Quantum dot-containing complex, ink composition comprising same, llight emitting device comprising same and electronic apparatus comprising same
Patent Information
- Application Number
- KR1020210181030
- Authority / Receiving Office
- KR · KR
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2021-12-16
- Publication Date
- 2026-09-15
- Estimated Expiration
- 2041-12-16
Smart Images

Figure 112021146221182-PAT00063_ABST
Abstract
Description
Technology Field
[0001] The invention relates to a quantum dot-containing composite, an ink composition containing the same, a light-emitting device containing the same, and an electronic device containing the same. Background Technology
[0002] Quantum dots are nanocrystals of semiconductor materials that exhibit a quantum confinement effect. When a quantum dot receives light from an excitation source and reaches an energy-excited state, it emits energy corresponding to its own energy band gap. At this time, since the wavelength varies depending on the particle size even for the same material, light in a desired wavelength range can be obtained by controlling the size of the quantum dot. Because it can exhibit characteristics such as excellent color purity and high luminous efficiency, it can be applied to various devices.
[0003] Quantum dots enable the realization of various colors and exhibit excellent luminescence characteristics by controlling particle size through the quantum confinement effect.
[0004] In addition, quantum dots can be utilized as materials that perform various optical functions (e.g., photoconversion functions) among optical components. Quantum dots are nanoscale semiconductor nanocrystals, and by controlling the size and composition of the nanocrystals, they can have different energy bandgaps and, accordingly, emit light of various emission wavelengths.
[0005] Optical components containing such quantum dots can have a thin film form, for example, a thin film patterned for each subpixel. Such optical components can also be utilized as color conversion components in devices containing various light sources.
[0006] Meanwhile, quantum dot ink as a photoluminescent material can be manufactured, for example, by directly dispersing quantum dots, which are photoconversion materials, into a monomer; however, in this case, dispersibility becomes an issue. The problem to be solved
[0007] The invention provides quantum dot-containing composites with improved absorption rate and light conversion efficiency. means of solving the problem
[0008] According to one aspect,
[0009] Quantum dots;
[0010] A first ligand and a second ligand coordinate to the surface of the quantum dot; comprising,
[0011] The first ligand is a hydrocarbon compound comprising a hydrophilic moiety and a lipophilic moiety, having an aspect ratio of 5 or more, and
[0012] The second ligand is a hydrocarbon compound comprising a hydrophilic moiety and a lipophilic moiety, with an aspect ratio of 4 or less, and
[0013] A quantum dot-containing complex is provided, wherein the hydrophile-lipophile balance (HLB) of the first ligand and the second ligand is independently 7 or greater:
[0014] The above aspect ratio = ligand length / ligand width
[0015] (Davies' method)
[0016] In the above formula,
[0017] m = number of hydrophilic moiety within the ligand molecule
[0018] H i = Coefficient of the i-th hydrophilic moiety
[0019] n = number of lipophilic moiety within the ligand molecule
[0020] According to other aspects of work,
[0021] An ink composition comprising the above quantum dot-containing complex, monomer, scatterer, and initiator is provided.
[0022] According to another aspect of work,
[0023] First electrode;
[0024] A second electrode facing the first electrode;
[0025] An intermediate layer interposed between the first electrode and the second electrode and including a light-emitting layer; comprising
[0026] A light-emitting device is provided, wherein the light-emitting layer comprises the quantum dot-containing complex.
[0027] According to another aspect of work,
[0028] An electronic device comprising the above quantum dot-containing complex is provided. Effects of the invention
[0029] The quantum dot-containing composite according to one embodiment has excellent absorption rate and light conversion efficiency. Brief explanation of the drawing
[0030] FIG. 1 is a diagram schematically showing the structure of a light-emitting element according to one embodiment. FIG. 2 is a cross-sectional view of a light-emitting device according to one embodiment of the present invention. FIG. 3 is a cross-sectional view of a light-emitting device according to another embodiment of the present invention. Specific details for implementing the invention
[0031] [Quantum Dot-Containing Complex]
[0032] A quantum dot-containing complex according to one aspect
[0033] Quantum dots;
[0034] A first ligand and a second ligand coordinate to the surface of the quantum dot; comprising,
[0035] The first ligand is a hydrocarbon compound comprising a hydrophilic moiety and a lipophilic moiety, having an aspect ratio of 5 or more, and
[0036] The second ligand is a hydrocarbon compound comprising a hydrophilic moiety and a lipophilic moiety, with an aspect ratio of 4 or less, and
[0037] The hydrophile-lipophile balance (HLB) of the first ligand and the second ligand may be 7 or more independently of each other.
[0038] The above aspect ratio = ligand length / ligand width
[0039] (Davies' method)
[0040] In the above formula,
[0041] m = number of hydrophilic moiety within the ligand molecule
[0042] H i = Coefficient of the i-th hydrophilic moiety
[0043] n = number of lipophilic moiety within the ligand molecule
[0045] The shape of the first ligand is rod-like compared to the shape of the second ligand, and numerically, the aspect ratio may be 5 or more. For example, the aspect ratio of the first ligand may be 5 to 20.
[0046] The shape of the second ligand is more spherical than the shape of the first ligand, and numerically, the aspect ratio may be 4 or less. For example, the aspect ratio of the second ligand may be 1 to 4.
[0047] The first and second ligands are hydrocarbon compounds composed of carbon and hydrogen, but may further include hydrophilic and lipophilic moiety containing elements other than carbon and hydrogen. Accordingly, the hydrocarbon compounds of the first and second ligands may further include, for example, oxygen, nitrogen, sulfur, etc., in addition to carbon and hydrogen.
[0048] The first and second ligands above coordinate the surface of the quantum dot, and the quantum dot-containing complex according to one embodiment of the present invention, which is coordinated with ligands having the aspect ratio as described above, has improved dispersibility.
[0049] Davis defined the hydrophilic-lipophilic-ratio value as < 7 + sum of hydrophilic moiety coefficients (H coefficients) - sum of lipophilic moiety coefficients (H coefficients).
[0050] According to one embodiment, the hydrophilic moiety is -SO4 - Na + , -COO - K + , -COO - Na + It may include tertiary amines, -COOH, -OH, -O-, =O, and any combination thereof.
[0051] Hydrophilic moiety -SO4 - Na + The coefficient of is 38.7, and the hydrophilic moiety -COO - K + The coefficient of is 21.1, and the hydrophilic moiety -COO - Na + The coefficient of is 19.1, the coefficient of the hydrophilic moiety tertiary amine is 9.4, the coefficient of the hydrophilic moiety -COOH is 2.1, the coefficient of the hydrophilic moiety -OH is 1.9, and the coefficients of the hydrophilic moiety -O- and =O are 1.3.
[0052] According to one embodiment, the lipophilic moiety may include -CH-, -CH2-, CH3-, =CH-, =CH2, and any combination thereof.
[0053] The coefficients of the lipophilic moiety -CH-, -CH2-, CH3-, =CH-, and =CH2 are 0.475.
[0054] When the hydrophilic-lipophilic-ratio values of the first ligand and the second ligand are independently 7 or higher, for example, when the quantum dot-containing complex is dispersed in a hydrophilic monomer, the dispersibility is good. For example, the hydrophilic-lipophilic-ratio values of the first ligand and the second ligand may be independently 7 to 18.
[0055] According to one embodiment, the first ligand and the second ligand may both include a COOH moiety at their terminals. For example, the first ligand and the second ligand may be coordinated to the quantum dot through the terminal COOH.
[0056] According to one embodiment, the first ligand may comprise two or more ethylene glycol moieties (OCH2CH2O). For example, when the first ligand comprises two or more ethylene glycol moieties (OCH2CH2O), the aspect ratio of the first ligand may be 5 or more and the hydrophilic-lipophilic-ratio may be 7 or more.
[0057] According to one embodiment, the first ligand may be 2,5,8,11,14-pentaoxaheptadecan-17-oic acid.
[0058] According to one embodiment, the second ligand may be mono-2-(acryloyloxy)ethyl succinate.
[0059] According to one embodiment, the ratio of the first ligand to the second ligand may be 5:4 to 1:8 (weight ratio). If the ratio of the first ligand to the second ligand deviates from the 5:4 range in which the first ligand is more abundant than the second ligand (e.g., the ratio of the first ligand to the second ligand is 6:4), the photoconversion efficiency of the quantum dot-containing complex decreases significantly. If the ratio of the second ligand to the first ligand deviates from the 1:8 range in which the second ligand is more abundant than the first ligand (e.g., the ratio of the first ligand to the second ligand is 1:8.5), the absorption rate and photoconversion efficiency decrease.
[0060] According to one embodiment, the ratio of the weight of the quantum dot and the total weight of the first ligand and the second ligand may be 10:1 to 10:4. If the total weight of the first ligand and the second ligand falls outside the 10:1 range toward the smaller side (e.g., the ratio of the weight of the quantum dot and the total weight of the first ligand and the second ligand is 10:0.5), the quantum dot may not be sufficiently coordinated by the ligand, resulting in a decrease in absorption rate and photoconversion efficiency. If the total weight of the first ligand and the second ligand falls outside the 10:4 range toward the larger side (e.g., the ratio of the weight of the quantum dot and the total weight of the first ligand and the second ligand is 10:5), the remaining ligand that fails to coordinate the quantum dot may have an adverse effect, resulting in a decrease in absorption rate and photoconversion efficiency.
[0061] Quantum dots are spherical semiconductor nanomaterials having a size of several to several hundred nanometers, and may include a core composed of a material with a small band gap and a shell arranged to surround the core.
[0062] According to one embodiment, the quantum dot may have a core-shell structure including a core including a first semiconductor crystal and a shell including a second semiconductor crystal, or may be a perovskite compound.
[0063] For example, the first semiconductor and the second semiconductor may independently include a group 12-16 compound, a group 13-15 compound, a group 14-16 compound, a group 14 compound, a group 11-13-16 compound, a group 11-12-13-16 compound, and any combination thereof.
[0064] For example, the first semiconductor and the second semiconductor are independently of each other, CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgS, MgSe; CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnS, MgZnSe; CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe;
[0065] GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb; GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP; GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb; InZnP;
[0066] SnS, SnSe, SnTe, PbS, PbSe, PbTe; SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe; SnPbSSe, SnPbSeTe, SnPbSTe;
[0067] Si, Ge, SiC, SiGe;
[0068] AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2; and any combination thereof may be included.
[0069] For example, the first semiconductor comprises GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and any combination thereof, and the second semiconductor comprises CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgS, MgSe, It may include CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnS, MgZnSe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and any combination thereof.
[0070] Meanwhile, the above perovskite compound is a material having a three-dimensional crystal structure related to the crystal structure of CaTiO3.
[0071] For example, the above perovskite can be represented by the following chemical formula 4:
[0072] <Chemical Formula 4>
[0073] [A][B m ][X]3
[0074] Among the above chemical formula 4
[0075] A is at least one monovalent organic-cation, a monovalent inorganic-cation, or any combination thereof, and
[0076] B is at least one type of divalent inorganic cation, and
[0077] m is a real number satisfying 0 < m ≤ 1, and
[0078] X is at least one type of monovalent anion.
[0079] The average particle size (D50) of the above quantum dots may be 2 to 10 nm.
[0080] The average particle size (D50) of the quantum dot-containing composite may be 40 nm to 1000 nm, for example, 50 nm to 1000 nm or 100 nm to 500 nm, or, as another example, 100 nm to 200 nm. When the average particle size of the quantum dot-containing composite satisfies the range described above, the quantum dot-containing composite can have excellent dispersion while containing a relatively large amount of quantum dots. The average particle size can be measured, for example, by laser diffraction. Since laser diffraction is well known, a description is omitted.
[0081] [Explanation of Fig. 1]
[0082] FIG. 1 schematically illustrates a cross-sectional view of a light-emitting element (10) according to one embodiment of the present invention. The light-emitting element (10) includes a first electrode (110), an intermediate layer (130), and a second electrode (150).
[0083] Hereinafter, the structure and manufacturing method of a light-emitting element (10) according to one embodiment of the present invention are described as follows with reference to FIG. 1.
[0084] [First electrode (110)]
[0085] A substrate may be additionally disposed on the lower part of the first electrode (110) of FIG. 1 or on the upper part of the second electrode (150). As the substrate, a glass substrate or a plastic substrate may be used. Alternatively, the substrate may be a flexible substrate and may include a plastic with excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphtalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0086] The first electrode (110) can be formed, for example, by providing a material for the first electrode on the substrate using a deposition method or a sputtering method. When the first electrode (110) is an anode, a material with a high work function that facilitates hole injection can be used as the material for the first electrode.
[0087] The first electrode (110) may be a reflective electrode, a semi-transparent electrode, or a transparent electrode. To form the first electrode (110) which is a transparent electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used as the material for the first electrode. Alternatively, to form the first electrode (110) which is a semi-transparent electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof may be used as the material for the first electrode.
[0088] The first electrode (110) may have a single-layer structure consisting of a single layer or a multi-layer structure including multiple layers. For example, the first electrode (110) may have a three-layer structure of ITO / Ag / ITO.
[0089] [Middle layer (130)]
[0090] An intermediate layer (130) is disposed on the upper portion of the first electrode (110). The intermediate layer (130) includes a light-emitting layer.
[0091] The above intermediate layer (130) may further include a hole transport region disposed between the first electrode (110) and the light-emitting layer and an electron transport region disposed between the light-emitting layer and the second electrode (150).
[0092] The above intermediate layer (130) may further include, in addition to various organic materials, metal-containing compounds such as organometallic compounds, inorganic materials such as quantum dots, etc.
[0093] Meanwhile, the intermediate layer (130) may include i) two or more emitting units sequentially stacked between the first electrode (110) and the second electrode (150), and ii) a charge generation layer disposed between the two emitting units. When the intermediate layer (130) includes the emitting units and charge generation layer as described above, the emitting element (10) may be a tandem emitting element.
[0094] [Middle layer (130) with a fixed transport area]
[0095] The hole transport region may have i) a monolayer structure consisting of a single layer made of a single material, ii) a monolayer structure consisting of a single layer containing multiple different materials, or iii) a multilayer structure including multiple layers containing multiple different materials.
[0096] The hole transport region above may include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, or any combination thereof.
[0097] For example, the hole transport region may have a multilayer structure of a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / light-emitting auxiliary layer, a hole injection layer / light-emitting auxiliary layer, a hole transport layer / light-emitting auxiliary layer, or a hole injection layer / hole transport layer / electron blocking layer stacked sequentially from the first electrode (110).
[0098] The hole transport region may include a compound represented by the following chemical formula 201, a compound represented by the following chemical formula 202, or any combination thereof:
[0099] <Chemical Formula 201>
[0100]
[0101] <Chemical Formula 202>
[0102]
[0103] Among the above chemical formulas 201 and 202,
[0104] L 201 to L 204 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and
[0105] L205 은, *-O-*', *-S-*', *-N(Q 201 )-*', at least one R 10a C1-C substituted or unsubstituted 20 alkylene group, at least one R 10a C2-C substituted or unsubstituted 20 alkenylene group, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and
[0106] xa1 to xa4 are independently one of integers 0 to 5, and
[0107] xa5 is one of integers from 1 to 10, and
[0108] R 201 to R 204 and Q 201 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and
[0109] R 201 and R 202 is optionally a single bond, at least one R 10a A C1-C5 alkylene group substituted or unsubstituted with or at least one R 10a Connected to each other through C2-C5 alkenylene groups substituted or unsubstituted, at least one R 10a C8-C substituted or unsubstituted 60 It can form polycyclic groups (e.g., carbazole groups, etc.) (e.g., refer to the following compound HT16, etc.),
[0110] R 203 and R 204is optionally a single bond, at least one R 10a A C1-C5 alkylene group substituted or unsubstituted with or at least one R 10a Connected to each other through C2-C5 alkenylene groups substituted or unsubstituted, at least one R 10a C8-C substituted or unsubstituted 60 It can form polycyclic groups, and
[0111] na1 can be one of integers from 1 to 4.
[0112] For example, each of the above chemical formulas 201 and 202 may include at least one of the group represented by the following chemical formulas CY201 to CY217:
[0113]
[0114] Among the above chemical formulas CY201 to CY217, R 10b and R 10c Descriptions of each of R in this specification 10a Refer to the explanation for, and ring CY 201 Inner ring CY 204 are independently of each other, C3-C 20 Carbocyclic group or C1-C 20 It is a heterocyclic group, and at least one hydrogen of the chemical formulas CY201 to CY217 is R as described in this specification. 10a It can be substituted or unsubstituted.
[0115] According to one embodiment, among the chemical formulas CY201 to CY217, the ring CY 201 Inner ring CY 204 It can be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group independently of each other.
[0116] According to another embodiment, each of the above formulas 201 and 202 may include at least one of the group represented by the formulas CY201 to CY203.
[0117] According to another embodiment, the formula 201 may each include at least one of the group represented by formulas CY201 to CY203 and at least one of the group represented by formulas CY204 to CY217.
[0118] According to another embodiment, xa1 in the above chemical formula 201 is 1, and R 201 is a group represented by one of the above chemical formulas CY201 to CY203, xa2 is 0, and R 202 may be a group represented by one of the above chemical formulas CY204 to CY207.
[0119] According to another embodiment, each of the above formulas 201 and 202 may not include the group represented by the above formulas CY201 to CY203.
[0120] According to another embodiment, each of the above formulas 201 and 202 may not include the group represented by formulas CY201 to CY203 and may include at least one of the group represented by formulas CY204 to CY217.
[0121] As another example, each of the above chemical formulas 201 and 202 may not include the group represented by the above chemical formulas CY201 to CY217.
[0122] For example, the hole transport region is one of the following compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PEDOT / PSS (Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), Pani / CSA (Polyaniline / Camphor sulfonic acid It may include (polyaniline / campersulfonic acid)), PANI / PSS (polyaniline / poly(4-styrenesulfonate)), or any combination thereof:
[0123]
[0124]
[0125]
[0126]
[0127]
[0128]
[0129]
[0130]
[0131]
[0132]
[0133] The thickness of the hole transport region may be about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. If the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the ranges described above, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.
[0134] The above-mentioned light-emitting auxiliary layer is a layer that increases light emission efficiency by compensating for the optical resonance distance according to the wavelength of light emitted from the light-emitting layer, and the above-mentioned electron blocking layer is a layer that prevents electron leakage from the hole transport region from the light-emitting layer. A material that can be included in the aforementioned hole transport region may be included in the light-emitting auxiliary layer and the electron blocking layer.
[0135] [p-dopant]
[0136] In addition to the material described above, the hole transport region may include a charge-generating material to improve conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region (e.g., in the form of a single layer consisting of the charge-generating material).
[0137] The above charge-generating material may be, for example, a p-dopant.
[0138] For example, the LUMO energy level of the above p-dopant may be -3.5 eV or less.
[0139] According to one embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, an element EL1 and an element EL2-containing compound, or any combination thereof.
[0140] Examples of the above quinone derivatives may include TCNQ, F4-TCNQ, etc.
[0141] Examples of the above cyano group-containing compounds may include HAT-CN, compounds represented by the following chemical formula 221, etc.
[0142]
[0143] <Chemical Formula 221>
[0144]
[0145] Of the above chemical formula 221,
[0146] R 221 to R 223 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and
[0147] The above R 221 to R 223 At least one of which is independently substituted with a cyano group; -F; -Cl; -Br; -I; a cyano group, -F, -Cl, -Br, -I, or any combination thereof C1-C 20 C3-C substituted with an alkyl group; or any combination thereof. 60 Carbocyclic group or C1-C 60 It can be a heterocyclic group.
[0148] Among the above-mentioned compounds containing elements EL1 and EL2, element EL1 may be a metal, a metalloid, or a combination thereof, and element EL2 may be a nonmetal, a metalloid, or a combination thereof.
[0149] Examples of the above metals are alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); Transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.); etc. may be included.
[0150] Examples of the above metalloids may include silicon (Si), antimony (Sb), tellurium (Te), etc.
[0151] Examples of the above nonmetals may include oxygen (O), halogens (e.g., F, Cl, Br, I, etc.).
[0152] For example, the above-mentioned element EL1 and element EL2-containing compounds may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metal tellurides, or any combination thereof.
[0153] Examples of the above metal oxides may include tungsten oxide (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxide (e.g., VO, V2O3, VO2, V2O5, etc.), molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxide (e.g., ReO3, etc.).
[0154] Examples of the above metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, etc.
[0155] Examples of the above alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, etc.
[0156] Examples of the above alkaline earth metal halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, etc.
[0157] Examples of the above transition metal halides include titanium halides (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3, VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halides (e.g., TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), and tungsten. Halides (e.g., WF3, WCl3, WBr3, WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), iron halides (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halides (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halides (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.),It may include silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.), etc.
[0158] Examples of the above-mentioned transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (e.g., InI3, etc.), tin halides (e.g., SnI2, etc.), etc.
[0159] Examples of the above lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3SmCl3, YbBr, YbBr2, YbBr3SmBr3, YbI, YbI2, YbI3, SmI3, etc.
[0160] Examples of the metalloid halides mentioned above may include antimony halides (e.g., SbCl5, etc.).
[0161] Examples of the above metal tellurides include alkali metal tellurides (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-transition metal tellurides (e.g., ZnTe, etc.), and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, It may include TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.
[0162] [Emitting layer in the middle layer (130)]
[0163] When the light-emitting element (10) is a full-color light-emitting element, the light-emitting layer may be patterned into a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer for each individual subpixel. Alternatively, the light-emitting layer may have a structure in which two or more layers among the red light-emitting layer, the green light-emitting layer, and the blue light-emitting layer are stacked in contact or spaced apart, or may have a structure in which two or more materials among the red light-emitting material, the green light-emitting material, and the blue light-emitting material are mixed without layer separation, thereby emitting white light.
[0164] The light-emitting layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0165] The content of the dopant in the above-mentioned light-emitting layer may be about 0.01 to about 15 parts by weight per 100 parts by weight of the host.
[0166] Meanwhile, the light-emitting layer may include a delayed fluorescent material. The delayed fluorescent material may act as a host or dopant in the light-emitting layer.
[0167] Alternatively, the light-emitting layer may include the above-described quantum dot-containing composite (hereinafter also referred to as "quantum dot").
[0168] Quantum dots are naturally dispersed in a dispersion medium, such as an organic solvent or a polymer resin, in a coordinated form. Any transparent medium that does not alter or reflect light and does not cause light absorption can be used as the dispersion medium without affecting the wavelength conversion performance of the quantum dots. For example, the organic solvent may include at least one of toluene, chloroform, and ethanol, and the polymer resin may include at least one selected from epoxy, silicone, polystyrene, and acrylate.
[0169] Unlike bulk materials, quantum dots possess discontinuous band gap energies due to the quantum confinement effect. Furthermore, quantum dots have the characteristic that the spacing between energy bands varies depending on their size; thus, even when using the same quantum dots, different sizes can emit light of different wavelengths. As the size of the quantum dot decreases, the band gap energy increases, and consequently, the wavelength of the emitted light becomes shorter. By utilizing these characteristics, light in a desired wavelength range can be obtained by controlling the size of the quantum dots through appropriate changes in the nanocrystal growth conditions. Therefore, by introducing such quantum dots into light-emitting devices, it is possible to realize light-emitting devices with high light efficiency and color purity.
[0170] If the above-described light-emitting layer includes a host and a dopant and does not include quantum dots, the color-converting layer described below may include a quantum dot-containing complex.
[0171] The thickness of the light-emitting layer may be about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer satisfies the range described above, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.
[0172] [Host]
[0173] The above host may include a compound represented by the following chemical formula 301:
[0174] <Chemical Formula 301>
[0175] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21
[0176] Among the above chemical formula 301,
[0177] Ar 301 and L 301 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and
[0178] xb11 is 1, 2, or 3, and
[0179] xb1 is one of integers from 0 to 5, and
[0180] R 301 Silver, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, at least one R 10a C1-C substituted or unsubstituted 60 alkyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkenyl group, at least one R 10a C2-C substituted or unsubstituted 60 alkynyl group, at least one R 10aC1-C substituted or unsubstituted 60 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group, at least one R 10a C1-C substituted or unsubstituted 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 ), -N(Q 301 )(Q 302 ), -B(Q 301 )(Q 302 ), -C(=O)(Q 301 ), -S(=O)2(Q 301 ), or -P(=O)(Q 301 )(Q 302 ) and,
[0181] xb21 is one of integers from 1 to 5, and
[0182] Q 301 to Q 303 For a description of each, refer to the description of Q1 in this specification.
[0183] For example, if xb11 in the above chemical formula 301 is 2 or more, then 2 or more Ar 301 They can be connected to each other through a single bond.
[0184] As another example, the host may include a compound represented by the following chemical formula 301-1, a compound represented by the following chemical formula 301-2, or any combination thereof:
[0185] <Chemical Formula 301-1>
[0186]
[0188] <Chemical Formula 301-2>
[0189]
[0190] Among the above chemical formulas 301-1 to 301-2,
[0191] Ring A 301 inner ring A304 are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and
[0192] X 301 is O, S, N-[(L 304 ) xb4 -R 304 ], C(R 304 )(R 305 ), or Si(R 304 )(R 305 ) and,
[0193] xb22 and xb23 are independently 0, 1, or 2, and
[0194] L 301 , xb1 and R 301 For descriptions thereof, refer to those described in this specification, and
[0195] L 302 to L 304 The descriptions regarding are independent of each other, the above L 301 Refer to the explanation for,
[0196] The descriptions for xb2 to xb4 are independent of each other, and refer to the description for xb1 above, and
[0197] R 302 to R 305 and R 311 to R 314 The explanation for each of the above R 301 Refer to the explanation for.
[0198] As another example, the host may include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. For example, the host may include a Be complex (e.g., compound H55 below), an Mg complex, a Zn complex, or any combination thereof.
[0199] As another example, the host may comprise one of the following compounds H1 to H124, ADN (9,10-Di(2-naphthyl)anthracene), MADN (2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), TBADN (9,10-di-(2-naphthyl)-2-t-butyl-anthracene), CBP (4,4'-bis(N-carbazolyl)-1,1'-biphenyl), mCP (1,3-di-9-carbazolylbenzene), TCP (1,3,5-tri(carbazol-9-yl)benzene), or any combination thereof:
[0200]
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211]
[0212]
[0213]
[0214] [Phosphorescent Dopant]
[0215] The above phosphorescent dopant may include at least one transition metal as a central metal.
[0216] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentate ligand, a hexate ligand, or any combination thereof.
[0217] The above phosphorescent dopant may be electrically neutral.
[0218] For example, the phosphorescent dopant may include an organometallic compound represented by the following chemical formula 401:
[0219] <Chemical Formula 401>
[0220] M(L 401 ) xc1 (L 402 ) xc2
[0221] <Chemical Formula 402>
[0222]
[0223] Among the above chemical formulas 401 and 402,
[0224] M is a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)), and
[0225] L 401 is a ligand represented by the above chemical formula 402, xc1 is 1, 2, or 3, and if xc1 is 2 or more, 2 or more L 401 They are identical or different from each other,
[0226] L 402 is an organic ligand, xc2 is 0, 1, 2, 3, or 4, and if xc2 is 2 or more, 2 or more L 402 are identical or different from each other,
[0227] X 401 and X 402 are independently nitrogen or carbon, and
[0228] Ring A401 and ring A 402 are independently of each other, C3-C 60 Carbocyclic group or C1-C 60 It is a heterocyclic group, and
[0229] T 401 is a single bond, -O-, -S-, -C(=O)-, -N(Q 411 )-, -C(Q 411 )(Q 412 )-, -C(Q 411 )=C(Q 412 )-, -C(Q 411 )= or =C= and,
[0230] X 403 and X 404 are independently of each other, chemical bonds (e.g., covalent bonds or coordinate bonds), O, S, N(Q 413 ), B(Q 413 ), P(Q 413 ), C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ) and,
[0231] Above Q 411 to Q 414 For descriptions regarding each, refer to the description of Q1 in this specification, and
[0232] R 401 and R 402 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, at least one R 10a C1-C substituted or unsubstituted 20 alkyl group, at least one R 10a C1-C substituted or unsubstituted 20 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group, at least one R 10a C1-C substituted or unsubstituted 60 Heterocyclic group, -Si(Q 401 )(Q402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ) or -P(=O)(Q 401 )(Q 402 ) and,
[0233] Above Q 401 to Q 403 For descriptions regarding each, refer to the description of Q1 in this specification, and
[0234] xc11 and xc12 are independently one of integers from 0 to 10, and
[0235] In the above chemical formula 402, * and *' are each binding sites with M in the above chemical formula 401.
[0236] For example, i) X in the above chemical formula 402 401 is nitrogen, and X 402 is carbon, or ii) X 401 and X 402 All of it can be nitrogen.
[0237] As another example, if xc1 in the above chemical formula 402 is 2 or more, then 2 or more L 401 Two of the rings A 401 is optionally, the connector T 402 Connected to each other through, or 2 rings A 402 is optionally, the connector T 403 They can be connected to each other through (see compounds PD1 to PD4 and PD7 below). The above T 402 and T 403 The descriptions for each of T in this specification 401 Refer to the explanation for.
[0238] L in the above chemical formula 401 402can be any organic ligand. For example, the above L 402 It may include a halogen group, a diketone group (e.g., acetylacetonate group), a carboxylic acid group (e.g., picolinate group), -C (=O), an isonitrile group, a -CN group, a phosphorus group (e.g., phosphine group, phosphite group, etc.), or any combination thereof.
[0239] The above phosphorescent dopant may include, for example, one of the following compounds PD1 to PD39, or any combination thereof:
[0240]
[0241]
[0242]
[0243]
[0244]
[0245]
[0246] [Fluorescent Dopant]
[0247] The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
[0248] For example, the fluorescent dopant may include a compound represented by the following chemical formula 501:
[0249] <Chemical Formula 501>
[0250]
[0251] Among the above chemical formula 501,
[0252] Ar 501 , L 501 to L 503 , R 501 and R 502 are independent of each other, at least one R 10aC3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and
[0253] xd1 to xd3 are independently 0, 1, 2, or 3, and
[0254] xd4 can be 1, 2, 3, 4, 5, or 6.
[0255] For example, Ar in the above chemical formula 501 501 It may include a condensed ring group in which three or more monocyclic groups are condensed together (e.g., anthracene group, chrysene group, pyrene group, etc.).
[0256] As another example, xd4 in the above chemical formula 501 can be 2.
[0257] For example, the fluorescent dopant may include one of the following compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:
[0258]
[0259]
[0260]
[0261]
[0262]
[0263]
[0264]
[0265] [Delayed Fluorescence]
[0266] The above-mentioned light-emitting layer may include a delayed fluorescent material.
[0267] In this specification, the delayed fluorescent material may be selected from any compound capable of emitting delayed fluorescence by a delayed fluorescence emission mechanism.
[0268] The delay fluorescent material included in the above-mentioned light-emitting layer can act as a host or a dopant depending on the type of other material included in the above-mentioned light-emitting layer.
[0269] According to one embodiment, the difference between the triplet energy level (eV) of the delay fluorescent material and the singlet energy level (eV) of the delay fluorescent material may be 0 eV or more and 0.5 eV or less. By satisfying the range described above, the reverse energy transfer (up-conversion) from the triplet state to the singlet state of the delay fluorescent material is effectively achieved, thereby improving the luminous efficiency of the light-emitting device (10).
[0270] For example, the above-mentioned delay fluorescent material comprises: i) at least one electron donor (e.g., a π-electron-excess C3-C such as a carbazole group). 60 cyclic group (π electron-rich C3-C 60 cyclic group) etc.) and at least one electron acceptor (e.g., sulfoxide group, cyano group, π electron-deficient nitrogenous C1-C 60 cyclic group (π electron-deficient nitrogen-containing C1-C 60 ii) a substance containing a cyclic group, etc., and ii) a C8-C containing two or more cyclic groups condensed while sharing boron (B). 60 It may include materials including polycyclic groups.
[0271] Examples of the above-mentioned delayed fluorescent materials may include at least one of the following compounds DF1 to DF9:
[0272]
[0273]
[0274] [Electronic transport region in the middle layer (130)]
[0275] The electron transport region may have i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a plurality of different materials, or iii) a multilayer structure including a plurality of layers containing a plurality of different materials.
[0276] The above electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0277] For example, the electron transport region may have a structure such as an electron transport layer / electron injection layer or a hole blocking layer / electron transport layer / electron injection layer stacked sequentially from the light-emitting layer.
[0278] The electron transport region (e.g., a hole blocking layer or electron transport layer among the electron transport regions) comprises at least one π electron-deficient nitrogen-containing C1-C 60 cyclic group (π electron-deficient nitrogen-containing C1-C 60 It may include metal-free compounds containing a cyclic group.
[0279] For example, the electron transport region may include a compound represented by the following chemical formula 601.
[0280] <Chemical Formula 601>
[0281] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21
[0282] Among the above chemical formula 601,
[0283] Ar 601 , and L 601are independent of each other, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group or at least one R 10a C1-C substituted or unsubstituted 60 It is a heterocyclic group, and
[0284] xe11 is 1, 2, or 3, and
[0285] xe1 is 0, 1, 2, 3, 4, or 5, and
[0286] R 601 is, at least one R 10a C3-C substituted or unsubstituted 60 Carbocyclic group, at least one R 10a C1-C substituted or unsubstituted 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), or -P(=O)(Q 601 )(Q 602 ) and,
[0287] Above Q 601 to Q 603 For descriptions regarding each, refer to the description of Q1 in this specification, and
[0288] xe21 is 1, 2, 3, 4, or 5, and
[0289] The above
[0290] Ar 601 , L 601 and R 601 At least one of them is independent of each other, at least one R 10a π electron-deficient nitrogenous C1-C substituted or unsubstituted 60 It could be a click group.
[0291] For example, if xe11 in the above chemical formula 601 is 2 or more, then 2 or more Ar 601They can be connected to each other through a single bond.
[0292] As another example, Ar in the above chemical formula 601 601 It may be a substituted or unsubstituted anthracene group.
[0293] As another example, the electron transport region may include a compound represented by the following chemical formula 601-1:
[0294] <Chemical Formula 601-1>
[0295]
[0296] In the above chemical formula 601-1,
[0297] X 614 is N or C(R 614 ) and, X 615 is N or C(R 615 ) and, X 616 is N or C(R 616 ) and, X 614 To X 616 At least one of them is N, and
[0298] L 611 to L 613 The explanation for each of the above L 601 Refer to the explanation for,
[0299] For descriptions of xe611 to xe613, refer to the description of xe1 above, and
[0300] R 611 to R 613 The explanation for each of the above R 601 Refer to the explanation for,
[0301] R 614 to R 616 They are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group, C1-C 20 Alkoxy group, at least one R 10a C3-C substituted or unsubstituted 60Carbocyclic group, or at least one R 10a C1-C substituted or unsubstituted 60 It can be a heterocyclic group.
[0302] For example, xe1 and xe611 to xe613 in the above chemical formulas 601 and 601-1 may be 0, 1, or 2 independently of each other.
[0303] The electron transport region may comprise one of the following compounds ET1 to ET45, BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-Diphenyl-1,10-phenanthroline), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
[0304]
[0305]
[0306]
[0307]
[0308]
[0309]
[0310]
[0311] The thickness of the electron transport region may be about 100 Å to about 5000 Å, for example, about 160 Å to about 4000 Å. If the electron transport region includes a hole blocking layer, an electron transport layer, or any combination thereof, the thickness of the hole blocking layer or the electron transport layer may be, independently of each other, about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. If the thickness of the hole blocking layer and / or the electron transport layer satisfies the ranges described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.
[0312] The above electron transport region (e.g., the electron transport layer among the electron transport regions) may further include a metal-containing material in addition to the material described above.
[0313] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ions of the alkali metal complex may be Li ions, Na ions, K ions, Rb ions, or Cs ions, and the metal ions of the alkaline earth metal complex may be Be ions, Mg ions, Ca ions, Sr ions, or Ba ions. The ligands coordinated to the metal ions of the alkali metal complex and the alkaline earth metal complex may independently include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0314] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compounds ET-D1 (LiQ) or ET-D2:
[0315]
[0316] The above electron transport region may include an electron injection layer that facilitates electron injection from the second electrode (150). The electron injection layer may be in direct contact with the second electrode (150).
[0317] The electron injection layer may have i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a plurality of different materials, or iii) a multilayer structure having a plurality of layers containing a plurality of different materials.
[0318] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0319] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0320] The alkali metal-containing compound, alkaline earth metal-containing compound and the rare earth metal-containing compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), tellurides, or any combination thereof of the alkali metal, alkaline earth metal, and rare earth metal, respectively.
[0321] The above alkali metal-containing compound may include alkali metal oxides such as Li2O, Cs2O, K2O, etc., alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc., or any combination thereof. The above alkaline earth metal-containing compound may include BaO, SrO, CaO, Ba x Sr 1-x O(x is 0 <x<1를 만족하는 실수임), Ba x Ca 1-x O(x is 0 <x<1를 만족하는 실수임) 등과 같은 알칼리 토금속 화합물을 포함할 수 있다. 상기 희토류 금속-함유 화합물은, YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, 또는 이의 임의의 조함을 포함할 수 있다. 또는, 상기 희토류 금속-함유 화합물은, 란타나이드 금속 텔루라이드를 포함할 수 있다. 상기 란타나이드 금속 텔루라이드의 예는, LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3등을 포함할 수 있다.
[0322] The above alkali metal complex, alkaline earth metal complex, and rare earth metal complex may comprise i) one of the ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and ii) a ligand bound to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0323] The electron injection layer described above may consist only of alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof, or may further include organic materials (e.g., compounds represented by the chemical formula 601).
[0324] According to one embodiment, the electron injection layer may be composed of i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, etc.
[0325] If the electron injection layer further comprises an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix containing the organic material.
[0326] The thickness of the electron injection layer may be about 1 Å to about 100 Å or about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.
[0327] [Second electrode (150)]
[0328] A second electrode (150) is disposed on the upper portion of the intermediate layer (130) as described above. The second electrode (150) may be a cathode, which is an electron injection electrode. In this case, a metal, alloy, electrically conductive compound, or any combination thereof having a low work function may be used as the material for the second electrode (150).
[0329] The second electrode (150) may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode (150) may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode.
[0330] The second electrode (150) may have a single-layer structure or a multi-layer structure having multiple layers.
[0331] [Capping layer]
[0332] A first capping layer may be disposed on the outer side of the first electrode (110), and / or a second capping layer may be disposed on the outer side of the second electrode (150). Specifically, the light-emitting element (10) may have a structure in which the first capping layer, the first electrode (110), the intermediate layer (130), and the second electrode (150) are stacked in order, a structure in which the first electrode (110), the intermediate layer (130), the second electrode (150), and the second capping layer are stacked in order, or a structure in which the first capping layer, the first electrode (110), the intermediate layer (130), the second electrode (150), and the second capping layer are stacked in order.
[0333] Light generated in the light-emitting layer of the intermediate layer (130) of the light-emitting element (10) can be emitted to the outside through the first electrode (110), which is a semi-transparent electrode or a transparent electrode, and the first capping layer, and light generated in the light-emitting layer of the intermediate layer (130) of the light-emitting element (10) can be emitted to the outside through the second electrode (150), which is a semi-transparent electrode or a transparent electrode, and the second capping layer.
[0334] The first capping layer and the second capping layer can serve to improve external light emission efficiency based on the principle of constructive interference. As a result, the light extraction efficiency of the light-emitting element (10) is increased, and the light emission efficiency of the light-emitting element (10) can be improved.
[0335] Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or higher (at 589 nm).
[0336] The first capping layer and the second capping layer may independently be an organic capping layer containing organic material, an inorganic capping layer containing inorganic material, or an organic-inorganic composite capping layer containing organic material and inorganic material.
[0337] At least one of the first capping layer and the second capping layer may independently comprise a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent comprising O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. According to one embodiment, at least one of the first capping layer and the second capping layer may independently comprise an amine group-containing compound.
[0338] For example, at least one of the first capping layer and the second capping layer may independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0339] According to another embodiment, at least one of the first capping layer and the second capping layer may independently comprise one of the compounds HT28 to HT33, one of the following compounds CP1 to CP6, β-NPB, or any of the same:
[0340]
[0341]
[0342] [Electronic device]
[0343] The light-emitting element may be included in various electronic devices. For example, an electronic device including the light-emitting element may be a light-emitting device, an authentication device, etc.
[0344] The electronic device (e.g., light-emitting device) may further include, in addition to the light-emitting element, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or color conversion layer may be disposed in at least one direction of propagation of light emitted from the light-emitting element. For example, the light emitted from the light-emitting element may be blue light or white light. Refer to the description of the light-emitting element above. According to one embodiment, the color conversion layer may include a quantum dot-containing composite according to one embodiment of the present invention.
[0345] The electronic device may include a first substrate. The first substrate may include a plurality of subpixel regions, the color filter may include a plurality of color filter regions corresponding to each of the plurality of subpixel regions, and the color conversion layer may include a plurality of color conversion regions corresponding to each of the plurality of subpixel regions.
[0346] A pixel defining film is placed between the plurality of subpixel regions above to define each subpixel region.
[0347] The above color filter may further include a plurality of color filter regions and a light-blocking pattern disposed between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light-blocking pattern disposed between the plurality of color conversion regions.
[0348] The plurality of color filter regions (or plurality of color conversion regions) comprises a first region emitting a first color light; a second region emitting a second color light; and / or a third region emitting a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the plurality of color filter regions (or plurality of color conversion regions) may include quantum dots. Specifically, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. Refer to the description of quantum dots as provided in this specification. The first region, the second region, and / or the third region may each further include scatterers.
[0349] For example, the light-emitting element may emit a first light, the first region may absorb the first light to emit a first-1 color light, the second region may absorb the first light to emit a second-1 color light, and the third region may absorb the first light to emit a third-1 color light. In this case, the first-1 color light, the second-1 color light, and the third-1 color light may have different maximum emission wavelengths. Specifically, the first light may be blue light, the first-1 color light may be red light, the second-1 color light may be green light, and the third-1 color light may be blue light.
[0350] The above electronic device may further include a thin-film transistor in addition to the light-emitting element described above. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, and either one of the source electrode and the drain electrode may be electrically connected to either one of the first electrode and the second electrode of the light-emitting element.
[0351] The above thin-film transistor may further include a gate electrode, a gate insulating film, etc.
[0352] The above active layer may include crystalline silicon, amorphous silicon, organic semiconductor, oxide semiconductor, etc.
[0353] The electronic device may further include a sealing portion for sealing a light-emitting element. The sealing portion may be disposed between the color filter and / or color conversion layer and the light-emitting element. The sealing portion allows light from the light-emitting element to be emitted to the outside while simultaneously blocking external air and moisture from penetrating the light-emitting element. The sealing portion may be a sealing substrate comprising a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer comprising one or more organic and / or inorganic layers. If the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
[0354] On the sealing portion, in addition to the color filter and / or color conversion layer, various functional layers may be additionally disposed depending on the application of the electronic device. Examples of the functional layers may include a touchscreen layer, a polarizing layer, etc. The touchscreen layer may be a pressure-sensitive touchscreen layer, a capacitive touchscreen layer, or an infrared touchscreen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual using biometric information (e.g., fingertip, pupil, etc.).
[0355] The above authentication device may further include means for collecting biometric information in addition to the light-emitting element as described above.
[0356] The above electronic device can be applied to various displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical devices (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram display devices, ultrasound diagnostic devices, endoscope display devices), fish finders, various measuring instruments, instruments (e.g., instruments for vehicles, aircraft, and ships), projectors, etc.
[0357] [Explanation of Figures 2 and 3]
[0358] FIG. 2 is a cross-sectional view of an electronic device (180) according to one embodiment of the present invention.
[0359] The electronic device (180) of FIG. 2 includes a substrate (100), a thin-film transistor (TFT), a light-emitting element, and a sealing portion (300) that seals the light-emitting element.
[0360] The substrate (100) may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer (210) may be disposed on the substrate (100). The buffer layer (210) may prevent the penetration of impurities through the substrate (100) and may serve to provide a flat surface on the upper surface of the substrate (100).
[0361] A thin-film transistor (TFT) may be disposed on the buffer layer (210). The thin-film transistor (TFT) may include an active layer (220), a gate electrode (240), a source electrode (260), and a drain electrode (270).
[0362] The active layer (220) may include an inorganic semiconductor, an organic semiconductor, or an oxide semiconductor such as silicon or polysilicon, and includes a source region, a drain region, and a channel region.
[0363] A gate insulating film (230) for insulating the active layer (220) and the gate electrode (240) may be disposed on the upper part of the active layer (220), and a gate electrode (240) may be disposed on the upper part of the gate insulating film (230).
[0364] An interlayer insulating film (250) may be disposed on the upper portion of the gate electrode (240). The interlayer insulating film (250) is disposed between the gate electrode (240) and the source electrode (260) and between the gate electrode (240) and the drain electrode (270) to insulate them.
[0365] A source electrode (260) and a drain electrode (270) may be disposed on the interlayer insulating film (250). The interlayer insulating film (250) and the gate insulating film (230) may be formed so as to expose the source region and the drain region of the active layer (220), and the source electrode (260) and the drain electrode (270) may be disposed to be in contact with the exposed source region and the drain region of the active layer (220).
[0366] Such a thin-film transistor (TFT) can be electrically connected to a light-emitting element to drive the light-emitting element and is covered and protected by a passivation layer (280). The passivation layer (280) may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light-emitting element is provided on the passivation layer (280). The light-emitting element includes a first electrode (110), an intermediate layer (130), and a second electrode (150).
[0367] The first electrode (110) may be disposed on the passivation layer (280). The passivation layer (280) may be disposed so as to expose a certain area without covering the entire drain electrode (270), and the first electrode (110) may be disposed to be connected to the exposed drain electrode (270).
[0368] A pixel defining film (290) including an insulating material may be disposed on the first electrode (110). The pixel defining film (290) exposes a predetermined area of the first electrode (110), and an intermediate layer (130) may be formed in the exposed area. The pixel defining film (290) may be a polyimide or polyacrylic-based organic film. Although not shown in FIG. 2, some or more layers of the intermediate layer (130) may extend to the upper part of the pixel defining film (290) and be disposed in the form of a common layer.
[0369] A second electrode (150) is disposed on the intermediate layer (130), and a capping layer (170) may be additionally formed on the second electrode (150). The capping layer (170) may be formed to cover the second electrode (150).
[0370] A sealing portion (300) may be disposed on the capping layer (170). The sealing portion (300) may be disposed on a light-emitting element and serve to protect the light-emitting element from moisture or oxygen. The sealing portion (300) may include an inorganic film comprising silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy resin (e.g., AGE (aliphatic glycidyl ether), etc.) or any combination thereof; or a combination of an inorganic film and an organic film.
[0371] FIG. 3 is a cross-sectional view of an electronic device (190) according to another embodiment of the present invention.
[0372] The electronic device (190) of FIG. 3 is the same electronic device as the light-emitting device of FIG. 2, except that a light-blocking pattern (500) and a functional area (400) are additionally disposed on the upper part of the encapsulation portion (300). The functional area (400) may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. According to one embodiment, the light-emitting element included in the electronic device of FIG. 3 may be a tandem light-emitting element.
[0373] [Manufacturing Method]
[0374] Each layer included in the hole transport region, each light-emitting layer, and each layer included in the electron transport region can be formed in a predetermined region using various methods such as vacuum deposition, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser thermal imaging (LITI).
[0375] When each layer included in the hole transport region, the emissive layer, and each layer included in the electron transport region are formed by vacuum deposition, the deposition conditions are, for example, a deposition temperature of about 100 to about 500°C, and about 10 -8 to about 10 -3 Within a vacuum level of torr and a deposition rate range of about 0.01 to about 100 Å / sec, the material to be included in the layer to be formed and the structure of the layer to be formed can be selected.
[0376] When forming each layer included in the hole transport region, the light-emitting layer, and each layer included in the electron transport region by spin coating, the coating conditions can be selected, for example, within a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature range of about 80°C to 200°C, taking into consideration the material to be included in the layer to be formed and the structure of the layer to be formed.
[0377] According to another aspect, the ink composition may include the quantum dot-containing complex, a monomer, a scatterer, and an initiator. The content of the monomer may be 70 to 150 parts by weight based on 100 parts by weight of the quantum dot-containing complex, the content of the scatterer may be 10 to 50 parts by weight based on 100 parts by weight of the quantum dot-containing complex, and the content of the initiator may be 0.1 to 10 parts by weight based on 100 parts by weight of the quantum dot-containing complex.
[0378] According to one embodiment, the monomer may be an acrylate-based compound, for example, 1,6-Hexanediol diacrylate.
[0379] The scatterer may be any ordinary particle that scatters light. The size of the scatterer may be, for example, 100 nm to 300 nm. If it is less than 100 nm or more than 300 nm, it may not be able to function as a scatterer.
[0380] The above initiator may be a radical compound commonly used in monomer polymerization.
[0381] The above ink composition can be used in solution processes such as spin coating and inkjet printing, and is suitable for solution processes when the content of each component is within the above range.
[0382] [General Definition of Substituents]
[0383] C3-C in this specification 60 A carbocyclic group refers to a cyclic group having 3 to 60 carbon atoms, consisting solely of carbon as ring-forming atoms, and C1-C 60 A heterocyclic group refers to a cyclic group having 1 to 60 carbon atoms that includes, in addition to carbon, a heteroatom as a ring-forming atom. The above C3-C 60 Carbocyclic group and C1-C 60Each heterocyclic group may be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed together. For example, the above C1-C 60 The number of ring-forming atoms in a heterocyclic group can be 3 to 61.
[0384] In this specification, the cyclic group is the above C3-C 60 Carbocyclic group and C1-C 60 Includes all heterocyclic groups.
[0385] In this specification, ð electron-excess C3-C 60 Cyclic group (ð electron-rich C3-C 60 A cyclic group refers to a cyclic group having 3 to 60 carbon atoms that does not contain *-N=*' as a ring-forming moiety, and ð electron-deficient nitrogen-containing C1-C 60 Cyclic group (ð electron-deficient nitrogen-containing C1-C 60 A cyclic group refers to a heterocyclic group having 1 to 60 carbon atoms containing *-N=*' as a ring-forming moiety.
[0386] for example,
[0387] The above C3-C 60The carbocyclic group may be i) group T1 or ii) a condensed ring group formed by the condensation of two or more groups T1 (e.g., cyclopentadiene group, adamantane group, norbornane group, benzene group, pentylene group, naphthalene group, azulene group, indacene group, acenaphtylene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, perylene group, pentapene group, heptylene group, naphthacene group, fisene group, hexacene group, pentacene group, rubicene group, coronene group, ovalene group, indene group, fluorene group, spiro-bifluorene group, benzofluorene group, indenophenanthrene group, or indenoanthracene group), and
[0388] The above C1-C 60A heterocyclic group is i) group T2, ii) a condensed ring group formed by the condensation of two or more groups T2, or iii) a condensed ring group formed by the condensation of one or more groups T2 and one or more groups T1 (e.g., pyrrole group, thiophene group, furan group, indole group, benzodole group, naphthoyndole group, isodole group, benzisoindole group, naphthoyisoindole group, benzocillol group, benzothiophene group, benzofuran group, carbazole group, dibenzocillol group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group, benzocillolocarbazole group, benzodolocarbazole group, benzoindolocarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthiophene group, Benzonaphthosilol group, benzofurodibenzofuran group, benzofurodibenzothiophen group, benzothienodibenzothiophen group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiaazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiaazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazolin group, benzoquinazolin group, phenanthroline group, sinoline group, phthalazine group, It may be the naftiridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluoren group, azadibenzocilol group, azadibenzothiophen group, azadibenzofuran group, etc.),
[0389] The above ð electron-excess C3-C 60A cyclic group is i) group T1, ii) a condensed ring group formed by condensing two or more groups T1 together, iii) group T3, iv) a condensed ring group formed by condensing two or more groups T3 together, or v) a condensed ring group formed by condensing one or more groups T3 and one or more groups T1 together (e.g., the above C3-C 60 Carbocyclic group, 1H-pyrrole group, Silol group, Borole group, 2H-pyrrole group, 3H-pyrrole group, Thiophene group, Furan group, Indole group, Benzoindole group, Naphthoyindole group, Isoindole group, Benzoisoindole group, Naphthoyisoindole group, Benzocilol group, Benzothiophene group, Benzofuran group, Carbazole group, Dibenzocilol group, Dibenzothiophene group, Dibenzofuran group, Indenocarbazole group, Indolocarbazole group, Benzofurocarbazole group, Benzothienocarbazole group, Benzocilolocarbazole group, Benzoindolocarbazole group, Benzocarbazole group, Benzonaphthofuran group, Benzonaphthothiophene group, Benzonaphtholilol group, Benzofurodibenzofuran group, It may be the benzopurodibenzothiophen group, benzothienodibenzothiophen group, etc.,
[0390] The above ð electron-deficient nitrogen-containing C1-C 60A cyclic group is i) group T4, ii) a condensed ring group formed by the condensation of two or more groups T4, iii) a condensed ring group formed by the condensation of one or more groups T4 and one or more groups T1, iv) a condensed ring group formed by the condensation of one or more groups T4 and one or more groups T3, or v) a condensed ring group formed by the condensation of one or more groups T4, one or more groups T1, and one or more groups T3 (e.g., pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiaazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiaazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, It may be the isoquinoline group, benzoquinoline group, benzisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazolin group, benzoquinazolin group, phenanthroline group, sinoline group, phthalazine group, naftiridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluoren group, azadibenzocilol group, azadibenzothiophen group, azadibenzofuran group, etc.),
[0391] The above group T1 is a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, norbornane (or, bicyclo[2.2.1]heptane)) group, norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.1.1]octane group, or a benzene group, and
[0392] The above group T2 is a furan group, a thiophene group, a 1H-pyrrole group, a silol group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazol group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiaazole group, a thiadiazole group, azasilol group, azaborol group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, It is a dihydropyrazine group, a tetrahydropyridazine group, or a dihydropyridazine group, and
[0393] The above group T3 is a furan group, a thiophene group, an 1H-pyrrole group, a silol group, or a borole group, and
[0394] The above group T4 may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazol group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiaazole group, a thiadiazole group, an azacilol group, an azaborol group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.
[0395] In this specification, the cyclic group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, ð electron-excess C3-C 60 Cyclic group or ð electron-deficient nitrogen-containing C1-C 60 The term "cyclic group" may be a group condensed to any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) depending on the structure of the chemical formula in which the term is used. For example, "benzene group" may be a benzo group, a phenyl group, a phenylene group, etc., which can be easily understood by a person skilled in the art depending on the structure of the chemical formula containing the "benzene group."
[0396] For example, 1 valence C3-C 60 Carbocyclic group and 1 valence C1-C 60 An example of a heterocyclic group is C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C1-C 60 It may include a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocondensed polycyclic group, and a divalent C3-C 60 Carbocyclic groups and 2 C1-C 60 An example of a heterocyclic group is C3-C 10 Cycloalkylene group, C1-C 10Heterocycloalkylene group, C3-C 10 Cycloalkenylene group, C1-C 10 Heterocycloalkenylene group, C6-C 60 Aryllene group, C1-C 60 It may include a heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic heterocondensed polycyclic group.
[0397] C1-C in this specification 60 The alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, n -Propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -Pentyl, tert -Pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -Isopentyl group, n - Hexyl group, isohexyl group, sec -hexyl group, tert -hexyl group, n - heptyl group, isoheptyl group, sec -Heptyl group, tert -Heptyl group, n -Octyl group, iso-octyl group, sec -Octyl group, tert -Octyl group, n -Nonilgi, Isononilgi, sec -Playing, tert -Playing, n - Decyl group, isodecyl group, sec -Desil, tert - Includes decyl groups, etc. C1-C in this specification. 60 The alkylene group is the C1-C 60 It refers to a divalent group having the same structure as an alkyl group.
[0398] C2-C in this specification 60 The alkenyl group is C2-C 60It refers to a monovalent hydrocarbon group comprising one or more carbon-carbon double bonds at the middle or terminal of an alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group, etc. In this specification, C2-C 60 The alkenylene group is the above C2-C 60 It refers to a divalent group having the same structure as an alkenyl group.
[0399] C2-C in this specification 60 The alkynyl group is C2-C 60 It refers to a monovalent hydrocarbon group comprising one or more carbon-carbon triple bonds at the middle or terminal of an alkyl group, and specific examples thereof include ethinyl groups, propynyl groups, etc. In this specification, C2-C 60 The alkynylene group is the above C2-C 60 It refers to a divalent group having the same structure as an alkynyl group.
[0400] C1-C in this specification 60 The alkoxy group is -OA 101 (Here, A 101 The above C1-C 60 It refers to a monovalent group having the chemical formula of an alkyl group, and specific examples thereof include a methoxy group, an ethoxy group, an isopropyloxy group, etc.
[0401] C3-C in this specification 10 A cycloalkyl group refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, norbornanyl group (or, a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.1.1]octyl group, etc. In this specification, C3-C 10 The cycloalkylene group is the C3-C above. 10It refers to a divalent group having the same structure as a cycloalkyl group.
[0402] C1-C in this specification 10 A heterocycloalkyl group refers to a monovalent cyclic group having 1 to 10 carbon atoms, comprising at least one heteroatom as a ring-forming atom in addition to a carbon atom, and specific examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, etc. In this specification, C1-C 10 The heterocycloalkylene group is the C1-C 10 It refers to a divalent group having the same structure as a heterocycloalkyl group.
[0403] C3-C in this specification 10 A cycloalkenyl group refers to a monovalent cyclic group having 3 to 10 carbon atoms, having at least one carbon-carbon double bond within the ring, but not having aromaticity; specific examples thereof include cyclopentenyl groups, cyclohexenyl groups, cycloheptenyl groups, etc. In this specification, C3-C 10 The cycloalkenylene group is the above C3-C 10 It refers to a divalent group having the same structure as a cycloalkenyl group.
[0404] C1-C in this specification 10 The heterocycloalkenyl group is a monovalent cyclic group having 1 to 10 carbon atoms, comprising, in addition to the carbon atom, at least one heteroatom as a ring-forming atom, and has at least one double bond within the ring. The C1-C 10 Specific examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazoleyl groups, 2,3-dihydrofuranyl groups, 2,3-dihydrothiophenyl groups, etc. In this specification, C1-C 10 The heterocycloalkenylene group is the above C1-C 10It refers to a divalent group having the same structure as a heterocycloalkenyl group.
[0405] C6-C in this specification 60 An aryl group refers to a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms, and C6-C 60 An arylene group refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. The above C6-C 60 Specific examples of aryl groups include phenyl group, pentalenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, Includes hepthalenyl group, naphthacenyl group, fisenyl group, hexacenyl group, penthacenyl group, rubisenyl group, coronenyl group, ovalenyl group, etc. The above C6-C 60 Aryl group and C6-C 60 If the arylene group contains two or more rings, the two or more rings can be condensed together.
[0406] C1-C in this specification 60 A heteroaryl group refers to a monovalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms, comprising at least one heteroatom as a ring-forming atom in addition to a carbon atom, and C1-C 60 A heteroarylene group refers to a divalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms, which additionally includes at least one heteroatom as a ring-forming atom in addition to the carbon atoms. 60 Specific examples of heteroaryl groups include pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolinyl groups, benzoquinolinyl groups, isoquinolinyl groups, benzisoquinolinyl groups, quinoxalinyl groups, benzoquinoxalinyl groups, quinazolinyl groups, benzoquinazolinyl groups, cinolinyl groups, phenanthrolinyl groups, phthalazinyl groups, naphthalidinyl groups, etc. The above C1-C60 heteroaryl group and C1-C 60 When a heteroarylene group contains two or more rings, the two or more rings can be condensed together.
[0407] In this specification, a monovalent non-aromatic condensed polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are condensed together, and the entire molecule contains only carbon as a ring-forming atom and has non-aromaticity. Specific examples of the monovalent non-aromatic condensed polycyclic group include indenyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, indenopenantrenyl groups, indenoanthracenyl groups, etc. In this specification, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
[0408] In this specification, a monovalent non-aromatic condensed heteropolycyclic group means a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are condensed together, and in addition to carbon atoms as ring-forming atoms, at least one heteroatom is included, and the entire molecule is non-aromatic. Specific examples of the above monovalent non-aromatic heterocondensed polycyclic group include: a pyrrole group, a thiophenyl group, a furanyl group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzocylol group, a benzothiophenyl group, a benzofuranyl group, a carbazole group, a dibenzocylol group, a dibenzothiophenyl group, a dibenzofuranyl group, azacarbazole group, azafluorenyl group, azadibenzocylol group, azadibenzothiophenyl group, azadibenzofuranyl group, a pyrazol group, an imidazole group, a triazole group, a tetrazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a thiadiazole group, Includes benzopyrazol group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, imidazopyridinyl group, imidazopyrimidinyl group, imidazotriazinyl group, imidazopyrazinyl group, imidazopyridazinyl group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group, benzosilolocarbazole group, benzindolocarbazole group, benzocarbazole group, benzonaphthofuranyl group, benzonaphthothiophenyl group, benzonaphthosilol group, benzofurodibenzofuranyl group, benzofurodibenzothiophenyl group, benzothienodibenzothiophenyl group, etc. In this specification, a divalent non-aromatic heterocondensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic heterocondensed polycyclic group.
[0409] C6-C in this specification 60 The aryloxy group is -OA 102 (Here, A 102 is the above C6-C 60 Pointing to arylgime), and the above C6-C 60arylthio is -SA 103 (Here, A 103 The above C6-C 60 It refers to the Arilgigiim).
[0410] C7-C in this specification 60 The arylalkyl group is -A 104 A 105 (Here, A 104 is C1-C 54 It is an alkylene group, and A 105 is C6-C 59 Referring to arylgiim), and C2-C in this specification 60 The heteroarylalkyl group is -A 106 A 107 (Here, A 106 C1-C 59 It is an alkylene group, and A 107 C1-C 59 It refers to a heteroaryl group.
[0411] "R" in this specification 10a "Is,
[0412] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group;
[0413] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12), or substituted or unsubstituted with any combination thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, or C1-C 60 Alkoxygenation;
[0414] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), or substituted or unsubstituted with any combination thereof, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, or C2-C 60 heteroarylalkyl group; or
[0415] -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q31 ), -S(=O)2(Q 31 ), or -P(=O)(Q 31 )(Q 32 );
[0416] It could be.
[0417] Q1 to Q3, Q in this specification 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 They are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; or deuterium, -F, cyano group, C1-C 60 Alkyl group, C1-C 60 C3-C substituted or unsubstituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof 60 Carbocyclic group; C1-C 60 Heterocyclic group; C7-C 60 Arylalkyl group; or C2-C 60 It may be a heteroarylalkyl group.
[0418] In this specification, a heteroatom refers to any atom other than a carbon atom. Examples of such heteroatoms include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0419] In this specification, third-row transition metals include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), or gold (Au), etc.
[0420] In this specification, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, and "ter-Bu" or "But " represents the tert-butyl group, and "OMe" represents the methoxy group.
[0421] In this specification, "biphenyl group" means "phenyl group substituted with a phenyl group." The "biphenyl group" is a substituent of "C6-C 60 It belongs to the "substituted phenyl group" which is an "aryl group".
[0422] In this specification, "terphenyl group" means "phenyl group substituted with a biphenyl group." The "terphenyl group" is a substituent of "C6-C 60 C6-C substituted with aryl groups 60 It belongs to the "substituted phenyl group" which is an "aryl group".
[0423] The maximum number of carbon atoms in the definition of a substituent is exemplary. For example, C1-C 60 The maximum number of carbon atoms in an alkyl group being 60 is exemplary, and the definition of an alkyl group is C1-C 20 The same applies to alkyl groups. The same applies to other cases.
[0424] In this specification, * and *' refer to bonding sites with adjacent atoms in the corresponding chemical formulas, unless otherwise defined.
[0425] Hereinafter, a compound and a light-emitting element according to one embodiment of the present invention will be described in more detail with reference to examples.
[0427] [Example]
[0428] fabrication of light-emitting devices
[0429] Preparation of quantum dot-containing complexes
[0430] (1) Quantum dot-containing complex of ligand 2,5,8,11,14-pentaoxaheptadecan-17-oic acid
[0431] 3 g of InP quantum dots coordinated with oleic acid were added to 100 ml of chloroform and stirred at room temperature for 1 hour. Subsequently, 0.9 g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid was added and stirred at 70°C for 2 hours to exchange the quantum dot coordination ligand from oleic acid to 2,5,8,11,14-pentaoxaheptadecan-17-oic acid.
[0432] Next, 300 ml of n-hexane was added, the resulting product was centrifuged (9500 rpm / 3 min), and the precipitate was vacuum dried to prepare a quantum dot-containing complex.
[0433] (2) Quantum dot-containing complex of ligands 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and 3-(2-(2-methoxyethoxy)ethoxy)propanoic acid (ligands 1:1 weight ratio)
[0434] A quantum dot-containing complex was prepared in an equivalent manner to (1) above, except that 0.45 g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and 0.45 g of 3-(2-(2-methoxyethoxy)ethoxy)propanoic acid were used as two ligands instead of 0.9 g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid ligand.
[0435] (3) Quantum dot-containing complex of ligands 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and mono-2-(Acryloyloxy)ethyl succinate (ligands in a 1:1 weight ratio)
[0436] A quantum dot-containing complex was prepared in an equivalent manner to (1) above, except that 0.45 g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and 0.45 g of mono-2-(Acryloyloxy)ethyl succinate were used as two ligands instead of 0.9 g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid ligand.
[0437] (4) Quantum dot-containing complex of ligands 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and mono-2-(Acryloyloxy)ethyl succinate (ligand weight ratio 1:2)
[0438] A quantum dot-containing complex was prepared in an equivalent manner to (1) above, except that 0.3g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and 0.6g of mono-2-(Acryloyloxy)ethyl succinate were used as two ligands instead of 0.9g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid ligand.
[0439] (5) Quantum dot-containing complex of ligands 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and mono-2-(Acryloyloxy)ethyl succinate (ligand weight ratio 1:4)
[0440] A quantum dot-containing complex was prepared in an equivalent manner to (1) above, except that 0.18 g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and 0.72 g of mono-2-(Acryloyloxy)ethyl succinate were used as two ligands instead of 0.9 g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid ligand.
[0441] (6) Quantum dot-containing complex of ligands 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and mono-2-(Acryloyloxy)ethyl succinate (ligand weight ratio 1:8)
[0442] A quantum dot-containing complex was prepared in an equivalent manner to (1) above, except that 0.1g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and 0.8g of mono-2-(Acryloyloxy)ethyl succinate were used as two ligands instead of 0.9g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid ligand.
[0443] (7) Quantum dot-containing complex of ligands 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and mono-2-(Acryloyloxy)ethyl succinate (ligands in a 6:4 weight ratio)
[0444] A quantum dot-containing complex was prepared in an equivalent manner to (1) above, except that 0.54 g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and 0.36 g of mono-2-(Acryloyloxy)ethyl succinate were used as two ligands instead of 0.9 g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid ligand.
[0445] (8) Quantum dot-containing complex of ligands 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and mono-2-(Acryloyloxy)ethyl succinate (ligand weight ratio 1:9)
[0446] A quantum dot-containing complex was prepared in an equivalent manner to (1) above, except that 0.09 g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid and 0.81 g of mono-2-(Acryloyloxy)ethyl succinate were used as two ligands instead of 0.9 g of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid ligand.
[0448] The aspect ratios and hydrophilic-lipophilic ratios of the related ligands are as follows.
[0450] Aspect ratio
[0451] Aspect ratio of oleic acid = 3.0
[0452] Length = 19.7 Å
[0453] Width = 6.57 Å
[0455] Aspect ratio of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid = 6.8
[0456] Length = 23 Å
[0457] Width = 3.4 Å
[0459] Aspect ratio of 3-(2-(2-methoxyethoxy)ethoxy)propanoic acid = 4.5
[0460] Length = 15.4 Å
[0461] Width = 3.4 Å
[0463] Aspect ratio of mono-2-(acryloyloxy)ethyl succinate = 3.2
[0464] Length = 15 Å
[0465] Width = 4.7 Å
[0467] Hydrophilic-lipophilic-non-hydrophilic
[0468] The hydrophilic-lipophilic ratio of oleic acid = 1.0
[0469] 7 + 2.1[-COOH] - 17x0.475[1 CH3-, 2 =CH-, 14 -CH2-] = 1.0
[0471] Hydrophilic-lipophilic ratio of 2,5,8,11,14-pentaoxaheptadecan-17-oic acid = 10.4
[0472] 7 + 2.1[-COOH] + 5x1.3[3 -O-] - 11x0.475[1 CH3-, 10 -CH2-] = 10.4
[0474] Hydrophilic-lipophilic ratio of 3-(2-(2-methoxyethoxy)ethoxy)propanoic acid = 9.7
[0475] 7 + 2.1[-COOH] + 3x1.3[3 -O-] - 7x0.475[1 CH3-, 6 -CH2-] = 9.7
[0477] Hydrophilic-lipophilic ratio of mono-2-(acryloyloxy)ethyl succinate = 11.4
[0478] 7 + 2.1[-COOH] + 4x1.3[2 -O-, 2 =O] - 6x0.475[1 CH2-, 1 =CH-, 4 -CH2-] = 11.4
[0480] Preparation of ink composition
[0481] (9) 0.5g of the quantum dot-containing complex of (1) and 0.5g of the monomer 1,6-Hexanediol diacrylate were stirred at room temperature for 12 hours, and then 0.1g of scattering agent TiO2 and 0.01g of initiator (TPO) were added and stirred for 3 more hours to prepare a quantum dot ink composition.
[0482] (10) A quantum dot ink composition was prepared in an equivalent manner to (9), except that 0.5g of the quantum dot-containing composite of (2) was used.
[0483] (11) A quantum dot ink composition was prepared in an equivalent manner to (9), except that 0.5g of the quantum dot-containing composite of (3) was used.
[0484] (12) A quantum dot ink composition was prepared in an equivalent manner to (9), except that 0.5g of the quantum dot-containing composite of (4) was used.
[0485] (13) A quantum dot ink composition was prepared in an equivalent manner to (9), except that 0.5g of the quantum dot-containing composite of (5) was used.
[0486] (14) A quantum dot ink composition was prepared in an equivalent manner to (9), except that 0.5g of the quantum dot-containing composite of (6) was used.
[0487] (15) A quantum dot ink composition was prepared in an equivalent manner to (9), except that 0.5g of the quantum dot-containing composite of (7) was used.
[0488] (16) A quantum dot ink composition was prepared in an equivalent manner to (9), except that 0.5g of the quantum dot-containing composite of (8) was used.
[0490] Meanwhile, the hydrophilic-lipophilic ratio of the monomer 1,6-Hexanediol diacrylate is 7.1.
[0492] Electronic device manufacturing
[0493] Comparative Example 1
[0494] As shown in FIG. 3, an electronic device was manufactured by forming a color conversion layer with a thickness of 10 micrometers using an inkjet with the quantum dot ink composition of (9) in the color conversion area, which is a functional area (400) on the upper part of the packaging part (300).
[0495] Comparative Example 2
[0496] An electronic device equivalent to Comparative Example 1 was manufactured except that the color conversion layer was formed using an inkjet with the quantum dot ink composition of (10) above.
[0497] Example 1
[0498] An electronic device equivalent to Comparative Example 1 was manufactured except that the color conversion layer was formed using an inkjet with the quantum dot ink composition of (11) above.
[0499] Example 2
[0500] An electronic device equivalent to Comparative Example 1 was manufactured except that the color conversion layer was formed using an inkjet with the quantum dot ink composition of (12) above.
[0501] Example 3
[0502] An electronic device equivalent to Comparative Example 1 was manufactured except that the color conversion layer was formed using an inkjet with the quantum dot ink composition of (13) above.
[0503] Example 4
[0504] An electronic device equivalent to Comparative Example 1 was manufactured except that the color conversion layer was formed using an inkjet with the quantum dot ink composition of (14) above.
[0505] Comparative Example 3
[0506] An electronic device equivalent to Comparative Example 1 was manufactured except that the color conversion layer was formed using an inkjet with the quantum dot ink composition of (15) above.
[0507] Comparative Example 4
[0508] An electronic device equivalent to Comparative Example 1 was manufactured except that the color conversion layer was formed using an inkjet with the quantum dot ink composition of (16) above.
[0510] To evaluate the characteristics of the electronic devices fabricated in Comparative Examples 1 to 4 and Examples 1 to 4, the absorption rate and light conversion efficiency at a current density of 10 mA / cm² were measured, and the results are shown in Table 1.
[0511] Absorption rate and light conversion efficiency were measured using the C9920-2-12 measuring device from Hamamatsu Photonics.
[0512] Ligands of quantum dot-containing complexes absorption rate 1) Photovoltaic conversion efficiency 2) Comparative Example 1 2,5,8,11,14-pentaoxaheptadecan-17-oic acid 78.4% 32.7% Comparative Example 2 2,5,8,11,14-pentaoxaheptadecan-17-oic acid: 3-(2-(2-methoxyethoxy)ethoxy)propanoic acid = 1:1 (weight ratio) 76.0% 27.0% Example 1 2,5,8,11,14-pentaoxaheptadecan-17-oic acid: mono-2-(acryloyloxy)ethyl succinate = 1:1 (weight ratio) 83.4% 36.8% Example 2 2,5,8,11,14-pentaoxaheptadecan-17-oic acid: mono-2-(acryloyloxy)ethyl succinate = 1:2 (weight ratio) 81.5% 36.4% Example 3 2,5,8,11,14-pentaoxaheptadecan-17-oic acid: mono-2-(acryloyloxy)ethyl succinate = 1:4 (weight ratio) 79.4% 36.9% Example 4 2,5,8,11,14-pentaoxaheptadecan-17-oic acid: mono-2-(acryloyloxy)ethyl succinate = 1:8 (weight ratio) 78.2% 35.6% Comparative Example 3 2,5,8,11,14-pentaoxaheptadecan-17-oic acid: mono-2-(acryloyloxy)ethyl succinate = 6:4 (weight ratio) 72.9% 30.0% Comparative Example 4 2,5,8,11,14-pentaoxaheptadecan-17-oic acid: mono-2-(acryloyloxy)ethyl succinate = 1:9 (weight ratio) 74.1% 29.5%
[0513] 1) The ratio of light from an organic light-emitting diode absorbed by the color conversion layer
[0514] 2) The ratio of converted absorbed light into light of a different wavelength
[0516] From Table 1 above, it can be seen that Examples 1 to 4 have superior absorption rates and light conversion efficiency compared to Comparative Examples 1 to 4. Explanation of the symbols
[0518] 10: Light-emitting element 110: First electrode 130: Middle layer 150: Second electrode
Claims
Claim 1 A quantum dot-containing complex comprising: a quantum dot; a first ligand and a second ligand coordinating the surface of the quantum dot; wherein the first ligand is a hydrocarbon compound comprising a hydrophilic moiety and a lipophilic moiety having an aspect ratio of 5 or more, and the second ligand is a hydrocarbon compound comprising a hydrophilic moiety and a lipophilic moiety having an aspect ratio of 4 or less, wherein the hydrophile-lipophile balance (HLB) of the first ligand and the second ligand is independently 7 or more, and the ratio of the first ligand and the second ligand is 1:2 to 1:8 (weight ratio): wherein the aspect ratio = ligand length / ligand width (Davies' method) In the above formula, m = number of hydrophilic moieties H within the ligand molecule i = Coefficient of the i-th hydrophilic moiety n = Number of lipophilic moiety within the ligand molecule. Claim 2 In claim 1, the hydrophilic moiety is -SO4 - Na + , -COO - K + , -COO - Na + Quantum dot-containing complex comprising , tertiary amine, -COOH, -OH, -O-, =O and any combination thereof. Claim 3 A quantum dot-containing complex according to claim 1, wherein the lipophilic moiety comprises -CH-, -CH2-, CH3-, =CH-, =CH2, and any combination thereof. Claim 4 A quantum dot-containing complex according to claim 1, wherein both the first ligand and the second ligand comprise a COOH moiety at their terminals. Claim 5 A quantum dot-containing complex according to claim 1, wherein the first ligand comprises two or more ethylene glycol moiety (OCH2CH2O). Claim 6 A quantum dot-containing complex according to claim 1, wherein the first ligand is 2,5,8,11,14-pentaoxaheptadecan-17-oic acid. Claim 7 A quantum dot-containing complex according to claim 1, wherein the second ligand is mono-2-(acryloyloxy)ethyl succinate. Claim 8 delete Claim 9 A quantum dot-containing complex according to claim 1, wherein the ratio of the weight of the quantum dot; and the total weight of the first ligand and the second ligand; is 10:1 to 10:
4. Claim 10 A quantum dot-containing complex according to claim 1, wherein the quantum dot has a core-shell structure including a core including a first semiconductor crystal and a shell including a second semiconductor crystal, or is a perovskite compound. Claim 11 In claim 10, the first semiconductor and the second semiconductor independently comprise a quantum dot-containing complex comprising a group 12-16 compound, a group 13-15 compound, a group 14-16 compound, a group 14 compound, a group 11-13-16 compound, a group 11-12-13-16 compound, and any combination thereof. Claim 12 In claim 10, the first semiconductor and the second semiconductor are independently of each other, CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgS, MgSe; CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnS, MgZnSe; CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe;GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb; GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP; GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb; Quantum dot-containing complex comprising InZnP;SnS, SnSe, SnTe, PbS, PbSe, PbTe; SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe; SnPbSSe, SnPbSeTe, SnPbSTe;Si, Ge, SiC, SiGe;AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2; and any combination thereof. Claim 13 In claim 10, the first semiconductor comprises GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and any combination thereof, and the second semiconductor comprises CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgS, Quantum dot-containing complex comprising MgSe, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnS, MgZnSe, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and any combination thereof. Claim 14 An ink composition comprising the quantum dot-containing complex of claim 1, a monomer, a scatterer, and an initiator. Claim 15 In claim 14, the above monomer comprises a hydrophilic moiety, an ink composition. Claim 16 In claim 14, the above monomer is an acrylate-based compound, an ink composition. Claim 17 In claim 14, the ink composition wherein the monomer is 1,6-Hexanediol diacrylate. Claim 18 A light-emitting device comprising: a first electrode; a second electrode opposite to the first electrode; an intermediate layer interposed between the first electrode and the second electrode and including a light-emitting layer, wherein the light-emitting layer comprises the quantum dot-containing composite of claim 1. Claim 19 An electronic device comprising the quantum dot-containing complex of claim 1. Claim 20 An electronic device according to claim 19, further comprising a color filter and a color conversion layer, wherein the color conversion layer comprises the quantum dot-containing complex.
Citation Information
Patent Citations
Quantum dot-containing complex, and light-emitting device and optical member and device including the same
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