Patent Application
20240032415
This application is based on and claims priority under 35 U.S.C. § 119 to Korean Patent Application No. 10-2022-0083983, filed on Jul. 7, 2022, in the Korean Intellectual Property Office, the disclosure of which is incorporated by reference herein in its entirety.
One or more embodiments relate to a light-emitting device, an electronic apparatus including the same, and an organometallic compound.
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 the light-emitting devices of the related art.
In a light-emitting device, a first electrode is located on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed 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 include an organometallic compound capable of providing high luminescence efficiency and a long lifespan, a light-emitting device having high luminescence efficiency and a long lifespan, and an electronic apparatus including the light-emitting device.
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.
According to one or more embodiments, a light-emitting device includes
According to one or more embodiments, an electronic apparatus includes the light-emitting device.
According to one or more embodiments, a consumer product includes the light-emitting device.
According to one or more embodiments, an organometallic compound may be represented by Formula 1
The above and other aspects, features, and advantages of certain embodiments will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
Reference will now be made in 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, 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.
According to one or more embodiments, a light-emitting device includes:
The detailed description of Formula 1 is the same as described in the present specification.
Since the light-emitting device includes an organometallic compound represented by Formula 1, the light-emitting device may have excellent luminescence efficiency and long lifespan characteristics.
For example, the organometallic compound may be included in the interlayer of the light-emitting device.
In an embodiment, the organometallic compound may be included in the emission layer of the light-emitting device.
In an embodiment, the light-emitting device may further include a second compound including at least one π electron-deficient nitrogen-containing C1-C60 cyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, and
The second compound to the fourth compound in the light-emitting device are the same as described in the present specification.
In an embodiment, the light-emitting device (for example, an emission layer of the light-emitting device) may include a second compound in addition to the organometallic compound. At least one of the organometallic compound and the second compound may include at least one deuterium. In an embodiment, the light-emitting device (for example, the emission layer in the light-emitting device) may each further include a third compound, a fourth compound, or any combination thereof, in addition to the organometallic compound and the second compound.
In an embodiment, the light-emitting device (for example, an emission layer of the light-emitting device) may include a third compound in addition to the organometallic compound. At least one of the organometallic compound and the third compound may include at least one deuterium. In an embodiment, the light-emitting device (for example, the emission layer in the light-emitting device) may further include a second compound, a fourth compound, or any combination thereof, in addition to the organometallic compound and the third compound.
In an embodiment, the light-emitting device (for example, the emission layer in the light-emitting device) may each further include a fourth compound, in addition to the organometallic compound. At least one of the organometallic compound and the fourth compound may include at least one deuterium. The fourth compound may improve color purity, luminescence efficiency, and lifespan characteristics of the light-emitting device. In an embodiment, the light-emitting device (for example, the emission layer in the light-emitting device) may each further include a second compound, a third compound, or any combination thereof, in addition to the organometallic compound and the fourth compound.
In an embodiment, the light-emitting device (for example, the emission layer in the light-emitting device) may each further include a second compound and a third compound, in addition to the organometallic compound. The second compound and the third compound may form an exciplex. At least one of the organometallic compound, the second compound, and the third compound may include at least one deuterium.
In an embodiment, a highest occupied molecular orbital (HOMO) energy level of the organometallic compound may be in a range of about −5.35 eV to about −5.15 eV or about −5.30 eV to about −5.20 eV.
In an embodiment, a lowest unoccupied molecular orbital (LUMO) energy level of the organometallic compound may be in a range of about −2.20 eV to about −1.80 eV or about −2.15 eV to about −1.90 eV.
The HOMO and LUMO energy levels may be evaluated via cyclic voltammetry analysis (for example, Evaluation Example 1) for the organometallic compound.
In an embodiment, the emission layer of the light-emitting device may include: i) the organometallic compound; and ii) the second compound, the third compound, the fourth compound, or any combination thereof, and the emission layer may emit blue light.
In an embodiment, a maximum emission wavelength of the blue light may be in a range of about 430 nm to about 475 nm, about 440 nm to about 475 nm, about 450 nm to about 475 nm, about 430 nm to about 470 nm, about 440 nm to about 470 nm, about 450 nm to about 470 nm, about 430 nm to about 465 nm, about 440 nm to about 465 nm, or about 450 nm to about 465 nm.
In an embodiment, an emission full width at half maximum (FWHM) of the blue light may be in a range of about 40 nm or less, about 5 nm to about 40 nm, about 10 nm to about 40 nm, about 15 nm to about 40 nm, about 20 nm to about 40 nm, about 5 nm to about 35 nm, about 10 nm to about 35 nm, about 15 nm to about 35 nm, about 20 nm to about 35 nm, about 5 nm to about 30 nm, about 10 nm to about 30 nm, about 15 nm to about 30 nm, about 20 nm to about 30 nm, about 5 nm to about 25 nm, about 10 nm to about 25 nm, about 15 nm to about 25 nm, or about 15 nm to about 23 nm.
In an embodiment, the blue light may be deep blue light.
In an embodiment, a CIEx coordinate (for example, a bottom emission CIEx coordinate) of the blue light may be in a range of about 0.125 to about 0.150 or about 0.130 to about 0.150.
In an embodiment, a CIEy coordinate (for example, a bottom emission CIEy coordinate) of the blue light may be in a range of about 0.120 to about 0.230.
Examples of the maximum emission wavelength and the CIEx and CIEy coordinates of the blue light may be referred to in Table 8 in the present specification.
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 following compounds may be excluded from the third compound.
In an embodiment, a difference between a triplet energy level (eV) of the fourth compound and a singlet energy level (eV) of the fourth compound may be about 0 eV or higher and about 0.5 eV or lower (or, about 0 eV or higher and about 0.3 eV or lower).
In an embodiment, the fourth compound may be a compound including at least one cyclic group including each of boron (B) and nitrogen (N) as a ring-forming atom.
In some embodiments, the fourth compound may be a C8-C60 polycyclic group-containing compound including at least two condensed cyclic groups that share a boron atom (B).
In an embodiment, the fourth compound may include a condensed ring in which at least one third ring may be condensed with at least one fourth ring,
the third ring may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norobornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and
the fourth ring may be a 1,2-azaborinine group, a 1,3-azaborinine group, a 1,4-azaborinine group, a 1,2-dihydro-1,2-azaborinine group, a 1,4-oxaborinine group, a 1,4-thiaborinine group, or a 1,4-dihydroborinine group.
In an embodiment, the third compound may not include a compound represented by Formula 3-1 described in the present specification.
In some embodiments, the second compound may include a compound represented by Formula 2:
In one or more embodiments, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
In some embodiments, the fourth compound may be a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
In some embodiments, the light-emitting device may satisfy at least one of Conditions 1 to 4:
Condition 1
LUMO energy level (eV) of third compound>LUMO energy level (eV) of organometallic compound
Condition 2
LUMO energy level (eV) of organometallic compound>LUMO energy level (eV) of second compound
Condition 3
HOMO energy level (eV) of organometallic compound>HOMO energy level (eV) of third compound
Condition 4
HOMO energy level (eV) of the third compound>HOMO energy level (eV) of the second compound
wherein each of the HOMO energy level and the LUMO energy level of each of the organometallic compound, the second compound, and the third compound may be a negative value, and may be measured according to a known method, for example, a method described in Evaluation Example 1 in the present specification.
In an embodiment, an absolute value of a difference between a LUMO energy level of the organometallic compound and a LUMO energy level of the second compound may be about 0.1 eV or higher and about 1.0 eV or lower, an absolute value of a difference between a LUMO energy level of the organometallic compound and a LUMO energy level of the third compound may be about 0.1 eV or higher and about 1.0 eV or lower, an absolute value of a difference between a HOMO energy level of the organometallic compound and a HOMO energy level of the second compound may be about 1.25 eV or lower (for example, about 1.25 eV or lower and about 0.2 eV or higher), and an absolute value of a difference between a HOMO energy level of the organometallic compound and a HOMO energy level of the third compound may be about 1.25 eV or lower (for example, about 1.25 eV or lower and about 0.2 eV or higher).
When the relationships between LUMO energy level and HOMO energy level satisfy the conditions as described above, the balance between holes and electrons injected into the emission layer can be made.
The light-emitting device may have a structure of a first embodiment or a second embodiment.
According to the first embodiment, the organometallic compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include a host, the organometallic compound may be different from the host, and the emission layer may emit phosphorescence or fluorescence emitted from the organometallic compound. That is, according to the first embodiment, the organometallic compound may be a dopant or an emitter. In an embodiment, the organometallic compound may be a phosphorescent dopant or a phosphorescent emitter.
Phosphorescence or fluorescence emitted from the organometallic compound may be blue light.
The emission layer may further include an auxiliary dopant. The auxiliary dopant may improve luminescence efficiency from the first compound by effectively transferring energy to the organometallic compound as a dopant or an emitter.
The auxiliary dopant may be different from the organometallic compound and the host.
In some embodiments, the auxiliary dopant may be a delayed fluorescence-emitting compound.
In some embodiments, the auxiliary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
According to the second embodiment, the organometallic compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include a host and a dopant, the organometallic compound, the host and the dopant may be different from one another, and the emission layer may emit phosphorescence or fluorescence (e.g., delayed fluorescence) from the dopant.
In an embodiment, the organometallic compound in the second embodiment may act as an auxiliary dopant that transfers energy to a dopant (or an emitter), not as a dopant.
In an embodiment, the organometallic compound in the second embodiment may act as an emitter and as an auxiliary dopant that transfers energy to a dopant (or an emitter).
For example, phosphorescence or fluorescence emitted from the dopant (or the emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (e.g., blue delayed fluorescence).
The dopant (or the emitter) in the second embodiment may be a phosphorescent dopant material (e.g., the organometallic compound represented by Formula 1, the organometallic compound represented by Formula 401, or any combination thereof) or any fluorescent dopant material (e.g., the compound represented by Formula 501, the compound represented by Formula 502, the compound represented by Formula 503, or any combination thereof).
In the first embodiment and the second embodiment, the blue light may have a maximum emission wavelength in a range of about 390 nm to about 500 nm, about 410 nm to about 490 nm, about 430 nm to about 480 nm, about 440 nm to about 475 nm, about 440 nm to about 465 nm, or about 450 nm to about 465 nm.
The auxiliary dopant in the first embodiment may include, e.g. the fourth compound represented by Formula 502 or Formula 503.
The host in the first embodiment and the second embodiment may be any host material (e.g., the compound represented by Formula 301, the compound represented by 301-1, the compound represented by Formula 301-2, or any combination thereof).
In some embodiments, the host in the first embodiment and the second embodiment may be the second compound, the third compound, or any combination thereof.
In an embodiment, the light-emitting device may further include a capping layer located outside the first electrode and/or outside the second electrode.
In an embodiment, the light-emitting device may further include at least one of a first capping layer located outside the first electrode and a second capping layer located outside the second electrode, and the organometallic compound represented by Formula 1 may be included in at least one of the first capping layer and the second capping layer.
More details for the first capping layer and/or second capping layer are the same as described in the present specification.
In an embodiment, the light-emitting device may further include:
The expression that an “(interlayer and/or a capping layer) includes at least one organometallic compound represented by Formula 1” as used herein may be construed as meaning that the “(interlayer and/or the capping layer) may include one organometallic compound of Formula 1 or two different organometallic compounds of Formula 1.”
In an embodiment, the interlayer and/or capping layer may include only Compound BD02 as the organometallic compound. In this regard, Compound BD02 may exist in the emission layer of the light-emitting device. In an embodiment, the interlayer may include, as the organometallic compound, Compound BD02 and Compound BD06. In this regard, Compound BD02 and Compound BD06 may exist in an identical layer (for example, Compound BD02 and Compound BD06 may all exist in an emission layer), or different layers (for example, Compound BD02 may exist in an emission layer and Compound BD06 may exist in an electron transport region).
The term “interlayer” as used herein refers to a single layer and/or all of a plurality of layers located between the first electrode and the second electrode of the light-emitting device.
Another aspect 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.
According to one or more embodiments, provided is a consumer product including the light-emitting device.
In an embodiment, the consumer product may be one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and/or light for signal, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a signboard.
One or more embodiments include an organometallic compound represented by Formula 1 The detailed description of Formula 1 is the same as described in the present specification.
Methods of synthesizing the organometallic compound may be easily understood to those of ordinary skill in the art by referring to Synthesis Examples and/or Examples described herein.
In Formula 1, M may be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu).
In an embodiment, M may be Pt.
In Formula 1, X1 to X4 may each independently be C or N.
In an embodiment, X1 may be C. In an embodiment, X1 in Formula 1 may be C, and C may be carbon of a carbene moiety.
In an embodiment, X1 in Formula 1 may be N.
In an embodiment, X2 and X3 may each be C, and X4 may be N.
In Formula 1, i) a bond between X1 and M may be a coordinate bond, and ii) one of a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M may be a coordinate bond and the other two may each be a covalent bond.
In an embodiment, a bond between X2 and M and a bond between X3 and M may each be a covalent bond, and a bond between X4 and M may be a coordinate bond.
In an embodiment, X4 may be N, and a bond between X4 and M may be a coordinate bond.
Ring CY1 to ring CY6 may each independently be a C4-C60 carbocyclic group or a C1-C60 heterocyclic group.
In an embodiment, ring CY1 may be a C1-C60 nitrogen-containing heterocyclic group.
In an embodiment, ring CY1 in Formula 1 may be i) an X1-containing 5-membered ring, ii) an X1-containing 5-membered ring in which at least one 6-membered ring is condensed, or iii) an X1-containing 6-membered ring.
That is, ring CY1 may include a 5-membered ring bonded to M in Formula 1 via X1. Here, the X1-containing 5-membered ring may be a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group, and the X1-containing 6-membered ring and the 6-membered ring which may be optionally condensed to the X1-containing 5-membered ring may each independently be a benzene group, a pyridine group, or a pyrimidine group.
In an embodiment, ring CY1 may be an X1-containing 5-membered ring, and the X1-containing 5-membered ring may be an imidazole group or a triazole group.
In an embodiment, ring CY1 may be an X1-containing 5-membered ring in which at least one 6-membered ring is condensed, and the X1-containing 5-membered ring in which the at least one 6-membered ring is condensed may be a benzimidazole group or an imidazopyridine group.
In an embodiment, ring CY1 may be an imidazole group, a triazole group, a benzimidazole group, or an imidazopyridine group.
For example, ring CY1 may be a benzimidazole group.
In an embodiment, rings CY2 to CY6 may each independently be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a benzofluorene group, a naphthobenzosilole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, a dibenzofluorene group, a dinaphthosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadibenzocarbazole group, an azadibenzofluorene group, or an azadinaphthosilole group.
In an embodiment, ring CY2 and ring CY4 may each independently be a benzene group, a pyridine group, or a pyrimidine group.
For example, ring CY2 may be a benzene group, and ring CY4 may be a pyridine group, and embodiments are not limited thereto.
In an embodiment, ring CY3, CY5, and CY6 may each independently be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group or, a fluorene group.
In an embodiment, the rings CY3, CY5 and CY6 may each independently be a benzene group, a pyridine group, or a pyrimidine group.
For example, ring CY3 may be a benzene group.
For example, ring CY5 may be a benzene group.
For example, ring CY6 may be a benzene group.
X51 in Formula 1 may be a single bond, *—N(R7)—*′, *—B(R7)—*′, *—P(R7)—*, *—C(R7)(R8)—*′, *—Si(R7)(R8)—*′, *—Ge(R7)(R8)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R7)═*′, *═C(R7)—*′ *—C(R7)═C(R8)—*′ *—C(═S)—*′, or *—C≡C—*′.
For example, X51 may be *—N(R7)—*′, *—B(R7)—*′, *—P(R7)—*′, *—C(R7)(R8)—*′, *—Si(R7)(R8)—*′, *—Ge(R7)(R8)—*′, *—S—*′, *—Se—*′, or *—O—*′.
In Formula 1, L1 may be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In an embodiment, L1 may be a benzene group, a naphthalene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one R10a.
b1 in Formula 1 indicates the number of L1(s), and may be an integer from 1 to 5. When b1 is 2 or more, two or more of L1(s) may be identical to or different from each other. In an embodiment, b1 may be 1 or 2.
In Formula 1, Y31 may be a single bond, O, S, N(RY31a), or C(RY31a)(RY31b), Y32 may be a single bond, O, S, N(RY32a), or C(RY32a)(RY32b), and at least one of Y31 and Y32 may be a single bond.
In an embodiment, any one of Y31 and Y32 may be a single bond. That is, i) Y31 is a single bond, and Y32 is O, S, N(RY32a), or C(RY32a)(RY32b), or ii) Y32 is a single bond, and Y31 is O, S, N(RY31a), or C(RY31a)(RY31b).
R1 to R8, RY31a, RY31b, RY32a, RY32b, and T1 in Formula 1 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, 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, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C7-C60 arylalkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroarylalkyl group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2).
a1, a2, a3, a4, a5, a6, c1, and n1 in Formula 1 may respectively indicate the numbers of groups represented by R1, R2, R3, R4, R5, R6, T1, and *-(L1)b1-(T1)c1, and may each independently be an integer from 0 to 20.
In an embodiment, a1 to a6 may each independently be 0, 1, 2, 3, 4, or 5.
In an embodiment, a5 may be 0, 1, or 2.
In an embodiment, c1 may be 1 or 2.
In an embodiment, n1 may be 0 or 1.
In an embodiment, c1 may be 2, and n1 may be 1.
In an embodiment, R1 to R8, RY31a, RY31b, RY32a, RY32b, and T1 may each independently be hydrogen, deuterium, —F, or a cyano group;
a C1-C20 alkyl group or a C3-C10 cycloalkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof; or
a phenyl group, a naphthyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl) phenyl group, or any combination thereof.
For example, R1 may be hydrogen, but embodiments are not limited thereto.
For example, R2 may be hydrogen, but embodiments are not limited thereto.
For example, R3 may be hydrogen, but embodiments are not limited thereto.
For example, at least one of R4 in the number of a4 may be a C1-C20 alkyl group, and the rest may be hydrogen, but embodiments are not limited thereto.
For example, R5 may be hydrogen, but embodiments are not limited thereto.
For example, R6 may be hydrogen, but embodiments are not limited thereto.
For example, RY31a, RY31b, RY32a, and RY32b may each independently be hydrogen, a C1-C20 alkyl group, or a C3-C10 cycloalkyl group; or a phenyl group unsubstituted or substituted with deuterium, C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, or a combination thereof, and embodiments are not limited thereto.
In an embodiment, the organometallic compound may be represented by Formula 1-1 or 1-2:
For example, in Formulae 1-1 and 1-2, R42 may be a C1-C20 alkyl group, and R41, R43, and R44 may each be hydrogen, and embodiments are not limited thereto.
In an embodiment, a group represented by
in Formula 1 may be a group represented by one of Formulae CY1-1 to CY1-42:
In an embodiment, X1 in Formulae CY1-1 to CY1-8 may be C, and X1 in Formulae CY1-9 to CY1-42 may be N.
In an embodiment, a group represented by
in Formula 1 may be a group represented by one of Formulae CY1(1) to CY1(8):
In an embodiment, a group represented by *-(L1)b1-(T1)c1 in Formula 1 may be a group represented by Formula CY1A:
In an embodiment, T11 and T12 may each independently be a phenyl group, a naphthyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, or any combination thereof.
In an embodiment, a group represented by *—(L1)b1-(T1)c1 in Formula 1 may be a group represented by Formula CY1(A):
For example, n1 may be 1, a group represented by *-(L1)b1-(T1)c1 in Formula 1 may be a group represented by Formula CY1A or CY1(A).
When the organometallic compound represented by Formula 1 has a bulky substituent (for example, a group represented by Formula CY1A or CY1(A) described in the present specification), the steric shielding effect (SSE) on the central transition metal M may be increased, so that excimer formation and/or exciplex formation with the host material in the light-emitting device can be substantially suppressed, providing a long lifespan and excellent luminescence efficiency to the light-emitting device.
In an embodiment, Z10 to Z22 may each independently be hydrogen, deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, or a (C1-C20 alkyl)phenyl group.
In an embodiment, a group represented by
in Formula 1 may be a group represented by one of Formulae CY2-1 to CY2-11:
In an embodiment, a group represented by
and a group represented by
in Formulae 1-1 and 1-2 may each independently be a group represented by one of Formulae CY2(1) to CY2(26):
In one or more embodiments, a group represented by
Formula 1 may be a group represented by one of Formulae CY3-1 to CY3-12.
In one or more embodiments,
For example, R31 and R32 in Formulae CYA(1) to CYA(6) may each independently be hydrogen or deuterium, and embodiments are not limited thereto.
For example, R33 to R36 in Formulae CYA(1) to CYA(6) may each independently be hydrogen or deuterium, and embodiments are not limited thereto.
For example, R5a and R5b in Formulae CYA(1) to CYA(6) may each independently be hydrogen or deuterium, and embodiments are not limited thereto.
In an embodiment, a group represented by in Formula 1 may be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, or a fluorene group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a deuterated C1-C20 alkyl group, a fluorinated C1-C20 alkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C1-C20 alkyl)phenyl group, or any combination thereof.
The triplet metal-centered (3MC) energy level of the organometallic compound may be 0.8 kcal/mol or more 1.5 kcal/mol or less, 0.8 kcal/mol or more 1.4 kcal/mol or less, or 0.8 kcal/mol or more 1.3 kcal/mol or less. An example of the energy level of the 3MC state may refer to Table 3 of the present specification.
The organometallic compound represented by Formula 1 may have, as a ligand, a condensed cyclic structure in which 5 rings or more are condensed (a condensed cyclic structure in which ring CY3, a nitrogen-containing ring, ring CY5, a ring including Y31 and Y32, and ring CY6 in Formula 1 are condensed together). As a result, the range of conjugation of the organometallic compound may be further expanded to provide a long lifespan for a light-emitting device. In addition, in the case of the organometallic compound, an anisotropic transition dipole moment is formed in the backbone direction in the molecule, so that the light generated when the light-emitting device is driven can be easily emitted to the outside, excellent luminescence efficiency may be provided.
In addition, in the case of the organometallic compound represented by Formula 1, a condensed ring is formed adjacent to ring CY4 (a ring CY5, a ring including Y31 and Y32, and ring CY6 in Formula 1 are sequentially condensed), and thus, compared to organometallic compounds in which a condensed ring is formed on ring CY3 (for example, Compound C of the present specification), the steric hindrance effect of the condensed cyclic structure on the bond between ring CY4 and M may be improved. As a result, the rigidity of the organometallic compound is increased and the energy level of the 3MC state is increased, and thus the stability of the organometallic compound is improved.
Therefore, by using the organometallic compound, an electronic device (for example, an organic light-emitting device) having a long lifespan and excellent luminescence efficiency may be realized.
b51 to b53 in Formula 2 indicate numbers of L51 to L53, respectively, and may each be an integer from 1 to 5. When b51 is 2 or more, two or more of L51(s) may be identical to or different from each other, when b52 is 2 or more, two or more of L52(s) may be identical to or different from each other, and when b53 is 2 or more, two or more of L53(s) may be identical to or different from each other. In an embodiment, b51 to b53 may each independently be 1 or 2.
L51 to L53 in Formula 2 may each independently be:
In an embodiment, in Formula 2, a bond between L51 and R51, a bond between L52 and R52, a bond between L53 and R53, a bond between two or more L51(s), a bond between two or more L52(s), a bond between two or more L53(s), a bond between L51 and carbon between X54 and X55 in Formula 2, a bond between L52 and carbon between X54 and X56 in Formula 2, and a bond between L53 and carbon between X55 and X56 in Formula 2 may each be a “carbon-carbon single bond.”
In Formula 2, X54 may be N or C(R54), X55 may be N or C(R55), X56 may be N or C(R56), and at least one of X54 to X56 may be N. R54 to R56 are the same as described above. In an embodiment, two or three of X54 to X56 may be N.
R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in the present specification may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, 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, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, a C7-C60 arylalkyl group unsubstituted or substituted with at least one R10a, a C2-C60 heteroarylalkyl group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2). Q1 to Q3 are the same as described in the present specification.
In an embodiment, i) R1 to R8, RY31a, RY31b, RY32a, RY32b and T1 in Formula 1, ii) R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 2, 3-1 to 3-5, 502, and 503, and iii) R10a may each independently be:
For example, in Formula 91,
In an embodiment, i) R1 to R8, RY31a, RY31b, RY32a, RY32b, and T1 in Formula 1 ii) R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 2, 3-1 to 3-5, 502, and 503, and iii) R10a may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a group represented by one of Formulae 9-1 to 9-19, a group represented by one of Formulae 10-1 to 10-246, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), or —P(═O)(Q1)(Q2) (wherein Q1 to Q3 are respectively the same as those described above):
In Formulae 3-1 to 3-5, 502, and 503, a71 to a74 and a501 to a504 may respectively indicate the number of R71(s) to R74(s) and R501 (s) to R504 (s), and a71 to a74 and a501 to a504 may each independently be an integer from 0 to 20. When a71 is 2 or greater, at least two R71(s) may be identical to or different from each other, when a72 is 2 or greater, at least two R72(s) may be identical to or different from each other, when a73 is 2 or greater, at least two R73(s) may be identical to or different from each other, when a74 is 2 or greater, may be identical to or different from each other R74(s) may be identical to or different from each other, when a501 is 2 or greater, at least two R501 (s) may be identical to or different from each other, when a502 is 2 or greater, at least two R502 (s) may be identical to or different from each other, when a503 is 2 or greater, at least two R503 (s) may be identical to or different from each other, and when a504 is 2 or greater, at least two R504 (s) may be identical to or different from each other. a71 to a74 and a501 to a504 may each independently be an integer from 0 to 8.
In Formula 1, i) two or more of R1 in the number of a1 may optionally be bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, ii) two or more of R2 in the number of a2 may optionally be bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, iii) two or more of R3 in the number of a3 may optionally be bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, iv) two or more of R4 in the number of a4 may optionally be bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, v) two or more of R5 in the number of a5 may optionally be bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, vi) two or more of R6 in the number of a6 may optionally be bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, and vii) two or more of R1 to R8, RY31a, RY31b, RY32a, and RY32b may optionally be bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In an embodiment, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 in Formula 2 may each not be a phenyl group.
In an embodiment, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 in Formula 2 may be identical to each other.
In an embodiment, a group represented by *-(L51)b51-R51 and a group represented by *-(L52)b52-R52 in Formula 2 may be different from each other.
In an embodiment, b51 and b52 in Formula 2 may each be 1, 2, or 3, and L51 and L52 may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, each unsubstituted or substituted with at least one R10a.
In an embodiment, R51 and R52 in Formula 2 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), or —Si(Q1)(Q2)(Q3), and
wherein Q1 to Q3 may each independently be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
In some embodiments,
For example,
R51a to R51e and R52a to R52e in Formulae CY51-1 to CY51-26 and Formulae CY52-1 to 52-26 may each independently be:
In Formulae 3-1 to 3-5, L81 to L85 may each independently be:
In some embodiments, in Formulae 3-1 and 3-2, a group represented by
may be represented by one of Formulae CY71-1(1) to CY71-1(8),
In an embodiment, the organometallic compound represented by Formula 1 may be one of Compounds BD01 to BD21:
In an embodiment, the second compound may be one of Compounds ETH1 to ETH96:
In an embodiment, the third compound may be one of Compounds HTH1 to HTH40:
In an embodiment, the fourth compound may be one of Compounds DFD1 to DFD29:
In the compounds described above, Ph represents a phenyl group, D5 represents substitution with five deuterium, and D4 represents substitution with four deuterium. For example, a group represented by
may be identical to a group represented by
[Description of
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
[First Electrode 110]
In
The first electrode 110 may be formed by, for example, depositing 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.
[Interlayer 130]
The interlayer 130 may be located on the first electrode 110. The interlayer 130 may include an emission layer.
The interlayer 130 may further include a hole transport region located between the first electrode 110 and the emission layer, and an electron transport region located between the emission layer and the second electrode 150.
The interlayer 130 may further include, in addition to various organic materials, a metal-containing compound such as an organometallic compound, an inorganic material such as quantum dots, or the like.
In an embodiment, 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 located between two neighboring 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.
[Hole Transport Region in Interlayer 130]
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:
For example, each of Formulae 201 and 202 may include at least one of groups represented by Formulae CY201 to CY217.
R10b and R10c in Formulae CY201 to CY217 are the same as described in connection with 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.
In one or more embodiments, 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 of groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formula 201 may include at least one of the groups represented by Formulae CY201 to CY203 and at least one of 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 of Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one of Formulae CY204 to CY207.
In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one of Formulae CY201 to CY203.
In one or more embodiments, each of Formulae 201 and 202 may not include a group represented by one of Formulae CY201 to CY203, and may include at least one of 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 of Formulae CY201 to CY217.
In an embodiment, the hole transport region may include one of 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 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 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, 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 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.
[p-Dopant]
The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of 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 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 are 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 are silicon (Si), antimony (Sb), and tellurium (Te).
Examples of the non-metal are oxygen (O) and halogen (for example, F, Cl, Br, I, etc.).
Examples of the compound including element EL1 and element EL2 are metal oxide, metal halide (for example, metal fluoride, metal chloride, metal bromide, or metal iodide), metalloid halide (for example, metalloid fluoride, metalloid chloride, metalloid bromide, or metalloid iodide), metal telluride, or any combination thereof.
Examples of the metal oxide are 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 are alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, and lanthanide metal halide.
Examples of the alkali metal halide are LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.
Examples of the alkaline earth metal halide are 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 are 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, AgI, etc.), and gold halide (for example, AuF, AuCl, AuBr, AuI, etc.).
Examples of the post-transition metal halide are 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 may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3 SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, and the like.
An example of the metalloid halide is antimony halide (for example, SbCl5, etc.).
Examples of the metal telluride are 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.).
[Emission Layer in Interlayer 130]
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 each other or are separated 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 with each other in a single layer to emit white light.
In an embodiment, the emission layer may include a host and a dopant (or emitter). In an embodiment, the emission layer may further include an auxiliary dopant that promotes energy transfer to a dopant (or emitter), in addition to the host and the dopant (or emitter). When the emission layer includes the dopant (or emitter) and the auxiliary dopant, the dopant (or emitter) and the auxiliary dopant are different from each other.
The organometallic compound represented by Formula 1 in the present specification may act as the dopant (or emitter), or may act as the auxiliary dopant.
An amount of the dopant (or emitter) in the emission layer 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.
In an embodiment, the emission 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. For example, the emission layer has a single-layered structure, and may include a mixture of host and dopant, but embodiments 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 these ranges, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
Host
The host in the emission layer may include the second compound or the third compound described in the present specification, or any combination thereof.
In an embodiment, the host may include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21 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 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 of 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:
In an embodiment, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
The host may have various modifications. For example, the host may include only one kind of compound, or may include two or more kinds of different compounds.
[Phosphorescent Dopant]
The emission layer may include, as a phosphorescent dopant, the organometallic compound represented by Formula 1 as described in the present specification.
In an embodiment, when the emission layer includes the organometallic compound represented by Formula 1 as described in the present specification, and the organometallic compound represented by Formula 1 as described in the present specification acts as an auxiliary dopant, the emission layer may include a phosphorescent dopant.
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:
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, or 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 of compounds PD1 to PD25, or any combination thereof:
[Fluorescent Dopant]
In an embodiment, when the emission layer includes the organometallic compound represented by Formula 1 as described in the present specification, and the organometallic compound represented by Formula 1 as described in the present specification acts as an auxiliary dopant, the emission layer may include a fluorescent dopant.
In an embodiment, when the emission layer includes the organometallic compound represented by Formula 1 as described in the present specification, and the organometallic compound represented by Formula 1 as described in the present specification acts as a phosphorescent dopant, the emission layer may include an auxiliary dopant.
The fluorescent dopant and the auxiliary dopant may each independently include an arylamine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
In an embodiment, the fluorescent dopant and the auxiliary dopant may each independently include a compound represented by 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.
In an embodiment, the fluorescent dopant and the auxiliary dopant may each include one of Compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:
In an embodiment, the fluorescent dopant and the auxiliary dopant may each independently include the fourth compound represented by Formula 502 or 503 as described in the present specification.
[Quantum Dot]
The emission layer may include a quantum dot.
The term “quantum dot” as used herein refers to a crystal of a semiconductor compound, and may include any material capable of emitting light of various emission wavelengths according to the size of the crystal.
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, or any process similar thereto.
The wet chemical process is a method including mixing a precursor material 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 or compound, or any combination thereof.
Examples of the Group II-VI semiconductor compound are a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, 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, or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, 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, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; a quaternary compound, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. Meanwhile, 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, InAlZnP, etc.
Examples of the Group III-VI semiconductor compound are: a binary compound, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, or InTe; a ternary compound, such as InGaS3, or InGaSe3; and any combination thereof.
Examples of the Group 1-III-VI semiconductor compound are: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, or AgAlO2; or any combination thereof.
Examples of the Group IV-VI semiconductor compound are: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; a quaternary compound, such as SnPbSSe, SnPbSeTe, or SnPbSTe; or any combination thereof.
The Group IV element or compound may include: a single element compound, such as Si or Ge; a binary compound, such as SiC 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.
Meanwhile, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is 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 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 toward the center of the core.
Examples of the shell of the quantum dot may be an oxide of metal, metalloid, or non-metal, a semiconductor compound, and any combination thereof. Examples of the oxide of metal, metalloid, or non-metal are a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, CO3O4, or NiO; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4; and any combination thereof. Examples of the semiconductor compound are, as described herein, a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; 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 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, since the light emitted through the quantum dot is emitted in all directions, the 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, or a nanoplate particle.
Since the energy band gap may be adjusted by controlling the size of the quantum dot, light having various 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 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 colors.
[Electron Transport Region in Interlayer 130]
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 transport region may include a buffer layer, a hole-blocking layer, an electron control layer, an electron transport 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, 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:
[Ar601]xe11-[(L601)xe1-R601]xe21 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:
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 of Compounds ET1 to ET46, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 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 layer are within these ranges, 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) 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 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, 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 be oxides, halides (for example, fluorides, chlorides, bromides, or iodides), 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, or K2O; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, 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), or the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, 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 are 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 of metal 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 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 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 RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, or the like.
When the electron injection layer further includes an organic material, 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 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, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
[Second Electrode 150]
The second electrode 150 may be located 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.
[Capping Layer]
A first capping layer may be located outside the first electrode 110, and/or a second capping layer may be located 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 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 of 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 of the first capping layer and the second capping layer may each independently include an amine group-containing compound.
For example, at least one of 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 of the first capping layer and the second capping layer may each independently include one of Compounds HT28 to HT33, one of Compounds CP1 to CP6, β-NPB, or any combination thereof:
[Film]
The organometallic compound represented by Formula 1 may be included in various films. According to one or more embodiments, a film including an organometallic compound represented by Formula 1 may be provided. The film may be, for example, an optical member (or 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, or like), a light-blocking member (for example, a light reflective layer, a light absorbing layer, or the like), a protective member (for example, an insulating layer, a dielectric layer, or the like).
[Electronic Apparatus]
The light-emitting device may be included in various electronic apparatuses. For example, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, 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 located in at least one direction in which light emitted from the light-emitting device travels. For example, the light emitted from the light-emitting device may be blue light or white light. For 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 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 emitting first color light, a second area emitting second color light, and/or a third area emitting 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 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 scatter.
For example, the light-emitting device may emit first light, the first area may absorb the first light to emit first-first color light, the second area may absorb the first light to emit second-first color light, and the third area may absorb the first light to emit 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 of the source electrode and the drain electrode may be electrically connected to any one of 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, or the like.
The activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.
The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located between the color filter and/or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and simultaneously prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate 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 functional layers may be additionally located 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, 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 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, or endoscope displays), fish finders, various measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and the like.
[Description of
The light-emitting apparatus of
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be located on the substrate 100. The buffer layer 210 may prevent penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
A TFT may be located 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 or polysilicon, an organic semiconductor, 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 located on the activation layer 220, and the gate electrode 240 may be located on the gate insulating film 230.
An interlayer insulating film 250 may be located on the gate electrode 240. The interlayer insulating film 250 may be located 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 located on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to 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 located in 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 located on the passivation layer 280. The passivation layer 280 may be located to expose a portion of the drain electrode 270, not fully covering the drain electrode 270, and the first electrode 110 may be located to be connected to the exposed portion of the drain electrode 270.
A pixel defining layer 290 including an insulating material may be located 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 or polyacrylic organic film. Although not shown in
The second electrode 150 may be located on the interlayer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
The encapsulation portion 300 may be located on the capping layer 170. The encapsulation portion 300 may be located on a light-emitting device to protect the light-emitting device from moisture 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, or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), or the like), or any combination thereof; or any combination of the inorganic films and the organic films.
The light-emitting apparatus of
[Manufacturing Method]
Respective layers included in the hole transport region, the emission layer, and respective layers included in 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, 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 with each other. For example, the C1-C60 heterocyclic group has 3 to 61 ring-forming atoms.
The “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 C3-C60 carbocyclic group may be i) group T1 or ii) a condensed cyclic group in which two or more groups T1 are condensed with each other (for example, a cyclopentadiene group, an adamantane group, a norbornane group, a benzene group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an 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 indenophenanthrene group, or an indenoanthracene group),
the C1-C60 heterocyclic group may be i) group T2, ii) a condensed cyclic group in which two or more groups T2 are condensed with each other, or iii) a condensed cyclic group in which at least one group T2 and at least one group T1 are condensed with each other (for example, 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, an azadibenzofuran group, etc.),
the π electron-rich C3-C60 cyclic group may be i) group T1, ii) a condensed cyclic group in which two or more groups T1 are condensed with each other, iii) group T3, iv) a condensed cyclic group in which two or more groups T3 are condensed with each other, or v) a condensed cyclic group in which at least one group T3 and at least one group T1 are condensed with each other (for example, the C3-C60 carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-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, etc.),
the π electron-deficient nitrogen-containing C1-C60 cyclic group may be i) group T4, ii) a condensed cyclic group in which two or more groups T4 are condensed with each other, iii) a condensed cyclic group in which at least one group T4 and at least one group T1 are condensed with each other, iv) a condensed cyclic group in which at least one group T4 and at least one group T3 are condensed with each other, or v) a condensed cyclic group in which at least one group T4, at least one group T1, and at least one group T3 are condensed with one another (for example, 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, an azadibenzofuran group, etc.),
group T1 may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or a bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a benzene group,
group T2 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group, or a dihydropyridazine group,
group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group, and
group T4 may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.
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 are 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 are 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 specific examples thereof are 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 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 in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof are 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 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 in the middle or at 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 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 are 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 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 specific examples are 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 the same structure as the C1-C10 heterocycloalkyl group.
The term C3-C10 cycloalkenyl group 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, and specific examples thereof are 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 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 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 are 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 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 are 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 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. 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 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. 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 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 the C6-C60 aryl group), and the term “C6-C60 arylthio group” as used herein indicates —SA103 (wherein A103 is the C6-C60 aryl group).
The term “C7-C60 arylalkyl group” 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 heteroarylalkyl 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:
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 in the present specification may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
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” 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, “ter-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 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.
11.5 g (1.0 eq.) of 2,6-dibromoaniline, 18.1 g (2.0 eq.) of [1,1′-biphenyl]-2-ylboronic acid, 1.1 g (0.020 eq) of tetrakis(triphenylphosphine) palladium(0), and potassium carbonate (3.0 eq.) were suspended in a mixed solution including 300 ml of tetrahydrofuran and 100 ml of distilled water and heated at a temperature of 80° C. in a nitrogen atmosphere for 24 hours. After cooling to room temperature, 300 mL of distilled water was added thereto, and the organic layer was extracted using ethylacetate, washed with saturated aqueous sodium chloride solution, and dried using magnesium sulfate. The resultant obtained therefrom was purified by column chromatography (1% methylene chloride/hexane (volume ratio 1:99)) to obtain Intermediate A-1 having the yield of 81%.
13.6 g (1.0 eq.) of Intermediate A-1, 9.4 g (1.1 eq) of 1-iodo-2-nitrobenzene, 0.60 g (0.020 eq) of Pd2(dba)3, 0.60 g (0.040 eq) of SPhos, and 5.3 g (1.6 eq) of sodium tert-butoxide were suspended in a toluene solvent, and then, heated in a nitrogen atmosphere for 12 hours at a temperature of 120° C. The resultant was cooled to room temperature, and then, 300 mL of distilled water was added thereto, and the organic layer was extracted using ethylacetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried by using magnesium sulfate. The resultant obtained therefrom was purified by column chromatography (% ethylacetate/hexane (volume ratio=5:95)) to obtain Intermediate A-2 having the yield of 78%.
13.9 g (1.0 eq.) of Intermediate A-2 was dissolved in 300 ml of ethanol, and then, 3.2 ml of 37% hydrochloric acid aqueous solution was added dropwise thereto. 3.2 g (1.0 eq.) of tin was added to the reaction mixture, and the temperature was raised, and stirred at 80° C. for 10 hours. When the reaction was completed, the temperature was dropped to room temperature, and neutralization was performed thereon using 1N aqueous sodium hydroxide solution, the organic layer was extracted with methylene chloride and distilled water, and the extracted organic layer was dried with magnesium sulfate to obtain Intermediate A-3 (yield: 75%). The obtained Intermediate A-3 was used in the next reaction without further purification.
Intermediate A-4 (yield: 77%) was synthesized in the same manner as used to synthesize Intermediates A-1 to A-3, except that 2,6-dibromo-4-tert-butylaniline, d5-phenylboronic acid, Intermediate A-4-1, and Intermediate A-4-2 were respectively used instead of 2,6-dibromoaniline, [1,1′-biphenyl]-2-ylboronic acid, Intermediate A-1, and Intermediate A-2.
Intermediate A-5-1 was synthesized in the same manner as used to synthesize Intermediate A-1, except that d5-phenylboronic acid (1 eq.) was used instead of [1,1′-biphenyl]-2-ylboronic acid (2 eq.).
8.1 g (1.0 eq.) of Intermediate A-5-1, 8.0 g (2.0 eq.) of 3,5-di-tert-butylphenyl boronic acid, [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloro[3-phenylallyl]palladium (II) (CX-31) (0.020 eq), and sodium carbonate 10.1 g (3.0 eq.) were suspended in a mixed solution including 300 ml of 1.4-dioxane and 100 ml of distilled water, and heated to 100° C. in a nitrogen atmosphere for 24 hours. After cooling to room temperature, 300 mL of distilled water was added thereto, and the organic layer was extracted using ethylacetate, washed with saturated aqueous sodium chloride solution, and dried using magnesium sulfate. The resultant obtained therefrom was purified by column chromatography (1% methylene chloride/hexane (volume ratio 1:99)) to obtain Intermediate A-5 having the yield of 95%.
Intermediate A-6 (yield: 85%) was synthesized in the same manner as used to synthesize Intermediate A-2 and Intermediate A-3, except that Intermediate A-5 and Intermediate A-6-1 were sequentially used in instead of Intermediate A-1.
Intermediate A-7-1 was synthesized in the same manner as used to synthesize Intermediate A-1, except that [1,1′-biphenyl]-3-ylboronic acid (1 eq.) was used instead of [1,1′-biphenyl]-2-ylboronic acid (2 eq.).
Intermediate A-7 was synthesized in the same manner as used to synthesize Intermediate A-5, except that Intermediate A-7-1 was used instead of Intermediate A-5-1 in Synthesis of Intermediate A-5.
Intermediate A-8 (yield: 87%) was synthesized in the same manner as used to synthesize Intermediate A-2 and A-3 except that Intermediate A-7 and Intermediate A-8-1 were sequentially used in instead of Intermediate A-1.
Intermediate A-9 (yield: 83%) was synthesized in the same manner as used to synthesize Intermediate A-3, except that [1,1′-biphenyl]-3-ylboronic acid, Intermediate A-9-1, and Intermediate A-9-2 were respectively used instead of [1,1′-biphenyl]-2-ylboronic acid, Intermediate A-1, and Intermediate A-2.
20 g (1.0 eq.) of 2-bromoa dibenzofuran was dissolved in 400 ml of tetrahydrofuran and cooled to −78° C., and n-butyllithium (2.5 M hexane solution) 39.0 ml (1.2 eq.) was added dropwise thereto. After stirring for 30 minutes, 12.5 ml of trimethylborate (1.4 eq.) was added dropwise thereto. The temperature was raised to room temperature, and then, the resultant was stirred for 12 hours, and 100 ml of 2N hydrochloric acid solution was added thereto complete the reaction. The resulting product was extracted with ethylacetate and dried over magnesium sulfate. The dried solid was dissolved in ether, solidified by adding hexane, and filtered to obtain 16.3 g of the target compound.
13.7 g (1.0 eq) of 1-bromo-4-methoxy-2-nitrobenzene, 16.0 g (1.3 eq) of Intermediate B-1, tetrakis triphenylphosphine palladium (Tetrakis(triphenylphosphine)palladium (0)) (0.05 eq), and potassium carbonate (2.0 eq) were suspended in a mixed solvent in which tetrahydrofuran and distilled water are mixed in a volume ratio of 2:1, and then, heated in a nitrogen atmosphere for 24 hours at a temperature of 85° C. The reaction mixture was cooled to room temperature, extracted with ethylacetate and water, and dried over magnesium sulfate. The resultant obtained therefrom was purified by column chromatography (20% methylenechloride/hexane (volume ratio 20:80)) to obtain the target compound with the yield of 75%.
10 g (1.0 eq) of Intermediate B-2 and 8.2 g (1.0 eq) of triphenylphosphine were dissolved in 200 ml of ortho-dichlorobenzene, and then, the temperature was raised to 180° C., followed by 12 hours of stirring. After completion of the reaction, the solvent was removed under reduced pressure, and two main products were separated by column chromatography to obtain Intermediate B-3-1 and Intermediate B-3-2 with yields of 20% and 18%, respectively.
11.3 g (1.0 eq) of Intermediate B-3-1, 8.42 g (1.0 eq) of 2-bromo tert-butylpyridine, 3.60 g (0.10 eq) of Pd2(dba)3, 3.23 g (0.2 eq) of SPhos, and 7.56 g (2.0 eq) of sodium tert-butoxide were suspended in toluene solvent and heated to 120° C. in a nitrogen atmosphere for 12 hours. The reaction mixture was cooled to room temperature, extracted with ethylacetate and water, and dried over magnesium sulfate. The purification was performed by column chromatography (5% ethylacetate/hexane (volume ratio=5:95)) to obtain a solid. The obtained solid was filtered after stirring for 2 hours in a suspended state in a solution including methylene chloride and hexane in a 5:95 volume ratio to obtain 13.3 g of the target compound.
13.3 g of Intermediate B-4 was dissolved in 130 ml of acetic acid, and then, 65 ml of bromine acid was added dropwise thereto. The reaction mixture was heated to 120° C. and stirred for 12 hours. When the reaction was completed, the solvent was removed therefrom under reduced pressure and neutralized with sodium hydroxide aqueous solution. The resulting solid was filtered, washed with distilled water, cold ethanol, and normal hexane in that order, and dried to obtain 13.1 g of the target compound.
12.9 (1.0 eq.) of Intermediate B-5, 9.3 ml (2.0 eq.) of 1,3-dibromobenzene, 0.61 g (0.1 eq.) of iodo copper, 1.26 g (0.1 eq.) of N,N′-bis(2-phenylphenyl) oxalamide (BPPO), and 13.4 g (2.0 eq.) of potassium phosphate were suspended in dimethylformamide solution, heated to 120° C. and stirred for 12 hours. The reaction mixture was filtered using celite, and then, the filtrate was subjected to reduced pressure to obtain a solid. The obtained solid was extracted with ethylacetate and water, washed several times with saturated chloride solution, and then the organic layer was dried with magnesium sulfate. The resulting product was purified by column chromatography (5% ethylacetate/hexane (volume ratio 5:95)) to obtain the target compound.
15 g (1.0 eq.) of Intermediate B-6, 10.0 g (1.1 eq.) of Intermediate A-3, 1.23 g (0.050 eq.) of Pd2(dba)3, 0.82 g (0.075 eq.) of SPhos, and 5.0 g (2.0 eq.) of sodium tert-butoxide were suspended in 100 ml of toluene and heated to 110° C. in a nitrogen atmosphere for 4 hours. The reaction mixture was cooled to room temperature, extracted with ethylacetate and water, and dried over magnesium sulfate. The resultant obtained therefrom was purified by column chromatography (10% ethylacetate/hexane (volume ratio=10:90)) to obtain the target compound.
4.0 g (1.0 eq.) of Intermediate B-7 was dissolving in 40 ml (50 eq.) of triethyl orthoformate, and then, 0.98 ml (1.2 eq.) of 12N hydrochloric acid was added dropwise thereto. The reaction mixture was heated to 80° C. and stirred for 12 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and an organic layer was extracted by using ethylacetate and distilled water. After drying with magnesium sulfate, the target compound was obtained by purification by column chromatography (5% methanol/methylene chloride (volume ratio=5:95)).
4.0 g (1.0 eq.) of Intermediate B-8 was dissolved in a mixed solvent including methanol and distilled water, and then ammonium hexafluorophosphate (3.0 eq.) was added thereto form a solid. The resultant was stirred for 30 minutes, and then filtered, washed with distilled water, and dried to obtain 4.2 g of the target compound.
2.0 g (1.00 eq.) of Intermediate B-9, 0.5 g (3.00 eq.) of sodium acetate, and 0.8 g (1.05 eq.) of Pt(COD)Cl2 were suspended in 85 ml of 1,4-dioxane, heated to 120° C., and stirred for 12 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and an organic layer was extracted by using ethylacetate and distilled water. The resulting product was dried with magnesium sulfate and purified by column chromatography (50% methylene chloride/hexane (volume ratio 50:50)) to obtain 0.45 g (0.391 mmol) of Compound BD02 with a yield of 22%.
0.54 g (0.462 mmol) of Compound BD05 was obtained at the yield of 24% in the same manner as in Synthesis Example of BD02, except that Intermediate A-4 was used instead of Intermediate A-3.
0.39 g (0.340 mmol) of Compound BD06 was obtained at the yield of 19% in the same manner as in Synthesis Example of BD02, except that Intermediate A-6 was used instead of Intermediate A-3.
0.55 g (0.455 mmol) of Compound BD07 was obtained at the yield of 25% in the same manner as in Synthesis Example of BD02, except that Intermediate A-8 was used instead of Intermediate A-3.
0.48 g (0.377 mmol) of Compound BD09 was obtained at the yield of 28% in the same manner as in Synthesis Example of BD02, except that Intermediate B-3-2 was used instead of Intermediate B-3-1.
0.32 g (0.251 mmol) of Compound BD16 was obtained at the yield of 19% in the same manner as in Synthesis Example of BD02, except that Intermediates B-1-1, B-2-1, B-3-3, B-4-1, B-5-1, B-6-1, A-9, B-7-1, B-8-1, and B-9-1 were sequentially used instead of Intermediates B-1, B-2, B-3-1, B-4, B-5, B-6, A-3, B-7, B-8, and B-9.
Intermediate CE1-1 was synthesized in the same manner as used to synthesize Intermediates B-4, B-5, and B-6, except that 2-methoxy-9H-carbazole, 9-(4-(tert-butyl)pyridin-2-yl)-2-methoxy-9H-carbazole, 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazol-2-ol, and 1-(3-bromophenyl)-1H-imidazole were sequentially used instead of Intermediate B-3-1, Intermediate B-4, Intermediate B-5, and 1,3-dibromobenzene.
Intermediate CE1-1 was dissolved in acetone solvent, and then, iodomethyl-d3 was added dropwise thereto, and stirred for 12 hours at room temperature, and then the solvent was removed therefrom under reduced pressure to synthesize Intermediate CE1-2.
1.2 g (1.791 mmol) of Compound A was obtained at the yield of 29% in the same manner as in Synthesis of Intermediate B-9 and Intermediate BD02, except that CE1-2 and Intermediate CE1-3 were sequentially used instead of Intermediate B-8 and Intermediate B-9.
8.3 g (14.2 mmol) of (3,5-di-tert-butylphenyl)(mesityl)iodonium trifluoromethanesulfonate, 8.3 g (14.2 mmol) of Compound CE1-1, and 0.18 g (0.6 mmol) of copper acetate were added to 50 ml of dimethylformamide and stirred at a temperature of 150° C. for 1 hour. When the reaction was completed, the solvent is removed therefrom under reduced pressure and the purification process was performed thereon by column chromatography (50% methylene chloride/acetone (volume ratio 50:50)) to synthesize 9.6 g of Intermediate CE2-1 with the yield of 80%.
9.0 g (10.6 mmol) of Intermediate CE2-1, 2.6 g (31.8 mmol) of sodium acetate, and 4.0 g (10.6 mmol) of Pt(COD)Cl2 were added to 480 ml of dimethylformamide, and the temperature was raised to 120° C. and the resultant solution was stirred for 15 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and an organic layer was extracted by using ethylacetate and distilled water. The resulting product was dried with magnesium sulfate and purified by column chromatography (50% methylene chloride/hexane (volume ratio 50:50)) to obtain 4.2 g of Compound B with the yield of 45%.
0.59 g of Compound C was obtained with the yield of 25% in the same manner as in the Synthesis of BD02, except that Intermediate CE3-1(1-methoxydibenzo[b,d]furan-4-yl)boronic acid, 1-bromo-2-nitrobenzene, Intermediate CE3-2, Intermediate CE3-3, Intermediate CE3-4, Intermediate CE3-5, Intermediate CE3-6, Intermediate A-11, Intermediate CE3-7, Intermediate CE3-8, and Intermediate CE3-9 were sequentially used instead of Intermediate B-1, 1-bromo-4-methoxy-2-nitrobenzene, Intermediate B-2, Intermediate B-3-1, Intermediate B-4, Intermediate B-5, Intermediate B-6, Intermediate A-3, Intermediate B-7, Intermediate B-8, and Intermediate B-9.
Results of measuring 1H NMR and high-resolution mass (HR-MS) of compounds synthesized in Synthesis Examples 2 to 7 and Comparative Synthesis Examples A to C were shown in Table 1. Synthesis methods for other compounds than the compounds described in the Synthesis Examples may be easily recognized by those skilled in the technical field by referring to the synthesis paths and source materials described above.
1H-NMR (CDCl3, 500 MHz)
Each of the HOMO and LUMO energy levels of Compounds BD02, BD05, BD06, BD07, BD09, BD16, A, B and C were evaluated according to the method shown in Table 2, and the results are shown in Table 3.
By using the DFT method of the Gaussian 09 program (with the structure optimization at the level of B3LYP, 6-311 G(d,p)), and 3MC state of the compounds synthesized according to Synthesis Examples above were simulated. The results thereof are shown in Table 3.
3MC (Kcal/mol)
After PMMA in CH2Cl2 solution and Compound BD02 (4 wt % relative to PMMA) were mixed, the result obtained therefrom was coated on a quartz substrate by using a spin coater and then heat-treated in an oven at 80° C., followed by cooling to room temperature, thereby manufacturing Film BD02 having a thickness of 40 nm. Films BD02, BD05, BD06, BD07, BD09, BD16, A, B, and C were manufactured in the same manner as used to manufacture film BD02, except that BD05, BD06, BD07, BD09, BD16, A, B, and C were each used instead of Compound BD02.
The photoluminescence spectrum of each of films BD02, BD05, BD06, BD07, BD09, BD16, A, B, and C was measured by using a Quantaurus-QY Absolute PL quantum yield spectrometer of Hamamatsu Inc. (equipped with a xenon light source, a monochromator, a photonic multichannel analyzer, and an integrating sphere, and using PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan)). During the measurement, an excitation wavelength was scanned from 320 nm to 380 nm at intervals of 10 nm, and a spectrum measured at the excitation wavelength of 340 nm was taken to obtain a maximum emission wavelength (emission peak wavelength) and FWHM of an organometallic compound included in each film, which were shown in Table 4.
From Table 4, it can be seen that in the case of Compounds BD02, BD05, BD06, BD07, BD09, and BD16, compared to Compounds A to C, the interaction between molecules is inhibited, and thus, the maximum emission wavelength was shortened, and/or, the emission FWHM was decreased.
As an anode, a glass substrate (product of Corning Inc.) with a 15 Ω/cm2 (1,200 Å) ITO formed thereon was cut to a size of 50 mm×50 mm×0.7 mm, sonicated using isopropyl alcohol and pure water each for 5 minutes, washed by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes, and then mounted on a vacuum deposition apparatus.
2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 600 Å, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred as “NPB”) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.
Compound BD02 (organometallic compound represented by Formula 1), Compound ETH2 (second compound), and Compound HTH29 (third compound) were vacuum-deposited on the hole transport layer to form an emission layer having a thickness of 350 Å. Here, an amount of Compound BD02 was 13 wt % based on the total weight (100 wt %) of the emission layer, and a weight ratio of Compound ETH2 to Compound HTH29 was adjusted to be 3.5:6.5.
Compound ETH34 was vacuum-deposited on the emission layer to form a hole-blocking layer having a thickness of 50 Å, and ET46 and LiQ were vacuum-deposited on the hole-blocking layer at a weight ratio of 4:6 to form an electron transport layer having a thickness of 310 Å. Next, Yb was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 15 Å, and then Mg was vacuum-deposited thereon to form a cathode having a thickness of 800 Å, thereby completing manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that, in forming the emission layer, compounds shown in Table 7 were used as the organometallic compound represented by Formula 1, the second compound, and the third compound.
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that, in forming the emission layer, compounds shown in Table 5 were used as the organometallic compound represented by Formula 1, the second compound, the third compound, and the fourth compound.
The driving voltage (V) at 1,000 cd/m2, color purity (CIEx,y), color conversion efficiency (cd/A/y), maximum emission wavelength (nm), and lifespan (T95) of the organic light-emitting devices manufactured in Examples F1 and F2 were measured using the Keithley MU 236 and the luminance meter PR650, and results are shown in Table 6. The lifespan (T95) in Table 6 indicates a time (hr) for the luminance to reach 95% of its initial luminance.
In Tables 5 and 6, the weight (wt %) per 100 wt % of the emission layer of each of the organometallic compound represented by Formula 1 and the fourth compound was also indicated.
Meanwhile,
The driving voltage (V) at 1,000 cd/m2, color purity (CIEx,y), color conversion efficiency (cd/A/y), maximum emission wavelength (nm), and lifespan (T95) of the organic light-emitting devices manufactured in Examples 1 to 6 were measured using the Keithley MU 236 and the luminance meter PR650, and results are shown in Table 8. The lifespan (T95) in Table 8 indicates a time (hr) for the luminance to reach 95% of its initial luminance.
In Tables 7 and 8, the weight (wt %) per 100 wt % of the emission layer of each of the organometallic compound represented by Formula 1 was also indicated.
Meanwhile, the electroluminescence spectra of Examples 1 to 6 and Comparative Examples A to C are shown in
From Table 8, it can be seen that the organic light-emitting devices of Examples 1 to 6 emit deep blue light, and compared to the organic light-emitting devices of Comparative Examples A to C, have an equivalent or higher level of driving voltage, color purity, and color conversion efficiency characteristics, and remarkably excellent lifespan characteristics.
The organometallic compound has excellent electrical characteristics, and thus a light-emitting device including the organometallic compound may have high luminescence efficiency and long lifespan.
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 as defined by the following claims.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2022-0083983 | Jul 2022 | KR | national |
