting layer can emit blue phosphorescence.
[0030] The light-emitting element may further include a capping layer disposed on the second electrode, the capping layer having a refractive index of 1.6 or higher.
[0031] One embodiment provides a light-emitting element, comprising: a first electrode; a second electrode disposed on the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode, comprising a first body and a second body that are different from each other, and a dopant comprising an organometallic complex, wherein the first body comprises a triazine core and at least one electron-accepting substituent substituted to the triazine core, the electron-accepting substituent being an aryl group substituted with a cyano or a halogen atom, or a six-membered heterocyclic group comprising a nitrogen atom as a cyclic atom.
[0032] The electron-accepting substituent may be represented by any one of EW-1 to EW-5 below.
[0033]
[0034] The first entity can be represented by the following chemical formula 1.
[0035] [Chemical Formula 1]
[0036]
[0037] In the chemical formula 1, Ar1 to Ar3 are each independently an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted), and at least one of Ar1 to Ar3 is an aryl group with 6 to 30 cyclic carbon atoms (including a halogen atom or a cyano group as a substituent) or a six-membered heterocyclic group (including a nitrogen atom as a cyclic atom).
[0038] The second entity can be represented by the following chemical formula 2.
[0039] [Chemical Formula 2]
[0040]
[0041] In the chemical formula 2, X is NR. a O or CR b R c R1 to R8, R a R b and R c R is independently composed of a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, an alkyl group with 1 to 20 carbon atoms (substituted or unsubstituted), an aryl group with 6 to 60 cyclic carbon atoms (substituted or unsubstituted), or a heterocyclic group with 2 to 60 cyclic carbon atoms (substituted or unsubstituted). a R b and R c At least one of them is represented by the following chemical formula A.
[0042] [Chemical Formula A]
[0043]
[0044] In the chemical formula A, m is an integer between 0 and 2, and Ar4 is a substituted or unsubstituted silyl group, an substituted or unsubstituted aryl group with 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group with 2 to 60 cyclic carbon atoms.
[0045] The dopant can be represented by the following chemical formula 3.
[0046] [Chemical Formula 3]
[0047]
[0048] In the chemical formula 3, Q1 to Q4 are each independently C or N, and the rings of C1 to C4 are each independently a hydrocarbon ring with 5 to 30 substituted or unsubstituted carbon atoms, or a heterocycle with 2 to 30 substituted or unsubstituted carbon atoms. Y is O or S, d1 to d4 are each independently an integer between 0 and 4, and R... 31 To R 34 Each group is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 1 to 30 substituted or unsubstituted cyclic carbon atoms, and may optionally be combined with adjacent groups to form a ring.
[0049] The light-emitting layer can emit blue phosphorescence.
[0050] One embodiment of the light-emitting element can exhibit long lifetime characteristics by including a hole transport host, an electron transport host, and a dopant material in the light-emitting layer. Attached Figure Description
[0051] Figure 1 This is a plan view showing a display device according to an embodiment.
[0052] Figure 2 This is a cross-sectional view of a display device according to an embodiment.
[0053] Figure 3 This is a schematic cross-sectional view of a light-emitting element according to one embodiment.
[0054] Figure 4 This is a schematic cross-sectional view of a light-emitting element according to one embodiment.
[0055] Figure 5 This is a schematic cross-sectional view of a light-emitting element according to one embodiment.
[0056] Figure 6 This is a schematic cross-sectional view of a light-emitting element according to one embodiment.
[0057] Figure 7 This is a cross-sectional view of a display device according to an embodiment.
[0058] Figure 8 This is a cross-sectional view of a display device according to an embodiment.
[0059] [Explanation of Labels in the Attached Image]
[0060] DD, DD-TD: Display device
[0061] ED: Light-emitting element; EL1: First electrode
[0062] EL2: Second electrode; HTR: Hole transport region
[0063] EML: Electron Transport Region of the Emitting Layer (ETR) Detailed Implementation
[0064] This invention can be modified in many ways and can have many forms. Specific embodiments are illustrated in the accompanying drawings and described in detail herein. However, it is not intended to limit the invention to the specific disclosed forms, and should be understood to include all modifications, equivalents, and substitutions encompassed by the spirit and scope of the invention.
[0065] In describing the figures, similar reference numerals are used for similar constituent elements. In the figures, the dimensions of the structures are shown enlarged compared to their actual dimensions for clarity of the invention. Terms such as "first," "second," etc., can be used to describe multiple constituent elements, but the constituent elements should not be limited by these terms. These terms are used only to distinguish one constituent element from another. For example, without departing from the scope of the invention, a first constituent element can be named a second constituent element, and similarly, a second constituent element can be named a first constituent element. Singular expressions include plural expressions unless the context clearly indicates a different meaning.
[0066] In this application, terms such as “comprising” or “having” should be understood as being intended to specify the presence of features, figures, steps, operations, constituent elements, components or combinations thereof as described in the specification, rather than pre-excluding the possibility of the presence or addition of one or more other features or figures, steps, operations, constituent elements, components or combinations thereof.
[0067] In this application, when referring to a layer, membrane, region, plate, or other portion as being "above" or "upper" another portion, this includes not only the case where it is "immediately above" the other portion, but also the case where other portions exist in between. Conversely, when referring to a layer, membrane, region, plate, or other portion as being "below" or "lower" of another portion, this includes not only the case where it is "immediately below" the other portion, but also the case where other portions exist in between. Furthermore, in this application, referring to being "arranged above" can include not only the case where it is arranged in the upper part, but also the case where it is arranged in the lower part.
[0068] In this specification, "substituted or unsubstituted" can mean that the substance is substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphonyl oxide, phosphonyl sulfide, alkyl, alkenyl, alkynyl, alkylcyclic, aryl, and heterocyclic groups. Furthermore, the substituents exemplified above can be either substituted or unsubstituted. For example, biphenyl can be interpreted as aryl or as a phenyl group substituted with a phenyl group.
[0069] In this specification, "forming a ring by bonding with adjacent groups" can refer to the situation where adjacent groups bond with each other 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, the rings formed by bonding with each other can connect with other rings to form a spirostructure.
[0070] In this specification, "adjacent group" can mean a substituent that is directly attached to the atom substituted by the corresponding substituent, another substituent that is substituted by the atom substituted by the corresponding substituent, or a substituent that is stereoscopically closest to the corresponding substituent. For example, in 1,2-dimethylbenzene, the two methyl groups can be interpreted as "adjacent groups"; in 1,1-diethylcyclopentane, the two ethyl groups can be interpreted as "adjacent groups"; and in 4,5-dimethylphenanthrene, the two methyl groups can be interpreted as "adjacent groups".
[0071] Examples of halogen atoms in this specification include fluorine, chlorine, bromine, or iodine atoms.
[0072] In this specification, alkyl groups can be straight-chain, 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, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2 - Hexyldecyl, 2-octyldecyl, undecyl, dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, hexadecyl, octadecyl, nonadecanyl, and triadecyl, etc., but not limited to these.
[0073] In this specification, cycloalkyl group refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. The cycloalkyl group can be a saturated cycloalkyl group with 5 to 20 carbon atoms in the ring.
[0074] In this specification, aryl represents any functional group or substituent derived from an aromatic hydrocarbon ring. Aryl groups can be monocyclic or polycyclic. The number of carbon atoms in the cyclic aryl group can be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, quinquephenyl, hexaphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, etc. It includes, but is not limited to, basic, and advanced technologies.
[0075] In this specification, the fluorene group can be substituted, or two substituents can combine with each other to form a spirostructure. Examples of fluorene group substitution are described below. However, this is not a limitation.
[0076]
[0077] In this specification, a heterocyclic group refers to any functional group or substituent derived from a ring comprising one or more of B, O, N, P, Si, and S as heteroatoms. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl groups. Aliphatic and aromatic heterocycles can be monocyclic or polycyclic.
[0078] In this specification, a heterocyclic group may include one or more of B, O, N, P, Si, and S as heteroatoms. When a heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be identical or different from each other. The heterocyclic group may be a monocyclic or polycyclic heterocyclic group, and includes the concept of heteroaryl groups. The number of cyclic carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.
[0079] In this specification, aliphatic heterocyclic groups may include one or more of B, O, N, P, Si, and S as heteroatoms. The number of cyclic carbon atoms in an aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups include ethylene oxide, thiocyclopropane, pyrrolyl, piperidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, thiaalkyl, tetrahydropyranyl, 1,4-dioxane, etc., but are not limited to these.
[0080] In this specification, a heteroaryl group may include one or more of B, O, N, P, Si, and S as a heteroatom. When a heteroaryl group includes two or more heteroatoms, these heteroatoms may be identical or different from each other. A heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heteroaryl group. The number of carbon atoms in the ring-forming structure of the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazole, N-arylcarbazole, and N-heteroarylcarbazole. N-alkylcarbazolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophene, dibenzothiophene, thiophene-thiophene, benzofuranyl, phenanthrolinel, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiazolyl, phenothiazinyl, dibenzothiophene, and dibenzofuranyl, etc., but not limited to these.
[0081] In this specification, except that the arylene group is divalent, the description of the aforementioned aryl group can be applied. Except that the heteroarylene group is divalent, the description of the aforementioned heteroarylene group can be applied.
[0082] In this specification, silane includes alkylsilane and arylsilane. Examples of silanes include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited thereto.
[0083] In this specification, the number of carbon atoms in an amino group is not particularly limited, but can be 1 to 30. Amino groups can include alkylamino, arylamino, or heteroarylamino groups. Examples of amino groups include methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthraylamino, etc., but are not limited to these.
[0084] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but can be 1 to 40, 1 to 30, or 1 to 20. For example, although the following structures are possible, it is not limited thereto.
[0085]
[0086] In this specification, the number of carbon atoms in the sulfinyl group and sulfonyl group is not particularly limited, but can be more than 1 and less than 30. The sulfinyl group can include alkyl sulfinyl group and aryl sulfinyl group. The sulfonyl group can include alkyl sulfonyl group and aryl sulfonyl group.
[0087] In this specification, a thiol group may include alkylthio and arylthio groups. A thiol group may refer to the case where a sulfur atom is bonded to the defined alkyl or aryl group. Examples of thiol groups include, but are not limited to, methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, and naphthylthio.
[0088] In this specification, an oxygen group can include alkoxy and aryloxy groups. An oxygen group can represent the combination of an oxygen atom with the defined alkyl or aryl group. An alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but can be, for example, 1 to 20 or 1 to 10. Examples of oxygen groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, and benzyloxy.
[0089] In this specification, the term "boron group" includes alkylboron group and arylboron group. Boron group can refer to the case where a boron atom is bonded to the defined alkyl or aryl group. Examples of boron groups include, but are not limited to, trimethylboron, triethylboron, tert-butyldimethylboron, triphenylboron, diphenylboron, and phenylboron.
[0090] In this specification, the alkenyl group can be straight-chain or branched. The number of carbon atoms is not particularly limited, but it is 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, styrylvinyl, etc., but are not limited to these.
[0091] In this specification, the number of carbon atoms in the amino group is not particularly limited, but can be more than 1 and less than 30. The amino group can include alkylamino and arylamino groups. Examples of amino groups include methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthraylamino, etc., but are not limited to these.
[0092] In this specification, the alkyl groups in alkylthio, alkylthionyl, alkylaryl, alkylamino, alkylboryl, alkylsilyl, and alkylamine are the same as the examples of alkyl groups mentioned above.
[0093] In this specification, the aryl groups in aryloxy (or “aryloxy”), arylthio, arylthionyloxy, arylamino, arylboryl, arylsilyl, and arylamine are the same as those in the examples of the aforementioned aryl groups.
[0094]
[0095] Hereinafter, an embodiment of the present invention will be described with reference to the accompanying drawings.
[0096] Figure 1 This is a plan view showing an embodiment of the display device DD. Figure 2 This is a cross-sectional view of a display device DD according to an embodiment. Figure 2 It is shown that... Figure 1 A cross-sectional view of the portion corresponding to the I-I' line.
[0097] The display device DD may include: a display panel DP; and an optical layer PP disposed on the display panel DP. The display panel DP includes light-emitting elements ED-1, ED-2, and ED-3. The display device DD may include multiple light-emitting elements ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP to control reflected light at the display panel DP caused by external light. The optical layer PP may, for example, include a polarizing layer or a color filter layer. Furthermore, unlike the case shown in the figures, in one embodiment of the display device DD, the optical layer PP may be omitted.
[0098] A base substrate BL can be disposed on the optical layer PP. The base substrate BL can be a component that provides a base surface for disposing the optical layer PP. The base substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited to this; the base substrate BL can be an inorganic layer, an organic layer, or a composite material layer. Furthermore, unlike the illustrated scenario, in one embodiment, the base substrate BL can be omitted.
[0099] The display device DD according to one embodiment may further include a filler layer (not shown). The filler layer (not shown) may be disposed between the display element layer DP-ED and the base substrate BL. The filler layer (not shown) may be an organic layer. The filler layer (not shown) may include at least one of acrylic resin, silicone resin and epoxy resin.
[0100] The display panel DP may include a base layer BS, a circuit layer DP-CL disposed on the base layer BS, and a display element layer DP-ED. The display element layer DP-ED may include: a pixel defining film PDL; light-emitting elements ED-1, ED-2, and ED-3 disposed between the pixel defining films PDL; and an encapsulation layer TFE disposed on the light-emitting elements ED-1, ED-2, and ED-3.
[0101] The base layer BS can be a component that provides a base surface for arranging the display element layer DP-ED. The base layer BS can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited to this; the base layer BS can be an inorganic layer, an organic layer, or a composite material layer.
[0102] In one embodiment, the circuit layer DP-CL is disposed on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors (not shown). The transistors (not shown) may each include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include switching transistors and driving transistors for driving the light-emitting elements ED-1, ED-2, and ED-3 of the display element layer DP-ED.
[0103] Each of the light-emitting elements ED-1, ED-2, and ED-3 may have the following characteristics. Figures 3 to 6 The structure of a light-emitting element ED according to one embodiment. Each of the light-emitting elements ED-1, ED-2, and ED-3 may include a first electrode EL1, a hole transport region HTR, light-emitting layers EML-R, EML-G, EML-B, an electron transport region ETR, and a second electrode EL2.
[0104] exist Figure 2An embodiment is shown below: the light-emitting layers EML-R, EML-G, and EML-B of light-emitting elements ED-1, ED-2, and ED-3 are arranged within the opening OH defined by the pixel-defining film PDL. The hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are provided as a common layer throughout the light-emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited to this, and... Figure 2 In a different embodiment, the hole transport region HTR and electron transport region ETR can be patterned and provided within the opening OH defined by the pixel defining film PDL. For example, in one embodiment, the hole transport region HTR, the light-emitting layers EML-R, EML-G, EML-B, and the electron transport region ETR of the light-emitting elements ED-1, ED-2, and ED-3 can be patterned using an inkjet printing method.
[0105] The encapsulation layer TFE can cover the light-emitting elements ED-1, ED-2, and ED-3. The encapsulation layer TFE can seal the display element layer DP-ED. The encapsulation layer TFE can be a thin-film encapsulation layer. The encapsulation layer TFE can be a single layer or composed of multiple stacked layers. The encapsulation layer TFE includes at least one insulating layer. According to one embodiment, the encapsulation layer TFE can include at least one inorganic film (hereinafter referred to as the encapsulation inorganic film). Furthermore, according to one embodiment, the encapsulation layer TFE can include at least one organic film (hereinafter referred to as the encapsulation organic film) and at least one encapsulation inorganic film.
[0106] Inorganic encapsulation films protect the display element layer (DP-ED) from moisture and oxygen, while organic encapsulation films protect the DP-ED from foreign matter such as dust particles. Inorganic encapsulation films may include, but are not specifically limited to, silicon nitride, silicon oxynitride, silicon oxide, titanium dioxide, or aluminum oxide. Organic encapsulation films may include acrylic compounds, epoxy compounds, etc. Organic encapsulation films may include photopolymerizable organic materials, but are not specifically limited to these.
[0107] The encapsulation layer TFE can be disposed on the second electrode EL2 and disposed to fill the opening OH.
[0108] Reference Figure 1 and Figure 2 The display device DD may include a non-light-emitting area NPXA and light-emitting areas PXA-R, PXA-G, and PXA-B. The light-emitting areas PXA-R, PXA-G, and PXA-B may be areas that emit light generated from light-emitting elements ED-1, ED-2, and ED-3, respectively. The light-emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other on a plane.
[0109] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B can be a region defined by a pixel-defining film (PDL). The non-light-emitting region NPXA is the region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and can be a region corresponding to the pixel-defining film (PDL). Furthermore, in this specification, the light-emitting regions PXA-R, PXA-G, and PXA-B can each correspond to a pixel. The pixel-defining film (PDL) can divide 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 can be distinguished by being arranged at the opening OH defined by the pixel-defining film (PDL).
[0110] The luminescent regions PXA-R, PXA-G, and PXA-B can be divided into multiple groups based on the color of the light generated by the luminescent elements ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In one embodiment of the display device DD, three light-emitting regions PXA-R, PXA-G, and PXA-B that emit red, green, and blue light are exemplarily shown. For example, one embodiment of the display device DD may include red light-emitting regions PXA-R, green light-emitting regions PXA-G, and blue light-emitting regions PXA-B that can be distinguished from each other.
[0111] In a display device DD according to one embodiment, a plurality of light-emitting elements ED-1, ED-2, and ED-3 can emit light in different wavelengths. For example, in one embodiment, the display device DD may include a first light-emitting element ED-1 that emits red light, a second light-emitting element ED-2 that emits green light, and a third light-emitting element ED-3 that emits blue light. That is, the red light-emitting area PXA-R, the green light-emitting area PXA-G, and the blue light-emitting area PXA-B of the display device DD can 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.
[0112] However, the embodiments are not limited thereto. The first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light of the same wavelength, or at least one of them may emit light of different wavelengths. For example, the first to third light-emitting elements ED-1, ED-2, and ED-3 may all emit blue light.
[0113] According to one embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B in the display device DD can be arranged in a stripe pattern. (See reference...) Figure 1Multiple red emitting regions PXA-R, multiple green emitting regions PXA-G, and multiple blue emitting regions PXA-B can be arranged along the second directional axis DR2. Alternatively, they can be arranged along the first directional axis DR1 in an alternating order of red emitting regions PXA-R, green emitting regions PXA-G, and blue emitting regions PXA-B.
[0114] exist Figure 1 and Figure 2 The illustration shows a scenario where the areas of the luminescent regions PXA-R, PXA-G, and PXA-B are all similar, but the embodiment is not limited to this. The areas of the luminescent regions PXA-R, PXA-G, and PXA-B can differ from each other depending on the wavelength of the emitted light. Furthermore, the areas of the luminescent regions PXA-R, PXA-G, and PXA-B can be represented as the areas when viewed from a plane defined by the first direction axis DR1 and the second direction axis DR2.
[0115] Furthermore, the arrangement of the luminescent regions PXA-R, PXA-G, and PXA-B is not limited to... Figure 1 As shown, the arrangement order of the red emitting areas PXA-R, green emitting areas PXA-G, and blue emitting areas PXA-B can be varied and provided according to the display quality characteristics required by the display device DD. For example, the arrangement of the emitting areas PXA-R, PXA-G, and PXA-B can be a pentile arrangement or a diamond arrangement.
[0116] Furthermore, the areas of the luminescent regions PXA-R, PXA-G, and PXA-B can be different from each other. For example, in one embodiment, the area of the green luminescent region PXA-G can be smaller than the area of the blue luminescent region PXA-B, but the embodiment is not limited to this.
[0117] the following, Figures 3 to 6 This is a schematic cross-sectional view of a light-emitting element according to one embodiment. The light-emitting element ED according to one embodiment may include: a first electrode EL1; a second electrode EL2 facing the first electrode EL1; and at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The at least one functional layer may include a hole transport region HTR, a light-emitting layer EML, and an electron transport region ETR stacked sequentially. That is, the light-emitting element ED of one embodiment may include a first electrode EL1, a hole transport region HTR, a light-emitting layer EML, an electron transport region ETR, and a second electrode EL2 stacked sequentially.
[0118] compared to Figure 3 , Figure 4A cross-sectional view of a light-emitting element (ED) according to an embodiment is shown, wherein the hole transport region (HTR) includes a hole injection layer (HIL) and a hole transport layer (HTL), and the electron transport region (ETR) includes an electron injection layer (EIL) and an electron transport layer (ETL). Furthermore, compared to... Figure 3 , Figure 5 A cross-sectional view of a light-emitting element (ED) according to an embodiment is shown, wherein the hole transport region (HTR) includes a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL), and the electron transport region (ETR) includes an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Compared to... Figure 4 , Figure 6 A cross-sectional view of a light-emitting element ED, including a capping layer CPL disposed on a second electrode EL2, is shown.
[0119] In one embodiment of the light-emitting element ED, the light-emitting layer EML may include an organometallic complex dopant and a plurality of host materials that are different from each other.
[0120] In a light-emitting element (ED) according to one embodiment, the first electrode EL1 is conductive. The first electrode EL1 can be formed of a metallic material, a metal alloy, or a conductive compound. The first electrode EL1 can be an anode or a cathode. However, the embodiment is not limited to this. Furthermore, the first electrode EL1 can be a pixel electrode. The first electrode EL1 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, it can include a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. When the first electrode EL1 is a semi-transparent or reflective electrode, the first electrode EL1 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, their compounds and mixtures (e.g., a mixture of Ag and Mg), and materials having a multilayer structure such as LiF / Ca or LiF / Al. Alternatively, the first electrode EL1 may be a multilayer structure including a reflective or semi-transparent film formed from the aforementioned materials and a transparent conductive film formed from indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto. Furthermore, the embodiments are not limited thereto; the first electrode EL1 may include the aforementioned metallic materials, a combination of two or more metallic materials selected from the aforementioned metallic materials, or oxides of the aforementioned metallic materials, etc. The thickness of the first electrode EL1 can be approximately up to approximately For example, the thickness of the first electrode EL1 can be approximately up to approximately
[0121] A hole transport region (HTR) is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer or a light-emitting auxiliary layer (not shown), and an electron blocking layer (EBL). The thickness of the hole transport region HTR can be, for example, approximately... up to approximately
[0122] The hole transport region (HTR) can have a single-layer structure composed of a single substance, a single-layer structure composed of multiple different substances, or a multi-layer structure composed of multiple different substances.
[0123] For example, the hole transport region HTR can have a single-layer structure of hole injection layer HIL or hole transport layer HTL, or it can have a single-layer structure composed of hole injection material and hole transport material. Furthermore, the hole transport region HTR can have a single-layer structure composed of multiple different materials, or it can have a structure consisting of hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / buffer layer (not shown), hole injection layer HIL / buffer layer (not shown), hole transport layer HTL / buffer layer (not shown), or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL, stacked sequentially from the first electrode EL1. However, the embodiments are not limited to these.
[0124] Hole transport regions (HTRs) can be formed using various methods, including vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).
[0125] In one embodiment of the light-emitting element ED, the hole transport region HTR may include the material of the hole transport region as described below.
[0126] The hole transport region (HTR) may include compounds represented by the following chemical formula H-1.
[0127] [Chemical formula H-1]
[0128]
[0129] In the chemical formula H-1, L1 and L2 can each be independently a directly linked aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). a and b can each be independently an integer from 0 to 10. Furthermore, when a or b is an integer of 2 or more, multiple L1 and L2 can each be independently an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted).
[0130] In chemical formula H-1, Ar1 and Ar2 can each be independently an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). Furthermore, in chemical formula H-1, Ar3 can be an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted).
[0131] The compound represented by the chemical formula H-1 can be a monoamine compound. Alternatively, the compound represented by the chemical formula H-1 can be a diamine compound comprising at least one of Ar1 to Ar3, with an amino group as a substituent. Furthermore, the compound represented by the chemical formula H-1 can be a carbazole compound comprising at least one of Ar1 and Ar2, with a substituted or unsubstituted carbazole group, or a fluorene compound comprising at least one of Ar1 and Ar2, with a substituted or unsubstituted fluorene group.
[0132] A compound represented by the chemical formula H-1 can be represented by any one of the compounds in the following compound group H. However, the compounds listed in the following compound group H are exemplary, and compounds represented by the chemical formula H-1 are not limited to those shown in the following compound group H.
[0133] [Compound Group H]
[0134]
[0135]
[0136]
[0137]
[0138] Hole transport region (HTR) may include phthalocyanine compounds such as copper phthalocyanine, N... 1 N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -Phenyl-N 4 N 4 -di-m-tolylphenyl-1,4-diamine)(DNTPD:N 1 N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 N 4-di-m-tolylbenzene-1,4-diamine), 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA: 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA: 4,4',4"-Tris(N,N-diphenylamino)triphenylamine), 4,4',4"-tris[N-(2-naphthyl)-N-phenylamine]triphenylamine 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]-triphenylamine, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA) sulfonicacid), polyaniline / poly(4-styrenesulfonate) (PANI / PSS: Polyaniline / Poly(4-styrenesulfonate)), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB: N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetra(pentafluoro) [4-Isopropyl-4'-methyldiphenyliodonium[Tetrakis(pentafluorophenyl)borate]], dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile, etc.
[0139] Furthermore, the hole transport region (HTR) may include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD: N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine), and 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA: 4,4'- Triphenylamine derivatives such as 4'-tris(N-carbazolyl)triphenylamine, N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB: N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), and 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC: 4,4′-Cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline]) hylphenyl)benzenamine]), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD: 4,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi: 9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl) Examples of carbazoles include 9-phenyl-9H-3,9'-bicarbazole (CCP: 9-phenyl-9H-3,9'-bicarbazole), 1,3-bis(N-carbazolyl)benzene (mCP: 1,3-Bis(N-carbazolyl)benzene), and 1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene (mDCP: 1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene).
[0140] The hole transport region HTR can be a compound comprising at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.
[0141] The thickness of the hole transport region (HTR) can be approximately up to approximately For example, it can be approximately up to approximately In the case where the hole transport region (HTR) includes a hole injection layer (HIL), the thickness of the hole injection layer (HIL) can be, for example, approximately... up to approximately In the case where the hole transport region (HTR) includes the hole transport layer (HTL), the thickness of the hole transport layer (HTL) can be approximately... up to approximately For example, in the case where the hole transport region HTR includes an electron blocking layer EBL, the thickness of the electron blocking layer EBL can be approximately up to approximately When the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) meet the ranges described above, satisfactory hole transport characteristics can be obtained without substantially increasing the driving voltage.
[0142] In addition to the substances mentioned above, the hole transport region (HTR) may also include a charge-generating substance to improve conductivity. The charge-generating substance may be uniformly or non-uniformly dispersed within the hole transport region (HTR). The charge-generating substance may, for example, be a p-dopant. The p-dopant may include, but is not limited to, at least one of metal halide compounds, quinone derivatives, metal oxides, and cyano-containing compounds. For example, p-dopers can include: metal halide compounds, such as CuI and RbI; quinone derivatives, such as tetracyanoquinone dimethylethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethylethane (F4-TCNQ); metal oxides, such as tungsten oxide and molybdenum oxide; and cyano-containing compounds, such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HATCN). -f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) and 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile), etc., but the examples are not limited thereto.
[0143] As previously mentioned, in addition to the hole injection layer (HIL) and the hole transport layer (HTL), the hole transport region (HTR) may also include at least one of a buffer layer (not shown) and an electron blocking layer (EBL). The buffer layer (not shown) can improve light emission efficiency by compensating for the resonant distance based on the wavelength of light emitted from the light-emitting layer (EML). The material included in the buffer layer (not shown) can be any material capable of being included in the hole transport region (HTR). The electron blocking layer (EBL) is a layer that prevents electrons from being injected from the electron transport region (ETR) into the hole transport region (HTR).
[0144] An emissive layer (EML) is provided on the hole transport region (HTR). The EML may have, for example, approximately up to approximately Or approximately up to approximately The thickness of the light-emitting layer (EML) is as follows. The EML can have a single-layer structure or a multi-layer structure with multiple layers stacked. In a multi-layer EML, the materials of the multiple layers can be different from each other or all the same, or at least one layer can be made of a different material than the rest.
[0145] In one embodiment of the light-emitting element (ED), the light-emitting layer (EML) may include a first body and a second body that are distinct from each other, as well as a dopant including an organometallic complex. Furthermore, in one embodiment of the light-emitting element (ED), where the EML comprises multiple layers, at least one layer may include the first body and the second body described later, as well as a dopant including an organometallic complex.
[0146] In one embodiment, the first body may be represented by the following chemical formula 1. That is, in one embodiment, the first body may include a triazine core.
[0147] [Chemical Formula 1]
[0148]
[0149] In Formula 1, Ar1 to Ar3 can each be independently an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). Furthermore, in Formula 1, at least one of Ar1 to Ar3 is an aryl group with 6 to 30 cyclic carbon atoms (including a halogen atom or a cyano group as a substituent) or a six-membered heterocyclic group (including a nitrogen atom as a cyclic atom). For example, at least one of Ar1 to Ar3 can be a phenyl group substituted with a halogen atom or a cyano group, or a six-membered heterocyclic group (including one or two nitrogen atoms as cyclic atoms). Additionally, the six-membered heterocyclic group can be a substituted or unsubstituted six-membered heterocyclic group.
[0150] In the first host represented by chemical formula 1, at least one of Ar1 to Ar3 may include an electron-accepting substituent. That is, a six-membered heterocyclic group including a halogen atom, a cyano group, or a nitrogen atom as a cyclic atom may be included in the first host as an electron-accepting substituent. For example, in the first host, at least one of Ar1 to Ar3 may include a phenyl group substituted with a fluorine atom, a phenyl group substituted with a cyano group, a pyridyl group, or a pyrimidinyl group, etc.
[0151] In one embodiment, at least one of Ar1 to Ar3 can be represented by any one of EW-1 to EW-5 described below. Furthermore, in EW-3 below, "Ph" represents phenyl. That is, in EW-3, the phenyl group can be substituted with a triphenylsilyl group.
[0152] The groups represented by EW-1 to EW-5 below can be electron-accepting substituents.
[0153]
[0154] In one embodiment, the first host material included in the light-emitting layer (EML) may be a compound comprising a triazine core and at least one electron-accepting substituent substituted into the triazine core. The first host material according to one embodiment, having such a compound structure, can exhibit high material stability.
[0155] The first host material according to one embodiment, represented by Chemical Formula 1, may include at least one electron-accepting substituent to reduce the electron density in the triazine moiety serving as the core. Accordingly, the binding force between the triazine and surrounding substituents increases, thereby exhibiting improved material stability. For example, in the absence of an electron-accepting substituent, the binding energy between the triazine and the substituent substituted into the triazine is approximately 2.7 eV, while for substituents including an electron-accepting group, the binding energy with the triazine increases to approximately 3.0 to 3.3 eV. That is, with the increase in binding energy, the stability of the first host material according to one embodiment is improved, and the lifetime of the light-emitting element in an embodiment including such a first host material can be increased.
[0156] The luminescent layer EML may include at least one of the compounds represented in compound group 1 below as a first host.
[0157] [Compound Group 1]
[0158]
[0159] The second entity can be represented by the following chemical formula 2.
[0160] [Chemical Formula 2]
[0161]
[0162] In chemical formula 2, X is NR. a O or CR b R c Furthermore, in chemical formula 2, R1 to R8, R a R b and R c It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, an alkyl group with 1 to 20 carbon atoms, an aryl group with 6 to 60 cyclic carbon atoms, or a heterocyclic group with 2 to 60 cyclic carbon atoms, which can be substituted or unsubstituted.
[0163] Furthermore, Ra R b and R c At least one of them is represented by the following chemical formula A.
[0164] [Chemical Formula A]
[0165]
[0166] That is, in one embodiment, when X is NR a At that time, R a Represented by chemical formula A, in one embodiment, where X is CR b R c At that time, R b and R c At least one of them can be represented by the chemical formula A.
[0167] In chemical formula A, m can be an integer between 0 and 2, and Ar4 can be a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group with 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group with 2 to 60 cyclic carbon atoms.
[0168] Furthermore, when m is 0, Ar4 can directly bind to the portion represented by Formula 2. When m is 1, Ar4 can bind to the portion represented by Formula 2 via a phenylene linker, and when m is 2, Ar4 can bind to the portion represented by Formula 2 via a divalent biphenyl linker.
[0169] For example, Ar4 can be a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted silyl, a substituted or unsubstituted phenyl, etc., but the examples are not limited thereto.
[0170] In chemical formula 2, R1 to R8 can be, for example, hydrogen atoms, substituted or unsubstituted carbazole groups, substituted silyl groups, etc. However, the examples are not limited thereto.
[0171] The luminescent layer EML may include at least one of the compounds represented in compound group 2 below as a second body.
[0172] [Compound Group 2]
[0173]
[0174] In one embodiment of the light-emitting element (ED), two host materials are simultaneously included in the light-emitting layer (EML). The first host material, represented by chemical formula 1, can be an electron transport host material, and the second host material, represented by chemical formula 2, can be a hole transport host material. This embodiment of the ED, by including both a first host material with excellent electron transport characteristics and a second host material with excellent hole transport characteristics in the light-emitting layer (EML), can effectively transfer energy to the dopant compound.
[0175] In one embodiment, the weight ratio of the first body to the second body in the total weight can be approximately 3:7 to approximately 7:3. When the contents of the first body and the second body satisfy the above ratio, the luminous efficiency and device lifetime can be increased because the charge balance characteristics within the light-emitting layer (EML) are improved.
[0176] In one embodiment of the light-emitting element ED, the dopant included in the light-emitting layer EML can be represented by the following chemical formula 3.
[0177] [Chemical Formula 3]
[0178]
[0179] The dopant of the light-emitting layer EML included in one embodiment can be an organometallic complex containing Pt as the central metal atom.
[0180] In chemical formula 3, Q1 to Q4 can be C or N independently, and the rings represented by C1 to C4 can be hydrocarbon rings with 5 to 30 carbon atoms that are substituted or unsubstituted, or heterocycles with 2 to 30 carbon atoms that are substituted or unsubstituted.
[0181] In chemical formula 3, Y is either O or S, and d1 to d4 are each an independent integer greater than 0 and less than 4. Furthermore, R... 31 To R 34 It can be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, an alkenyl group with 2 to 20 carbon atoms, an aryl group with 6 to 30 carbon atoms, or a heteroaryl group with 1 to 30 carbon atoms, and can optionally be combined with adjacent groups to form a ring.
[0182] Furthermore, chemical formula 3 can be represented by the following chemical formula 3-1.
[0183] [Chemical Formula 3-1]
[0184]
[0185] In chemical formula 3-1, Q 11 Q 31 Q 32 And Q 33 They can be N and NR independently. 11 CR 12 CR 12 R 13 BR 14 Or BR 14 R 15 In chemical formula 3-1, R 11 To R 15 It can be independently composed of hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted amino groups, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted cyclic carbon groups with 6 to 30 carbon atoms, or substituted or unsubstituted cyclic carbon groups with 1 to 30 carbon atoms, and can selectively combine with adjacent groups to form a ring. Furthermore, in chemical formula 3-1, the portion indicated by the dashed line (______) corresponds to the portion that selectively forms a double bond.
[0186] In one embodiment, R 11 To R 15 The components can be methyl, tert-butyl, substituted phenyl, etc., independently, but the examples are not limited thereto.
[0187] In chemical formula 3-1, Y, C4 ring, R 31 R 32 R 34 d1, d2, and d4 can be applied to the same content as defined in the above chemical formula 3.
[0188] The light-emitting layer EML may include at least one of the compounds represented in compound group 3 below as a dopant.
[0189] [Compound Group 3]
[0190]
[0191] In one embodiment of the light-emitting element (ED), the light-emitting layer (EML) can be provided by co-depositing the two host materials and the dopant material described above. In one embodiment, the EML comprising a first host material represented by chemical formula 1, a second host material represented by chemical formula 2, and a dopant material represented by chemical formula 3 can emit blue light. For example, in one embodiment of the ED, the EML comprising a first host material, a second host material, and a dopant material of chemical formula 3 can emit phosphorescence; specifically, the EML can emit blue phosphorescence.
[0192] One embodiment of the light-emitting element (ED) may include a first host to exhibit improved lifetime characteristics, the first host being an electron transport host having a triazine core and at least one electron-accepting substituent bonded to the triazine core. Furthermore, one embodiment of the light-emitting element (ED) may exhibit good luminous efficiency characteristics and excellent device lifetime characteristics through an emissive layer (EML) of a material comprising the aforementioned first host, second host, and a combination of dopants of Formula 3.
[0193] In addition to the first body, the second body, and the dopant of Formula 3, which includes an organometallic complex, the light-emitting element ED according to one embodiment may also include the light-emitting layer material described below. The light-emitting layer material described below may also be included in the same light-emitting layer as the light-emitting layer including the first body, the second body, and the dopant of Formula 3, or may be included in other light-emitting layers that are separate from it.
[0194] For example, light-emitting elements (EDs) may also include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, etc. Derivatives, dihydrobenzanthracene derivatives, or benzo[9,10]phenanthrene derivatives are known luminescent layer materials. Specifically, the luminescent layer EML may include anthracene derivatives or pyrene derivatives.
[0195] In addition, Figures 3 to 6 In one embodiment of the light-emitting element ED, the light-emitting layer EML may include a compound represented by the following chemical formula E-1. The compound represented by the following chemical formula E-1 can be used as a fluorescent host material.
[0196] [Chemical Formula E-1]
[0197]
[0198] In chemical formula E-1, R 31 To R 40It can be independently composed of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted silyl groups, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted oxygen groups, substituted or unsubstituted mercapto groups, substituted or unsubstituted cyclic aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted cyclic aryl groups having 2 to 30 carbon atoms, and can optionally be combined with adjacent groups to form a ring. Furthermore, R 31 To R 40 It can combine with adjacent groups to form saturated or unsaturated hydrocarbon rings. Furthermore, R... 31 To R 40 It can combine with adjacent substituents or adjacent benzene rings to form condensation rings. In chemical formula E-1, c and d can each be an independent integer greater than 0 and less than 5. Chemical formula E-1 can be represented by any one of the following compounds E1 to E19.
[0199]
[0200]
[0201] Furthermore, the chemical formula E-1 can be represented by any one of the following compounds.
[0202]
[0203]
[0204] In one embodiment, the luminescent layer (EML) may include a compound represented by the following chemical formula E-2a or E-2b. The compound represented by the following chemical formula E-2a or E-2b may be used as a phosphorescent host material.
[0205] [Chemical formula E-2a]
[0206]
[0207] In the chemical formula E-2a, 'a' can be an integer from 0 to 10, and 'La' can be a directly bonded, substituted or unsubstituted cyclic aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted cyclic aryl group with 2 to 30 cyclic carbon atoms. Furthermore, when 'a' is an integer of 2 or more, multiple 'La's can each independently be a substituted or unsubstituted cyclic aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted cyclic aryl group with 2 to 30 cyclic carbon atoms.
[0208] Furthermore, in chemical formula E-2a, A1 to A5 can each be independently N or CR. i R a To R i It can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, an alkyl group with 1 to 20 carbon atoms, an alkenyl group with 2 to 20 carbon atoms, an aryl group with 6 to 30 carbon atoms, or a heteroaryl group with 2 to 30 carbon atoms, and can optionally be combined with adjacent groups to form a ring. R a To R i It can combine with adjacent groups to form hydrocarbon rings or heterocycles that include N, O, S, etc. as cyclic atoms.
[0209] Furthermore, in chemical formula E-2a, two or three selected from A1 to A5 can be N, and the rest can be CR. i .
[0210] [Chemical formula E-2b]
[0211]
[0212] In chemical formula E-2b, Cbz1 and Cbz2 can be independently either an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 cyclic carbon atoms. b It can be a directly bonded, substituted or unsubstituted cyclic aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group with 2 to 30 carbon atoms. b can be an integer from 0 to 10. When b is an integer of 2 or more, multiple L... b It can be independently a cyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms.
[0213] A compound represented by chemical formula E-2a or E-2b may be represented by any one of the compounds in the following compound group E-2. However, the compounds listed in the following compound group E-2 are exemplary, and compounds represented by chemical formula E-2a or E-2b are not limited to those shown in the following compound group E-2.
[0214] [Compound Group E-2]
[0215]
[0216]
[0217]
[0218] The luminescent layer EML can also include common materials known in the art as the host material. For example, the luminescent layer EML can include bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO: Bis[2-(diphenylphosphino)phenyl]ether oxide), 4,4'-bis(carbazol-9-yl)biphenyl (CBP: 4,4'-Bis(carbazol-9-yl)biphenyl), 1,3-bis(carbazol-9-yl)benzene (mCP: 1,3-Bis(carbazol-9-yl)benzene), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF: 2,8-Bis(diphenylphosphoryl)dibenzo[b,d]furan). The main substance is at least one of uran), 4,4',4”-tris(carbazol-9-yl)-triphenylamine (TCTA: 4,4',4”-Tris(carbazol-9-yl)-triphenylamine) and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi: 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene).However, it is not limited to this; for example, tris(8-hydroxyquinolino)aluminum (Alq3: tris(8-hydroxyquinolino)aluminum), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP: 4,4'-bis(N-carbazolyl)-1,1'-biphenyl), poly(N-vinylcabazole) (PVK: poly(N-vinylcabazole)), 9,10-di(naphthalene-2-yl)anthracene (ADN: 9,10-di(naphthalene-2-yl)anthracene), 4,4',4"-tris(carbazol-9-yl)-triphenylamine (TCTA: 4,4',4"-Tris(carbazol-9-yl)-triphenylamine), and 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TP) can be used. Bi: 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene), 2-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN: 2-tert-butyl-9,10-di(naphth-2-yl)anthracene), distyrylarylene (DSA: distyrylarylene), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP: 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl), 2-methyl-9,10-bis(naphth-2-yl)anthracene (MADN: 2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), hexaphenylcyclotriphosphazene (CP1: Hexaphenyl) Cyclotriphosphazene, 1,4-bis(triphenylsilyl)benzene (UGH2: 1,4-Bis(triphenylsilyl)benzene), hexaphenylcyclotrisiloxane (DPSiO3: Hexaphenylcyclotrisiloxane), octaphenylcyclotetrasiloxane (DPSiO4: Octaphenylcyclotetrasiloxane), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF: 2,8-Bis(diphenylphosphoryl)dibenzofuran) and other similar compounds are used as the main materials.
[0219] The emissive layer EML may also include compounds represented by the chemical formulas Ma or Mb. These compounds can be used as phosphorescent dopant materials.
[0220] [Chemical formula Ma]
[0221]
[0222] In the chemical formula Ma, Y1 to Y4 and Z1 to Z4 are each independently CR1 or N, and R1 to R4 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxygen group, an alkyl group with 1 to 20 carbon atoms, an alkenyl group with 2 to 20 carbon atoms, an aryl group with 6 to 30 cyclic carbon atoms, or a heteroaryl group with 2 to 30 cyclic carbon atoms, and can optionally be combined with adjacent groups to form a ring. In the chemical formula Ma, m is 0 or 1, and n is 2 or 3. In the chemical formula Ma, when m is 0, n is 3; when m is 1, n is 2.
[0223] Compounds represented by the chemical formula Ma can be used as red or green phosphorescent dopants.
[0224] Compounds represented by the chemical formula Ma can be represented by any one of the following compounds M-a1 to M-a23. However, compounds M-a1 to M-a23 are exemplary, and compounds represented by the chemical formula Ma are not limited to those represented by compounds M-a1 to M-a23.
[0225]
[0226]
[0227] Compounds M-a1 and M-a2 can be used as red dopant materials, while compounds M-a3 to M-a5 can be used as green dopant materials.
[0228] [Chemical formula Mb]
[0229]
[0230] In the chemical formula Mb, Q1 to Q4 are independently C or N, and C1 to C4 are independently hydrocarbon rings with 5 to 30 substituted or unsubstituted carbon atoms, or heterocycles with 2 to 30 substituted or unsubstituted carbon atoms. 21 To L 24 Each can be independently represented as direct binding, *-O-*, *-S-*, etc. The substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, the substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or the substituted or unsubstituted cyclic aryl group having 2 to 30 carbon atoms, wherein e1 to e4 are independently 0 or 1. R 31 To R 39 Each of the following groups is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted cyclic carbon atoms, and may optionally be combined with adjacent groups to form a ring, wherein d1 to d4 are independently integers of 0 to 4.
[0231] Compounds represented by the chemical formula Mb can be used as blue or green phosphorescent dopants.
[0232] A compound represented by the chemical formula Mb can be represented by any of the compounds listed below. However, the compounds listed below are exemplary, and the compound represented by the chemical formula Mb is not limited to the compounds represented by the compounds listed below.
[0233]
[0234] In the compound, R, R 38 and R 39 It can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cyclic carbon group with 6 to 30 carbon atoms, or a heteroaryl group with 2 to 30 carbon atoms.
[0235] Furthermore, it may include at least one of the following compounds containing a dopant material with Pt as the central metal.
[0236]
[0237] The emissive layer (EML) may also include a compound represented by any one of the following chemical formulas: Fa to Fc. The compounds represented by the following chemical formulas: Fa to Fc can be used as fluorescent dopant materials.
[0238] [Chemical formula Fa]
[0239]
[0240] In the chemical formula Fa, the components are selected from R. aTo R j The two in can be replaced independently by *-NAr1Ar2. In R a To R j In *-NAr1Ar2, the remaining groups not substituted by * can be independently hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted amino groups, alkyl groups with 1 to 20 carbon atoms (substituted or unsubstituted), aryl groups with 6 to 30 cyclic carbon atoms (substituted or unsubstituted), or heteroaryl groups with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). In *-NAr1Ar2, Ar1 and Ar2 can be independently independently aryl groups with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or heteroaryl groups with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). For example, at least one of Ar1 and Ar2 can be a heteroaryl group including O or S as a cyclic atom.
[0241] The luminescent layer EML may include at least one of the following compounds FD1 to FD22 as a fluorescent dopant.
[0242]
[0243]
[0244]
[0245] [Chemical formula Fb]
[0246]
[0247] In the chemical formula Fb, R a and R b It can be independently a hydrogen atom, a deuterium atom, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted cyclic carbon atoms, and can optionally be combined with adjacent groups to form a ring.
[0248] In the chemical formula Fb, U and V can be, independently, either substituted or unsubstituted cyclic hydrocarbon rings with 5 to 30 carbon atoms, or substituted or unsubstituted cyclic heterocycles with 2 to 30 carbon atoms.
[0249] In the chemical formula Fb, the number of rings represented by U and V can be independently 0 or 1. For example, in the chemical formula Fb, when the number of U or V is 1, it means that in the part described as U or V, one ring forms a condensed ring; when the number of U or V is 0, it means that there are no rings described as U or V. Specifically, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the condensed ring of the fluorene core having the chemical formula Fb can be a tetracyclic cyclic compound. Furthermore, when the number of U and V is both 0, the condensed ring of the fluorene core having the chemical formula Fb can be a tricyclic cyclic compound. Furthermore, when the number of U and V is both 1, the condensed ring of the fluorene core having the chemical formula Fb can be a pentacyclic cyclic compound.
[0250] In the chemical formula Fb, Ar1 to Ar4 can be independently aryl groups with 6 to 30 cyclic carbon atoms, either substituted or unsubstituted, or heteroaryl groups with 2 to 30 cyclic carbon atoms.
[0251] [Chemical formula Fc]
[0252]
[0253] In the chemical formula Fc, A1 and A2 are independently O, S, Se, or NR, respectively. m R m It can be a hydrogen atom, a deuterium atom, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted cyclic carbon atoms. R1 to R 11 Each group is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxygen group, a substituted or unsubstituted thio group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms, and may optionally be combined with adjacent groups to form a ring.
[0254] In the chemical formula Fc, A1 and A2 can independently combine with substituents of adjacent rings to form condensed rings. For example, when A1 and A2 are independently NR... m In this case, A1 can combine with R4 or R5 to form a ring. Furthermore, A2 can combine with R7 or R8 to form a ring.
[0255] In one embodiment, the light-emitting layer EML may further include styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene (BCzVB: 1,4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB: 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi: N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylaniline). L-benzenamine, 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi: 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl), perylene and its derivatives (e.g., 2,5,8,11-tetra-t-butylperylene (TBP: 2,5,8,11-tetra-t-butylperylene)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene) are known dopant materials.
[0256] The light-emitting layer (EML) may also include known phosphorescent dopant materials. For example, phosphorescent dopant can be a metal complex including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm). Specifically, iridium(III)bis(4,6-difluorophenylpyridinato-N,C2')picolinate (FIrpic: iridium(III)bis(4,6-difluorophenylpyridinato-N,C2')picolinate), iridium(III)bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III) (Fir6: Bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III)), or platinumoctaethyl porphyrin (PtOEP: platinumoctaethyl porphyrin) can be used as phosphorescent dopants. However, the examples are not limited to these.
[0257] That is, the light-emitting element (ED) of one embodiment includes a first body, a second body, and a dopant represented by chemical formula 3, and can exhibit improved lifetime characteristics through the compound structure characteristics of the first body. Furthermore, in addition to the combination of the first body, the second body, and the dopant material represented by chemical formula 3 in one embodiment, the aforementioned light-emitting layer material may also be included.
[0258] exist Figures 3 to 6 In one embodiment of the light-emitting element ED, an electron transport region (ETR) is provided on the light-emitting layer (EML). The electron transport region (ETR) may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL), but the embodiment is not limited thereto.
[0259] The electron transport region (ETR) can have a single-layer structure composed of a single substance, a single-layer structure composed of multiple different substances, or a multi-layer structure composed of multiple different substances.
[0260] For example, the electron transport region (ETR) can have a single-layer structure of either the electron injection layer (EIL) or the electron transport layer (ETL), or it can have a single-layer structure composed of an electron injection material and an electron transport material. Furthermore, the ETR can have a single-layer structure composed of multiple different materials, or it can have a structure of electron transport layer ETL / electron injection layer EIL, hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL stacked sequentially from the emitting layer (EML), but it is not limited to these. The thickness of the ETR can, for example, be approximately... up to approximately
[0261] Electron transport regions (ETRs) can be formed using various methods, including vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).
[0262] The electron transport region (ETR) may include compounds represented by the following chemical formula ET-1.
[0263] [Chemical formula ET-1]
[0264]
[0265] In the chemical formula ET-1, at least one of X1 to X3 is N, and the rest are CR. a R a Ar1 to Ar3 can be hydrogen atoms, deuterium atoms, alkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, aryl groups with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or heteroaryl groups with 2 to 30 substituted or unsubstituted cyclic carbon atoms.
[0266] In chemical formula ET-1, a to c can each be an integer from 0 to 10 or less. In chemical formula ET-1, L1 to L3 can each be an arylene group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroarylene group with 2 to 30 substituted or unsubstituted cyclic carbon atoms, respectively, through direct linkage. Furthermore, when a to c are integers of 2 or more, L1 to L3 can each be an arylene group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroarylene group with 2 to 30 substituted or unsubstituted cyclic carbon atoms, respectively.
[0267] Electron transport region (ETR) compounds may include anthracene compounds. However, they are not limited to this; for example, ETRs may include tris(8-hydroxyquinolino)aluminum, 1,3,5-tris[(3-pyridyl)-phen-3-yl]benzene, and 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine. ine), 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi: 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP: 2,9-Dim ethyl-4,7-diphenyl-1,10-phenanthroline), 4,7-diphenyl-1,10-phenanthroline (Bphen: 4,7-Diphenyl-1,10-phenanthroline), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ: 3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ: 4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD: 2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), bis(2-methyl-8-quinolino-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq: Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olate)aluminum), bis(benzoquinolin-10-olate)beryllium (Bebq2: berylliumbis(benzoquinolin-10-olate)), 9,10-di(naphthalene-2-yl)anthracene (ADN: 9,10-di(naphthalene-2-yl)anthracene), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB: (1,3-Bis[3,5-di(pyridin-3-yl)phenyl]benzene), and mixtures thereof.
[0268] The electron transport region (ETR) may include at least one of the following compounds: ET1 to ET36.
[0269]
[0270]
[0271]
[0272]
[0273] Furthermore, the electron transport region (ETR) can include: metal halides, such as LiF, NaCl, CsF, RbCl, RbI, CuI, KI, etc.; lanthanide group metals, such as Yb, etc., and can include co-deposited materials of said metal halides and lanthanide group metals. For example, the ETR can include KI:Yb, RbI:Yb, etc., as co-deposited materials. In addition, the ETR can use metal oxides such as Li₂O, BaO, or lithium 8-hydroxyl-Lithiumquinolate (Liq), but the embodiments are not limited to these. The ETR can also be composed of a mixture of electron transport material and insulating organometallic salt. The organometallic salt can be a material with an energy band gap of approximately 4 eV or higher. Specifically, for example, organometallic salts may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.
[0274] In addition to the materials mentioned above, the electron transport region (ETR) may also include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP: 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline) and 4,7-diphenyl-1,10-phenanthroline (Bphen: 4,7-Diphenyl-1,10-phenanthroline), but the embodiments are not limited thereto.
[0275] The electron transport region (ETR) can be a compound comprising at least one of the electron injection layer (EIL), the electron transport layer (ETL), and the hole blocking layer (HBL).
[0276] In the case where the electron transport region ETR includes the electron transport layer ETL, the thickness of the electron transport layer ETL can be approximately up to approximately For example, it can be approximately up to approximately When the thickness of the electron transport layer (ETL) meets the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in the driving voltage. When the electron transport region (ETL) includes an electron injection layer (EIL), the thickness of the EIL can be approximately... up to approximately About up to approximately When the thickness of the electron injection layer (EIL) meets the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.
[0277] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 can be a common electrode. The second electrode EL2 can be a cathode or an anode, but the embodiments are not limited thereto. For example, if the first electrode EL1 is an anode, the second electrode EL2 can be a cathode, and if the first electrode EL1 is a cathode, the second electrode EL2 can be an anode.
[0278] The second electrode EL2 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. In the case where the second electrode EL2 is a transmissive electrode, it can be composed of a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO).
[0279] When the second electrode EL2 is a semi-transparent or reflective electrode, it may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W, their compounds and mixtures (e.g., AgMg, AgYb, or MgYb), and materials having a multilayer structure of LiF / Ca or LiF / Al. Alternatively, the second electrode EL2 may be a multilayer structure comprising a reflective or semi-transparent film formed from the aforementioned materials and a transparent conductive film formed from indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. For example, the second electrode EL2 may include the aforementioned metallic materials, a combination of two or more metallic materials selected from the aforementioned metallic materials, or oxides of the aforementioned metallic materials.
[0280] Although not shown, the second electrode EL2 can be connected to the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.
[0281] Furthermore, in one embodiment, a capping layer CPL may be disposed on the second electrode EL2 of the light-emitting element ED. The capping layer CPL may be multilayer or single-layer.
[0282] In one embodiment, the capping layer CPL can be an organic layer or an inorganic layer. For example, when the capping layer CPL includes inorganic materials, the inorganic materials may include: alkali metal compounds, such as LiF; alkaline earth metal compounds, such as MgF2; and SiON, SiN. X SiO y wait.
[0283] For example, when the capping layer CPL includes an organic compound, the organic compound may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15: N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA: 4,4',4"-Tris(carbazol-9-yl)triphenylamine), etc., or may include epoxy resin or acrylate such as methacrylate. However, the embodiments are not limited thereto, and the capping layer CPL may include at least one of compounds P1 to P5 as described below.
[0284]
[0285] Furthermore, the refractive index of the capping layer CPL can be 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 can be 1.6 or higher.
[0286] Figure 7 as well as Figure 8 These are cross-sectional views of a display device according to one embodiment. Hereinafter, in conjunction with the reference... Figure 7 and Figure 8 When describing a display device according to one embodiment, the description will not repeat the descriptions of the above-described display device. Figures 1 to 6 The content repeated in the explanation should be explained mainly based on the differences.
[0287] Reference Figure 7 According to one embodiment, the display device DD may include a display panel DP including a display element layer DP-ED, a light control layer CCL and a color filter layer CFL disposed on the display panel DP.
[0288] exist Figure 7 In one embodiment shown, the display panel DP may include a base layer BS, a circuit layer DP-CL disposed on the base layer BS, and a display element layer DP-ED, wherein the display element layer DP-ED may include a light-emitting element ED.
[0289] The light-emitting element (ED) may include: a first electrode EL1; a hole transport region HTR disposed on the first electrode EL1; a light-emitting layer EML disposed on the hole transport region HTR; an electron transport region ETR disposed on the light-emitting layer EML; and a second electrode EL2 disposed on the electron transport region ETR. Furthermore, Figure 7 The structure of the light-emitting element ED shown can be applied in the same way as described above. Figures 4 to 6 The structure of the light-emitting element.
[0290] Reference Figure 7 The emissive layer EML can be disposed within the opening OH defined by the pixel defining film PDL. For example, the emissive layers EML provided corresponding to each emissive region PXA-R, PXA-G, and PXA-B, divided by the pixel defining film PDL, can emit light of the same wavelength. In a display device DD according to one embodiment, the emissive layer EML can emit blue light. Furthermore, unlike the illustrated case, in one embodiment, the emissive layer EML can be provided as a common layer throughout the entire emissive region PXA-R, PXA-G, and PXA-B.
[0291] The light control layer (CCL) can be disposed on the display panel (DP). The light control layer (CCL) may include a light converter. The light converter may be a quantum dot or a phosphor, etc. The light converter can convert the wavelength of the received light and emit it. That is, the light control layer (CCL) may be a layer including quantum dots or a layer including phosphors.
[0292] The optical control layer (CCL) may include multiple optical control units CCP1, CCP2, and CCP3. The optical control units CCP1, CCP2, and CCP3 may be spaced apart from each other.
[0293] Reference Figure 7 A segmented pattern BMP can be arranged between the light control units CCP1, CCP2, and CCP3 that are separated from each other, but the embodiment is not limited to this. Although in Figure 7 The diagram shows a case where the segmentation pattern BMP does not overlap with the light control units CCP1, CCP2, and CCP3, but the edges of the light control units CCP1, CCP2, and CCP3 may overlap with at least a portion of the segmentation pattern BMP.
[0294] The light control layer CCL may include: a first light control unit CCP1, including a first quantum dot QD1 that converts first-color light provided by the light-emitting element ED into second-color light; a second light control unit CCP2, including a second quantum dot QD2 that converts first-color light into third-color light; and a third light control unit CCP3 that transmits first-color light.
[0295] In one embodiment, the first light control unit CCP1 can provide red light as a second color light, and the second light control unit CCP2 can provide green light as a third color light. The third light control unit CCP3 can transmit blue light, which is the first color light provided from the light-emitting element ED, to provide blue light. For example, the first quantum dot QD1 can be a red quantum dot, and the second quantum dot QD2 can be a green quantum dot. The same content as described above can be applied to quantum dots QD1 and QD2.
[0296] Furthermore, the optical control layer CCL may also include a scatterer SP. The first optical control unit CCP1 may include a first quantum dot QD1 and a scatterer SP, the second optical control unit CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third optical control unit CCP3 may not include a quantum dot but may include a scatterer SP.
[0297] The scatterer SP can be inorganic particles. For example, the scatterer SP can include at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer SP can include any one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or it can be a mixture of two or more substances selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.
[0298] Each of the first light control unit CCP1, the second light control unit CCP2, and the third light control unit CCP3 may include base resins BR1, BR2, and BR3 for dispersing quantum dots QD1, QD2, and scatterers SP. In one embodiment, the first light control unit CCP1 may include the first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second light control unit CCP2 may include the second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third light control unit CCP3 may include scatterers SP dispersed in the third base resin BR3. The base resins BR1, BR2, and BR3, as media for dispersing quantum dots QD1, QD2, and scatterers SP, may be composed of various resin compositions commonly referred to as binders. For example, the base resins BR1, BR2, and BR3 may be acrylic resins, polyurethane resins, silicone resins, epoxy resins, etc. The base resins BR1, BR2, and BR3 may be 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.
[0299] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 serves to prevent the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 may be disposed on the light control units CCP1, CCP2, and CCP3 to prevent them from being exposed to moisture / oxygen. Furthermore, the barrier layer BFL1 may cover the light control units CCP1, CCP2, and CCP3. Additionally, a barrier layer BFL2 may also be provided between the light control units CCP1, CCP2, and CCP3 and the filters CF1, CF2, and CF3 (described later).
[0300] Barrier layers BFL1 and BFL2 may include at least one inorganic layer. That is, barrier layers BFL1 and BFL2 may be formed from inorganic materials. For example, barrier layers BFL1 and BFL2 may be formed from silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, and silicon nitride, or a metal thin film that ensures light transmittance. Furthermore, barrier layers BFL1 and BFL2 may also include an organic film. Barrier layers BFL1 and BFL2 may consist of a single layer or multiple layers.
[0301] In one embodiment of the display device DD, the color filter layer CFL can be disposed on the light control layer CCL. For example, the color filter layer CFL can be disposed directly on the light control layer CCL. In this case, the blocking layer BFL2 can be omitted.
[0302] The color filter layer CFL may include a light-shielding portion BM and filters CF1, CF2, and CF3. Furthermore, the color filter layer CFL may also include a blocking layer BFL2. The color filter layer CFL may include: a first filter CF1 that allows the transmission of a second color light; a second filter CF2 that allows the transmission of a third color light; and a third filter CF3 that allows the transmission of a first color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. Each of the filters CF1, CF2, and CF3 may include a photosensitive polymer and a pigment or dye. The first filter CF1 may include a red pigment or dye, the second filter CF2 may include a green pigment or dye, and the third filter CF3 may include a blue pigment or dye. However, the embodiments are not limited thereto; the third filter CF3 may not include any pigment or dye. The third filter CF3 may include a photosensitive polymer and may not include any pigment or dye. The third filter CF3 may be transparent. The third filter CF3 can be formed from a transparent photosensitive resin.
[0303] Furthermore, in one embodiment, the first filter CF1 and the second filter CF2 can be yellow filters. The first filter CF1 and the second filter CF2 can be provided integrally without distinguishing them from each other.
[0304] The light-shielding portion BM can be a black matrix. The light-shielding portion BM can be formed from organic or inorganic light-shielding materials containing black pigments or dyes. The light-shielding portion BM can prevent light leakage and define the boundaries between adjacent filters CF1, CF2, and CF3. Furthermore, in one embodiment, the light-shielding portion BM can be formed from a blue filter.
[0305] The first to the third filters CF1, CF2, and CF3 can be arranged to correspond to the red emitting area PXA-R, the green emitting area PXA-G, and the blue emitting area PXA-B, respectively.
[0306] A base substrate BL can be disposed on the color filter layer CFL. The base substrate BL can be a component that provides a base surface for disposing the color filter layer CFL and the light control layer CCL, etc. The base substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited to this, and the base substrate BL can be an inorganic layer, an organic layer, or a composite material layer. Furthermore, unlike the illustrated case, in one embodiment, the base substrate BL can be omitted.
[0307] Figure 8 This is a cross-sectional view showing a portion of a display device according to one embodiment. Figure 8 It shows the relationship with Figure 7 A cross-sectional view of a portion of the display panel DP. In a display device DD-TD of one embodiment, the light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The light-emitting element ED-BT may include: a first electrode EL1 and a second electrode EL2 facing each other; and a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3, which are provided by being stacked sequentially 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 may include a light-emitting layer EML (Emitting Material Layer). Figure 7 ), with an EML light-emitting layer sandwiched in the middle ( Figure 7 The hole transmission region (HTR) and electron transmission region (ETR) are arranged accordingly.
[0308] That is, the light-emitting element ED-BT of the display device DD-TD included in one embodiment can be a light-emitting element with a tandem structure including multiple light-emitting layers.
[0309] exist Figure 8 In one embodiment shown, the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can all be blue light. However, the embodiment is not limited to this, and the wavelengths of the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can be different from each other. For example, a light-emitting element ED-BT comprising multiple light-emitting structures OL-B1, OL-B2, and OL-B3 that emit light in different wavelengths can emit white light.
[0310] Charge generation layers CGL1 and CGL2 can be arranged between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. Charge generation layers CGL1 and CGL2 may include p-type charge generation layers and / or n-type charge generation layers.
[0311] At least one of the light-emitting structures OL-B1, OL-B2, and OL-B3 in the display device DD-TD included in one embodiment can utilize the combination of materials of the light-emitting layer according to one embodiment described above. That is, at least one of the light-emitting structures OL-B1, OL-B2, and OL-B3 can include, in the light-emitting layer, the first substrate as an electron transport substrate, the second substrate as a hole transport substrate, and a dopant represented by chemical formula 3.
[0312] The display device DD-TD according to an embodiment of the present invention can exhibit improved lifespan characteristics by including a material combination comprising the light-emitting layer EML as described above.
[0313] Hereinafter, a light-emitting element according to an embodiment of the present invention and a first body included in a light-emitting element according to an embodiment will be specifically described with reference to embodiments and comparative examples. Furthermore, the embodiments shown below are examples to aid in understanding the present invention, and the scope of the present invention is not limited thereto.
[0314] [Example]
[0315] 1. The synthesis of the first subject
[0316] <Synthesis of Compound ET01>
[0317] According to one embodiment, compound ET01 can be synthesized by, for example, the steps of the following reaction formula.
[0318]
[0319] (Synthesis of intermediate compound 1)
[0320] 1,3-Dibromo-5-chlorobenzene (10 g) and tetrahydrofuran (THF) were added to a round-bottom flask (RBF), and n-butyllithium (nBuLi) (2 M in hexane, 1.2 eq) was slowly added dropwise at room temperature, followed by stirring for 30 minutes. Triphenylsilyl chloride (1.5 eq) and tetrahydrofuran (THF) were then added to the RBF. The reaction solution was then refluxed for two hours, cooled to room temperature, quenched dropwise with water, and stirred for 30 minutes. The resulting solid was filtered and washed with distilled water, methanol, and hexane to obtain intermediate compound 1 (yield 84%). [C] 24 H 18 BrClSi[M]+: Calculated: 448.00, Measured: 447]
[0321] (Synthesis of intermediate compound 2)
[0322] Intermediate compound 1 (12 g), CuCN (1.2 equivalents), Pd2(dba)3 (0.02 equivalents), and DPPF (1.2 equivalents) were added to a round-bottom flask (RBF) and stirred at 120 °C for 12 hours in toluene (150 mL). After the reaction was complete, the solvent was removed by silica filtration with methylene chloride. Intermediate compound 2 (76% yield) was obtained by column chromatography with methylene chloride:hexane [(1:3)] and drying. 25 H 18 ClNSi[M]+: Calculated: 395.09, Measured: 394]
[0323] (Synthesis of intermediate compound 3)
[0324] Intermediate compound 2 (8 g) and tetrahydrofuran (THF) (100 mL) were added to a round-bottom flask (RBF), and n-butyllithium (nBuLi) (2 M in hexane, 17 mL, 1.2 equivalents) was slowly added dropwise at -78 °C. Trimethyl borate (1.5 equivalents) was then slowly added dropwise after 40 minutes. The reaction solution was slowly heated to room temperature and stirred overnight. After quenching with water and NH4Cl solution, it was washed with EA / H2O and dried over MgSO4. Subsequently, intermediate compound 3 (88% yield) was obtained by column chromatography using dichloromethane (MC):ethyl acetate (EA). [C] 25 H 20 BNO2Si[M]+: Calculated: 405.14, Measured: 404]
[0325] (Synthesis of intermediate compound 4)
[0326] 9H-carbazole (2 equivalents) and tetrahydrofuran (THF) were added to a round-bottom flask (RBF), and n-butyllithium (nBuLi) (2M in hexane, 2.2 equivalents) was slowly added dropwise at room temperature, followed by stirring for 30 minutes. 2,4,6-trichlorotriazine (1 equivalent) and tetrahydrofuran (THF) were added to the round-bottom flask (RBF), and the prepared lithium carbazole solution was slowly added dropwise over 30 minutes using a dropping funnel. After refluxing the reaction solution for 2 hours, the reaction solution was cooled to room temperature and stirred for 30 minutes after quenching with water. The resulting solid was filtered and washed with distilled water, methanol, and hexane to obtain intermediate compound 4 (yield 82%). [C] 27 H 16 ClN5[M]+: Calculated: 445.91, Measured: 444]
[0327] (Synthesis of compound ET01)
[0328] Intermediate compound 3 (1 equivalent), intermediate compound 4 (1.1 equivalent), Pd(PPh3)4 (0.05 equivalent), K2CO3 (2.5 equivalent), tetrahydrofuran (THF) (400 mL), and H2O (100 mL) were added to a round-bottom flask (RBF) and stirred under reflux at 100 °C overnight. After the reaction was complete, EA / H2O was added and stirred for 30 minutes. The organic layer was then separated using a separatory funnel. The organic layer was dried with MgSO4 and filtered through dichloromethane to obtain silica. The resulting solid was filtered and dried using MeOH. The dried solid was dissolved in 100 mL of toluene by heating and solidified by dropwise addition of a 1:1 solution of ether and hexane (100 mL). The solid was redissolved in dichloromethane (MC) (400 mL) and hexane (400 mL) was added, followed by slow recrystallization to synthesize compound ET01 (yield 84.1%). [C] 52 H 34 N6Si [M]+: Calculated: 770.26, Measured: 769]
[0329] <Synthesis of Compound ET02>
[0330] According to one embodiment, compound ET02 can be synthesized, for example, by the steps of the following reaction formula.
[0331]
[0332] (Synthesis of intermediate compound 5)
[0333] 3-(bromophenyl)triphenylsilane (1 equivalent) and tetrahydrofuran (THF) (150 mL) were added to a round-bottom flask (RBF). Then, n-butyllithium (nBuLi) (2 M in hexane, 17 mL, 1.2 equivalent) was slowly added dropwise at -78 °C, followed by the slow addition of trimethylborate (1.5 equivalent) after 40 minutes. The reaction solution was then slowly heated to room temperature and stirred overnight, followed by quenching with water and NH4Cl solution and washing with EA / H2O. The solution was then dried over MgSO4 and purified by column chromatography with MC:EA to obtain intermediate compound 5 (77% yield). [C] 24 H 21 BO2Si[M]+: Calculated: 380.33, Measured: 379
[0334] (Synthesis of intermediate compound 6)
[0335] Intermediate compound 6 was obtained using the same method as intermediate compound 4, but with only 1 equivalent of 9H-carbazole (yield 85%). [C] 15 H8Cl2N4[M]+: Calculated value: 314.01, Measured value: 313]
[0336] (Synthesis of compound ETO2)
[0337] Intermediate compound 6 (1 equivalent), Pd(PPh3)4 (0.05 equivalent), K2CO3 (2.1 equivalent), tetrahydrofuran (THF) (400 mL), and H2O (100 mL) were added to a round-bottom flask (RBF) and stirred. After cooling to 0 °C, a 1 M solution of intermediate compound 3 dissolved in tetrahydrofuran (THF) was added dropwise. The temperature was then slowly raised to room temperature and stirred for 6 hours. Next, intermediate compound 5 (1.1 equivalent) was added and the mixture was refluxed at 100 °C with stirring overnight. After the reaction was complete, EA / H2O was added and the mixture was stirred for 30 minutes. The organic layer was then separated using a separatory funnel. After drying with MgSO4, the solid was filtered through dichloromethane and then filtered and dried using MeOH. The dried solid was dissolved in toluene (100 mL) by heating and then solidified by dropwise addition of a 1:1 solution of dichloromethane (MC):hexane (100 mL). The solid was then redissolved in dichloromethane (MC) and purified by column chromatography using MC:EA to synthesize compound ET02 (yield 51%). [C] 64 H45 N5Si2[M]+: Calculated: 939.32, Measured: 938.
[0338] Synthesis of Compound ET03
[0339] According to one embodiment, compound ET03 can be synthesized, for example, by the steps of the following reaction formula.
[0340]
[0341] Intermediate compound 6 (1 equivalent), intermediate compound 3 (2.2 equivalent), Pd(PPh3)4 (0.05 equivalent), K2CO3 (2.5 equivalent), tetrahydrofuran (THF) (400 mL), and H2O (100 mL) were added to a round-bottom flask (RBF) and refluxed with stirring at 100 °C overnight. After the reaction was complete, EA / H2O was added and the mixture was stirred for 30 minutes. Only the organic layer was separated using a separatory funnel. The solid was then dried with MgSO4 and filtered through dichloromethane to obtain silica. The resulting solid was then filtered through MeOH and dried. The dried solid was dissolved in toluene (100 mL) by heating and solidified by dropwise addition of a 1:1 solution of diethyl ether and hexane (100 mL). The solid was redissolved in dichloromethane (MC) (400 mL) and hexane (400 mL) was added, followed by slow recrystallization to synthesize compound ET03 (yield 84.1%). [C] 65 H 44 N6Si2[M]+ Calculation: 964.32, Measurement: 963]
[0342] Synthesis of Compound ET05
[0343] According to one embodiment, compound ET05 can be synthesized, for example, by the steps of the following reaction formula.
[0344]
[0345] 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (1 equivalent), (3-cyanophenyl)boronic acid (1.2 equivalent), Pd(PPh3)4 (0.05 equivalent), K2CO3 (1.5 equivalent), tetrahydrofuran (THF) (200 mL), and H2O (50 mL) were added to a round-bottom flask (RBF) and stirred under reflux at 100 °C for one day (Overnight). After the reaction was complete, EA / H2O was added, and the mixture was stirred for 30 minutes. The organic layer was separated using a separatory funnel. The mixture was then dried over MgSO4 and filtered through dichloromethane to remove silica. The resulting solid was then filtered through MeOH and dried. The dried solid was dissolved in toluene (100 mL) by heating and then solidified by adding dropwise a solution of ether and hexane in a 1:1 ratio (100 mL). The solid was then redissolved in dichloromethane (MC) (200 mL) and hexane (400 mL) was added, followed by slow recrystallization to synthesize compound ET05 (yield 89%).
[0346] [C 34 H 20 N6[M]+: Calculation: 512.17, Measurement: 511]
[0347] Synthesis of Compound ET09
[0348] According to one embodiment, compound ET09 can be synthesized, for example, by the steps of the following reaction formula.
[0349]
[0350] In the synthesis of compound ET05, compound ET09 was synthesized using the same method as that used for compound ET05, except that (3-fluorophenyl)boronicacid was used instead of (3-cyanophenyl)boronic acid. The yield was 81%. [C] 33 H 20 FN5[M]+: Calculation: 505.17, Measurement: 504]
[0351] 2. Manufacturing and evaluation of light-emitting elements
[0352] (Manufacturing of light-emitting elements)
[0353] ITO glass substrates were cut to size 50mm × 50mm × 0.5mm and ultrasonically cleaned for 10 minutes each with isopropanol and pure water. Afterward, they were further cleaned by irradiation with ultraviolet light for 10 minutes and exposure to ozone. The ITO glass substrates were then placed in a vacuum deposition apparatus. m-MTDATA, a known material, was deposited on the ITO glass substrates under vacuum. The thickness forms a hole injection layer. Then, by using... A hole transport layer is formed by vacuum deposition of NPB to a certain thickness. This is achieved by simultaneously depositing a first substrate, a second substrate, and a dopant on top of the hole transport layer. A light-emitting layer is formed by a thickness of [amount missing]. Then, by [action missing] on top of the light-emitting layer... An electron transport layer was formed by depositing ETL1 to a certain thickness, and by using The second electrode was formed by vacuum deposition of Mg to a certain thickness. The materials used to manufacture the light-emitting element are shown below. Furthermore, light-emitting elements of the embodiments and comparative examples were manufactured using different first host materials.
[0354]
[0355] (Characteristic evaluation of light-emitting elements)
[0356] The lifetime (T95) of the manufactured light-emitting elements was evaluated. The evaluated lifetime characteristics were used as a measure of luminance from 1000 cd / m². 2 The component lifetime (T95) is expressed as the time it takes for the baseline to decrease to 95% of its original level. At 10 mA / cm² 2 The component lifetime (T95) was measured by continuous driving at a current density, and the unit is hour.
[0357] Table 1 shows the material combinations in the light-emitting layers of the embodiments and comparative examples, and the device lifetime characteristics based thereon. Furthermore, in Comparative Examples 1-1, 2-1, and 3-1, the comparative compound ET-C1 described below was used as the first host material; in Comparative Examples 1-2, 2-2, and 3-2, the comparative compound ET-C2 described below was used as the first host material. The remaining second host and dopant configurations were the same as in the embodiments.
[0358] <Comparative Compounds>
[0359]
[0360] Table 1
[0361]
[0362] Referring to the results in Table 1, it can be seen that, compared to the comparative examples, the device lifetime of the embodiments in which the light-emitting layer according to one embodiment includes a first body of a triazine derivative substituted with at least one electron-accepting substituent is improved. Furthermore, it can be seen that the embodiments in which the light-emitting layer includes a combination of a first body, a second body, and an organometallic complex exhibit superior device lifetime characteristics compared to the comparative examples.
[0363] This improved lifetime is believed to be due to the fact that, in the two co-deposited host materials, the first host, acting as the electron transport host, includes electron-accepting substituents substituted into the triazine framework compared to the first host materials of the comparative examples (ET-C1, ET-C2), thereby increasing the bond dissociation energy. Specifically, according to one embodiment, the first host material must include electron-accepting substituents to enhance the binding force between the triazine core and the substituents, thereby increasing the nonpolar covalent bonding characteristics of the bond, which can raise the bond dissociation energy to 3.0 eV to 3.3 eV. This is believed to improve the material stability of the first host, thereby increasing the lifetime of the light-emitting element in embodiments including this material.
[0364] According to one embodiment, a light-emitting element can exhibit improved lifetime characteristics by including a light-emitting layer having a combination of the proposed first body, a second body, and a dopant.
[0365] Although the above description has been made with reference to preferred embodiments of the present invention, it will be understood by those skilled in the art or those with ordinary knowledge of the art that various modifications and alterations can be made to the present invention without departing from the spirit and technical scope of the invention as set forth in the claims.
[0366] Therefore, the scope of the present invention should not be limited to the contents described in the detailed description of the specification, but should be determined by the claims.
Claims
1. A light-emitting element, comprising: First electrode; The second electrode is disposed on the first electrode; as well as The light-emitting layer, disposed between the first electrode and the second electrode, comprises a first substrate represented by the following chemical formula 1, a second substrate different from the first substrate, and a dopant comprising an organometallic complex: [Chemical Formula 1] , In the chemical formula 1, Ar1 to Ar3 are each independently an aryl group with 6 to 30 cyclic carbon atoms (either substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (either substituted or unsubstituted). At least one of Ar1 to Ar3 is an aryl group with 6 to 30 cyclic carbon atoms, including a halogen atom or a cyano group as a substituent, or a six-membered heterocyclic group including a nitrogen atom as a cyclic atom. The dopant is represented by the following chemical formula 3: [Chemical Formula 3] , In the chemical formula 3, Q1 to Q4 are each independently C or N. The C1 to C4 rings are each independently a hydrocarbon ring with 5 to 30 cyclic carbon atoms, either substituted or unsubstituted, or a heterocycle with 2 to 30 cyclic carbon atoms, either substituted or unsubstituted. Y is either O or S. d1 to d4 are each an independent integer greater than 0 and less than 4. R 31 To R 34 Each group is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 1 to 30 substituted or unsubstituted cyclic carbon atoms, and may optionally be combined with adjacent groups to form a ring.
2. The light-emitting element as described in claim 1, wherein, At least one of Ar1 to Ar3 is represented by any one of the following EW-1 to EW-5: 。 3. The light-emitting element as described in claim 1, wherein, The second entity is represented by the following chemical formula 2: [Chemical Formula 2] , In the chemical formula 2, X is NR a O or CR b R c , R1 to R8, R a R b and R c Each of the following can be independently composed of a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, an alkyl group with 1 to 20 carbon atoms (substituted or unsubstituted), an aryl group with 6 to 60 cyclic carbon atoms (substituted or unsubstituted), or a heterocyclic group with 2 to 60 cyclic carbon atoms (substituted or unsubstituted). R a R b and R c At least one of them is represented by the following chemical formula A: [Chemical Formula A] , In the chemical formula A, m is an integer greater than 0 and less than 2. Ar4 is a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 cyclic carbon atoms.
4. The light-emitting element as described in claim 1, wherein, Chemical formula 3 is represented by the following chemical formula 3-1: [Chemical Formula 3-1] , In the chemical formula 3-1, Q 11 Q 31 Q 32 And Q 33 N and NR are independent of each other. 11 CR 12 CR 12 R 13 BR 14 Or BR 14 R 15 , R 11 To R 15 Each group is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 1 to 30 substituted or unsubstituted cyclic carbon atoms, and may optionally be combined with adjacent groups to form a ring. Y, C4 ring, R 31 R 32 R 34 d1, d2, and d4 are defined in the same way as in the chemical formula 3.
5. The light-emitting element as claimed in claim 1, wherein, The weight ratio of the first body to the second body is 3:7 to 7:
3.
6. The light-emitting element as claimed in claim 1, wherein, The first body includes at least one of the compounds represented in compound group 1 below: [Compound Group 1] 。 7. The light-emitting element as claimed in claim 1, wherein, The second body includes at least one of the compounds represented in compound group 2 below: [Compound Group 2] 。 8. The light-emitting element as claimed in claim 1, wherein, The dopant includes at least one of the compounds represented in compound group 3 below: [Compound Group 3] 。 9. The light-emitting element as claimed in claim 1, wherein, The light-emitting layer emits blue phosphorescence.
10. The light-emitting element as claimed in claim 1, wherein, Also includes: A capping layer, disposed on the second electrode, has a refractive index of 1.6 or higher.
11. A light-emitting element, comprising: First electrode; The second electrode is disposed on the first electrode; as well as The light-emitting layer, disposed between the first electrode and the second electrode, comprises a first substrate and a second substrate that are distinct from each other, and a dopant comprising an organometallic complex. The first body comprises a triazine core and at least one electron-accepting substituent substituted into the triazine core. The electron-accepting substituent is an aryl group substituted with a cyano or halogen atom, or a six-membered heterocyclic group including a nitrogen atom as a cyclic atom. The dopant is represented by the following chemical formula 3: [Chemical Formula 3] , In the chemical formula 3, Q1 to Q4 are each independently C or N. The C1 to C4 rings are each independently a hydrocarbon ring with 5 to 30 cyclic carbon atoms, either substituted or unsubstituted, or a heterocycle with 2 to 30 cyclic carbon atoms, either substituted or unsubstituted. Y is either O or S. d1 to d4 are each an independent integer greater than 0 and less than 4. R 31 To R 34 Each group is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 1 to 30 substituted or unsubstituted cyclic carbon atoms, and may optionally be combined with adjacent groups to form a ring.
12. The light-emitting element as claimed in claim 11, wherein, The electron-accepting substituent is represented by any one of the following EW-1 to EW-5: 。 13. The light-emitting element as claimed in claim 11, wherein, The first entity is represented by the following chemical formula 1: [Chemical Formula 1] , In the chemical formula 1, Ar1 to Ar3 are each independently an aryl group with 6 to 30 cyclic carbon atoms (either substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (either substituted or unsubstituted). At least one of Ar1 to Ar3 is an aryl group with 6 to 30 cyclic carbon atoms, including a halogen atom or a cyano group as a substituent, or a six-membered heterocyclic group including a nitrogen atom as a cyclic atom.
14. The light-emitting element as claimed in claim 11, wherein, The second entity is represented by the following chemical formula 2: [Chemical Formula 2] , In the chemical formula 2, X is NR a O or CR b R c , R1 to R8, R a R b and R c Each of the following can be independently composed of a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, an alkyl group with 1 to 20 carbon atoms (substituted or unsubstituted), an aryl group with 6 to 60 cyclic carbon atoms (substituted or unsubstituted), or a heterocyclic group with 2 to 60 cyclic carbon atoms (substituted or unsubstituted). R a R b and R c At least one of them is represented by the following chemical formula A: [Chemical Formula A] , In the chemical formula A, m is an integer greater than 0 and less than 2. Ar4 is a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 cyclic carbon atoms.
15. The light-emitting element as claimed in claim 11, wherein, The first body includes at least one of the compounds represented in compound group 1 below: [Compound Group 1] 。 16. The light-emitting element as claimed in claim 11, wherein, The second body includes at least one of the compounds represented in compound group 2 below: [Compound Group 2] 。 17. The light-emitting element as claimed in claim 11, wherein, The dopant includes at least one of the compounds represented in compound group 3 below: [Compound Group 3] 。 18. The light-emitting element as claimed in claim 11, wherein, The light-emitting layer emits blue phosphorescence.
Citation Information
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