Patent Grant
12201016
This application claims the benefit of Korean Patent Application No. 10-2019-0028854, filed on Mar. 13, 2019, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein in its entirety by reference.
One or more embodiments relate to an organometallic compound, an organic light-emitting device including the organometallic compound, and an apparatus including the organic light-emitting device.
Organic light-emitting devices are self-emission devices that produce full-color images, and also have wide viewing angles, high contrast ratios, short response times, as well as excellent characteristics in terms of brightness, driving voltage, and response speed.
In an example, an organic light-emitting device includes a first electrode disposed on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode, which are sequentially disposed on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.
One or more embodiments include an organometallic compound, an organic light-emitting device including the organometallic compound, and an apparatus including the organic 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.
An aspect of the present disclosure provides an organometallic compound represented by Formula 1:
M11(L11)n11(L12)n12. <Formula 1>
In Formula 1,
In Formula 1-1,
Another aspect of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the organometallic compound described above.
Another aspect of the present disclosure provides an apparatus including: a thin-film transistor including a source electrode, a drain electrode, and an activation layer; and the organic light-emitting device described above, wherein the first electrode of the organic light-emitting device is electrically connected to one of the source electrode and the drain electrode of the thin-film transistor.
These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings in which:
The present disclosure will now be described more fully with reference to exemplary embodiments. The disclosure may, however, be embodied in many different forms and should not be construed as being limited to the embodiments set forth herein rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the disclosure to those skilled in the art. Features, and how to achieve them of the inventive concept will become apparent by reference to the embodiment that will be described later in detail, together with the accompanying drawings. This embodiments may, however, be embodied in many different forms and should not be limited to the exemplary embodiments.
Hereinafter, embodiments are described in detail by referring to the attached drawings, and in the drawings, like reference numerals denote like elements, and a redundant explanation thereof will not be provided herein.
As used herein, the singular forms “a,” “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
It will be further understood that the terms “comprises” and/or “comprising” used herein specify the presence of stated features or components, but do not preclude the presence or addition of one or more other features or components.
It will be understood that when a layer, region, or component is referred to as being “on” or “onto” another layer, region, or component, it may be directly or indirectly formed on the other layer, region, or component. That is, for example, intervening layers, regions, or components may be present.
Sizes of elements in the drawings may be exaggerated for convenience of explanation. In other words, since sizes and thicknesses of components in the drawings are arbitrarily illustrated for convenience of explanation, the following embodiments of the present disclosure are not limited thereto.
The term “an organic layer” as used herein refers to a single layer and/or a plurality of layers disposed between a first electrode and a second electrode of an organic light-emitting device. A material included in the “organic layer” is not limited to an organic material.
An organometallic compound according to an embodiment is represented by Formula 1 below:
M(L11)xc1(L12)xc2. <Formula 1>
In Formula 1,
For example, M11 in Formula 1 may be selected from platinum (Pt), palladium (Pd), copper(Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm), but embodiments of the present disclosure are not limited thereto.
In one embodiment, M11 in Formula 1 may be selected from Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, and Os, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, M11 in Formula 1 may be selected from Pt, Pd, Cu, Ag, Au, Ru, and Os, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, M11 in Formula 1 may be selected from Pt, Pd, Ru, Os, but embodiments of the present disclosure are not limited thereto:
In Formula 1-1, X11 to X13 may each independently be selected from a single bond, *—O—*′, *—S—*′, *—C(B11)(B12)—*′, *—Si(B11)(B12)—*, *—B(B11)—*′, *—N(B11)—*′, and *—P(B11)—*′, and B11 and B12 may be understood by referring to a detailed description thereof to be provided later.
For example, X11 to X13 in Formula 1-1 may each independently be selected from a single bond, *—O—*′, *—S—*′, *—C(B11)(B12)—*′, and *—N(B11)—*′, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, at least one selected from X11 to X13 in Formula 1-1 may be a single bond, but embodiments of the present disclosure are not limited thereto.
In one embodiment, in Formula 1-1,
In one embodiment, X11 to X13 in Formula 1-1 may be a single bond, but embodiments of the present disclosure are not limited thereto.
Y11 to Y14 in Formula 1-1 may each independently be nitrogen (N) or carbon (C).
T11 to T14 in Formula 1-1 may each independently be selected from a single bond, *—O—*′, *—S—*′, *—C(B13)(B14)—*′, *—Si(B13)(B14)—*′, *—B(B13)—*′, *—N(B13)—*′, and *—P(B13)—*′, and B13 and B14 may be understood by referring to a detailed description thereof to be provided later.
For example, T11 to T14 in Formula 1-1 may each independently be selected from a single bond, *—O—*′, and *—S—*′, but are not limited thereto.
In one or more embodiments, T11 to T14 in Formula 1-1 may be a single bond, but embodiments of the present disclosure are not limited thereto.
ring A11 to ring A20 in Formula 1-1 may each independently be selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group.
For example, ring A11 to ring A20 in Formula 1-1 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed with each other, iv) a condensed ring in which at least two second rings are condensed with each other, or v) a condensed ring in which at least one first ring and at least one second ring are condensed with each other.
The first ring may be selected from a cyclopentane group, a cyclopentene group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a borole group, a phosphole group, a silole group, a germole group, a selenophene group, an oxazole group, a dihydroxazole group, an isoxazole group, a dihydroisoxazole group, an oxadiazole group, a dihydroxadiazole group, an isoxadiazole group, a dihydroisoxadiazole group, an oxatriazole group, a dihydroxatriazole group, an isoxatriazole group, a dihydroisoxatriazole group, a thiazole group, a dihydrothiazole group, an isothiazole group, a dihydroisothiazole group, a thiadiazole group, a dihydrothiadiazole group, an isothiadiazole group, a dihydroisothiadiazole group, a thiatriazole group, a dihydrothiatriazole group, an isothiatriazole group, a dihydroisothiatriazole group, a pyrazole group, a dihydropyrazole group, an imidazole group, a dihydroimidazole group, a triazole group, a dihydrotriazole group, a tetrazole group, a dihydrotetrazole group, an azasilole group, a diazasilol group, and a triazasilole group, but embodiments of the present disclosure are not limited thereto.
The second ring may be selected from a cyclohexane group, a cyclohexene group, a cyclohexadiene group, an admantane group, a norbornane group, a norbornene group, a benzene group, a pyridine group, a dihydropyridine group, a tetrahydropyridine group, a pyrimidine group, a dihydropyrimidine group, a tetrahydropyrimidine group, a pyrazine group, a dihydropyrazine group, a tetrahydropyrazine group, a pyridazine group, a dihydropyridazine group, a tetrahydropyridazine group, and a triazine group, but embodiments of the present disclosure are not limited thereto.
In one embodiment, ring A11 to ring A20 in Formula 1-1 may each independently be selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an indole group, a carbazole group, an indenopyridine group, an indolopyridine group, a benzofuropyridine group, a benzothienopyridine group, a benzosilolopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuropyrimidine group, a benzothienopyrimidine group, a benzosilolopyrimidine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a cinnoline group, a phthalazine group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a dihydroimidazole group, a triazole group, a dihydrotriazole group, an oxazole group, a dihydroxazole group, an isoxazole group, a thiazole group, a dihydrothiazole group, an isothiazole group, an oxadiazole group, a dihydroxadiazole group, a thiadiazole group, a dihydrothiadiazole group, a benzopyrazole group, a benzimidazole group, a dihydrobenzimidazole group, an imidazopyridine group, an imidazopyrimidine group, an imidazopyrazine group, a benzoxazole group, a dihydrobenzoxazole group, a benzothiazole group, a dihydrobenzothiazole group, a benzoxadiazole group, a dihydrobenzoxadiazole group, a benzothiadiazole group, and a dihydrobenzothiadiazole group, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, in Formula 1-1, ring A11 to ring A14 may each independently be selected from a benzene group, a naphthalene group, an indene group, a fluorene group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, an indole group, a carbazole group, an indenopyridine group, an indolopyridine group, a benzofuropyridine group, a benzothienopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuropyrimidine group, a benzothienopyrimidine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a cinnoline group, a phthalazine group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a dihydroimidazole group, a triazole group, a dihydrotriazole group, an oxazole group, a dihydroxazole group, an isoxazole group, a thiazole group, a dihydrothiazole group, an isothiazole group, an oxadiazole group, a dihydroxadiazole group, a thiadiazole group, a dihydrothiadiazole group, a benzopyrazole group, a benzimidazole group, a dihydrobenzimidazole group, an imidazopyridine group, an imidazopyrimidine group, an imidazopyrazine group, a benzoxazole group, a dihydrobenzoxazole group, a benzothiazole group, a dihydrobenzothiazole group, a benzoxadiazole group, a dihydrobenzoxadiazole group, a benzothiadiazole group, and a dihydrobenzothiadiazole group, and
In one or more embodiments, ring A11 to ring A14 in Formula 1-1 may each independently be represented by one of Formulae 2-1 to 2-43, but embodiments are not limited thereto:
In Formulae 2-1 to 2-43,
In one embodiment, in Formula 101, a group represented by
may be a group represented by Formula 3-11, a group represented by
may be a group represented by Formula 3-21, a group represented by
may be a group represented by Formula 3-31, and a group represented by
may be a group represented by Formula 3-41, but embodiments of the present disclosure are not limited thereto:
In Formulae 3-11, 3-21, 3-31, and 3-41,
In one embodiment, in Formula 1-1, a group represented by
may be a group represented by one selected from Formulae 10-1 to 10-15, a group represented by
may be a group represented by one selected from Formulae 11-1 to 11-15, and a group represented by
may be a group represented by one selected from Formulae 12-1 to 12-15:
In Formulae 10-1 to 10-15, 11-1 to 11-15, and 12-1 to 12-15,
For example, in Formulae 10-1 to 10-15, 11-1 to 11-15, and 12-1 to 12-15, R15 to R20 may each independently be selected from:
In Formula 1-1, B11 to B14 and R11 to R20 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), and —P(═S)(Q1)(Q2), and
For example, in Formula 1-1, B11 to B14 and R11 to R20 may each independently be selected from:
In one embodiment, in Formula 1-1, B11 to B14 and R11 to R20 may each independently be selected from:
In Formulae 5-1 to 5-138,
In one embodiment, in Formula 1-1, B11 to B14 and R11 to R20 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, and a group represented by one of Formulae 9-1 to 9-16;
In Formulae 6-1 to 6-257,
In one embodiment, in Formula 1-1, R11 to R14 may each independently be selected from:
In one embodiment, in Formula 1-1, R15 to R20 may each independently be selected from:
In Formula 1-1, b11 to b20 may each independently be an integer from 1 to 10.
In Formula 1-1, *1 to *4 each indicate a binding site to M11.
In Formula 1-1, * and *′ each indicate a binding site to a neighboring atom.
In one embodiment, in Formula 1, L11 may be a ligand represented by Formula 1-11, but embodiments of the present disclosure are not limited thereto:
In Formula 1-11,
For example, in Formula 1-11, ring A11 to ring A14 may each independently be selected from a benzene group, a naphthalene group, an indene group, a fluorene group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, an indole group, a carbazole group, an indenopyridine group, an indolopyridine group, a benzofuropyridine group, a benzothienopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuropyrimidine group, a benzothienopyrimidine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a cinnoline group, a phthalazine group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a dihydroimidazole group, a triazole group, a dihydrotriazole group, an oxazole group, a dihydroxazole group, an isoxazole group, a thiazole group, a dihydrothiazole group, an isothiazole group, an oxadiazole group, a dihydroxadiazole group, a thiadiazole group, a dihydrothiadiazole group, a benzopyrazole group, a benzimidazole group, a dihydrobenzimidazole group, an imidazopyridine group, an imidazopyrimidine group, an imidazopyrazine group, a benzoxazole group, a dihydrobenzoxazole group, a benzothiazole group, a dihydrobenzothiazole group, a benzoxadiazole group, a dihydrobenzoxadiazole group, a benzothiadiazole group, and a dihydrobenzothiadiazole group, and
In one or more embodiments, L11 in Formula 1 may be a ligand represented by Formula 1-21, but embodiments of the present disclosure are not limited thereto:
In Formula 1-21,
For example, in Formula 1-21, ring A11 to ring A14 may each independently be selected from a benzene group, a naphthalene group, an indene group, a fluorene group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, an indole group, a carbazole group, an indenopyridine group, an indolopyridine group, a benzofuropyridine group, a benzothienopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuropyrimidine group, a benzothienopyrimidine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a cinnoline group, a phthalazine group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a dihydroimidazole group, a triazole group, a dihydrotriazole group, an oxazole group, a dihydroxazole group, an isoxazole group, a thiazole group, a dihydrothiazole group, an isothiazole group, an oxadiazole group, a dihydroxadiazole group, a thiadiazole group, a dihydrothiadiazole group, a benzopyrazole group, a benzimidazole group, a dihydrobenzimidazole group, an imidazopyridine group, an imidazopyrimidine group, an imidazopyrazine group, a benzoxazole group, a dihydrobenzoxazole group, a benzothiazole group, a dihydrobenzothiazole group, a benzoxadiazole group, a dihydrobenzoxadiazole group, a benzothiadiazole group, and a dihydrobenzothiadiazole group,
L12 in Formula 1 may be selected from a monodentate ligand and a bidentate ligand.
For example, L12 in Formula 1 may be a ligand represented by one of Formulae 7-1 to 7-11, but embodiments of the present disclosure are not limited thereto:
In Formulae 7-1 to 7-11,
For example, ring A71 and ring A72 in Formula 7-1 may each independently be selected from a benzene group, a naphthalene group, an imidazole group, a benzimidazole group, a pyridine group, a pyrimidine group, a triazine group, a quinoline group, and an isoquinoline group, but embodiments of the present disclosure are not limited thereto.
For example, in Formula 7-1, X72 and X79 may be N, but embodiments of the present disclosure are not limited thereto.
For example, in Formula 7-7, X73 may be C(Q73), X74 may be C(Q74), X75 may be C(Q75), X76 may be C(Q76), and X77 may be C(Q77), but embodiments of the present disclosure are not limited thereto.
For example, in Formula 7-8, X78 may be N(Q78), and X79 may be N(Q79), but embodiments of the present disclosure are not limited thereto.
For example, in Formulae 7-2, 7-3, and 7-8, Y71 and Y72 may each independently be selected from a substituted or unsubstituted methylene group and a substituted or unsubstituted phenylene group, but embodiments of the present disclosure are not limited thereto.
For example, in Formulae 7-1 and 7-2, Z71 and Z72 may each independently be O, but embodiments of the present disclosure are not limited thereto.
For example, in Formula 7-4, Z73 may be P, but embodiments of the present disclosure are not limited thereto.
For example, in Formulae 7-1 to 7-8, R71 to R80 and Q73 to Q79 may each independently be selected from:
In one embodiment, L12 in Formula 1 may be represented by one of Formulae 8-1 to 8-11, but embodiments of the present disclosure are not limited thereto:
In Formula 1, n11 indicates the number of L11, wherein n11 may be 1.
In Formula 1, n12 indicates the number of L12, wherein n12 may be selected from 0, 1, and 2. When n12 is two, a plurality of L12(s) may be identical to or different from each other.
In one embodiment, in Formula 1, n11 may be 1, and n12 may be 0.
In one or more embodiments, in Formula 1, n11 may be 1, and n12 may be 2.
In one or more embodiments, in Formula 1, M11 may be selected from Pt and Pd, n11 may be 1, and n12 may be 0.
In one embodiment, the organometallic compound represented by Formula 1 may be selected from compounds BD1 to BD80 of Group I below, but embodiments of the present disclosure are not limited thereto:
Since the organometallic compound essentially includes a ring including A15, X11, and A16, a ring including A17, X12, and A18, and a ring including A19, X13, and A20, that is, includes three condensed rings as a linker, the formation of exciplex with a host is hindered, as compared with a compound including two condensed rings as a linker. Therefore, the efficiency of an electronic device (for example, an organic light-emitting device) including the organometallic compound may be improved.
The organometallic compound may emit blue light having a maximum emission wavelength in a range of about 430 nm or more and about 470 nm or less.
A synthesis method for the organometallic compound represented by Formula 1 would be apparent to those of ordinary skill in the art by referring to the following examples.
At least one of the organometallic compound of Formula 1 may be used between a pair of electrodes of an organic light-emitting device. Accordingly, provided is an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode. The organic layer includes an emission layer, wherein the organic layer includes at least one organometallic cyclic compound represented by Formula 1.
The expression “(an organic layer) includes at least one of organometallic compounds” as used herein may include a case in which “(an organic layer) includes identical organometallic compounds represented by Formula 1” and a case in which “(an organic layer) includes two or more different organometallic compounds represented by Formula 1”.
For example, the organic layer may include, as the organometallic compound, only Compound 1. In this regard, Compound 1 may exist only in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the organometallic compound, Compound 1 and Compound 2. In one or more embodiments, Compound 1 and Compound 2 may both exist in an identical layer (for example, Compound 1 and Compound 2 may both exist in an emission layer), or may exist in different layers (for example, Compound 1 may exist in an emission layer and Compound 2 may exist in an electron transport layer).
The organic layer includes i) a hole transport region that is disposed between the first electrode (anode) and the emission layer and includes at least one of a hole injection layer, a hole transport layer, a buffer layer, and an electron blocking layer, and/or ii) an electron transport region that is disposed between the emission layer and the second electrode (cathode) and includes at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. The emission layer may include at least one of organometallic compounds represented by Formula 1.
In one or more embodiments, at least one of the hole transport region and the emission layer may include at least one selected from an arylamine-containing compound, an acridine-containing compound, and a carbazole-containing compound, and/or
at least one of the emission layer and the electron transport region may include at least one selected from a silicon-containing compound, a phosphine oxide-containing compound, a sulfur oxide-containing compound, a phosphorus oxide-containing compound, a triazine-containing compound, a pyrimidine-containing compound, a pyridine-containing compound, a dibenzofuran-containing compound, and a dibenzothiophene-containing compound.
[Description of
Hereinafter, the structure of the organic light-emitting device 10 according to an embodiment and a method of manufacturing the organic light-emitting device 10 will be described in connection with
[First Electrode 110]
In
The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be selected from materials with a high work function to facilitate hole injection.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming a first electrode may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combinations thereof, but embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming a first electrode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combinations thereof, but embodiments of the present disclosure are not limited thereto.
The first electrode 110 may have a single-layered structure, or a multi-layered structure including two or more layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.
[Organic Layer 150]
The organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emission layer.
The organic layer 150 may further include a hole transport region between the first electrode 110 and/or the emission layer, and an electron transport region between the emission layer and the second electrode 190.
[Hole Transport Region in Organic Layer 150]
The hole transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.
For example, the hole transport region may have a single-layered structure including a single layer including a plurality of different materials, or a multi-layered structure having a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein for each structure, constituting layers are sequentially stacked from the first electrode 110 in this stated order, but the structure of the hole transport region is not limited thereto.
The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, and a compound represented by Formula 202:
In Formulae 201 and 202,
For example, in Formula 202, R201 and R202 may optionally be linked via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R203 and R204 may optionally be linked via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.
In one embodiment, in Formulae 201 and 202,
In one or more embodiments, xa1 to xa4 may each independently be 0, 1, or 2.
In one or more embodiments, xa5 may be 1, 2, 3, or 4.
In one or more embodiments, R201 to R204 and Q201 may each independently be selected from a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group; and
In one or more embodiments, at least one selected from R201 to R203 in Formula 201 may each independently be selected from:
In one or more embodiments, in Formula 202, i) R201 and R202 may be linked via a single bond, and/or ii) R203 and R204 may be linked via a single bond.
In one or more embodiments, in Formula 202, at least one selected from R201 to R204 may each independently be selected from:
The compound represented by Formula 201 may be represented by Formula 201A:
In one embodiment, the compound represented by Formula 201 may be represented by Formula 201A(1) below, but embodiments of the present disclosure are not limited thereto:
In one embodiment, the compound represented by Formula 201 may be represented by Formula 201A-1 below, but embodiments of the present disclosure are not limited thereto:
In one embodiment, the compound represented by Formula 202 may be represented by Formula 202A:
In one embodiment, the compound represented by Formula 202 may be represented by Formula 202A-1:
In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,
The hole transport region may include at least one compound selected from Compounds HT1 to HT39, but embodiments of the present disclosure are not limited thereto:
A thickness of the hole transport region may be from about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, 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 flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may include the materials as described above.
[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 homogeneously or non-homogeneously dispersed in the hole transport region.
The charge-generation material may be, for example, a p-dopant.
In one embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of −3.5 eV or less.
The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto.
For example, the p-dopant may include at least one selected from:
In Formula 221,
When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.
The emission layer may include a host and a dopant. The dopant may include the organometallic compound represented by Formula 1. In one or more embodiments, the dopant may further include, in addition to the organometallic compound represented by Formula 1, at least one of a phosphorescent dopant and a fluorescent dopant:
An amount of the dopant 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, but embodiments of the present disclosure are not limited thereto.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
[Host in Emission Layer]
In one or more embodiments, the host may include a compound represented by Formula 301 below.
[Ar301]xb11-[(L301)xb1-R301]xb21 <Formula 301>
In Formula 301,
In one embodiment, Ar301 in Formula 301 may be selected from:
When xb11 in Formula 301 is two or more, two or more Ar301(s) may be linked via a single bond.
In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or 301-2:
In Formulae 301-1 to 301-2,
For example, L301 to L304 in Formulae 301, 301-1, and 301-2 may each independently be selected from:
In one embodiment, R301 to R304 in Formulae 301, 301-1, and 301-2 may each independently be selected from:
In one embodiment, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (for example, Compound H55), a Mg complex, and a Zn complex.
The host may be selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), 4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide(POPCPA), and Compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:
In one or more embodiments, the host may include at least one selected from a silicon-containing compound (for example, BCPDS or the like used in Examples) and a phosphine oxide-containing compound (for example, POPCPA or the like used in Examples).
The host may include one type of compounds only or two or more different types of compounds (for example, the constituent hosts in Examples are BCPDS and POPCPA). As such, embodiments may be modified in various ways.
In one or more embodiments, an amount of the host in the emission layer may be greater than that of the organometallic compound represented by Formula 1 which is a dopant.
[Electron Transport Region in Organic Layer 150]
The electron transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.
For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein for each structure, constituting layers are sequentially stacked from an emission layer. However, embodiments of the structure of the electron transport region are not limited thereto.
The hole transport region may include the second compound as described above.
In one embodiment, the hole transport region may include a buffer layer. The buffer layer may directly contact the emission layer, and may include the second compound.
In one or more embodiments, the electron transport region may include a buffer layer, an electron transport layer, and an electron injection layer, which are stacked in this stated order on the emission layer. The buffer layer may include the second compound as described above.
The electron transport region (for example, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-depleted nitrogen-containing ring.
The “π electron-depleted nitrogen-containing ring” indicates a C1-C60 heterocyclic group having at least one *—N═*′ moiety as a ring-forming moiety.
For example, the “π electron-depleted nitrogen-containing ring” may be i) a 5-membered to 7-membered heteromonocyclic group having at least one *—N═*′ moiety, ii) a heteropolycyclic group in which two or more 5-membered to 7-membered heteromonocyclic groups each having at least one *—N═*′ moiety are condensed with each other, or iii) a heteropolycyclic group in which at least one of 5-membered to 7-membered heteromonocyclic groups, each having at least one *—N═*′ moiety, is condensed with at least one C5-C60 carbocyclic group.
Examples of the π electron-depleted nitrogen-containing ring include an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, an indazole, a purine, a quinoline, an isoquinoline, a benzoquinoline, a phthalazine, a naphthyridine, a quinoxaline, a quinazoline, a cinnoline, a phenanthridine, an acridine, a phenanthroline, a phenazine, a benzimidazole, an isobenzothiazole, a benzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a triazine, thiadiazole, an imidazopyridine, an imidazopyrimidine, and an azacarbazole, but are not limited thereto.
For example, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21 <Formula 601>
In Formula 601,
In one embodiment, at least one selected from Ar601(s) in the number of xe11 and R601(s) in the number of xe21 may include the π electron-depleted nitrogen-containing ring.
In one embodiment, ring Ar601 in Formula 601 may be selected from:
When xe11 in Formula 601 is two or more, two or more ring Ar601(s) may be linked via a single bond.
In one or more embodiments, ring Ar601 in Formula 601 may be an anthracene group.
In one or more embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:
In Formula 601-1,
In one embodiment, L601 and L611 to L613 in Formulae 601 and 601-1 may each independently be selected from:
In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
In one or more embodiments, R601 and R611 to R613 in Formulae 601 and 601-1 may each independently be selected from:
The electron transport region may include at least one compound selected from Compounds ET1 to ET36, but embodiments of the present disclosure are not limited thereto:
In one or more embodiments, the electron transport region may include at least one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-dphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), NTAZ, diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1), and 3P-T2T:
A thickness of the buffer layer, the hole blocking layer, or the electron control layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, the electron blocking layer may have excellent electron blocking characteristics or electron control characteristics without a substantial increase in driving voltage.
A thickness of the electron transport layer may be from about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, satisfactory electron transport 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 at least one selected from alkali metal complex and alkaline earth-metal complex. The alkali metal complex may include a metal ion selected from a Li ion, a Na ion, a K ion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex may include a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Sr ion, and a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be selected from a hydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxy diphenyl oxadiazole, a hydroxy diphenylthiadiazole, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, LiQ) or ET-D2:
The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may directly contact the second electrode 190.
The electron injection layer may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof.
The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but embodiments of the present disclosure are not limited thereto.
The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.
The alkali metal compound, the alkaline earth-metal compound, and the rare earth metal compound may be selected from oxides and halides (for example, fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth-metal, and the rare earth metal.
The alkali metal compound may be selected from alkali metal oxides, such as Li2O, Cs2O, or K2O, and alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, or RbI. In one embodiment, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but embodiments of the present disclosure are not limited thereto.
The alkaline earth-metal compound may be selected from alkaline earth-metal oxides, such as BaO, SrO, CaO, BaxSr1-xO (0<x<1), or BaxCa1-xO (0<x<1). In one embodiment, the alkaline earth-metal compound may be selected from BaO, SrO, and CaO, but embodiments of the present disclosure are not limited thereto.
The rare earth metal compound may be selected from YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, and TbF3. In one embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but embodiments of the present disclosure are not limited thereto.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include an ion of alkali metal, alkaline earth-metal, and rare earth metal as described above, and a ligand coordinated with a metal ion of the alkali metal complex, the alkaline earth-metal complex, or the rare earth metal complex may be selected from hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
The electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When a thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without substantial increase in driving voltage.
[Second Electrode 190]
The second electrode 190 may be disposed on the organic layer 150 having such a structure. The second electrode 190 may be a cathode which is an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be selected from metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function.
The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 190 may have a single-layered structure, or a multi-layered structure including two or more layers.
[Description of
Regarding
In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in an emission layer may pass through the first electrode 110 and the first capping layer 210 toward the outside, wherein the first electrode 110 may be a semi-transmissive electrode or a transmissive electrode. In the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in an emission layer may pass through the second electrode 190 and the second capping layer 220 toward the outside, wherein the second electrode 190 may be a semi-transmissive electrode or a transmissive electrode.
The first capping layer 210 and the second capping layer 220 may increase external luminescent efficiency according to the principle of constructive interference.
The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.
At least one selected from the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrine derivatives, phthalocyanine derivatives, a naphthalocyanine derivatives, alkali metal complexes, and alkaline earth-based complexes. The carbocyclic compound, the heterocyclic compound, and the amine-based compound may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include an amine-based compound.
In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.
In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from Compounds HT28 to HT33 and Compounds CP1 to CP5, but embodiments of the present disclosure are not limited thereto:
Hereinbefore, the organic light-emitting device according to an embodiment has been described in connection with
Layers constituting the hole transport region, an emission layer, and layers constituting the electron transport region may be formed in a certain region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.
When layers constituting the hole transport region, 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 by taking into account a material to be included in a layer to be formed, and the structure of a layer to be formed.
When layers constituting the hole transport region, an emission layer, and layers constituting the electron transport region are formed by spin coating, the spin coating may be performed at a coating speed of about 2000 rpm to about 5000 rpm and at a heat treatment temperature of about 80° C. to about 200° C. by taking into account a material to be included in a layer to be formed, and the structure of a layer to be formed.
[Apparatus]
The organic light-emitting device may be included in various apparatuses.
One of the source electrode and the drain electrode may be electrically connected to the first electrode of the organic light-emitting device.
The thin-film transistor may further include a gate electrode, a gate insulating layer, or the like.
The activation layer may include crystalline silicon, amorphous silicon, organic semiconductor, oxide semiconductor, or the like, but embodiments of the present disclosure are not limited thereto.
The apparatus may further include a sealing part that seals the light-emitting device. The sealing part may implement an image from the light-emitting device, and prevent outside air and moisture from penetrating into the light-emitting device. The sealing part may be a sealing substrate including a transparent glass or a plastic substrate. The sealing part may be a thin-film encapsulation layer including a plurality of organic layers and/or a plurality of inorganic layers. When the sealing part is the thin-film encapsulation layer, the entire flat display device may be made flexible.
For example, the apparatus may be used as an light-emitting device, an authentication apparatus, or an electronic device.
The light-emitting apparatus may be used as various displays, light sources, and the like.
The authentication apparatus may be, for example, a biometric authentication apparatus for authenticating an individual by using biometric information of a biometric body (for example, a finger tip, a pupil, or the like). The authentication apparatus may further include, in addition to the organic light-emitting device, a biometric information collector.
The electronic apparatus may be applied to personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram (ECG) displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and the like, but embodiments of the present disclosure are not limited thereto.
The term “first-row transition metal of the Periodic Table of Elements” as used herein refers to a fourth-row element of the Periodic Table of Element and belonging to a d-block, and examples thereof include scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and zinc (Zn).
The term “second-row transition metal of the Periodic Table of Elements” as used herein refers to a fifth-row element of the Periodic Table of Element and belonging to a d-block, and examples thereof include yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), and cadmium (Cd).
The term “third-row transition metal of the Periodic Table of Elements” as used herein refers to a sixth-row element of the Periodic Table of Element and belonging to a d-block and an f-block, and examples thereof include lanthanum (La), samarium (Sm), europium (Eu), terbium (Tb), thulium (Tm), ytterbium (Yb), lutetium (Lu), hafnium (Hf), tantalum (Ta), tungsten(W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pr), gold (Au), and mercury (Hg).
The term “C1-C60 alkyl group” as used herein refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The term “C1-C60 alkylene group” as used herein 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 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 include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group” as used herein refers to a 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 monocyclic group having 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C3-C10 cycloalkylene group” as used herein 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 monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Non-limiting examples of the C1-C10 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-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 having 6 to 60 carbon atoms, and a C6-C60 arylene group used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other. The term “C7-C60 alkyl heteroaryl group” as used herein refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms. Non-limiting examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. 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 “C2-C60 alkyl heteroaryl group” as used herein refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group.
The term “C6-C60 aryloxy group” as used herein refers to —OA102 (wherein A102 is the C6-C60 aryl group), and a C6-C60 arylthio group used herein indicates —SA103 (wherein A103 is the C6-C60 aryl group).
The term “C1-C60 heteroaryloxy group” as used herein indicates —OA104 (wherein A104 is the C1-C6 heteroaryl group), and the term “C6-C60 heteroarylthio group” as used herein indicates —SA105 (wherein A105 is the C1-C60 heteroaryl group).
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 with each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. A detailed example of the monovalent non-aromatic condensed polycyclic group is a fluorenyl 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.
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, at least one heteroatom selected from N, O, Si, P, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. An example of the monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl 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.
The term “C5-C60 carbocyclic group” as used herein refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms in which a ring-forming atom is a carbon atom only. The term “C5-C60 carbocyclic group” as used herein refers to an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C5-C60 carbocyclic group may be a ring, such as benzene, a monovalent group, such as a phenyl group, or a divalent group, such as a phenylene group. In one or more embodiments, depending on the number of substituents connected to the C5-C60 carbocyclic group, the C5-C60 carbocyclic group may be a trivalent group or a quadrivalent group.
The term “C1-C60 heterocyclic group” as used herein refers to a group having the same structure as the C5-C60 carbocyclic group, except that as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S is used in addition to carbon (the number of carbon atoms may be in a range of 1 to 60).
In the present specification, at least one substituent of the substituted C5-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, the substituted C3-C10 cycloalkylene group, the substituted C1-C10 heterocycloalkylene group, the substituted C3-C10 cycloalkenylene group, the substituted C1-C10 heterocycloalkenylene group, the substituted C6-C60 arylene group, the substituted C1-C60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkyl aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
The term “Ph” as used herein refers to a phenyl group, the term “Me” as used herein refers to a methyl group, the term “Et” as used herein refers to an ethyl group, the term “ter-Bu” or “But” as used herein refers to a tert-butyl group, and the term “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 phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.
* and *′ as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula.
Hereinafter, a compound according to embodiments and an organic light-emitting device according to embodiments will be described in detail with reference to Synthesis Examples and Examples. The wording “B was used instead of A” used in describing Synthesis Examples refers to that an identical molar equivalent of B was used in place of A.
Compound BD1 was synthesized with reference to the Scheme I.
(1) Synthesis of Intermediate 1-1
Compound A reacted with nBuLi and then reacted with 3-bromo benzaldehyde to synthesize Intermediate 1-1. Intermediate 1-1 was identified by LC-MS.
C19H15BrO: M+1 340.15.
(2) Synthesis of Intermediate 1-2
Intermediate 1-1 reacted with pyridinium chlorochromate (cas: 26299-14-9) under a dichloromethane solvent at room temperature to synthesize Intermediate 1-2. Intermediate 1-2 was identified by LC-MS.
C19H13BrO: M+1 337.13.
(3) Synthesis of Intermediate 1-3
2-bromo pyridine (cas: 109-04-6) was activated with magnesium under an iodine catalyst and reacted with Intermediate 1-2 to synthesize Intermediate 1-3. Intermediate 1-3 was identified by LC-MS.
C24H18BrNO: M+1 417.57.
(4) Synthesis of Intermediate 1-4
Intermediate 1-3 reacted with hydrochloride (cas: 7647-01-0) under an AcOH solvent to obtain Intermediate 1-4. Intermediate 1-4 was identified by LC-MS.
C24H16BrN: M+1 399.92.
(5) Synthesis of Intermediate 1-5
Compound A reacted with nBuLi and then reacted with isophthalaldehyde to synthesize Intermediate 1-5. Intermediate 1-5 was identified by LC-MS.
C32H26O2: M+1 443.18.
(6) Synthesis of Intermediate 1-6
Intermediate 1-5 reacted with pyridinium chlorochromate (cas: 26299-14-9) under a dichloromethane solvent at room temperature to synthesize Intermediate 1-6. Intermediate 1-6 was identified by LC-MS.
C32H22O2: M+1 438.53.
(7) Synthesis of Intermediate 1-7
Intermediate 1-4 reacted with nBuLi and then reacted with Intermediate 1-6 to synthesize Intermediate 1-7. Intermediate 1-7 was identified by LC-MS.
C56H39NO2: M+1 757.95.
(8) Synthesis of Intermediate 1-8
Intermediate 1-7 reacted with pyridinium chlorochromate (cas: 26299-14-9) under a dichloromethane solvent to synthesize Intermediate 1-8. Intermediate 1-8 was identified by LC-MS.
C56H37NO: M+1 739.90.
(9) Synthesis of Intermediate 1-9
Intermediate 1-8 reacted with imidazole (cas: 288-32-4) and potassium carbonate to synthesize Intermediate 1-9. Intermediate 1-9 was identified by LC-MS.
C59H41N3O: M+1 808.22.
(10) Synthesis of Intermediate 1-10
Intermediate 1-9 reacted with pyridinium chlorochromate (cas: 26299-14-9) under a dichloromethane solvent at room temperature to synthesize Intermediate 1-9. Intermediate 1-10 was identified by LC-MS.
C59H39N3: M+1 789.99.
(11) Synthesis of Intermediate 1-11
Intermediate 1-10 reacted with iodide methane (cas: 74-88-4) under an acetone solvent to synthesize Intermediate 1-11. Intermediate 1-11 was identified by LC-MS.
C60H42N3: M+1 805.22.
(12) Synthesis of Compound BD1
Intermediate 1-11, dichloro(1,5-cyclooctadiene)platinum(ii), and sodium acetate reached with each other under a 1,4-dioxane solvent at a temperature of 160° C. to synthesize Compound BD1. Compound BD1 was identified by LC-MS.
C60H39N3Pt: M+1 997.08.
Compound BD2 was synthesized with reference to the Scheme II and Synthesis Example 1.
Compounds BD2 was identified by LC-MS.
C61H41N3Pt: M+1 1011.12.
Compound BD3 was synthesized with reference to the Scheme III and Synthesis Example 1.
Compounds BD3 was identified by LC-MS.
C63H45N3Pt: M+1 1039.25.
Compound BD4 was synthesized with reference to the Scheme IV and Synthesis Example 1.
Compound BD4 was identified by LC-MS.
C64H47N3Pt: M+1 1053.24.
Compound BD5 was synthesized with reference to the Scheme V and Synthesis Example 1.
Compound BD5 was identified by LC-MS.
C61H41N3Pt: M+1 1011.12.
As an anode, an ITO substrate, on which ITO/Ag/ITO were deposited, was cut to a size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The ITO substrate was provided to a vacuum deposition apparatus.
Compound 2-TNATA was vacuum-deposited on the ITO substrate to form a hole injection layer having a thickness of 60 nm, and NPB was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 30 nm.
BCPDS (bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane) (host) and Compound BD1 (dopant) were co-deposited on the hole transport layer at a weight ratio of 10:1 to form an emission layer having a thickness of 25 nm.
BAlq was deposited on the emission layer to form a hole blocking layer having a thickness of 5 nm, Alq3 was deposited on the hole blocking layer to form an electron transport layer having a thickness of 25 nm, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 0.5 nm, and Al was deposited on the electron injection layer to form a cathode having a thickness of 150 nm, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that Compounds shown in Table 1 were each used in forming an emission layer.
The driving voltage (V), current density (mA/cm2), luminescent efficiency (cd/A), maximum emission wavelength (nm), and lifespan (Tso) of the organic light-emitting devices manufactured according to Example 1 and Comparative Examples 1 to 4 at 1,000 cd/m2 by using Keithley MU 236 and a luminance meter PR650, and results thereof are shown in Table 1. In Table 1, the lifespan (Tso) indicates an amount of time that lapsed when luminance was 90% of initial luminance (100%).
BD1
C1
C2
C3
C4
Referring to Table 1, it is confirmed that the current efficiency and lifespan of the organic light-emitting device of Example 1 are more excellent than those of the organic light-emitting devices of Comparative Examples 1 to 4.
The organic light-emitting device may have high efficiency and a 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 |
|---|---|---|---|
| 10-2019-0028854 | Mar 2019 | KR | national |
| Number | Name | Date | Kind |
|---|---|---|---|
| 8187729 | Murakami et al. | May 2012 | B2 |
| 9617291 | Li et al. | Apr 2017 | B2 |
| 9847498 | Brooks et al. | Dec 2017 | B2 |
| 9920242 | Li | Mar 2018 | B2 |
| 10033003 | Li et al. | Jul 2018 | B2 |
| 10056567 | Li | Aug 2018 | B2 |
| 20120043546 | Oh | Feb 2012 | A1 |
| 20130168656 | Tsai | Jul 2013 | A1 |
| 20180090692 | Kang et al. | Mar 2018 | A1 |
| 20190019964 | Jeon et al. | Jan 2019 | A1 |
| 20190027699 | Ko et al. | Jan 2019 | A1 |
| 20190044085 | Jeong et al. | Feb 2019 | A1 |
| Number | Date | Country |
|---|---|---|
| 2006-060198 | Mar 2006 | JP |
| 10-1548382 | Aug 2015 | KR |
| Entry |
|---|
| Analog electronic technology, ISBN 978-7-04-029791-1, pp. 157-159, Jul. 31, 2010. |
| Number | Date | Country | |
|---|---|---|---|
| 20200295279 A1 | Sep 2020 | US |
