Patent Grant
12082491
This application claims priority to and benefits of Korean Patent Application No. 10-2020-0004944 under 35 U.S.C. § 119, filed on Jan. 14, 2020 in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.
Embodiments relate to an organometallic compound and an organic light-emitting device including the same.
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, and excellent characteristics in terms of brightness, driving voltage, and response speed, compared to devices in the art.
The organic light-emitting device may include 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.
Provided are novel organometallic compounds and organic light-emitting devices including the same.
Embodiments will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the embodiments of the disclosure.
In an embodiment, an organometallic compound represented by Formula 1 is provided.
In Formula 1
In an embodiment, an organic light-emitting device may include a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic light-emitting device includes the organometallic compound.
In an embodiment, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode. 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. The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
In an embodiment, the emission layer may include the organometallic compound.
In an embodiment, the emission layer may emit blue light having a maximum emission wavelength of about 400 nm to about 500 nm.
In an embodiment, the emission layer may include a hose and a dopant, and the dopant may include the organometallic compound.
In an embodiment, the hole transport region may include a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of less than about −3.5 cV.
In an embodiment, the electron transport region may include the electron transport layer and the electron injection layer, and at least one of the electron transport layer and the electron injection layer may further include at least one selected from the group consisting 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.
The above and other aspects, features, and advantages of embodiments of the disclosure will be more apparent from the following description taken in conjunction with the drawings.
Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings. In this regard, the embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are described below, by referring to the figures, to explain aspects of the invention.
Like reference numerals refer to like elements throughout. In the drawings, the dimensions of structures are exaggerated for clarity of illustration. It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Thus, a first element could be termed a second element without departing from the teachings of the invention. Similarly, a second element could be termed a first element. As used herein, the singular forms are intended to include the plural forms as well, unless the context clearly indicates otherwise.
As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items for the purpose of its meaning and interpretation. 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. For example, “A and/or B” may be understood to mean A, B, or A and B. The terms “and” and “or” may be used in the conjunctive or disjunctive sense and may be understood to be equivalent to “and/or”. Throughout the disclosure, the expression “at least one of a, b or c” indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.
The phrase “at least one of” is intended to include the meaning of “at least one selected from the group consisting of” for the purpose of its meaning and interpretation. For example, “at least one of A and B” may be understood to mean A, B, or A and B. When preceding a list of elements, the term, “at least one of,” modifies the entire list of elements and does not modify the individual elements of the list.
It will be further understood that the terms “comprises,” “comprising,” “includes,” and/or “including,” when used in this specification, specify the presence of stated features, numerals, steps, operations, elements, parts, or the combination thereof, but do not preclude the presence or addition of one or more other features, numerals, steps, operations, elements, parts, or the combination thereof.
It will be further understood that when a layer, a film, a region, a plate, etc. is referred to as being “on” or “above” another part, it can be directly on the other part, or intervening elements may also be present. It will also be understood that when a layer, a film, a region, a plate, etc. is referred to as being “under” or “below” another part, it can be directly under the other part, or intervening elements may also be present. When an element is referred to as being disposed on another element, it can be disposed under the other element.
The spatially relative terms “below”, “beneath”, “lower”, “above”, “upper”, or the like, may be used herein for ease of description to describe the relations between one element or component and another element or component as illustrated in the drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation, in addition to the orientation depicted in the drawings. For example, in the case where a device illustrated in the drawing is turned over, the device positioned “below” or “beneath” another device may be placed “above” another device. Accordingly, the illustrative term “below” may include both the lower and upper positions. The device may also be oriented in other directions and thus the spatially relative terms may be interpreted differently depending on the orientations.
Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by those skilled in the art to which this disclosure pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and will not be interpreted in an ideal or excessively formal sense unless clearly defined in the specification.
An aspect of the disclosure provides an organometallic compound represented by Formula 1 below:
M1 and M2 in Formula 1 may each independently 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).
According to an embodiment, the M1 may be Pt or Pd. For example, M1 may be Pt. For example, M1 may be Pd.
According to an embodiment, M2 may be selected from Rh, Ir, Os, and Ru. For example, M2 may be Ir.
A1 to A4 and B1 to B4 in Formula 1 may each independently be selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group.
In an embodiment, A1 to A4 and B1 to B4 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, cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole 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 dihydropyridine 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 phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a 2,3-dihydroimidazole group, a triazole group, a 2,3-dihydrotriazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.
According to an embodiment, A1 to A4 and B1 to B4 may each independently be selected from groups represented by one of Formulae 2-1 to 2-43.
In Formulae 2-1 to 2-43,
According to an embodiment, B1 to B4 may each independently be a group represented by one of Formulae 3-1 and 3-2:
In Formulae 3-1 and 3-2,
According to an embodiment, A1 to A4 and B1 to B4 may each independently be selected from a benzene group, a pyridine group, an imidazole group, a 2,3-dihydroimidazole group, an imidazopyrimidine group, and a benzimidazole group.
For example, A1 to A4 may each independently be selected from a benzene group and a pyridine group. In embodiments, B1 to B4 may each independently be selected from an imidazole group, a 2,3-dihydroimidazole group, an imidazopyrimidine group, and a benzimidazole group.
X11 to X16 in Formula 1 may each independently be C or N.
According to an embodiment, X11 to X16 may each be C.
Y10, Y11, Y12, Y20, Y21, Y30, Y31, Y32, Y40, Y41, Y50, Y51, Y60, Y61, Y70, Y71, Y80, and Y81 in Formula 1 may each independently be C or N.
A bond between M1 and X11, a bond between M1 and Y10, a bond between M1 and Y50, and a bond between M1 and Y60 may each independently be a covalent bond or a coordination bond.
According to an embodiment, two of the bond between M1 and X11, the bond between M1 and Y10, the bond between M1 and Y50, and the bond between M1 and Y60 may be covalent bonds, and the other two bonds may be coordination bonds.
For example, a bond between M1 and X11 may be a covalent bond, a bond between M1 and Y10 may be a covalent bond, a bond between M1 and Y50 may be a coordination bond, and a bond between M1 and Y60 may be a coordination bond.
A bond between M2 and X14, a bond between M2 and Y20, a bond between M2 and Y30, a bond between M2 and Y40, a bond between M2 and Y70, and a bond between M2 and Y80 may each independently be a covalent bond or a coordination bond.
According to an embodiment, three of the bond between M2 and X14, the bond between M2 and Y20, the bond between M2 and Y30, the bond between M2 and Y40, the bond between M2 and Y70, and the bond between M2 and Y80 may be covalent bonds, and the other three bonds may be coordination bonds.
For example, a bond between M2 and X14 may be a covalent bond, a bond between M2 and Y20 may be covalent bond, a bond between M2 and Y30 may be a coordination bond, a bond between M2 and Y40 may be a covalent bond, a bond between M2 and Y70 may be a coordination bond, and a bond between M2 and Y80 may be a coordination bond.
According to an embodiment, two of the bond between M1 and X11, the bond between M1 and Y10, the bond between M1 and Y50, and the bond between M1 and Y60 are covalent bonds, and the other two bonds are coordination bond, and three of the bond between M2 and X14, the bond between M2 and Y20, the bond between M2 and Y30, the bond between M2 and Y40, the bond between M2 and Y70, and the bond between M2 and Y80 may be covalent bonds, and the other three bonds may be coordination bonds. Thus, the organometallic compound does not have a salt form including cations and anions, and may be electrically neutral.
T1 in Formula 1 may be selected from a single bond, *—O—*′, *—S—*′, *—C(R1)(R2)—*′, *—C(R1)═*, *═C(R1)—*, *—C(R1)═C(R2)—*, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*, *—B(R1)—*′, *—N(R1)—*′, *—P(R1)—*′, *—Si(R1)(R2)—*′, *—P(═O)(R1)—*′, and *—Ge(R1)(R2)—*′.
According to an embodiment, T1 may be a single bond, *—O—*′, *—S—*′, *—N(R1)—*′, *—C(R1)(R2)—*′, *—Si(R1)(R2)—*′, and *—B(R1)—*′.
According to an embodiment, T1 may be selected from *—O—*′ and *—S—*′. For example, T1 may be *—O—*′. In embodiments, T1 may be *—S—*′.
R1, R2, R10, R20, R30, R40, R50, R60, R70, and R80 in Formula 1 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 hydrazino group, a hydrazino 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 C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —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).
According to an embodiment, R1, R2, R10, R20, R30, R40, R50, R60, R70, and R80 may each independently be selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
According to an embodiment, R1, R2, R10, R20, R30, R40, R50, R60, R70, and R80 may each independently be selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
In Formulae 5-1 to 5-26 and 6-1 to 6-55,
According to an embodiment, R1, R2, R10, R20, R30, R40, R50, R60, R70, and R80 may each independently be selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
According to an embodiment, R1, R2, R10, R20, R30, R40, R50, R60, R70, and R80 may each independently be selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C20 alkyl group, and a C1-C20 alkoxy group.
Two or more neighboring substituents selected from the group consisting of R1, R2, R10, R20, R30, R40, R50, R60, R70, and R80 in Formula 1 may optionally be linked together to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group.
According to an embodiment, two or more neighboring substituents selected from the group consisting of R1, R2, R10, R20, R30, R40, R50, R60, R70, and R80 may optionally be linked together to form any one group selected from: a cyclopentane group, a cyclohexane group, a benzene group, a naphthylene group, a fluorene group, a pyridine group, a pyrimidine group, a triazine group, or a carbazole group; and
According to an embodiment, two or more neighboring substituents selected from the group consisting of R1, R2, R10, R20, R30, and R40 may optionally be linked together to form a cyclopentane group, a cyclohexane group, a benzene group, a naphthylene group, a fluorene group, a pyridine group, a pyrimidine group, a triazine group, or a carbazole group.
According to an embodiment, two or more neighboring substituents selected from the group consisting of R1, R2, R10, R20, R30, and R40 may optionally be linked together to form a benzene group, a naphthylene group, a fluorene group, a pyridine group, a pyrimidine group, a triazine group, or a carbazole group.
In Formula 1, a10, a20, a30, a40, a50, a60, a70, and a80 may each independently be an integer from 1 to 8.
According to an embodiment, the organometallic compound may be represented by Formula 2:
In Formula 2,
According to an embodiment, the organometallic compound represented by Formula 1 may be selected from Compounds BD1 to BD20, but embodiments are not limited thereto:
The organometallic compound represented by Formula 1 contains two metal atoms, and the ligands coordinated to these metal atoms are linked to each other, thereby providing excellent molecular stability due to a rigid structure. In organometallic compounds represented by Formula 1, the formation of excimers is inhibited due to a structure in which the angle of the ligands with respect to the metal atom is tilted. Thus, the efficiency and lifespan of an organic light-emitting device using the organometallic compound may be improved.
The organometallic compound may emit blue light. For example, the organometallic compound may emit blue light having a maximum emission wavelength of about 400 nm to about 500 nm. For example, the maximum emission wavelength may be from about 440 nm to about 470 nm (a bottom emission CIEx,y color coordinate of 0.05), but embodiments are not limited thereto. Accordingly, the organometallic compound represented by Formula 1 may be useful for the manufacturing of an organic light-emitting device.
Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Examples provided below.
At least one of such organometallic compounds represented by Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound may be included in an emission layer. The organometallic compound included in the emission layer may act as a dopant. In embodiments, the organometallic compound of Formula 1 may be used as a material for a capping layer located outside a pair of electrodes of an organic light-emitting device.
An aspect of the disclosure provides an organic light-emitting device that may include: a first electrode; a second electrode facing the first electrode; an organic layer disposed between the first electrode and the second electrode; and at least one organometallic compound represented by Formula 1. For example, the organic layer includes at least one of the organometallic compounds.
The expression “(an organic layer) includes at least one of organometallic compounds” 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 be the organometallic compound, and may include 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 this regard, Compound 1 and Compound 2 may exist in an identical layer (for example, Compound 1 and Compound 2 may all exist in an emission layer), or different layers (for example, Compound 1 may exist in an emission layer and Compound 2 may exist in an electron transport region).
In an embodiment,
The term “organic layer” used herein refers to a single layer and/or all layers between the first electrode and the second electrode of the organic light-emitting device. A material included in “the organic layer” is not limited to an organic material.
In an embodiment, the emission layer may include the organometallic compound represented by Formula 1. The emission layer may further include a host, and an amount of the host of the emission layer may be greater than the amount of the organometallic compound in the emission layer.
In an embodiment, the hole transport region may include an electron blocking layer, and the electron blocking layer may include the organometallic compound; or
In an embodiment, the hole transport region may include a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of −3.5 eV or less.
In an embodiment, the electron transport region may include an electron transport layer and an electron injection layer, and
[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 a first electrode 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 are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflectable 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 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 located on the first electrode 110. The organic layer 150 may include an emission layer.
The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 190.
[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 different materials, or iii) a multi-layered structure having multiple layers including 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 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 below, and a compound represented by Formula 202 below:
In Formulae 201 and 202,
For example, in Formula 202, R201 and R202 may optionally be linked to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R203 and R204 may optionally be linked to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.
In an 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 an integer from 201 may each independently be selected from:
In one or more embodiments, in Formula 202, i) R201 and R202 may be linked to each other via a single bond, and/or ii) R203 and R204 may be linked to each other via a single bond.
In one or more embodiments, R201 to R204 in Formula 202 may be selected from:
In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A below:
In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A(1) below, but embodiments are not limited thereto:
In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A-1 below, but embodiments are not limited thereto:
In one or more embodiments, the compound represented by Formula 202 may be represented by Formula 202A below:
In one or more embodiments, the compound represented by Formula 202 may be represented by Formula 202A-1 below:
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 compounds to be included in the hole transport region are not limited thereto:
A thickness of the hole transport region may be in a range of about 100 Å to about 10,000 Å. For example, the thickness of the hole transport region may be in a range of about 100 Å to about 1,000 Å. When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å. For example, the thickness of the hole injection layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the hole transport layer may be in a range of 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 an embodiment, a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be −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 are not limited thereto.
In an embodiment, the p-dopant may include at least one selected from:
In Formula 221,
[Emission Layer in Organic Layer 150]
When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other.
In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.
The emission layer may include a host and a dopant. The dopant may include at least one selected from a phosphorescent dopant and a fluorescent dopant.
An amount of a dopant in the emission layer may be, based on about 100 parts by weight of the host, in the range of about 0.01 to about 15 parts by weight, 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, the thickness of the emission layer may be in a range of 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 an embodiment, Ar301 in Formula 301 may be selected from:
When xb11 in Formula 301 is two or more, two or more of Ar301(s) may be linked via a single bond.
In one or more embodiments, the compound represented by Formula 301 may be represented by one of Formula 301-1 or Formula 301-2:
In Formulae 301-1 and 301-2
A301 to A304 may each independently be selected from a benzene ring, a naphthalene ring, a phenanthrene ring, a fluoranthene ring, a triphenylene ring, a pyrene ring, a chrysene ring, a pyridine ring, a pyrimidine ring, an indene ring, a fluorene ring, a spiro-bifluorene ring, a benzofluorene ring, a dibenzofluorene ring, an indole ring, a carbazole ring, a benzocarbazole ring, a dibenzocarbazole ring, a furan ring, a benzofuran ring, a dibenzofuran ring, a naphthofuran ring, a benzonaphthofuran ring, a dinaphthofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a naphthothiophene ring, a benzonaphthothiophene ring, and a dinaphthothiophene ring,
For example, L301 to L304 in Formulae 301, 301-1, and 301-2 may each independently be selected from:
In an embodiment, R301 to R304 in Formulae 301, 301-1, and 301-2 may each independently be selected from:
In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (for example, Compound H55), an Mg complex, and a Zn complex.
The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and at least one selected from Compounds H1 to H55, but embodiments are not limited thereto:
[Phosphorescent Dopant Included in Emission Layer in Organic Layer 150]
The phosphorescent dopant may include an organometallic complex represented by Formula 401 below:
In Formulae 401 and 402,
In an embodiment, A401 and A402 in Formula 402 may each independently be selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group, and a dibenzothiophene group.
In one or more embodiments, in Formula 402, i) X401 may be nitrogen and X402 may be carbon, or ii) X401 and X402 may each be nitrogen at the same time.
In one or more embodiments, R401 and R402 in Formula 402 may each independently be selected from:
In one or more embodiments, when xc1 in Formula 401 is two or more, two A401(s) in two or more L401(s) may optionally be linked to each other via X407, which is a linking group, two A402(s) may optionally be linked to each other via X408, which is a linking group (see Compounds PD1 to PD4 and PD7). X407 and X408 may each independently be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q413)-*′, *—C(Q413)(Q414)-*′, or *—C(Q413)=C(Q414)-*′ (wherein Q413 and Q414 may each independently be hydrogen, deuterium, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group), but embodiments are not limited thereto.
L402 in Formula 401 may be a monovalent, divalent, or trivalent organic ligand. For example, L402 may be selected from halogen, diketone (for example, acetylacetonate), carboxylic acid (for example, picolinate), —C(═O), isonitrile, —CN, and phosphorus (for example, phosphine, or phosphite), but embodiments are not limited thereto.
In one or more embodiments, the phosphorescent dopant may be selected from, for example, Compounds PD1 to PD25, but embodiments are not limited thereto:
[Fluorescent Dopant in Emission Layer]
The fluorescent dopant may include an arylamine compound or a styrylamine compound.
The fluorescent dopant may include a compound represented by Formula 501 below.
In Formula 501,
In an embodiment, Ar501 in Formula 501 may be selected from:
In one or more embodiments, L501 to L503 in Formula 501 may each independently be selected from:
In one or more embodiments, R501 and R502 in Formula 501 may each independently be selected from:
In one or more embodiments, xd4 in Formula 501 may be 2, but embodiments are not limited thereto.
For example, the fluorescent dopant may be selected from Compounds FD1 to FD22:
In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but embodiments are not limited thereto.
[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 different materials, or iii) a multi-layered structure having multiple layers including 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 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 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-deficient nitrogen-containing ring include an imidazole ring, a pyrazole ring, a thiazole ring, an isothiazole ring, an oxazole ring, an isoxazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an indazole ring, a purine ring, a quinoline ring, an isoquinoline ring, a benzoquinoline ring, a phthalazine ring, a naphthyridine ring, a quinoxaline ring, a quinazoline ring, a cinnoline ring, a phenanthridine ring, an acridine ring, a phenanthroline ring, a phenazine ring, a benzimidazole ring, an isobenzothiazole ring, a benzoxazole ring, an isobenzoxazole ring, a triazole ring, a tetrazole ring, an oxadiazole ring, a triazine ring, a thiadiazole ring, an imidazopyridine ring, an imidazopyrimidine ring, and an azacarbazole ring, but are not limited thereto.
For example, the electron transport region may include a compound represented by Formula 601 below:
[Ar601]xe11-[(L601)xe1-R601]xe21 <Formula 601>
In Formula 601,
In an embodiment, at least one of Ar601(s) in the number of xe11 and R601(s) in the number of xe21 may include the π electron-deficient nitrogen-containing ring.
In an embodiment, ring Ar601 in Formula 601 may be selected from:
When xe11 in Formula 601 is 2 or more, two or more Ar601(s) may be linked to each other via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be an anthracene group.
In one or more embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:
In Formula 601-1,
In an 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 are not limited thereto:
In one or more embodiments, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ.
A thickness of the buffer layer, a thickness of the hole blocking layer, and a thickness of the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å. For example, the thickness of the buffer layer, the thickness of the hole blocking layer, and the thickness of the electron control layer may each independently be in a range of about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are each within these ranges, excellent hole blocking characteristics or excellent electron control characteristics may be obtained without a substantial increase in driving voltage.
A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the electron transport layer may be in a range of about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.
The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include at least one selected from 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 diphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but embodiments 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 contact (e.g., 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 different materials, or iii) a multi-layered structure having multiple layers including 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 an 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 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, or KI. In an embodiment, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but embodiments 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 an embodiment, the alkaline earth-metal compound may be selected from BaO, SrO, and CaO, but embodiments are not limited thereto.
The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3 and TbF3. In an embodiment, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but embodiments 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 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, the thickness of the electron injection layer may be in a range of about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.
[Second Electrode 190]
The second electrode 190 is located 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 a metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function.
The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, and IZO, but embodiments 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
An organic light-emitting device 20 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, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer 210 toward the outside, and 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, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer 220 toward the outside.
The first capping layer 210 and the second capping layer 220 may increase external emission 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 an 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 an 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 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 2,000 rpm to about 5,000 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.
[Definitions of Substituents]
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 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. 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. 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 two or more rings may be fused to each other.
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. 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 two or more rings may be condensed with each other.
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 refers to —SA103 (wherein A103 is the C6-C60 aryl 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 that includes only carbon as a ring-forming atom and consists of 5 to 60 carbon atoms. The C5-C60 carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C5-C60 carbocyclic group may be a benzene ring, 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. For example, the term “benzene group” may represent a benzene ring, a phenyl group, a phenylene group, or a trivalent or tetravalent group corresponding thereto, and the like.
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 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 C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
The term “Ph” as used herein 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.
Starting material 1-0, 1,2,4,5-tetrabromobenzene (cas: 636-28-2) and BPPO were reacted in the presence of CuI, K3PO4, and a DMSO solvent at a temperature of 160° C. Intermediate 1-1 was confirmed by LC-MS.
C12H6Br4O: M+1 481.75
Intermediate 1-1 was reacted with imidazole (cas: 288-13-1) and potassium carbonate to synthesize Intermediate 1-2. Intermediate 1-2 was confirmed by LC-MS.
C24H18N8O: M+1 434.19
Intermediate 1-2 was reacted with iodide methane (cas: 74-88-4) in the presence of acetone as a solvent to synthesize Intermediate 1-3. Intermediate 1-3 was confirmed by LC-MS.
C28H3014N80: M+1 1001.89
Intermediate 1-3 was reacted with dichloro(1,5-cyclooctadiene)platinum(II) in the presence of sodium acetate and dioxen solvent as a solvent at a temperature of 160° C. Intermediate 1-4 was confirmed by LC-MS.
C28H2612N8OPt: M+1 939.25
Starting material 2-0 was reacted with 2,6-dibromopyridine (cas: 626-05-1), Pd2(dba)3, Sphos, and K3PO4 in the presence of a toluene solvent at a temperature of 120° C. Intermediate 2-1 was confirmed by LC-MS.
C15H7F4N3: M+1 305.09
Intermediate 1-4, Intermediate 2-1, IrCl3·3H2O, and K2CO3 were dissolved in a propionic acid, and the mixture was stirred at a temperature of 140° C. for 12 hours. The reaction was completed and a solvent was removed therefrom under reduced pressure, and an extraction process was performed thereon with methylene chloride and distilled water. An organic layer was washed 3 times with distilled water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Compound BD1 was confirmed by LC-MS.
C43H28F43rN11 OPt: M+1 1178.17
Compounds BD2 to BD20 were synthesized in the substantially the same method as used to synthesize the intermediate of Compound BD1, except for the starting material.
The compounds synthesized according to Synthesis Examples above were identified by 1H NMR and MS/FAB, and results are shown in Table 1 below.
1H NMR (CDCl3, 400 MHz)
Synthesis methods of compounds other than Compounds shown in Table 1 may also be easily recognized by those of ordinary skill in the art by referring to the synthesis mechanisms and source materials described above.
As a substrate and an anode, a glass substrate with 15 Ωcm2 (1,200 Å) ITO thereon, which was manufactured by Corning Inc., was cut to a size of 50 mm×50 mm×0.7 mm, and the glass substrate was sonicated by using isopropyl alcohol and pure water for 5 minutes each, and then ultraviolet (UV) light was irradiated for 30 minutes thereto and ozone was exposed thereto for cleaning. The resultant glass substrate was loaded onto a vacuum deposition apparatus.
2-TNATA was vacuum-deposited on an ITO anode on the glass substrate to form an hole injection layer having a thickness of 600 Å, and NPB was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.
Bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane) (BCPDS) and (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA) (the weight ratio of BCPDS to POPCPA was 1:1), which were co-hosts, and Compound 1, which was a dopant, were co-deposited on the hole transport layer at a co-host to dopant weight ratio of 90:10 to form an emission layer having a thickness of 300 Å.
Diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) was deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å, Alq3 was deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and A1 was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 3,000 Å, 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 in forming an emission layer, for use as a dopant, corresponding compounds shown in Table 1 were used instead of Compound 1.
The driving voltage, current density, luminance, emission efficiency, emission color, and maximum emission wavelength of the organic light-emitting devices manufactured according to Examples 1 and 2, and Comparative Examples 1 to 3 were measured by using Kethley SMU 236 and a luminance photometer PR650, and results thereof are shown in Table 2.
Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 5 had a low driving voltage and high current density and high emission efficiency. The organic light-emitting devices of Example 1 to 5 showed a lower driving voltage and higher current density than the organic light-emitting devices of Comparative Examples 1 and 3.
The organic light-emitting device including the organometallic compound may have a low driving voltage, high luminance, high efficiency, high color purity, 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.
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