Patent Application
20250223283
One or more aspects of embodiments of the present disclosure relate to a compound and an organic light-emitting device including the same.
Organic light-emitting devices are self-emission devices that have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of brightness, driving voltage, and/or response speed, compared to devices in the related art.
The organic light-emitting device may include a first electrode disposed (positioned) on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode, which are sequentially disposed on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, may then recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state, thereby generating light.
One or more aspects of embodiments of the present disclosure are directed toward a hole transport compound having high efficiency characteristics compared to the already existing compounds and a device including the hole transport compound.
Additional aspects 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 an embodiment of the present disclosure,
In Formula 1,
According to another embodiment of the present disclosure, an organic light-emitting including: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer is provided, wherein the organic layer includes the compound of Formula 1.
According to another embodiment of the present disclosure, an electronic apparatus includes:
The above and other aspects, features, and advantages of certain embodiments of the 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 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.
Expressions such as “at least one of,” “one of,” and “selected from,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list. Further, the use of “may” when describing embodiments of the present invention may refer to “one or more embodiments of the present invention.”
An embodiment of the present disclosure provides a compound represented by Formula 1:
In Formula 1,
In the heteroaryl group and the heteroarylene group, a carbazolyl group and a carbazolylene group are excluded. For example, Formula 1 may include only one carbazole moiety.
Regarding the carbazole moiety in Formula 1 according to an embodiment, a benzene moiety (ring) not binding to L2 is in an unsubstituted state.
In one embodiment, Ar1 and Ar2 in Formula 1 may each independently be selected from a substituted or unsubstituted C6-C60 aryl group and a substituted or unsubstituted C1-C60 heteroaryl group.
In one embodiment, Ar1 may be selected from Formulae 2a to 2c:
In Formulae 2a to 2c,
In one embodiment, Z11 in Formula 2a may be a substituted or unsubstituted C6-C60 aryl group.
In one embodiment, Z11 in Formula 2a may be selected from —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, and groups represented by Formulae 3a and 3b:
In Formulae 3a and 3b,
In one embodiment, Ar2 in Formula 1 may be a substituted or unsubstituted C6-C60 aryl group, and for example, may be a C6-C60 aryl group substituted with —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, and/or a hydrazone group. For example, Ar2 in Formula 1 may be a C6-C60 aryl group substituted with —F, —Cl, —Br, and/or —I.
In one embodiment, L1 and L2 in Formula 1 may each independently be a substituted or unsubstituted C6-C60 arylene group. For example, L1 and L2 in Formula 1 may each independently be selected from: phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-fluorene-benzofluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, and a ovalenylene group, and
In one embodiment, Formula 1 may be Formula 2:
In Formula 2,
In one embodiment, Formula 1 may be Formula 3:
In Formula 3,
In one embodiment, Formula 1 may be Formula 4:
In Formula 4,
In one embodiment, Formula 1 may be Formula 5:
In Formula 5,
In one embodiment, the compound of Formula 1 may be one of compounds illustrated below:
The expression “(an organic layer) includes at least one compound” as used herein may include a case in which “(an organic layer) includes one or more identical compounds represented by Formula 1” and a case in which “(an organic layer) includes two or more different compounds represented by Formula 1”
For example, an organic layer may include, as the compound of Formula 1, only Compound 1. Here, Compound 1 may exist (e.g., may be included) only in an emission layer of an organic light-emitting device. In one or more embodiments, an organic layer may include, as the compound of Formula 1, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may exist in an identical (same) layer (for example, Compound 1 and Compound 2 may both exist in an emission layer), or in different layers (for example, Compound 1 may exist in an emission layer and Compound 2 may exist in an electron transport region).
Another embodiment of the present disclosure provides an organic light-emitting device including:
In one embodiment,
In one embodiment, the emission layer may be a fluorescence emission layer. For example, the emission layer may be a blue fluorescence emission layer.
In one embodiment, the compound of Formula 1 may be used in a hole transport region, for example, in a hole transport layer.
Another embodiment of the present disclosure provides an electronic apparatus including: a thin-film transistor; and the organic light-emitting device, wherein the thin-film transistor includes a source electrode, a drain electrode, an activation layer, and a gate electrode, and the first electrode of the organic light-emitting device is in electrical connection with at least one of the source electrode and the drain electrode of the thin-film transistor.
The term “an organic layer” as used herein may refer to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of an organic light-emitting device. A material included in the “organic layer” is not limited to an organic material.
Hereinafter, the structure of the organic light-emitting device 10 according to an embodiment and a method of manufacturing the organic light-emitting device 10 will be described in connection with
In
The first electrode 110 may be formed by depositing or sputtering a material to form the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material to form the first electrode 110 may be selected from materials with a high work function to facilitate hole injection.
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 to form a first electrode may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combinations thereof, but embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material to form the first electrode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combinations thereof, but embodiments of the present disclosure are not limited thereto.
The first electrode 110 may have a single-layered structure, or a multi-layered structure including two or more layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.
The organic layer 150 may be disposed on the first electrode 110. The organic layer 150 may include an emission layer.
The organic layer 150 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 190.
The hole transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.
For example, the hole transport region may have a single-layered structure including a single layer including a plurality of different materials, or a multi-layered structure having 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, wherein for each structure, constituting layers are sequentially stacked from the first electrode 110 in this stated order, but the structure of the hole transport region is not limited thereto.
The hole transport region may include the compound of Formula 1.
The hole transport region may further include, for example, in addition to the compound of Formula 1, a compound described below.
In one embodiment, the hole transport region may include at least one selected from 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), and polyaniline/poly(4-styrenesulfonate) (PANI/PSS):
A thickness of the hole transport region may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, and for example, about 100 Å to about 1500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, satisfactory (or suitable) 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 flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may each independently include any of the materials as described above.
p-dopant
The hole transport region may further include, in addition to the materials described above, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
The charge-generation material may be, for example, a p-dopant.
In one embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of −3.5 ev or less.
The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto.
In one embodiment, the p-dopant may include at least one selected from:
In Formula 221,
When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, 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 selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from 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 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 at least one selected from a phosphorescent dopant and a fluorescent dopant.
In the emission layer, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
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 this range, excellent (or suitable) light-emission characteristics may be obtained without a substantial increase in driving voltage.
The emission layer may include a quantum dot.
In one or more embodiments, the host may include a compound represented by Formula 301 below.
[Ar301]xb11-[(L301)xb1-R301]xb21. Formula 301
In Formula 301,
In one embodiment, Ar301 in Formula 301 may be selected from:
When xb11 in Formula 301 is 2 or more, two or more Ar301(s) may be linked to each other via a single bond.
In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2:
In Formulae 301-1 and 301-2,
For example, L301 to L304 in Formulae 301, 301-1, and 301-2 may each independently be selected from:
In one embodiment, R301 to R304 in Formulae 301, 301-1, and 301-2 may each independently be selected from:
In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (for example, Compound H55), a Mg complex, and a Zn complex.
The host may include at least one selected from 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), and Compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:
The phosphorescent dopant may include an organometallic complex represented by Formula 401:
In Formulae 401 and 402,
In one embodiment, A401 and A402 in Formula 402 may each independently be selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group, and a dibenzothiophene group.
In one or more embodiments, in Formula 402, i) X401 may be nitrogen, and X402 may be carbon, or ii) X401 and X402 may each be nitrogen at the same time.
In one or more embodiments, R401 and R402 in Formula 402 may each independently be selected from:
In one or more embodiments, when xc1 in Formula 401 is 2 or more, two A401(s) in two or more L401(s) may optionally be linked to each other via X407, which is a linking group, and/or two A402(s) in two or more L401(s) may optionally be linked to each other via X408, which is a linking group (see e.g., Compounds PD1 to PD4 and PD7). X407 and X408 may each independently be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q413)-*′, *—C(Q413)(Q414)-*′, and/or *—C(Q413)═C(Q414)-*′ (wherein Q413 and Q414 may each independently be hydrogen, deuterium, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and/or a naphthyl group), but are not limited thereto.
L402 in Formula 401 may be a monovalent, divalent, and/or trivalent organic ligand. For example, L402 may be selected from halogen, diketone (for example, acetylacetonate), carboxylic acid (for example, picolinate), —C(═O), isonitrile, —CN, and phosphorus (for example, phosphine and/or phosphite), but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, the phosphorescence dopant may be selected from, for example, Compounds PD1 to PD25, but embodiments of the present disclosure are not limited thereto:
The fluorescent dopant may include an arylamine compound and/or a styrylamine compound.
The fluorescent dopant may include a compound represented by Formula 501:
In Formula 501,
In one embodiment, Ar501 in Formula 501 may be selected from:
In one or more embodiments, L501 to L503 in Formula 501 may each independently be selected from:
In one or more embodiments, R501 and R502 in Formula 501 may each independently be selected from:
In one or more embodiments, xd4 in Formula 501 may be 2, but embodiments of the present disclosure are not limited thereto.
For example, the fluorescent dopant may be selected from Compounds FD1 to FD22:
In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but embodiments of the present disclosure are not limited thereto:
The emission layer may include a quantum dot selected from a IV-VI group compound, a IV group element, and a IV group compound. The IV-VI group compound may be selected from: a binary compound selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe, and any mixture thereof; a ternary compound selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and any mixture thereof; and a quaternary compound selected from SnPbSSe, SnPbSeTe, SnPbSTe, and any mixture thereof. The IV group element may be selected from Si, Ge, and any mixture thereof. The IV group compound may be a binary compound selected from SiC, SiGe, and any mixture thereof.
The binary compound, the ternary compound, or the quaternary compound may each independently exist in particles at uniform concentration, or may exist in the same particle in a state in which a concentration distribution is partially different. In addition, the binary compound, the ternary compound, or the quaternary compound may each independently have a core-shell structure, in which one quantum dot surrounds another quantum dot. An interface between the core and the shell may have a concentration gradient in which the concentration of atoms existing in the shell decreases toward the center.
In one or more embodiments, the quantum dot may have a core-shell structure including a core with the above-described nanoparticles and a shell surrounding the core. The shell of the quantum dot may serve as a protective layer for maintaining semiconductor characteristics by preventing or reducing chemical degeneration of the core, and/or may serve as a charging layer for imparting electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multilayer. An interface between the core and the shell may have a concentration gradient in which the concentration of atoms existing in the shell decreases toward the center. Examples of the shell of the quantum dot may include a metal oxide, a non-metal oxide, a semiconductor compound, and combinations thereof.
For example, examples of the metal oxide and non-metal oxide may include a binary compound (such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and/or NiO), and a ternary compound (such as MgAl2O4, CoFe2O4, NiFe2O4, and/or CoMn2O4), but embodiments of the present disclosure are not limited thereto.
Examples of the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, and the like, but embodiments of the present disclosure are not limited thereto.
A full width of half maximum (FWHM) of an 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. When the FWHM of the emission wavelength spectrum of the quantum dot is within this range, color purity and/or color reproduction may be improved.
In some embodiments, light emitted through such quantum dot is irradiated in omnidirection, thereby improving a wide viewing angle. More specifically, a spherical, pyramidal, multi-arm, and/or cubic nanoparticle, a nanotube, a nanowire, a nanofiber, and/or nanoplate particle may be used.
The quantum dot may adjust the color of emitted light according to the particle size. Therefore, the quantum dot may emit various emission colors such as blue, red, and/or green.
The electron transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
The electron transport region may include at least one selected from a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.
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 an electron transport layer/electron injection layer structure, wherein for each structure, constituting layers are sequentially stacked from an emission layer. However, embodiments of the structure of the electron transport region are not limited thereto.
The electron transport region (for example, a buffer layer, a hole blocking layer, an electron control layer, and/or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-depleted nitrogen-containing ring.
The “π electron-depleted nitrogen-containing ring” may refer to a C1-C60 heterocyclic group having at least one *—N═*′ moiety as a ring-forming moiety.
For example, the “π electron-depleted nitrogen-containing ring” may be i) a 5-membered to 7-membered heteromonocyclic group having at least one *—N═*′ moiety, ii) a heteropolycyclic group in which two or more 5-membered to 7-membered heteromonocyclic groups, each having at least one *—N═*′ moiety, are condensed with each other, or iii) a heteropolycyclic group in which at least one of 5-membered to 7-membered heteromonocyclic groups, each having at least one *—N═*′ moiety, is condensed with at least one C5-C60 carbocyclic group.
Examples of the π electron-depleted nitrogen-containing ring include an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, an indazole, a purine, a quinoline, an isoquinoline, a benzoquinoline, a phthalazine, a naphthyridine, a quinoxaline, a quinazoline, a cinnoline, a phenanthridine, an acridine, a phenanthroline, a phenazine, a benzimidazole, an isobenzothiazole, a benzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a triazine, a thiadiazole, an imidazopyridine, an imidazopyrimidine, and an azacarbazole, but are not limited thereto.
For example, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21. Formula 601
In Formula 601,
In one embodiment, at least one of Ar601(s) in the number of xe11 and at least one of R601(s) in the number of xe21 may each independently include the π electron-depleted nitrogen-containing ring.
In one embodiment, Ar601 in Formula 601 may be selected from:
When xe11 in Formula 601 is 2 or more, two or more Ar601(s) may be linked to each other via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be an anthracene group.
In one or more embodiments, a compound represented by Formula 601 may be represented by Formula 601-1:
In Formula 601-1,
In one embodiment, L601 and L611 to L613 in Formulae 601 and 601-1 may each independently be selected from:
In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, and/or 2.
In one or more embodiments, R601 and R611 to R613 in Formula 601 and 601-1 may each independently be selected from:
The electron transport region may include at least one compound selected from Compounds ET1 to ET36, but embodiments of the present disclosure are not limited thereto:
In one or more embodiments, the electron transport region may include at least one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-dphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ:
In one embodiment, the electron transport region may include a phosphine oxide-containing compound (for example, TSPO1 used in the following examples and/or the like), but embodiments of the present disclosure are not limited thereto. In one embodiment, the phosphine oxide-containing compound may be used in a hole blocking layer in the electron transport region, but embodiments of the present disclosure are not limited thereto.
Thicknesses of the buffer layer, the hole blocking layer, and the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within any of these ranges, the electron transport region may have excellent (or suitable) hole blocking characteristics and/or electron control characteristics without a substantial increase in driving voltage.
A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory (or suitable) electron transport characteristics 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 at least one selected from an alkali metal complex and an alkaline earth-metal complex. The alkali metal complex may include a metal ion selected from a Li ion, a Na ion, a K ion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex may include a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Sr ion, and a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be selected from a hydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, LiQ) and/or Compound ET-D2:
The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.
The electron injection layer may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, and/or Cs. In one or more embodiments, the alkali metal may be Li and/or Cs, but embodiments of the present disclosure are not limited thereto.
The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.
The alkali metal compound, the alkaline earth-metal compound, and the rare earth metal compound may be selected from oxides and halides (for example, fluorides, chlorides, bromides, and/or iodides) of the alkali metal, the alkaline earth-metal, and the rare earth metal, respectively.
The alkali metal compound may be selected from alkali metal oxides (such as Li2O, Cs2O, and/or K2O), and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and/or KI). In one embodiment, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but embodiments of the present disclosure are not limited thereto.
The alkaline earth-metal compound may be selected from alkaline earth-metal oxides, such as BaO, SrO, CaO, BaxSr1-xO (0<x<1), and/or BaxCa1-xO (0<x<1). In one embodiment, the alkaline earth-metal compound may be selected from BaO, SrO, and CaO, but embodiments of the present disclosure are not limited thereto.
The rare earth metal compound may be selected from YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3 and TbF3. In one embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but embodiments of the present disclosure are not limited thereto.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may respectively include an ion of alkali metal, alkaline earth-metal, and rare earth metal as described above, and a ligand coordinated with a metal ion of the alkali metal complex, the alkaline earth-metal complex, or the rare earth metal complex may be selected from hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
The electron injection layer may include (e.g., may consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal 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. When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal compound, the alkaline earth-metal compound, the rare earth metal compound, the alkali metal complex, the alkaline earth-metal complex, the rare earth metal complex, or any combinations thereof may be homogeneously or non-homogeneously 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, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory (or suitable) electron injection characteristics without a substantial increase in driving voltage.
The second electrode 190 may be disposed on the organic layer 150 having the structure according to embodiments of the present disclosure. The second electrode 190 may be a cathode, which is an electron injection electrode, and in this regard, a material to form the second electrode 190 may be selected from a metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function.
The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 190 may have a single-layered structure, or a multi-layered structure including two or more layers.
Regarding
In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in an emission layer may pass through the first electrode 110 and the first capping layer 210 toward the outside, wherein the first electrode 110 may be a semi-transmissive electrode or a transmissive electrode. In the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in an emission layer may pass through the second electrode 190 and the second capping layer 220 toward the outside, wherein the second electrode 190 may be a semi-transmissive electrode or a transmissive electrode.
The first capping layer 210 and the second capping layer 220 may increase external luminescent efficiency according to the principle of constructive interference.
The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material. The organic capping layer may include polyethylene tetephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acryl-based resin (e.g., polymethylmethacrylate, polyacrylic acid, etc), or any combination thereof.
At least one selected from the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrine derivatives, phthalocyanine derivatives, a naphthalocyanine derivatives, alkali metal complexes, and alkaline earth-based complexes. The carbocyclic compound, the heterocyclic compound, and/or the amine-based compound may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include an amine-based compound.
In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from Compounds HT28 to HT33 and Compounds CP1 to CP5, but embodiments of the present disclosure are not limited thereto.
Hereinbefore, the organic light-emitting device according to an embodiment has been described in connection with
Layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region may be formed in a certain region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.
When layers constituting the hole transport region, the 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, by taking into account a material to be included in a layer to be formed, and the structure of a layer to be formed.
When layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region are formed by spin coating, the spin coating may be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80° C. to 200° C., by taking into account a material to be included in a layer to be formed, and the structure of a layer to be formed.
The organic light-emitting device may be included in various suitable apparatuses. For example, a light-emitting apparatus, an authentication apparatus, and/or an electronic apparatus, which includes the organic light-emitting device, may be provided.
The light-emitting apparatus may further include, in addition to the organic light-emitting device, a thin film transistor including a source electrode and a drain electrode. One of the source electrode and the drain electrode of the thin film transistor may be electrically connected to one of the first electrode and the second electrode of the organic light-emitting device. The light-emitting apparatus may be used as various suitable displays, light sources, and/or the like.
The authentication apparatus may be, for example, a biometric authentication apparatus for authenticating an individual by using biometric information of a biometric body (for example, a finger tip, a pupil, and/or the like).
The authentication apparatus may further include, in addition to the organic light-emitting device, a biometric information collector.
The electronic apparatus may be applied to 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 (ECG) displays, ultrasonic diagnostic devices, and/or endoscope displays), fish finders, various measuring instruments, meters (for example, meters for a vehicle, an aircraft, and/or a vessel), projectors, and/or the like, but embodiments of the present disclosure are not limited thereto.
The term “C1-C60 alkyl group” as used herein may refer to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The term “C1-C60 alkylene group” as used herein may refer to a divalent group having the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as used herein may refer to a hydrocarbon group having at least one carbon-carbon double bond, for example, in the middle and/or at the terminus of the C2-C60 alkyl group, and non-limiting examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein may refer to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein may refer to a hydrocarbon group having at least one carbon-carbon triple bond, for example, in the middle and/or at the terminus of the C2-C60 alkyl group, and non-limiting examples thereof include an ethynyl group, and a propynyl group. The term “C2-C60 alkynylene group” as used herein may refer to a divalent group having the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group” as used herein may refer to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and non-limiting examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C3-C10 cycloalkyl group” as used herein may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C3-C10 cycloalkylene group” as used herein may refer to a divalent group having the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as used herein may refer to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and 1 to 10 carbon atoms as the remaining ring-forming atoms, and non-limiting 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 may refer to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” as used herein may refer to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein may refer to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein may refer to a monovalent monocyclic group that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms as the remaining ring-forming atoms, and at least one carbon-carbon double bond in its ring. Non-limiting 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-C1a heterocycloalkenylene group” as used herein may refer to a divalent group having the same structure as the C1-C1a heterocycloalkenyl group.
The term “C6-C60 aryl group” as used herein may refer to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. The term “C6-C60 arylene group” used herein may refer to a divalent group having the same structure as the C6-C60 aryl group. When the C6-C60 aryl group and the C6-C6a arylene group each independently include two or more rings, the respective rings may be fused to each other.
The term “C1-C60 heteroaryl group” as used herein may refer to a monovalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms (as the remaining ring-forming atoms). Non-limiting 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, and an isoquinolinyl group. The term “C1-C60 heteroarylene group” as used herein may refer to a divalent group having the same structure as the C1-C60 heteroaryl group. When the C1-C6a heteroaryl group and the C1-C60 heteroarylene group each independently include two or more rings, the respective rings may be condensed (fused) with each other.
The term “C6-C60 aryloxy group” as used herein may refer to a group represented by —OA102 (wherein A102 is the C6-C60 aryl group), and a C6-C60 arylthio group used herein may refer to a group represented by —SA103 (wherein A103 is the C6-C60 aryl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein may refer to a monovalent group having two or more rings condensed with each other, only carbon atoms as ring-forming atoms (for example, having 8 to 60 carbon atoms), and no aromaticity in its entire molecular structure (i.e. the overall structure is non-aromatic). A non-limiting example of the monovalent non-aromatic condensed polycyclic group is a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein may refer to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein may refer to a monovalent group having two or more rings condensed to each other, at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, other than carbon atoms (for example, 1 to 60 carbon atoms), and no aromaticity in its entire molecular structure (i.e. the overall structure is non-aromatic). A non-limiting example of the monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein may refer to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C4-C60 carbocyclic group” as used herein may refer to a monocyclic or polycyclic group having 4 to 60 carbon atoms in which ring-forming atoms carbon atoms only. The term “C4-C60 carbocyclic group” as used herein may refer to an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C4-C60 carbocyclic group may be a ring (such as benzene), a monovalent group (such as a phenyl group), or a divalent group (such as a phenylene group). In one or more embodiments, depending on the number of substituents connected to the C4-C60 carbocyclic group, the C4-C60 carbocyclic group may be a trivalent group or a quadrivalent group.
The term “C1-C60 heterocyclic group” as used herein may refer to a group having the same structure as the C4-C60 carbocyclic group, except that as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S is used, in addition to carbon atoms (the number of carbon atoms may be in a range of 1 to 60).
In the present specification, at least one substituent of the substituted C4-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, the substituted C3-C10 cycloalkylene group, the substituted C1-C10 heterocycloalkylene group, the substituted C3-C10 cycloalkenylene group, the substituted C1-C10 heterocycloalkenylene group, the substituted C6-C60 arylene group, the substituted C1-C60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-Cia cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
The term “Ph” as used herein may refer to a phenyl group, the term “Me” as used herein may refer to a methyl group, the term “Et” as used herein may refer to an ethyl group, the term “ter-Bu” or “But” as used herein may refer to a tert-butyl group, the term “OMe” as used herein may refer to a methoxy group, and “D” may refer to deuterium.
The term “biphenyl group” as used herein may refer to “a phenyl group substituted with a phenyl group. In other words, the “biphenyl group” may be a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group” as used herein may refer to “a phenyl group substituted with a biphenyl group. In other words, the “terphenyl group” may be a 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.
Hereinafter, a compound according to embodiments and an organic light-emitting device according to embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was used instead of A” used in describing Synthesis Examples may refer to an identical molar equivalent of B being used in place of A.
50 mmol (14.37 g) of triphenylmethyl chloride and aniline (12.5 ml) were heated in an Ar condition at a temperature of 220° C. After 20 minutes of the reaction, the reaction solution was cooled to a temperature of 95° C., and 2.0 M HCl (240 ml) and methanol (200 ml) were added thereto, and a reaction was additionally allowed to go for 30 minutes, thereby obtaining 13.2 g (83%) of Reactant Compound A through purification.
Reactant Compound A (6.6 g), 2-bromo-9-phenyl-9H-carbazole (5.3 g), Pd2(dba)3 (1.06 g), P(t-Bu)3 (0.30 g), and NaOtBu (4.78 g) were dissolved in toluene (150 ml), and then, the mixed solution was stirred at a temperature of 90° C. for 1 hour. The reaction solution was cooled to room temperature, and the reaction was terminated with water. Then, an extraction process was performed thereon three times by using ethylether. An organic layer separated therefrom was dried by using anhydrous sulfur magnesium, and then, distilled under reduced pressure. A residue obtained therefrom was separated and purified by column chromatography, thereby obtaining Intermediate 1-1 (5.76 g, yield: 60%). Compound 1 (2.6 g, yield: 40%) was also obtained in the same (or substantially the same) manner as in the synthesis of Intermediate 1-1, except that bromo benzene (1.8 g) was used instead of 2-bromo-9-phenyl-9H-carbazole, and Intermediate 1-1 (5.76 g) was used instead of Reactant Compound A.
Compound 24 (4.1 g, yield: 57%) was obtained in the same (or substantially the same) manner as in the synthesis of Compound 1, except that 3-bromo-1,1′-biphenyl (2.7 g) was used instead of bromo benzene.
Compound 42 (3.5 g, yield: 44%) was obtained in the same (or substantially the same) manner as in the synthesis of Compound 1, except that 3-(4-bromophenyl)-9-phenyl-9H-carbazole (4.9 g) and 4-bromo-1,1′-biphenyl (2.6 g) were used instead of 2-bromo-9-phenyl-9H-carbazole and bromo benzene, respectively.
Compound 46 (3.6 g, yield: 47%) was obtained in the same (or substantially the same) manner as in the synthesis of Compound 42, except that bromonaphthalene (2.45 g) was used instead of 4-bromo-1,1′-biphenyl.
Compound 63 (3.2 g, yield: 44%) was obtained in the same (or substantially the same) manner as in the synthesis of Compound 1, except that 3-(3-bromophenyl)-9-phenyl-9H-carbazole (4.97 g) and 2-bromo-1,1′-biphenyl (2.33 g) were used instead of 2-bromo-9-phenyl-9H-carbazole and bromo benzene, respectively.
4-bromoaniline (5.16 g) was dissolved in DMF (200 ml) after performing nitrogen blowing thereon, and then, n-Buli (14 ml) was added dropwise thereto at a temperature of −78° C. The mixed solution was stirred for 1 hour, and trimethyl borate (4.15 g) was added thereto at room temperature to allow a reaction overnight. The reaction was terminated with water, and HCl was added thereto to allow a reaction to go for additional 1 hour. Then, an extraction process was performed thereon three times by using ether. An organic layer separated therefrom was dried by using anhydrous sulfur magnesium, and then, distilled under reduced pressure. A residue obtained therefrom was re-crystallized by using MC, thereby obtaining Intermediate B-1 (6.45 g, yield: 52%).
Intermediate B-1 (6.45 g), Pd(PPh3)4, (1.00 g), K2CO3 (6.72 g), and 1-bromo-4-iodobenzene (4.91 g) were dissolved in THF/H2O (100 ml/25 ml), and the mixed solution was stirred at a temperature 80° C. for 12 hours. The reaction solution was cooled to room temperature, and the reaction was terminated with water. Then, an extraction process was performed thereon three times by using ethylether. An organic layer separated therefrom was dried by using anhydrous sulfur magnesium, and then, distilled under reduced pressure. A residue obtained therefrom was separated and purified by column chromatography, thereby obtaining Reactant Compound B (4.65 g, yield: 67%).
Reactant Compound B (6.17 g), 2-bromo-9-phenyl-9H-carbazole (4.02 g), Pd2(dba)3 (1.35 g), P(t-Bu)3 (0.30 g), and NaOtBu (4.26 g) were dissolved in toluene (80 ml), and then, the mixed solution was stirred at a temperature of 90° C. for 1 hour. The reaction solution was cooled to room temperature, and the reaction was terminated with water. Then, an extraction process was performed thereon three times by using ethylether. An organic layer separated therefrom was dried by using anhydrous sulfur magnesium, and then, distilled under reduced pressure. A residue obtained therefrom was separated and purified by column chromatography, thereby obtaining Intermediate 81-1 (6.5 g, yield: 67%). Compound 81 (3.76 g, yield: 65%) was also obtained in the same (or substantially the same) manner as in the synthesis of Intermediate 81-1, except that bromo benzene (3.07 g) instead of 2-bromo-9-phenyl-9H-carbazole, and Intermediate 81-1 (3.48 g) were used instead of Reactant Compound B.
Compound 108 (3.2 g, yield: 44%) was obtained in the same (or substantially the same) manner as in the synthesis of Compound 81, except that 2-bromo-9,9-dimethyl-9H-fluorene (2.33 g) was used instead of bromo benzene.
The compounds synthesized according to Synthesis Examples were identified by 1H NMR and MS/FAB, and results thereof are shown in Table 1.
Compounds other than the compounds shown in Table 1 should be easily recognized (and synthesized) by one of ordinary skill in the art with reference to the synthetic routes and the raw materials above.
1H NMR (CDCl3, 400 MHz)
As an anode, a glass substrate (Corning, Inc.), on which ITO was formed to a thickness of 15 Ω/cm2 (1,200 Å), was cut to a size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then, cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the glass substrate was provided to a vacuum deposition apparatus.
2-TNATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 600 Å, and then, 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as 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 300 Å.
9,10-di(naphthalen-2-yl)anthracene (hereinafter, referred to as DNA), as a blue phosphorescence host, and 4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (hereinafter, referred to as DPAVBi), as a blue phosphorescence dopant, were co-deposited at a weight ratio of 98:2 on the hole transport layer to form an emission layer having a thickness of 300 Å.
Then, Alq3 was deposited on the emission layer to form an electron transport layer having a thickness of 300 Å, LiF, which is a halogenated alkali metal, was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was deposited on the electron injection layer to a thickness of 3,000 Å (cathode electrode) to form a LiF/Al electrode, thereby completing the manufacture of an organic light-emitting device.
An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 100 was used instead of NPB in forming a hole transport layer.
An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 101 was used instead of NPB in forming a hole transport layer.
An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 102 was used instead of NPB in forming a hole transport layer.
An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 103 was used instead of NPB in forming a hole transport layer.
An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 104 was used instead of NPB in forming a hole transport layer.
An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 1 was used instead of NPB in forming a hole transport layer.
An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 24 was used instead of NPB in forming a hole transport layer.
An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 42 was used instead of NPB in forming a hole transport layer.
An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 46 was used instead of NPB in forming a hole transport layer.
An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 63 was used instead of NPB in forming a hole transport layer.
An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 81 was used instead of NPB in forming a hole transport layer.
An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 108 was used instead of NPB in forming a hole transport layer.
The driving voltage, luminance, efficiency, and lifespan of the organic light-emitting devices manufactured according to Examples 1 to 7 and Comparative Examples 1 to 6 were measured, and results thereof are shown in Table 2.
Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 7 showed excellent results compared to those of Comparative Examples 1 to 6.
According to the one or more embodiments, an organic light-emitting device including a compound represented by Formula 1 showed excellent efficiency and improved lifespan.
As used herein, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.
In addition, the terms “substantially,” “about,” and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art.
Also, any numerical range recited herein is intended to include all subranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
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 their equivalents.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2019-0105269 | Aug 2019 | KR | national |
This application is a continuation of U.S. application Ser. No. 16/812,164, filed on Mar. 6, 2020, which claims priority to and the benefit of Korean Patent Application No. 10-2019-0105269, filed on Aug. 27, 2019, in the Korean Intellectual Property Office, the entire contents of both of which are incorporated herein by reference.
| Number | Date | Country | |
|---|---|---|---|
| Parent | 16812164 | Mar 2020 | US |
| Child | 19091629 | US |
