Patent Application
20230189544
This application claims priority to and the benefit of Korean Patent Application No. 10-2021-0176939, filed on Dec. 10, 2021, in the Korean Intellectual Property Office, the entire content of which is hereby incorporated by reference.
One or more embodiments of the present disclosure include a light-emitting device including a heterocyclic compound and an electronic apparatus including the light-emitting device.
Self-emissive devices among light-emitting devices have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of luminance, driving voltage, and response speed compared to other the light-emitting devices of the related art.
In a light-emitting device, a first electrode is on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially on the first electrode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to produce excitons. The excitons may transition from an excited state to a ground state, thus generating light.
One or more embodiments of the present disclosure relate to a light-emitting device including a heterocyclic compound and an electronic apparatus including the light-emitting device.
Additional aspects of embodiments will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one or more embodiments, a light-emitting device includes a first electrode,
In Formula 1, X may be O or S,
According to one or more embodiments, an electronic apparatus includes the light-emitting device.
According to one or more embodiments, provided is a heterocyclic compound represented by Formula 1 (hereinafter referred to as “first compound represented by Formula 1” or “first compound”).
The above and other aspects and features of certain embodiments of the present disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects of embodiments of the present description. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression “at least one of a, b or c” indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.
The light-emitting device may include: first electrode; second electrode facing the first electrode;
X in Formula 1 may be O or S.
Y1 in Formula 1 may be B or N.
In an embodiment, Y1 in Formula 1 may be N.
In Formula 1, R1 to R4 may each independently be:
In Formula 1-1, L1 may be a single bond, a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group, each unsubstituted or substituted with at least one R10a,
At least one of R2(s) in the number of a2 and R3(s) in the number of a3 may be a group represented by Formula 1-2.
When at least one of R2(s) in the number of a2 and R3(s) in the number of a3 is a group represented by Formula 1-2, the other R2(s) and R3(s), that is, groups that are not represented by Formula 1-2 among R2(s) and R3(s), may be groups excluding the groups represented by Formula 1-2 among the above-described R1 to R4.
For example, when one R3 is a group represented by Formula 1-2, R2 in the number of a2 and R3 in the number of a3-1 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, or a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a; —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2); or a group represented by Formula 1-1.
In an embodiment, in Formula 1, R1 may be a group represented by Formula 1-1. For example, R1 may be a group represented by Formula 1-1, and one of R3(s) in the number of a3 may be a group represented by Formula 1-2.
In one or more embodiments, in Formula 1,
For example, in Formula 1,
In the case of i) and iv), at least one of R2(s) in the number of a2 may be a group represented by Formula 1-1, or R2(s) in the number of a2 may be a group excluding the groups represented by Formulae 1-1 and 1-2 among the above-described R1 to R4.
In the case of ii), at least one of R3(s) in the number of a3 may be a group represented by Formula 1-1, or R3(s) in the number of a3 may be a group excluding the groups represented by Formulae 1-1 and 1-2 among the above-described R1 to R4.
In one or more embodiments, in Formula 1, R2 may be: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; or
a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, or a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a.
In an embodiment, in Formula 1, R4 may be: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; or
a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, or a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a.
For example, in Formula 1, R4 may be hydrogen, but embodiments are not limited thereto.
In an embodiment, in Formula 1-1,
For example, R11 in Formula 1-1 and R13 and R14 in Formula 1-2 may each independently be:
In an embodiment, in Formula 1-1,
In one or more embodiments, in Formula 1-2, Y2 may be N.
In an embodiment, in Formula 1-2, R13 and R14 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, or a C1-C20 alkoxy group; or a C1-C20 alkyl group or a C1-C20 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof. For example, R13 and R14 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group.
For example, in Formula 1, a group represented by
may be a group represented by one selected from Formulae 1A-1 to 1A-4:
For example, in Formula 1, a group represented by
may be a group represented by one selected from Formulae 1B-1 to 1B-4:
[00113] wherein, in Formulae 1B-1 to 1B-4, R41 to R44 are respectively the same as in the description of R31,
In an embodiment, the heterocyclic compound represented by Formula 1 may be one selected from the compounds below, but embodiments of the present disclosure are not limited thereto:
In an embodiment, the second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
In an embodiment, the second compound may include a compound represented by Formula 2 (hereinafter may also be referred to as “heterocyclic compound represented by Formula 2”):
[00119] wherein, in Formula 2, X51 may be N or C(Rx51), X52 may be N or C(Rx52), X53 may be N or C(Rx53), and at least one selected from X51 to X53 may be N,
In an embodiment, as a second compound, a compound including at least one TT electron-deficient nitrogen-containing C1-C60 cyclic group, which is different from the compound represented by Formula 2, may further be included in addition to the compound represented by Formula 2.
In one or more embodiments, as the second compound, only a compound represented by Formula 2 may be included.
In an embodiment, in Formula 2, two of X51 to X53 may be N, each of X51 to X53 may be N.
In an embodiment, RX51 to RX53 in Formula 2 may each independently be hydrogen.
In an embodiment, L51 to L53 in Formula 2 may each independently be: a single bond;
For example, in Formula 2, L51 to L53 may each independently be a single bond, or a benzene group or a carbazole group unsubstituted or substituted with at least one R10a
In an embodiment, R53 in Formula 2 may be a cyclopentadiene group, an adamantane group, norbornane group, a benzene group, a pentalene group, a naphthalene group, an azulene group, an indacene group, acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentaphene group, a heptalene group, a naphthacene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indeno phenanthrene group, or an indenoanthracene group; or
a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, or an azadibenzofuran group, each unsubstituted or substituted with at least one R10a.
For example, R53 in Formula 2 may be a benzene group or a carbazole group unsubstituted or substituted with at least one R10a
In an embodiment, in Formula 2,
In an embodiment, T1 to T3 in Formula 2-1 may be a benzene group unsubstituted or substituted with at least one R10a.
In an embodiment, T1 to T3 in Formula 2-1 may be identical to or different from each other.
In an embodiment, b51 to b53 in Formula 2 may each independently be 1 or 2.
In an embodiment, the heterocyclic compound represented by Formula 2 may be one selected from the compounds below, but embodiments of the present disclosure are not limited thereto:
The term “R10a” as used herein may be:
The first compound represented by Formula 1 is a heterocyclic compound having a core in which benzofuran or benzothiophene is condensed together with dibenzoborole or carbazole, electric characteristics are controlled according to the introduction position and number of cyclic substituents, thereby facilitating hole transport. In the first compound represented by Formula 1, at least one of R2(s) in the number of a2 and R3(s) in the number of a3 may be a heterocyclic substituent (e.g., a group represented by Formula 1-2), which can increase a triplet energy level of the first compound represented by Formula 1, wherein such a substituent may be directly bound to the core to facilitate control of the electric characteristics of the first compound, thereby particularly improving luminescence efficiency of phosphorescent and delayed fluorescence devices in which triplet energy levels are used in a light-emitting mechanism.
In addition, by using a second compound (for example, the heterocyclic compound represented by Formula 2) including a TT electron-deficient nitrogen-containing C1-C60 cyclic group, in combination with the first compound, electron transport and hole transport may be facilitated and a charge balance in the emission layer may be improved or optimized, and thus, by accelerating the formation of excitons in the emission layer, luminescence efficiency may be improved, and by reducing currents used at the same luminance, the light-emitting device lifespan may be improved.
For example, by using the second compound in combination with the first compound represented by Formula 1, an electronic device (for example, an organic light-emitting device) having improved luminescence efficiency and lifespan characteristics may be realized.
Synthesis methods of the heterocyclic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples and/or Examples provided below.
At least one heterocyclic compound represented by Formula 1 may be used in a light-emitting device (for example, an organic light-emitting device). For example, provided is a light-emitting device including: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emission layer; and a heterocyclic compound represented by Formula 1 as described herein.
In some embodiments,
In an embodiment, the heterocyclic compound represented by Formula 1 may be included between the first electrode and the second electrode of the light-emitting device.
In an embodiment, the heterocyclic compound represented by Formula 1 may be included in the interlayer of the light-emitting device, for example, the emission layer of the interlayer.
In an embodiment, the light-emitting device may include: the first compound represented by Formula 1; and the second compound including at least one TT electron-deficient nitrogen-containing C1-C60 cyclic group.
In one or more embodiments, the first compound represented by Formula 1 and the second compound including at least one TT electron-deficient nitrogen-containing C1-C60 cyclic group may be included between the first electrode and the second electrode.
In one or more embodiments, the interlayer of the light-emitting device, for example, the emission layer of the interlayer may include the first compound and the second compound.
In an embodiment, the emission layer of the light-emitting device may include a host, and the host may include the first compound and the second compound. In other words, the first compound and the second compound may act as a host.
In one or more embodiments, the emission layer of the light-emitting device may further include a dopant, a sensitizer, or any combination thereof. For example, the emission layer may include a host, and may further include a dopant, a sensitizer, or any combination thereof.
For example, the first compound and the second compound may each independently be, according to other materials included in the emission layer, a dopant or a sensitizer.
In one or more embodiments, the emission layer of the light-emitting device may further include a phosphorescent emitter, a prompt fluorescence emitter, a delayed fluorescence (for example, Thermally Activated Delayed Fluorescence (TADF)) emitter, or any combination thereof.
In one or more embodiments, the emission layer of the light-emitting device may further include a transition metal-containing organometallic compound, a boron (B)-containing compound, or any combination thereof.
For example, the transition metal-containing organometallic compound and the boron (B)-containing compound may each independently be a dopant or a sensitizer according to other materials included in the emission layer.
For example, the transition metal-containing organometallic compound may be a phosphorescent dopant.
For example, the emission layer may emit phosphorescence or fluorescence emitted from the transition metal-containing organometallic compound or the boron (B)-containing compound, and the transition metal-containing organometallic compound and the boron (B)-containing compound may each independently be a phosphorescent emitter, a prompt fluorescence emitter, or a delayed fluorescence(for example, TADF) emitter.
For example, the transition metal-containing organometallic compound may be a phosphorescent emitter and the boron (B)-containing compound may be a delayed fluorescence emitter.
In one or more embodiments, the transition metal-containing organometallic compound may include platinum and a tetradentate ligand bound to the platinum. For example, the transition metal-containing organometallic compound may be an organometallic compound represented by Formula 401 as described herein.
In one or more embodiments, the boron (B)-containing compound may be a C8-C60 polycyclic group-containing compound including at least two condensed cyclic groups that share a boron atom (B).
The emission layer may emit red light, green light, blue light, and/or white light. For example, the emission layer may emit blue light. The blue light may have a maximum emission wavelength of, for example, about 370 nm to about 490 nm, about 380 nm to about 490 nm, about 390 nm to about 490 nm, about 400 nm to about 490 nm, or about 430 nm to about 490 nm.
In an embodiment, the light-emitting device may include a capping layer outside the first electrode and/or outside the second electrode.
In an embodiment, the light-emitting device may further include at least one selected from a first capping layer outside the first electrode and a second capping layer outside the second electrode, and at least one selected from the first capping layer and the second capping layer may include the heterocyclic compound represented by Formula 1 and/or the second compound. More details for the first capping layer and/or second capping layer are the same as described in the present specification.
The wording “(interlayer and/or capping layer) includes the heterocyclic compound represented by Formula 1,” as used herein, may be understood as “(interlayer and/or capping layer) may include one kind of heterocyclic compound represented by Formula 1 or two different kinds of heterocyclic compounds, each represented by Formula 1.”
For example, the interlayer and/or capping layer may include Compound 1 only as the heterocyclic compound represented by Formula 1. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In an embodiment, the interlayer may include Compounds 1 and 2 as the heterocyclic compound represented by Formula 1. In this regard, Compounds 1 and 2 may be present in the same layer (for example, all of Compounds 1 and 2 may be present in the emission layer), or may be present in different layers (for example, Compound 1 may be present in the emission layer and Compound 2 may be present in the electron transport region).
The term “interlayer,” as used herein, refers to a single layer and/or all of a plurality of layers between the first electrode and the second electrode of the light-emitting device.
Another aspect of embodiments provides an electronic apparatus including the light-emitting device. The electronic apparatus may further include a thin-film transistor. For example, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, wherein the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In an embodiment, the electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. For more details on the electronic apparatus, related descriptions provided herein may be referred to.
Hereinafter, the structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 will be described with reference to
In
The first electrode 110 may be formed by, for example, depositing and/or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high-work function material that facilitates injection of holes.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof.
The first electrode 110 may have a single-layered structure consisting of a single layer or a multi-layered structure including a plurality of layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
The interlayer 130 may be on the first electrode 110. The interlayer 130 may include an emission layer.
The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 150.
The interlayer 130 may further include, in addition to various suitable organic materials, a metal-containing compound such as an organometallic compound, an inorganic material such as quantum dots, and/or the like.
In one or more embodiments, the interlayer 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 between the two or more emitting units. When the interlayer 130 includes emitting units and a charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region may have: i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer consisting of a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
For example, the hole transport region may have a multi-layered structure including a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, the layers of each structure being stacked sequentially from the first electrode 110.
The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[00207] wherein, in Formulae 201 and 202,
For example, each of Formulae 201 and 202 may include at least one selected from groups represented by Formulae CY201 to CY217:
In Formulae CY201 to CY217, R10b and R10c may each be the same as described with respect to R10a, ring CY201 to ring CY204 may each independently be a C3-C20 carbocyclic group or a C1-C20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R10a as described above.
In an embodiment, ring CY201 to ring CY204 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In one or more embodiments, each of Formulae 201 and 202 may include at least one selected from groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formula 201 may include at least one selected from the groups represented by Formulae CY201 to CY203 and at least one selected from the groups represented by Formulae CY204 to CY217.
In one or more embodiments, in Formula 201, xa1 may be 1, R201 may be a group represented by one selected from Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one selected from Formulae CY204 to CY207.
In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one selected from Formulae CY201 to CY203.
In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one selected from Formulae CY201 to CY203, and may include at least one selected from the groups represented by Formulae CY204 to CY217.
In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one selected from Formulae CY201 to CY217.
In an embodiment, the hole transport region may include one selected from Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 30 Å to about 9,000 Å, about 40 Å to about 9,000 Å, about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 5 Å to about 2,000 Å, about 10 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 are within these ranges, suitable or satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer, and the electron blocking layer may block or reduce the leakage of electrons from an emission layer to a hole transport region. Materials that may be included in the hole transport region may be included in the emission auxiliary layer and the electron blocking layer.
The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties (e.g., electrically conductive properties). The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer consisting of a charge-generation material).
The charge-generation material may be, for example, a p-dopant.
For example, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be -3.5 eV or less.
In one or more embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including element EL1 and element EL2, or any combination thereof.
Examples of the quinone derivative are TCNQ, F4-TCNQ, etc.
Examples of the cyano group-containing compound are HAT-CN, and a compound represented by Formula 221:
In Formula 221,
In the compound including element EL1 and element EL2, element EL1 may be metal, metalloid, or any combination thereof, and element EL2 may be non-metal, metalloid, or any combination thereof.
Examples of the metal include an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metal (for example, 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.); post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), etc.); and lanthanide metal (for example, 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.).
Examples of the metalloid include silicon (Si), antimony (Sb), and tellurium (Te).
Examples of the non-metal include oxygen (O) and halogen (for example, F, Cl, Br, I, etc.).
Examples of the compound including element EL1 and element EL2 include metal oxide, metal halide (for example, metal fluoride, metal chloride, metal bromide, and/or metal iodide), metalloid halide (for example, metalloid fluoride, metalloid chloride, metalloid bromide, and/or metalloid iodide), metal telluride, or any combination thereof.
Examples of the metal oxide include tungsten oxide (for example, WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxide (for example, VO, V2O3, VO2, V2O5, etc.), molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), and rhenium oxide (for example, ReO3, etc.).
Examples of the metal halide include alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, and lanthanide metal halide.
Examples of the alkali metal halide include LiF, NaF, KF, RbF, CsF, LiCI, NaCl, KCI, RbCI, CsCI, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.
Examples of the alkaline earth metal halide include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2
Examples of the transition metal halide include titanium halide (for example, TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halide (for example, HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halide (for example, VF3, VCl3, VBr3, VI3, etc.), niobium halide (for example, NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halide (for example, TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halide (for example, CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halide (for example, MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halide (for example, WF3, WCl3, WBr3, WI3, etc.), manganese halide (for example, MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halide (for example, TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halide (for example, ReF2, ReCl2, ReBr2, ReI2, etc.), iron halide (for example, FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halide (for example, RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halide (for example, OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halide (for example, CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halide (for example, RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halide (for example, IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halide (for example, NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halide (for example, PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halide (for example, PtF2, PtCl2, PtBr2, PtI2, etc.), copper halide (for example, CuF, CuCl, CuBr, CuI, etc.), silver halide (for example, AgF, AgCl, AgBr, Agl, etc.), and gold halide (for example, AuF, AuCl, AuBr, AuI, etc.).
Examples of the post-transition metal halide include zinc halide (for example, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halide (for example, InI3, etc.), and tin halide (for example, SnI2, etc.).
Examples of the lanthanide metal halide include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3 SmCl3, YbBr, YbBr2, YbBr3 SmBr3, YbI, YbI2, YbI3, and SmI3
An example of the metalloid halide includes antimony halide (for example, SbCl5, etc.).
Examples of the metal telluride include alkali metal telluride (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal telluride (for example, 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 telluride (for example, ZnTe, etc.), and lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact (e.g., physically contact) each other or are spaced apart from each other to emit white light. In one or more embodiments, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed together with each other in a single layer to emit white light.
The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescence dopant, or any combination thereof.
The amount of the dopant in the emission layer may be from about 0.01 part by weight to about 15 parts by weight based on 100 parts by weight of the host.
In one or more embodiments, the emission layer may include a quantum dot.
In some embodiments, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may act as a host or a dopant in the emission layer.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
The host in the emission layer may include the first compound or the second compound described in the present specification, or any combination thereof.
In an embodiment, the host may include a compound represented by Formula 301 below:
In Formula 301,
For example, when xb11 in Formula 301 is 2 or more, two or more of Ar301(s) may be linked to each other via a single bond.
In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
In Formulae 301-1 and 301-2,
In one or more embodiments, the host may include an alkali earth metal complex, a post-transition metal complex, or any combination thereof. For example, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or any combination thereof.
In an embodiment, the host may include one selected from Compounds H1 to H124, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof:
The host may have various suitable modifications. For example, the host may include only one kind of compound, or may include two or more kinds of different compounds.
In one or more embodiments, the phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
The phosphorescent dopant may be electrically neutral.
For example, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[00283] wherein, in Formulae 401 and 402,
For example, in Formula 402, i) X401 may be nitrogen, and X402 may be carbon, or ii) each of X401 and X402 may be nitrogen.
In one or more embodiments, when xc1 in Formula 402 is 2 or more, two ring A401 (s) in two or more of L401 (s) may be optionally linked to each other via T402, which is a linking group, and two ring A402(s) may be optionally linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each be the same as described herein with respect to T401.
L402 in Formula 401 may be an organic ligand. For example, L402 may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or any combination thereof.
The phosphorescent dopant may include, for example, one selected from compounds PD1 to PD40, or any combination thereof:
The fluorescence dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
For example, the fluorescence dopant may include a compound represented by Formula 501:
[00302] wherein, in Formula 501,
For example, Ar501 in Formula 501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, or a pyrene group) in which three or more monocyclic groups are condensed together.
In one or more embodiments, xd4 in Formula 501 may be 2.
For example, the fluorescence dopant may include: one selected from Compounds FD1 to FD36; DPVBi; DPAVBi; or any combination thereof:
The emission layer may include a delayed fluorescence material.
In the present specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescent light based on a delayed fluorescence emission mechanism.
The delayed fluorescence material included in the emission layer may act as a host or a dopant depending on the type (or kind) of other materials included in the emission layer.
In one or more embodiments, the difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be greater than or equal to 0 eV and less than or equal to 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material satisfies the above-described range, up-conversion from a triplet state to a singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be improved.
For example, the delayed fluorescence material may include i) a material including at least one electron donor (for example, a Π electron-rich C3-C60 cyclic group, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, or a Π electron-deficient nitrogen-containing C1-C60 cyclic group), and ii) a material including a C8-C60 polycyclic group in which two or more cyclic groups are condensed together while sharing boron (B).
Examples of the delayed fluorescence material may include at least one selected from Compounds DF1 to DF10:
The emission layer may include quantum dots.
The term “quantum dots,” as used herein, refers to crystals of a semiconductor compound, and may include any suitable material capable of emitting light of various suitable emission wavelengths according to the size of the crystals.
A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, and/or any suitable process similar thereto.
The wet chemical process is a method including mixing a precursor material together with an organic solvent and then growing a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled through a process which costs lower, and is easier than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE),
The quantum dot may include Group II-VI semiconductor compounds, Group III-V semiconductor compounds, Group III-VI semiconductor compounds, Group I-III-VI semiconductor compounds, Group IV-VI semiconductor compounds, a Group IV element and/or compound, or any combination thereof.
Examples of the Group II-VI semiconductor compound include a binary compound, such as CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and/or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, and/or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and/or HgZnSTe; or any combination thereof.
Examples of the Group III-V semiconductor compound may include: a binary compound, such as GaN, GaP, GaAs, GaSb, AIN, AIP, AlAs, AlSb, InN, InP, InAs, and/or InSb; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AINP, AINAs, AINSb, AIPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and/or InPSb; a quaternary compound, such as GaAINP, GaAINAs, GaAINSb, GaAIPAs, GaAIPSb, GalnNP, GalnNAs, GalnNSb, GalnPAs, GalnPSb, InAINP, InAINAs, InAINSb, InAIPAs, and/or InAIPSb; or any combination thereof. In some embodiments, the Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including a Group II element are InZnP, InGaZnP, InAIZnP, etc.
Examples of the Group III-VI semiconductor compound include: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, and/or InTe; a ternary compound, such as InGaS3, and/or InGaSe3; and any combination thereof.
Examples of the Group I-III-VI semiconductor compound include: a ternary compound, such as AgInS, AgInS2, CulnS, CuInS2, CuGaO2, AgGaO2, and/or AgAlO2; or any combination thereof.
Examples of the Group IV-VI semiconductor compound include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, and/or PbTe; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, and/or SnPbTe; a quaternary compound, such as SnPbSSe, SnPbSeTe, and/or SnPbSTe; or any combination thereof.
The Group IV element and/or compound may include: a single element compound, such as Si and/or Ge; a binary compound, such as SiC and/or SiGe; or any combination thereof.
Each element included in a multi-element compound such as the binary compound, the ternary compound, and the quaternary compound may be present at a uniform concentration or non-uniform concentration in a particle.
In some embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is uniform (e.g., substantially uniform), or a core-shell dual structure. For example, the material included in the core and the material included in the shell may be different from each other.
The shell of the quantum dot may act as a protective layer that prevents or reduce chemical degeneration of the core to maintain semiconductor characteristics, and/or as a charging layer that imparts electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. The interface between the core and the shell may have a concentration gradient in which the concentration of an element existing in the shell decreases along a direction toward the center of the core.
Examples of the shell of the quantum dot may be an oxide of metal, metalloid, and/or non-metal, a semiconductor compound, and any combination thereof. Examples of the oxide of metal, metalloid, and/or non-metal include a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and/or NiO; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, and/or CoMn2O4; and any combination thereof. Examples of the semiconductor compound include, as described herein, Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; and any combination thereof. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AIP, AlSb, or any combination thereof.
A full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dot may be about 45 nm or less, for example, about 40 nm or less, for example, about 30 nm or less, and within these ranges, color purity or color reproducibility may be increased. In addition, because the light emitted through the quantum dot is emitted in all directions (e.g., substantially all directions), a wide viewing angle may be improved.
In addition, the quantum dot may be in the form of a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, and/or a nanoplate particle.
Because the energy band gap may be adjusted by controlling the size of the quantum dot, light having various suitable wavelength bands may be obtained from the quantum dot emission layer. Accordingly, by using quantum dots of different sizes, a light-emitting device that emits light of various suitable wavelengths may be implemented. In one or more embodiments, the size of the quantum dot may be selected to emit red, green and/or blue light. In addition, the size of the quantum dot may be configured to emit white light by combination of light of various suitable colors.
The electron transport region may have: i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer consisting of a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The electron transporting region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transporting layer, an electron injection layer, or any combination thereof.
For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, the constituting layers of each structure being sequentially stacked from an emission layer.
In an embodiment, the electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer, and/or the electron transport layer in the electron transport region) may include a metal-free compound including at least one Π electron-deficient nitrogen-containing C1-C60 cyclic group.
For example, the electron transport region may include a compound represented by Formula 601 below:
[00339] wherein, in Formula 601,
For example, when xe11 in Formula 601 is 2 or more, two or more of Ar601(s) may be linked to each other via a single bond.
In other embodiments, Ar601 in Formula 601 may be a substituted or unsubstituted anthracene group.
In other embodiments, the electron transport region may include a compound represented by Formula 601-1:
[00350] wherein, in Formula 601-1,
For example, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
The electron transport region may include one selected from Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAIq, TAZ, NTAZ, or any combination thereof:
A thickness of the electron transport region may be from about 100 Å to about 5,000 Å, for example, about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be from 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 from about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, suitable or satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of an alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and the metal ion of an alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) and/or ET-D2:
The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may directly contact (e.g., physically contact) the second electrode 150.
The electron injection layer may have: i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer consisting of a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
The electron injection layer may include an alkali metal, alkaline earth metal, a rare earth metal, an alkali metal-containing compound, 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.
The alkali metal may include Li, a 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.
The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include oxides, halides (for example, fluorides, chlorides, bromides, and/or iodides), and/or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
The alkali metal-containing compound may include: alkali metal oxides, such as Li2O, Cs2O, and/or K2O; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and/or KI; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1—xO (wherein x is a real number satisfying the condition of 0<x<1), BaxCa1—xO (wherein x is a real number satisfying the condition of 0<x<1), and/or the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, Scl3, TbI3, or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include lanthanide metal telluride. Examples of the lanthanide metal telluride include 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, and Lu2Te3.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one selected from ions of the alkali metal, the alkaline earth metal, and the rare earth metal and ii), as a ligand bonded to the metal ion, for example, a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenyl benzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
The electron injection layer may include (e.g., consist of) 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, as described above. In one or more embodiments, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).
In one or more embodiments, the electron injection layer may include (e.g., consist of): i) an alkali metal-containing compound (for example, an alkali metal halide); or ii) a) an alkali metal-containing compound (for example, 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 Rbl:Yb co-deposited layer, and/or the like.
When the electron injection layer further includes an organic material, alkali metal, alkaline earth metal, rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a 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 including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the ranges described above, suitable or satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be on the interlayer 130 having a structure as described above. The second electrode 150 may be a cathode, which is an electron injection electrode, and as the material for the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low-work function, may be used.
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 semi-transmissive electrode, or a reflective electrode.
The second electrode 150 may have a single-layered structure or a multi-layered structure including a plurality of layers.
A first capping layer may be outside the first electrode 110, and/or a second capping layer may be outside the second electrode 150. In particular, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in the stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in the stated order.
Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110 which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer. Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150 which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.
The first capping layer and the second capping layer may increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.
Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or more (at a wavelength of 589 nm).
The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
At least one selected from the first capping layer and the second capping layer may each independently include carbocyclic compounds, heterocyclic compounds, amine group-containing compounds, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or any combination thereof. Optionally, the carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one selected from the first capping layer and the second capping layer may each independently include an amine group-containing compound.
For example, at least one selected from the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
In one or more embodiments, at least one selected from the first capping layer and the second capping layer may each independently include one selected from Compounds HT28 to HT33, one selected from Compounds CP1 to CP6, [β-NPB, or any combination thereof:
The heterocyclic compound represented by Formula 1 may be included in various suitable films. Accordingly, another aspect of embodiments of the present disclosure provides a film including the heterocyclic compound represented by Formula 1. The film may be, for example, an optical member (e.g., a light control means) (for example, a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, and/or the like), a light-blocking member (for example, a light reflective layer, a light absorbing layer, and/or the like), a protective member (for example, an insulating layer, a dielectric layer, and/or the like).
The light-emitting device may be included in various suitable electronic apparatuses. For example, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, and/or the like.
The electronic apparatus (for example, a light-emitting apparatus) may further include, in addition to the light-emitting device, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be in at least one traveling direction of light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light or white light. For more details on the light-emitting device, related description provided above may be referred to. In one or more embodiments, the color conversion layer may include a quantum dot. The quantum dot may be, for example, a quantum dot as described herein.
The electronic apparatus may include a first substrate. The first substrate may include a plurality of subpixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the subpixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the subpixel areas.
A pixel-defining film may be located among the subpixel areas to define each of the subpixel areas.
The color filter may further include a plurality of color filter areas and light-shielding patterns located among the color filter areas, and the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns located among the color conversion areas.
The plurality of color filter areas (or the plurality of color conversion areas) may include a first area that emits a first color light, a second area that emits a second color light, and/or a third area that emits 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 from one another. 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 areas (or the plurality of color conversion areas) may include quantum dots. In particular, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include a quantum dot. For more details on the quantum dot, related descriptions provided herein may be referred to. The first area, the second area, and/or the third area may each include a scatterer (e.g., a light scatterer).
For example, the light-emitting device may emit a first light, the first area may absorb the first light to emit a first-first color light, the second area may absorb the first light to emit a second-first color light, and the third area may absorb the first light to emit a third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. In particular, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device as described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein any one selected from the source electrode and the drain electrode may be electrically connected to any one selected from the first electrode and the second electrode of the light-emitting device.
The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.
The activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and/or the like.
The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be between the color conversion layer and/or color filter and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and concurrently (e.g., simultaneously) prevents or reduces penetration of ambient air and/or moisture into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate and/or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic apparatus may be flexible.
Various suitable functional layers may be additionally on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the use of the electronic apparatus. Examples of the functional layers may include a touch screen layer, a polarizing layer, and the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, and/or an infrared touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by using biometric information of a living body (for example, fingertips, pupils, etc.).
The authentication apparatus may further include, in addition to the light-emitting device as described above, a biometric information collector.
The electronic apparatus may be applied to various suitable displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, and/or endoscope displays), fish finders, various suitable measuring instruments, meters (for example, meters for a vehicle, an aircraft, and/or a vessel), projectors, and/or the like.
The light-emitting apparatus of
The substrate 100 may be a flexible substrate, a glass substrate, and/or a metal substrate. A buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
A TFT may be on the buffer layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The activation layer 220 may include an inorganic semiconductor such as silicon and/or polysilicon, an organic semiconductor, and/or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
A gate insulating film 230 for insulating the activation layer 220 from the gate electrode 240 may be on the activation layer 220, and the gate electrode 240 may be on the gate insulating film 230.
An interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270, to insulate from one another.
The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may expose the source region and the drain region of the activation layer 220, and the source electrode 260 and the drain electrode 270 may be in contact (e.g., physical contact) with the exposed portions of the source region and the drain region of the activation layer 220.
The TFT is electrically connected to a light-emitting device to drive the light-emitting device, 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 any combination thereof. A light-emitting device is provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may expose a portion of the drain electrode 270, not fully covering the drain electrode 270, and the first electrode 110 may be connected to the exposed portion of the drain electrode 270.
A pixel defining layer 290 including an insulating material may be on the first electrode 110. The pixel defining layer 290 may expose a certain region of the first electrode 110, and an interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide and/or polyacrylic organic film. In some embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 to be in the form of a common layer.
The second electrode 150 may be on the interlayer 130, and a capping layer 170 may be additionally on the second electrode 150. The capping layer 170 may cover the second electrode 150.
The encapsulation portion 300 may be on the capping layer 170. The encapsulation portion 300 may be on a light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), and/or the like), or any combination thereof; or any combination of the inorganic films and the organic films.
The light-emitting apparatus of
The layers included in the hole transport region, the emission layer, and the layers included in the electron transport region may be formed in a certain region by using various suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, laser-induced thermal imaging, and/or the like.
When layers constituting the hole transport region, an emission layer, and layers constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10-8 torr to about 10-3 torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.
The term “C3-C60 carbocyclic group,” as used herein, refers to a cyclic group consisting of carbon only as a ring-forming atom and having three to sixty carbon atoms, and the term “C1-C60 heterocyclic group,” as used herein, refers to a cyclic group that has one to sixty carbon atoms and further has, in addition to carbon, a heteroatom as a ring-forming atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed together with each other. For example, the C1-C60 heterocyclic group has 3 to 61 ring-forming atoms.
The term “cyclic group,” as used herein, may include the C3-C60 carbocyclic group, and the C1-C60 heterocyclic group.
The term “π electron-rich C3-C60 cyclic group,” as used herein, refers to a cyclic group that has three to sixty carbon atoms and does not include *—N═*’ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C1-C60 cyclic group,” as used herein, refers to a heterocyclic group that has one to sixty carbon atoms and includes *—N═*’ as a ring-forming moiety.
For example,
The terms “the cyclic group, ” “the C3-C60 carbocyclic group, ” “the C1-C60 heterocyclic group, ” “the π electron-rich C3-C60 cyclic group,” or “the π electron-deficient nitrogen-containing C1-C60 cyclic group,” as used herein, refer to a group condensed to any cyclic group, a monovalent group, or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of a formula for which the corresponding term is used. For example, the “benzene group” may be a benzo group, a phenyl group, a phenylene group, or the like, which may be easily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
Examples of the monovalent C3-C60 carbocyclic group and the monovalent C1-C60 heterocyclic group include a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group. Examples of the divalent C3-C60 carbocyclic group and the monovalent C1-C60 heterocyclic group include a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group,” as used herein, refers to a linear or branched aliphatic hydrocarbon monovalent group that has one to sixty carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. The term “C1-C60 alkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group,” as used herein, refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond at a main chain (e.g., in the middle) or at a terminal end (e.g., the terminus) of the C2-C60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group,” as used herein, refers to a divalent group having substantially the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group,” as used herein, refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond at a main chain (e.g., in the middle) or at a terminal end (e.g., the terminus) of the C2-C60 alkyl group, and examples thereof include an ethynyl group and a propynyl group. The term “C2-C60 alkynylene group,” as used herein, refers to a divalent group having substantially the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group,” as used herein, refers to a monovalent group represented by -OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C3-C10 cycloalkyl group,” as used herein, refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term “C3-C10 cycloalkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group,” as used herein, refers to a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group,” as used herein, refers to a monovalent cyclic group that has three to ten carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity (e.g., is not aromatic), and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group,” as used herein, refers to a divalent group having substantially the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group,” as used herein, refers to a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having at least one carbon-carbon double bond in the cyclic structure thereof. Examples of the C1-C10 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group,” as used herein, refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group,” as used herein, refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term “C6-C60 arylene group,” as used herein, refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Examples of the C6-C60 aryl group include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be condensed together with each other.
The term “C1-C60 heteroaryl group,” as used herein, refers to a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. The term “C1-C60 heteroarylene group,” as used herein, refers to a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be condensed together with each other.
The term “monovalent non-aromatic condensed polycyclic group,” as used herein, refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure (e.g., is not aromatic when considered as a whole). Examples of the monovalent non-aromatic condensed polycyclic group are an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indeno anthracenyl group. The term “divalent non-aromatic condensed polycyclic group,” as used herein, refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group described above.
The term “monovalent non-aromatic condensed heteropolycyclic group,” as used herein, refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and having non-aromaticity in its entire molecular structure (e.g., is not aromatic when considered as a whole). Examples of the monovalent non-aromatic condensed heteropolycyclic group include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphtho indolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group,” as used herein, refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group described above.
The term “C6-C60 aryloxy group,” as used herein, indicates -OA102 (wherein A102 is a C6-C60 aryl group), and the term “C6-C60 arylthio group,” as used herein, indicates -SA103 (wherein A103 is a C6-C60 aryl group).
The term “C7-C60 aryl alkyl group,” as used herein, refers to -A104A105 (where A104 may be a C1-C54 alkylene group, and A105 may be a C6-C59 aryl group), and the term C2-C60 heteroaryl alkyl group” used herein refers to -A106A107 (where A106 may be a C1-C59 alkylene group, and A107 may be a C1-C59 heteroaryl group).
The term “R10a,” as used herein, refers to:
The term “heteroatom,” as used herein, refers to any atom other than a carbon atom. Examples of the heteroatom are O, S, N, P, Si, B, Ge, Se, and any combinations thereof.
The term “third-row transition metal,” as used herein, includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and the like.
“Ph,” as used herein, refers to a phenyl group, “Me,” as used herein, refers to a methyl group, “Et,” as used herein, refers to an ethyl group, “tert-Bu” or “But,” as used herein, refers to a tert-butyl group, and “OMe,” as used herein, refers to a methoxy group.
The term “biphenyl group,” as used herein, refers to “a phenyl group substituted with a phenyl group.” In other words, the “biphenyl group” is a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group,” as used herein, refers to “a phenyl group substituted with a biphenyl group”. In other words, the “terphenyl group” is a substituted phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.
* and *’, as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.
Hereinafter, compounds according to embodiments and light-emitting devices according to embodiments will be described in more detail with reference to the following synthesis examples and examples. The wording “B was used instead of A” used in describing Synthesis Examples means that an identical molar equivalent of B was used in place of A.
Pd(OAc)2 (0.1 eq), [(t-Bu)3PH]BF4 (0.15 eq), K2CO3 (5 eq), and toluene (0.1 M, 1 eq reagent basis) were added to 3-bromo-12H-benzo[4,5]thieno[2,3-a]carbazole (1 eq) and 3-bromo-1,1′-biphenyl (1.2 eq) in a flask and the resultant mixture was stirred for 24 hours while refluxing. The resultant reaction mixture was cooled to room temperature, an extraction process was performed thereon by using methylene chloride (MC), and then washing was carried out with distilled water. After drying with MgSO4, a residue obtained by distillation under reduced pressure was separated by column chromatography, thereby obtaining Intermediate 1 (12-([1,1′-biphenyl]-3-yl)-3-bromo-12H-benzo[4,5]thieno[2,3-a]carbazole)(yield of 79.9 %). Intermediate 1 was confirmed with liquid chromatography-mass spectrometry (LC-MS).
Pd(dba)3 (0.06 eq), (t-Bu)3P (0.09 eq), t-BuONa (4.4 eq), and toluene (0.1 M, 1 eq reagent basis) were added to Intermediate 1 (1 eq) and 9H-carbazole (1.2 eq) in a flask and the resultant mixture was stirred for 24 hours while refluxing. The resultant reaction mixture was cooled to room temperature, an extraction process was performed thereon by using methylene chloride (MC), and then washing was carried out with distilled water. After drying with MgSO4, a residue obtained by distillation under reduced pressure was separated by column chromatography, thereby obtaining HT-01 (yield of 90.5 %). HT-01 was confirmed by LC-MS.
Pd(dba)3 (0.06 eq), (t-Bu)3P (0.09 eq), t-BuONa (4.4 eq) and toluene (0.1 M, 1 eq reagent basis) were added to Intermediate 1 (1 eq) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.2 eq) in a flask, and the resultant mixture was stirred for 26 hours while refluxing. The resultant reaction mixture was cooled to room temperature, an extraction process was performed thereon by using methylene chloride (MC), and then washing was carried out with distilled water. After drying with MgSO4, a residue obtained by distillation under reduced pressure was separated by column chromatography, thereby obtaining HT-02 (yield of 79.8 %). HT-02 was confirmed by LC-MS.
Pd(dba)3 (0.06 eq), (t-Bu)3P (0.1 eq), t-BuONa (4.4 eq), and toluene (0.1 M, 1 eq reagent basis) were added to 12-([1,1′-biphenyl]-3-yl-2′,3′,4′,5′,6′-d5)-3-bromo-12H-benzo[4,5]thieno[2,3-a]carbazole (1 eq) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.2 eq) in a flask and stirred for 26 hours while refluxing. The resultant reaction mixture was cooled to room temperature, an extraction process was performed thereon by using methylene chloride (MC), and then washing was carried out with distilled water. After drying with MgSO4, a residue obtained by distillation under reduced pressure was separated by column chromatography, thereby obtaining HT-03 (yield of 71.9 %). HT-03 was confirmed by LC-MS.
(C42H13D13N2S : [M]+ 603.82)
1H-NMR and MS/FAB of the compounds used in Synthesis Examples 1 to 3 and Comparative Examples are shown in Table 1. Synthesis methods for other compounds than the compounds shown in Table 1 may be easily recognized by those skilled in the technical field by referring to the synthesis paths and source material materials described above.
1H-NMR (CDCl3 , 500 MHz)
HOMO energy, LUMO energy, simulation maximum emission wavelength (λmaxsim), and experimental maximum emission wavelength (λmaxexp) of compounds used in Synthesis Examples 1 to 3 and Comparative Examples below were measured, and results thereof are shown in Table 3.
Particularly, the HOMO and LUMO energy levels were evaluated according to the method described in Table 2, and λmaxsim and λmaxexp were evaluated by using a density functional theory (DFT) method of the Gaussian 09 program (with structure optimization at a B3LYP, 6-311 G(d,p) level of theory, e.g., using the B3LYP hybrid functional and 6-311 G(d,p) basis set).
An ITO glass substrate was cut to a size of 50 mm x 50 mm x 0.5 mm, ultrasonically cleaned with isopropyl alcohol and pure water each for 10 minutes, and then cleaned by irradiation of ultraviolet rays and exposure to ozone for 10 minutes. Then, the ITO glass substrate was loaded onto a vacuum deposition apparatus.
m-MTDATA was vacuum-deposited on the ITO glass substrate to form a hole injection layer having a thickness of 40 Å, and NPB, which is a hole transport material, was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 10 Å. The first compound, the second compound, and Dopant-1 (DF10) were simultaneously vacuum-deposited to a weight ratio of 46:46:8 on the hole transport layer to form an emission layer having a thickness of 300 Å. Subsequently, ET1 was deposited on the emission layer to form an electron transport layer having a thickness of 300 Å and Al was vacuum-deposited on the electron transport layer to form an Al electrode having a thickness of 1,200 Å (cathode), thereby completing the manufacture of an organic electroluminescent device.
Materials used in the above-described organic electroluminescent light-emitting device may be represented by the formula below.
The light-emitting device was manufactured in substantially the same manner as in Example 1 except that, when forming the emission layer, the compounds in Table 4 were used as the first compound, the second compound, and the dopant. Among the compounds in Table 4, Dopant-2 is PD40.
To evaluate the characteristics of the organic electroluminescent device according to the Examples and Comparative Examples, the luminescence efficiency (cd/A) and lifespan (T90) of the organic light-emitting device at a current density of 10 mA/cm2 were each measured by using a Keithley MU 236 and a luminance meter PR650, and the result thereof are each shown in Table 4. In Table 4, the lifespan (T90) is a measure of the time (hr) taken for the luminance to reach 90 % of the initial luminance.
From Table 4, it can be seen that, compared to the organic light-emitting devices of Comparative Examples 1 to 6 using one type (or kind) of host and of Comparative Examples 7 to 10 in which the first compound does not satisfy Formula 1, the organic light-emitting devices of Examples 1 to 14 including the first compound represented by Formula 1 and the second compound including at least one π electron-deficient nitrogen-containing C1-C60 cyclic group have improved luminescence efficiency and lifespan characteristics due to accelerated formation of excitons in the emission layer.
Although the present disclosure has been described with reference to the Synthesis Examples and Examples, these examples are provided for illustrative purposes only, and one of ordinary skill in the art should understand that these examples may have various suitable modifications and other examples equivalent thereto. Accordingly, the scope of the present disclosure should be determined by the appended claims, and equivalents thereof.
A light-emitting device may have excellent luminescence efficiency and luminescence lifespan by using the heterocyclic compound, and the light-emitting device may be used in manufacturing a high-quality electronic apparatus.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the following claims, and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2021-0176939 | Dec 2021 | KR | national |
