Patent Application
20230363274
This application claims priority under 35 U.S.C. § 119 to Korean Patent Application No. 10-2022-0055743, filed on May 4, 2022, in the Korean Intellectual Property Office, the disclosure of which is incorporated by reference herein in its entirety.
The disclosure relates to a condensed cyclic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.
Organic light-emitting devices are self-emissive devices, which have improved characteristics in terms of viewing angles, response time, luminance, driving voltage, and response speed, and produce full-color images.
In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer that is arranged between the anode and the cathode and includes an emission layer. A hole transport region may be arranged between the anode and the emission layer, and an electron transport region may be arranged between the emission layer and the cathode. Holes provided from the anode move toward the emission layer through the hole transport region, and electrons provided from the cathode move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transition from an excited state to the ground state to thereby generate light.
Provided are a novel condensed cyclic compound, an organic light-emitting device including the same, and an electronic 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 of the disclosure.
According to an aspect of the disclosure, provided is a condensed cyclic compound represented by Formula 1:
According to another aspect of the disclosure, an organic light-emitting device includes a first electrode, a second electrode, and an organic layer arranged between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one condensed cyclic compound.
The condensed cyclic compound may be included in the emission layer of the organic layer, and the condensed cyclic compound included in the emission layer may serve as a host.
According to another aspect of the disclosure, an electronic apparatus includes the organic light-emitting device.
The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the FIGURE which is a schematic cross-sectional view of an organic light-emitting device according to an embodiment.
Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the FIGURES, to explain aspects. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
It will be understood that when an element is referred to as being “on” another element, it can be directly on the other element or intervening elements may be present therebetween In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.
It will be understood that, although the terms “first,” “second,” “third” etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Thus, “a first element,” “component,” “region,” “layer” or “section” discussed below could be termed a second element, component, region, layer or section without departing from the teachings herein.
The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, “a,” “an,” “the,” and “at least one” do not denote a limitation of quantity, and are intended to cover both the singular and plural, unless the context clearly indicates otherwise. For example, “an element” has the same meaning as “at least one element,” unless the context clearly indicates otherwise.
“Or” means “and/or.” As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.
Furthermore, relative terms, such as “lower” or “bottom” and “upper” or “top,” may be used herein to describe one element's relationship to another element as illustrated in the FIGURE. It will be understood that relative terms are intended to encompass different orientations of the device in addition to the orientation depicted in the FIGURE. For example, if the device in the
“About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ±30%, 20%, 10% or 5% of the stated value.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. 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 the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded Thus, the regions illustrated in the FIGURE are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.
According to an aspect of the disclosure, a condensed cyclic compound may be represented by Formula 1:
CY1, CY3 and CY4 in Formula 1 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, CY1, CY3 and CY4 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide 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 triazole 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 benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
In an embodiment, CY1, CY3 and CY4 may each independently be a benzene group, a naphthalene group, or a pyridine group.
Y1 in Formula 1 may be O, S, or Se.
L1 in Formula 1 may be a single bond, a substituted or unsubstituted C3-C60 carbocyclic group, or a substituted or unsubstituted C1-C60 heterocyclic group.
For example, L1 may be: a single bond; or
In an embodiment, L1 may be: a single bond; or a benzene group, a naphthalene group, or a pyridine group, each unsubstituted or substituted with at least one R10a.
n1 in Formula 1 may be an integer from 1 to 3.
T3 and T4 in Formula 1 may each independently be a group represented by Formula 1A:
Details of Formula 1A may be as described herein.
a3 and a4 in Formula 1 may each independently be an integer from 0 to 10.
In an embodiment, the sum of a3 and a4 may be 1 or more.
For example, the sum of a3 and a4 may be 1 or 2.
R1, R3, R4, and R21 to R23 in Formula 1 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 C2-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), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), or —P(═O)(Q8)(Q9).
In an embodiment, R1, R3, R4, and R21 to R23 may each independently be:
In an embodiment, R1, R3, R4, and R21 to R23 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
In Formulae 9-1 to 9-39 and 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-350, * may indicate a binding site to a neighboring atom, Ph may be a phenyl group, TMS may be a trimethylsilyl group, and TMG may be a trimethylgermyl group.
In an embodiment, at least one of b1 R1(s) and R21 to R23 may be a substituted or unsubstituted C6-C12 aryl group.
In an embodiment, at least one of R1 and R21 to R23 may be: a phenyl group or a naphthyl group; or a phenyl group or a naphthyl group, each substituted with deuterium, a cyano group, a C1-C10 alkyl group, a phenyl group, or any combination thereof.
In an embodiment, one of R1 and R21 to R23 may be a substituted or unsubstituted C6-C12 aryl group.
b1, b3, and b4 in Formula 1 may each independently be an integer from 1 to 10.
In an embodiment, the condensed cyclic compound may be represented by Formula 1-1:
In Formula 1-1,
In one or more embodiments, at least one of R11 to R14 and R21 to R23 in Formula 1-1 may be: a phenyl group or a naphthyl group; or a phenyl group or a naphthyl group, each substituted with deuterium, a cyano group, a C1-C10 alkyl group, a phenyl group, or any combination thereof.
In an embodiment, a moiety represented by
in Formula 1 may be a group represented by one of Formulae 2-1 to 2-20:
In Formulae 2-1 to 2-20,
CY5 and CY6 in Formula 1A may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, CY5 and CY6 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide 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 triazole 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 benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
In an embodiment, CY5 and CY6 may each independently be a benzene group, a naphthalene group, or a pyridine group.
L2 in Formula 1A may be a single bond, a substituted or unsubstituted C3-C60 carbocyclic group, or a substituted or unsubstituted C1-C60 heterocyclic group.
In an embodiment, L2 may be: a single bond; or
In an embodiment, L2 may be: a single bond; or a benzene group, a naphthalene group, or a pyridine group, each unsubstituted or substituted with at least one R10a.
n2 in Formula 1A may be an integer from 1 to 3.
R5 and R6 in Formula 1A may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 C2-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), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), or —P(═O)(Q8)(Q9).
In an embodiment, R5 and R6 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF5, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
In an embodiment, R5 and R6 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
b5 and b6 in Formula 1A may each independently be an integer from 1 to 10.
* in Formula 1A may indicate a binding site to a neighboring atom.
In an embodiment, Formula 1A may be a group represented by one of Formulae 1A-1 to 1A-8:
In Formulae 1A-1 to 1A-8,
In an embodiment, the condensed cyclic compound may be represented by one of Formulae 3-1 to 3-4:
In Formulae 3-1 to 3-4,
In an embodiment, the condensed cyclic compound may be one of Compounds 1 to 500:
The condensed cyclic compound according to the disclosure satisfies the structure of Formula 1 as described above, and includes a substituent represented by Formula 1 A (e.g., carbazole). Due to such a structure, the condensed cyclic compound represented by Formula 1 may have a high triplet energy level and excellent thermal stability and charge mobility characteristics. Accordingly, an electronic device, for example, an organic light-emitting device, using the condensed cyclic compound represented by Formula 1 may have low driving voltage, high efficiency, and long lifespan characteristics.
A highest occupied molecular orbital (HOMO) energy level, a lowest unoccupied molecular orbital (LUMO) energy level, an S1 energy level, and a T1 energy level of some compounds of the condensed cyclic compound represented by Formula 1 are evaluated by using the Gaussian 09 program with the molecular structure optimization obtained by B3LYP-based density functional theory (DFT), and results thereof are shown in Table 1.
From Table 1, it is confirmed that the condensed cyclic compound represented by Formula 1 has such electric characteristics that are suitable for use as a host for an electronic device, for example, an organic light-emitting device.
In an embodiment, a maximum emission wavelength (emission peak wavelength, λmax) of an emission peak of an emission spectrum or electroluminescence spectrum of the condensed cyclic compound may be in a range of about 400 nm to about 490 nm.
Synthesis methods of the condensed cyclic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples provided below.
Accordingly, the condensed cyclic compound represented by Formula 1 may be suitable for use as a host in an organic layer, for example, an emission layer, of an organic light-emitting device. Thus, another aspect of the disclosure provides an organic light-emitting device including: a first electrode; a second electrode; and an organic layer arranged between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one condensed cyclic compound represented by Formula 1.
The organic light-emitting device may have excellent driving voltage, excellent efficiency characteristics, and excellent lifespan characteristics by having the organic layer including the condensed cyclic compound represented by Formula 1 as described above.
The condensed cyclic compound represented by Formula 1 may be used between a pair of electrodes of the organic light-emitting device. For example, the condensed cyclic compound represented by Formula 1 may be included in the emission layer. In this regard, the condensed cyclic compound may serve as a host, and the emission layer may further include a dopant (that is, an amount of the condensed cyclic compound represented by Formula 1 may be less than an amount of the dopant in the emission layer).
The dopant may be a fluorescent dopant, a phosphorescent dopant, or any combination thereof. For example, the dopant may be a phosphorescent dopant.
In an embodiment, the emission layer may include a host, a fluorescent dopant, and a phosphorescent dopant, and the condensed cyclic compound may be included in the host. In this regard, the phosphorescent dopant may be a sensitizer compound that is used together with a fluorescent dopant to transfer excitons to the fluorescent dopant.
In an embodiment, the emission layer may emit blue light. For example, the emission layer may emit blue light having a maximum emission wavelength in a range of about 400 nm to about 490 nm.
The expression “(an organic layer) includes at least one of condensed cyclic compounds” as used herein may include a case in which “(an organic layer) includes identical condensed cyclic compounds represented by Formula 1” and a case in which “(an organic layer) includes two or more different condensed cyclic compounds represented by Formula 1.”
For example, the organic layer may include, as the condensed cyclic compound, only Compound 1. In this regard, Compound 1 may be present in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the condensed cyclic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be present in an identical layer (e.g., both Compound 1 and Compound 2 may be present in the emission layer).
The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode. Alternatively, the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
For example, in the organic light-emitting device, 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 arranged between the first electrode and the emission layer and an electron transport region arranged between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
The term “organic layer” as used herein refers to a single layer and/or a plurality of layers arranged between the first electrode and the second electrode of the organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.
The
A substrate may be additionally arranged under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in organic light-emitting devices available in the art may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
The first electrode 11 may be, for example, formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but embodiments are not limited thereto.
The organic layer 15 may be arranged on the first electrode 11.
The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
The hole transport region may be arranged between the first electrode 11 and the emission layer.
The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.
The hole transport region may include a only hole injection layer or only a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, wherein, for each structure, respective layers are sequentially stacked in this stated order from the first electrode 11.
When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB) deposition.
When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature in a range of about 100° C. to about 500° C., a vacuum pressure in a range of about 10−8 torr to about 10−3 torr, and a deposition rate in a range of about 0.01 Å/sec to about 100 Å/sec, but embodiments are not limited thereto.
When the hole injection layer is formed by spin coating, the coating conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the coating conditions may include a coating speed in a range of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature for removing a solvent after coating in a range of about 80° C. to about 200° C., but embodiments are not limited thereto.
Conditions for forming the hole transport layer and the electron blocking layer may be the same as the conditions for forming the hole injection layer.
The hole transport region may include, for example, at least one of m-MTDATA, TDATA, 2-TNATA, NPB, 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, a compound represented by Formula 202, or a combination thereof:
Ar101 and Ar102 in Formula 201 may each independently be:
xa and xb in Formula 201 may each independently be an integer from 0 to 5, or may each independently be 0, 1, or 2. For example, xa may be 1, and xb may be 0, but embodiments are not limited thereto.
R101 to R108, R111 to R119, and R121 to R124 in Formulae 201 and 202 may each independently be:
R109 in Formula 201 may be:
In an embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments are not limited thereto:
R101, R111, R112, and R109 in Formula 201A may each be as defined herein.
For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include Compounds HT1 to HT20, but embodiments 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, about 100 Å to about 1,000 Å. When the hole transport region includes at least one of 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 10,000 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 hole transport region may further include, in addition to the materials described above, a charge-generation material for improving 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. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments are not limited thereto. For example, non-limiting examples of the p-dopant may include: a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ), or F6-TCNNQ; a metal oxide, such as a tungsten oxide or a molybdenum oxide; and a cyano group-containing compound, such as Compound HT-D1 or Compound F12, but embodiments are not limited thereto:
The hole transport region may further include a buffer layer.
The buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer to improve the efficiency of an organic light-emitting device.
Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer, though the deposition or coating conditions may vary according to a material that is used.
When the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be selected from materials for the hole transport region described above and materials for a host to be described below, but embodiments are not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may be mCP, which will be described below.
The emission layer may include a host and a dopant, and the host may include the condensed cyclic compound represented by Formula 1.
The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
In an embodiment, the emission layer may include a host, a fluorescent dopant, and a phosphorescent dopant, and the condensed cyclic compound may be included in the host. In this regard, the phosphorescent dopant may be a sensitizer compound that is used together with a fluorescent dopant to transfer excitons to the fluorescent dopant.
For example, the phosphorescent dopant may be a blue dopant.
The phosphorescent dopant may include at least one transition metal as a central metal.
The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
The phosphorescent dopant may be electrically neutral.
In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 31:
M31 in Formula 31 may be a transition metal.
In an embodiment, M31 may be Pt, Pd, or Au.
In Formula 31, X31 to X34 may each independently be C or N, and
In an embodiment, a bond between X31 and M31 may be a coordinate bond.
In an embodiment, X31 may be C, and a bond between X31 and M31 may be a coordinate bond. That is, X31 in Formula 31 may be C in a carbene moiety.
CY31 to CY34 in Formula 31 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In an embodiment, CY31 to CY34 may each independently be:
In Formula 31, L31 may be a single bond, a double bond, *—N(R35a)—*′, *—B(R35a)—*′, *—P(R35a)—*′, *—C(R35a)(R35b)—*′, *—Si(R35a)(R35b)—*′, *—Ge(R35a)(R35b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R35a)═*′, *═C(R35a)—*′, *—C(R35a)═C(R35b)—*′, *—C(═S)—*′, *—C═C—*′, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
n31 to n34 in Formula 31 may each independently be an integer from 0 to 5, and three or more of n31 to n34 may each independently be an integer from 1 to 5.
In Formula 31, when n31 is 0, L31 may not be present, when n32 is 0, L32 may not be present, when n33 is 0, L33 may not be present, and when n34 is 0, L34 may not be present.
In Formula 31, when n31 is 2 or more, two or more of L31(s) may be identical to or different from each other, when n32 is 2 or more, two or more of L32(s) may be identical to or different from each other, when n33 is 2 or more, two or more of L33(s) may be identical to or different from each other, and when n34 is 2 or more, two or more of L34(s) may be identical to or different from each other.
R31 to R34, R35a, R35b, R36a, R36b, R37a, R37b, R38a, and R38b in Formula 31 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 aryl alkyl 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 heteroaryl alkyl 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), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9).
In an embodiment, R31 to R34, R35a, R35b, R36a, R36b, R37a, R37b, R38a, and R38b may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a cyano group (CN), a nitro group, an amino group, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 31-1 or Formula 31-2:
b31 to b34 in Formula 31 may each independently be an integer from 0 to 20.
In Formula 31, two or more of b31 R31(s) may optionally be bonded to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
Two or more of R31 to R34, R35a, R35b, R36a, R36b, R37a, R37b, R38a, and R38b may optionally be bonded to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a, and
In Formulae 31-1 and 31-2,
In an embodiment, R311 to R317 in Formulae 31-1 and 31-2 may each independently be:
For example, at least one of R311 to R317 in Formulae 31-1 and 31-2 may include:
In one or more embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 51:
M51(L51)n51(L52)n52 Formula 51.
For example, M51 may be a first-row transition metal, a second-row transition metal, or a third-row transition metal.
In one or more embodiments, M51 may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
In an embodiment, M51 may be Ir, Pt, Os, or Rh.
In Formula 51, L51 may be a ligand represented by Formula 51A, and L52 may be a ligand represented by Formula 51B:
Details of Formulae 51A and 51B may be as described herein.
n51 in Formula 51 may be 1, 2, or 3, wherein, when n51 is 2 or more, two or more of L51 (s) may be identical to or different from each other.
n52 in Formula 51 may be 0, 1, or 2, wherein, when n52 is 2, two of L52(s) may be identical to or different from each other.
The sum of n51 and n52 in Formula 51 may be 2 or 3. For example, the sum of n51 and n52 may be 3.
In an embodiment, in Formula 51, i) M51 may be Ir, and the sum of n51 and n52 may be 3; or ii) M51 may be Pt, and the sum of n51 and n52 may be 2.
In one or more embodiments, in Formula 51, M51 may be Ir, and i) n51 may be 1, and n52 may be 2, or ii) n51 may be 2, and n52 may be 1.
L51 and L52 in Formula 51 may be different from each other.
Y51 to Y54 in Formulae 51A and 51B may each independently be C or N. For example, Y51 and Y53 may each be N, and Y52 and Y54 may each be C.
CY51 to CY54 in Formulae 51A and 51B may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
For example, CY51 to CY54 may each independently be i) a third ring, ii) a fourth ring, iii) a condensed ring in which two or more third rings are condensed with each other, iv) a condensed ring in which two or more fourth rings are condensed with each other, or v) a condensed ring in which at least one third ring is condensed with at least one fourth ring,
In one or more embodiments, ring CY51 to ring CY54 in Formulae 51A and 51B may each independently be a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzogermole group, a benzoselenophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzogermole group, a dibenzoselenophene group, a benzofluorene group, a benzocarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a naphthobenzosilole group, a naphthobenzoborole group, a naphthobenzophosphole group, a naphthobenzogermole group, a naphthobenzoselenophene group, a dibenzofluorene group, a dibenzocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dinaphthosilole group, a dinaphthoborole group, a dinaphthophosphole group, a dinaphthogermole group, a dinaphthoselenophene group, an indenophenanthrene group, an indolophenanthrene group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a phenanthrobenzosilole group, a phenanthrobenzoborole group, a phenanthrobenzophosphole group, a phenanthrobenzogermole group, a phenanthrobenzoselenophene group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindene group, an azaindole group, an azabenzofuran group, an azabenzothiophene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzogermole group, an azabenzoselenophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzogermole group, an azadibenzoselenophene group, an azabenzofluorene group, an azabenzocarbazole group, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azanaphthobenzosilole group, an azanaphthobenzoborole group, an azanaphthobenzophosphole group, an azanaphthobenzogermole group, an azanaphthobenzoselenophene group, an azadibenzofluorene group, an azadibenzocarbazole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadinaphthosilole group, an azadinaphthoborole group, an azadinaphthophosphole group, an azadinaphthogermole group, an azadinaphthoselenophene group, an azaindenophenanthrene group, an azaindolophenanthrene group, an azaphenanthrobenzofuran group, an azaphenanthrobenzothiophene group, an azaphenanthrobenzosilole group, an azaphenanthrobenzoborole group, an azaphenanthrobenzophosphole group, an azaphenanthrobenzogermole group, an azaphenanthrobenzoselenophene group, an azadibenzothiophene 5-oxide group, an aza9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide 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 benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a phenanthroline group, a phenanthridine group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, an azasilole group, an azaborole group, an azaphosphole group, an azagermole group, an azaselenophene group, a benzopyrrole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzisothiazole group, a benzoxadiazole group, a benzothiadiazole group, a pyridinopyrrole group, a pyridinopyrazole group, a pyridinoimidazole group, a pyridinoxazole group, a pyridinoisoxazole group, a pyridinothiazole group, a pyridinoisothiazole group, a pyridinoxadiazole group, a pyridinothiadiazole group, a pyrimidinopyrrole group, a pyrimidinopyrazole group, a pyrimidinoimidazole group, a pyrimidinoxazole group, a pyrimidinoisoxazole group, a pyrimidinothiazole group, a pyrimidinoisothiazole group, a pyrimidinoxadiazole group, a pyrimidinothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, a norbornene group, a benzene group condensed with a cyclohexane group, a benzene group condensed with norbornane group, a pyridine group condensed with a cyclohexane group, or a pyridine group condensed with a norbornane group.
In an embodiment, CY51 and CY53 may be different from each other.
In one or more embodiments, CY52 and CY54 may be different from each other.
In one or more embodiments, CY51 to CY54 may be different from each other.
R51 to R54 in Formulae 51A and 51B may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 C1-C60 alkylthio 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9). Q1 to Q9 may each be as defined herein.
In an embodiment, R51 to R54 in Formulae 51A and 51B may each independently be:
In one or more embodiments, R51 to R54 may each independently be:
In Formulae 51A and 51B, b51 to b54 may indicate the numbers of R51(s) to R54(s), respectively, and may each independently be an integer from 0 to 20. When b51 is 2 or more, two or more of R51(s) may be identical to or different from each other, when b52 is 2 or more, two or more of R52(s) may be identical to or different from each other, when b53 is 2 or more, two or more of R53(s) may be identical to or different from each other, and when b54 is 2 or more, two or more of R54(s) may be identical to or different from each other. For example, b51 to b54 may each independently be an integer from 0 to 8.
In an embodiment, the phosphorescent dopant may be one of Compounds P1 to P52:
When the phosphorescent dopant is selected from Compounds P1 to P52, exciplex formation with the host compound described above may be facilitated. For example, when the phosphorescent dopant includes a bulky substituent (e.g., a tert-butyl group, a cumyl group, etc.), exciplex formation may be facilitated by having an energy level similar to that of the host compound. In the case of the phosphorescent dopant, a gap between a LUMO level of an electron transporting (ET) host and a HOMO level of the phosphorescent dopant may be reduced, thereby facilitating exciplex formation.
In an embodiment, the emission layer may further include a fluorescent dopant. For example, the fluorescent dopant may be a thermally activated delayed fluorescence dopant and a blue dopant.
The fluorescent dopant may have a difference between a triplet energy level and a singlet energy level of 0.4 eV or less.
In an embodiment, the fluorescent dopant may be a luminescence emitter that may emit light by receiving excitons from an exciplex of the host and the phosphorescent dopant according to embodiments so that the received excitons transition to a ground state.
In an embodiment, the fluorescent dopant may be a compound represented by Formula 41:
In Formula 41,
In an embodiment, R41 to R49 may each independently be:
In an embodiment, Formula 41 may be selected from Formulae 41-1 to 41-8:
In Formulae 41-1 to 41-8,
In an embodiment, the fluorescent dopant may be selected from Compounds D1 to D30:
In an embodiment, an amount of the fluorescent dopant included in the emission layer may be in a range of 0 wt % to about 5 wt %.
An amount (weight) of the dopant in the emission layer may be in a range of about 0.1 part by weight to about 20 parts by weight based on 100 parts by weight of the emission layer.
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, and a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light, and various modifications are possible.
When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 part by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments are not limited thereto.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, excellent luminescence characteristics may be obtained without a substantial increase in driving voltage.
Next, an electron transport region may be arranged on the emission layer.
The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but embodiments are not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be the same as the conditions for forming the hole injection layer.
When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAIq, but embodiments are not limited thereto:
A thickness of the hole blocking 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 thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may further include at least one of BCP, Bphen, Alq3, BAIq, TAZ, and NTAZ:
In one or more embodiments, the electron transport layer may include at least one of Compounds ET1 to ET25, but embodiments are not limited thereto:
A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Λ to about 500 Å. When the thickness of the electron transport layer is within these ranges, excellent electron transporting characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may further include, in addition to the materials described above, a metal-containing material.
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 19.
The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 19 may be arranged on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be a metal, an alloy, an electrically conductive compound, or a combination thereof, which has a relatively low work function. For example, lithium (L1), magnesium (Mg), aluminum (AI), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the second electrode 19. In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
Hereinbefore, the organic light-emitting device 10 has been described with reference to the FIGURE, but embodiments are not limited thereto.
According to another aspect of the disclosure, provided is a diagnostic composition including at least one of the condensed cyclic compound represented by Formula 1.
The condensed cyclic compound represented by Formula 1 may provide high luminescence efficiency, and accordingly, the diagnostic composition including the condensed cyclic compound may have high diagnostic efficiency.
The diagnostic composition may be used in various applications, such as a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic 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, a hexyl group, and the like. 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 “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, an isopropyloxy group, and the like.
The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group formed by substituting 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, a butenyl group, and the like. 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 formed by substituting 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, a propynyl group, and the like. 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 “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, a cycloheptyl group, and the like. 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, P, Si, and S as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. 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, a cycloheptenyl group, and the like. 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 of N, O, P, Si, B, Se, Te, Ge, S, or any combination thereof as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in the ring thereof. Examples of the C1-C10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. 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 the term “C6-C60 arylene group” as 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, a chrysenyl group, and the like. 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 “C7-C60 alkylaryl group” as used herein refers to a C6-C60 aryl 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 cyclic aromatic system that has at least one of N, O, P, Si, B, Se, Te, Ge, S, or any combination thereof as a ring-forming atom, and 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 of N, O, P, B, Se, Te, Ge, S, or any combination thereof as a ring-forming atom, and 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, an isoquinolinyl group, and the like. 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 fused to each other. The term “C2-C60 alkylheteroaryl 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 the term “C6-C60 arylthio group” as used herein refers to -SA103 (wherein A103 is the C6-C60 aryl group).
The term “C1-C60 heteroaryloxy group” as used herein refers to -OA104 (wherein A104 is the C1-C60 heteroaryl group), and the term “C1-C60 heteroarylthio group” as used herein refers to -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 that has two or more condensed rings and only carbon atoms (e.g., the number of carbon atoms may be in a range of 8 to 60) as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. 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 that has two or more condensed rings and a heteroatom selected from B, N, O, P, Si, B, Se, Te, Ge, S, or any combination thereof and carbon atoms (e.g., the number of carbon atoms may be in a range of 1 to 60) as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group and the like. 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-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group including 5 to 30 carbon atoms only as ring-forming atoms. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group.
The term “C1-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group including 1 to 30 carbon atoms and at least one heteroatom selected from N, O, P, Si, B, Se, Te, Ge, S, or any combination thereof as ring-forming atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group.
As used herein, the number of carbons in each group that is substituted (e.g., C1-C60) excludes the number of carbons in the substituent. For example, a C1-C60 alkyl group can be substituted with a C1-C60 alkyl group. The total number of carbons included in the C1-C60 alkyl group substituted with the C1-C60 alkyl group is not limited to 60 carbons. In addition, more than one C1-C60 alkyl substituent may be present on the C1-C60 alkyl group. This definition is not limited to the C1-C60 alkyl group and applies to all substituted groups that recite a carbon range.
At least one substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 heterocyclic 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 alkylaryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkylheteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:
Hereinafter, a compound and an organic light-emitting device according to embodiments will be described in detail with reference to Synthesis Examples and Examples, but the disclosure is not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of A used was identical to an amount of B used, in terms of a molar equivalent.
9 g of 8-bromo-1-fluorodibenzo[b,d]furan, 5.0 g of phenylboronic acid, 1.2 g of Pd(PPh3)4, and 9.4 g of potassium carbonate were added to 100 ml of 1,4-dioxane and 50 ml of distilled water, and the mixture was refluxed while heating in a nitrogen atmosphere. After reacting for 18 hours, the reaction mixture was cooled to room temperature, and an organic layer was separated therefrom and purified by column chromatography to obtain Intermediate 33-1 (5.5 g, 21.0 mmol).
5 g of Intermediate 33-1, 6.4 g of 9H-3,9′-bicarbazole, and 12.4 g of cesium carbonate were added to 65 ml of N-methyl-2-pyrrolidone, and the mixture was stirred at 180° C. for 6 hours. After cooling to room temperature, water was added thereto, and the resulting solid was filtered under reduced pressure and purified by column chromatography to obtain Compound 33 (8.5 g, 14.7 mmol).
LC/MS [M]+ 574.2
Intermediate 35-1 (8.5 g, 25.1 mmol) was obtained in the same manner as in the synthesis of Intermediate 33-1, except that 20 g of [1,1′-biphenyl]-3-ylboronic acid was used instead of phenylboronic acid.
Compound 35 (9.6 g, 14.8 mmol) was obtained in the same manner as in the synthesis of Compound 33, except that 7 g of Intermediate 35-1 was used instead of Intermediate 33-1.
LC/MS [M]+ 650.2
Compound 7 (10.4 g, 18.1 mmol) was obtained in the same manner as in the synthesis of Compound 35, except that 9H-2,9′-bicarbazole was used instead of 9H-3,9′-bicarbazole.
LC/MS [M]+ 650.2
Intermediate 410-1 (9.0 g, 25.9 mmol) was obtained in the same manner as in the synthesis of Intermediate 33-1, except that ([1,1′-biphenyl]-3-yl-d9)boronic acid was used instead of phenylboronic acid.
Compound 410 (13.9 g, 20.6 mmol) was obtained in the same manner as in the synthesis of Compound 33, except that Intermediate 410-1 was used instead of Intermediate 33-1, and 9H-3,9′-bicarbazole-d15 was used instead of 9H-3,9′-bicarbazole.
LC/MS [M]+ 674.4
Compound 91 (6.3 g, 7.7 mmol) was obtained in the same manner as in the synthesis of Compound 35, except that 5.1 g of 9H-3,9′:3′,9″-tercarbazole was used instead of 9H-3,9′-bicarbazole.
LC/MS [M]+ 815.3
A glass substrate with a 1,500 Å-thick indium tin oxide (ITO) electrode (first electrode, anode) formed thereon was cleaned by distilled water ultrasonication. After the distilled water ultrasonication, ultrasonic cleaning was performed using solvents, such as isopropyl alcohol, acetone, and methanol, and the glass substrate was dried and transferred to a plasma cleaner. Then, the glass substrate was cleaned by using oxygen plasma for 5 minutes, and transferred to a vacuum depositor.
Compound HT3 and Compound HT-D2 were co-deposited on the ITO electrode of the glass substrate to form a hole injection layer having a thickness of 100 Å, Compound HT3 was deposited on the hole injection layer to form a hole transport layer having a thickness of 1,300 Å, and mCP was deposited on the hole transport layer to form an electron blocking layer having a thickness of 100 Å, thereby forming a hole transport region.
A host and a dopant were co-deposited at a weight ratio of 85:15 on the hole transport region to form an emission layer having a thickness of 300 Å. The host included a first host (Compound 33) and a second host (E1), and the weight ratio of the first host to the second host was adjusted to 6:4.
BCP was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 100 Å, Compound ET3 and LiQ were co-vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and an Al second electrode (cathode) having a thickness of 1,200 Å was formed on the electron injection layer, 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 2 were each used instead of Compound 33 in forming an emission layer.
The T95 lifespan (at 1,000 nit, hr), which indicates the time taken until the initial luminance is reduced to 95%, of each of the organic light-emitting devices manufactured in Examples 1 to 5 and Comparative Examples 1 to 3 was evaluated and measured using a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). Results thereof were converted into relative values (%) and are shown in Table 2.
From Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 5 had excellent lifespan characteristics, as compared with the organic light-emitting devices of Comparative Examples 1 to 3.
A glass substrate with a 1,500 Å-thick indium tin oxide (ITO) electrode (first electrode, anode) formed thereon was cleaned by distilled water ultrasonication. After the distilled water ultrasonication, ultrasonic cleaning was performed using solvents, such as isopropyl alcohol, acetone, and methanol, and the glass substrate was dried and transferred to a plasma cleaner. Then, the glass substrate was cleaned by using oxygen plasma for 5 minutes, and transferred to a vacuum depositor.
Compound HT3 and Compound HT-D2 were co-deposited on the ITO electrode of the glass substrate to form a hole injection layer having a thickness of 100 Å, Compound HT3 was deposited on the hole injection layer to form a hole transport layer having a thickness of 1,300 Å, and mCP was deposited on the hole transport layer to form an electron blocking layer having a thickness of 100 Å, thereby forming a hole transport region.
A host, a phosphorescent dopant (P31), and a fluorescent dopant (D3) were co-deposited at a weight ratio of 85:14:1 on the hole transport region to form an emission layer having a thickness of 300 Å. The host included a first host (Compound 33) and a second host (E1), and the weight ratio of the first host to the second host was adjusted to 6:4.
BCP was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 100 Å, Compound ET3 and LiQ were co-vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and an Al second electrode (cathode) having a thickness of 1,200 Å was formed on the electron injection layer, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in the same manner as in Example 6, except that compounds shown in Table 3 were each used instead of Compound 33 in forming an emission layer.
The T95 lifespan (at 1,000 nit, hr), which indicates the time taken until the initial luminance is reduced to 95%, of each of the organic light-emitting devices manufactured in Examples 6 to 10 and Comparative Example 4 was evaluated and measured using a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). Results thereof were converted into relative values (%) and are shown in Table 3.
From Table 3, it was confirmed that the organic light-emitting devices of Examples 6 to 10 had excellent lifespan characteristics, as compared with the organic light-emitting device of Comparative Example 4.
As described above, the condensed cyclic compound may have excellent thermal stability and charge mobility characteristics, and thus, an electronic device, for example, an organic light-emitting device, including the condensed cyclic compound may have low driving voltage and high efficiency characteristics. Accordingly, by using the condensed cyclic compound, a high-quality organic light-emitting device may be realized.
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 FIGURE, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2022-0055743 | May 2022 | KR | national |
