Patent Application
20230080626
This application claims the benefit of Japanese Patent Application No. 2020-216557, filed on Dec. 25, 2020, in the Japanese Patent Office and Korean Patent Application No. 10-2021-0087429, filed on Jul. 2, 2021, in the Korean Intellectual Property Office, the disclosures of which are incorporated by reference herein in their entirety.
The present disclosure relates to condensed cyclic compounds, organic light-emitting devices including the condensed cyclic compounds, and electronic apparatuses including the organic light-emitting devices.
Organic light-emitting devices are self-emissive devices that have wide viewing angles, high contrast ratios, and short response times, exhibit excellent characteristics in terms of 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 may move toward the emission layer through the hole transport region, and electrons provided from the cathode 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 transition from an excited state to a ground state, thereby generating light.
Provided are condensed cyclic compounds having excellent luminescence efficiency and high color purity and organic light-emitting devices including the condensed cyclic compounds.
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 an embodiment, provided is a condensed cyclic compound represented by Formula 1:
In Formula 1,
Ar1 to Ar5 are each independently a C6-C60 carbocyclic group or a C1-C60 heterocyclic group,
R1 to R5 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2), wherein R1(s) in the number of n1, R2(s) in the number of n2, R3(s) in the number of n3, R4(s) in the number of n4, and R5(s) in the number of n5 are identical to or different from each other,
n1 to n5 are each independently an integer from 0 to 8,
the sum of n1 to n5 is 1 or more,
two of two or more R1(s) when n1 is 2 or more; two of two or more R2(s) when n2 is 2 or more; two of two or more R3(s) when n3 is 2 or more; two of two or more R4(s) when n4 is 2 or more; and two of two or more R5(s) when n5 is 2 or more are respectively optionally linked to each other or linked together via a single bond to form a C8-C60 polycyclic group unsubstituted or substituted with at least one R10a,
R10a is:
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), and
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, or a phenyl group, a biphenyl group, or any combination thereof.
According to an aspect of another embodiment, provided is an organic light-emitting device including: a first electrode; a second electrode; and an interlayer arranged between the first electrode and the second electrode and including an emission layer, wherein the interlayer includes at least one condensed cyclic compound.
According to an aspect of another embodiment, provided is an electronic apparatus including 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 accompanying drawings, in which:
Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the specification. 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 a group 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 Figures It will be understood that relative terms are intended to encompass different orientations of the device in addition to the orientation depicted in the Figures For example, if the device in one of the figures is turned over, elements described as being on the “lower” side of other elements would then be oriented on “upper” sides of the other elements The exemplary term “lower,” can therefore, encompasses both an orientation of “lower” and “upper,” depending on the particular orientation of the figure Similarly, if the device in one of the figures is turned over, elements described as “below” or “beneath” other elements would then be oriented “above” the other elements The exemplary terms “below” or “beneath” can, therefore, encompass both an orientation of above and below.
“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 figures 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.
An aspect of the present disclosure provides a condensed cyclic compound represented by Formula 1:
wherein, in Formula 1,
Ar1 to Ar5 may each independently be a C6-C60 carbocyclic group or a C1-C60 heterocyclic group.
In an embodiment, Ar1 to Ar5 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 isooxazole 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 one or more embodiments, Ar5 in Formula 1 may be a benzene group, a naphthalene group, an anthracene group, or any combination thereof.
In one or more embodiments, a moiety represented by
in Formula 1 may be a group represented by one of Formulae 1-1 to 1-4:
wherein, in Formulae 1-1 to 1-4,
a portion indicated with a dotted line refers to bonding to a neighboring part of Formula 1, and
R5a to R5f may respectively be the same as described in connection with R1 to R5.
In one or more embodiments, Ar1 to Ar5 may be a benzene group, a naphthalene group, an anthracene group, or any combination thereof.
In one or more embodiments, Ar1 to Ar5 may each independently be a benzene group.
In an embodiment, a group represented by
in Formula 1 may be represented by one of Formulae 1-2-1 to 1-2-19:
In one or more embodiments, the group represented by
in Formula 1 may be represented by one of Formulae 1-2-1 to 1-2-12, 1-2-14, 1-2-16, 1-2-18, and 1-2-19.
In Formula 1, R1 to R5 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2), wherein R1(s) in the number of n1, R2(s) in the number of n2, R3(s) in the number of n3, R4(s) in the number of n4, and R5(s) in the number of n5 may be identical to or different from each other. R10a may be the same as described herein.
Q1 to Q3 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
In an embodiment, R1 to R5 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C30 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C30 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C30 arylthio group unsubstituted or substituted with at least one R10a, or —N(Q1)(Q2), and
Q1 and Q2 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C20 alkoxy group; or a C3-C30 carbocyclic group or a C1-C30 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof. R10a may be the same as described herein.
In an embodiment, at least one of R1 to R4 may be —N(Q1)(Q2), and
Q1 and Q2 may each independently be a benzene group or a naphthalene group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
In Formula 1, n1 to n5 may each independently be an integer from 0 to 8.
In an embodiment, n1 and n3 may each independently be an integer from 0 to 4.
In an embodiment, n2 and n4 may each independently be an integer from 0 to 3.
In an embodiment, n5 may be an integer from 0 to 2.
In Formula 1, the sum of n1 to n5 may be 1 or more.
In an embodiment, the sum of n1 to n4 may be 1 or more.
In an embodiment, n1 to n4 may each independently be 0 or 1, and n5 may be 0.
In Formula 1, two of two or more R1(s) when n1 is 2 or more; two of two or more R2(s) when n2 is 2 or more; two of two or more R3(s) when n3 is 2 or more; two of two or more R4(s) when n4 is 2 or more; and two of two or more R5(s) when n5 is 2 or more may respectively be optionally linked to each other or linked together via a single bond to form a C8-C60 polycyclic group unsubstituted or substituted with at least one R10a.
In an embodiment, the condensed cyclic compound represented by Formula 1 may be represented by Formula 2:
In Formula 2,
Ar1 to Ar4, R1 to R5, and n1 to n4 may respectively be the same as described herein,
X1 and X2 may each independently be C or N,
n52 may be an integer from 0 to 2,
the sum of n1 to n4 and n52 may be 1 or more, and
two of two or more R1(s) when n1 is 2 or more; two of two or more R2(s) when n2 is 2 or more; two of two or more R3(s) when n3 is 2 or more; two of two or more R4(s) when n4 is 2 or more; and two R5(s) when n52 is 2 may respectively be optionally linked to each other or linked together via a single bond to form a C8-C60 polycyclic group unsubstituted or substituted with at least one R10a.
In an embodiment, each of X1 and X2 in Formula 2 may C.
In one or more embodiment, the compound represented by Formula 1 may be represented by Formula 3:
In Formula 3,
R11 to R14 may respectively be the same as described in connection with R1,
R21 to R23 may respectively be the same as described in connection with R2,
R31 to R34 may respectively be the same as described in connection with R3,
R41 to R43 may respectively be the same as described in connection with R4,
R51 and R52 may respectively be the same as described in connection with R5,
at least one of R11 to R14, R21 to R23, R31 to R34, R41 to R43, R51, and R52 may not be hydrogen, and
two of R11 to R14, R21 to R23, R31 to R34, R41 to R43, R51, and R52 may optionally be linked to each other or linked together via a single bond to form a C8-C60 polycyclic group unsubstituted or substituted with at least one R10a.
In an embodiment, at least one of R13, R22, R33, and R42 in Formula 2 may not be hydrogen.
In one or more embodiments, the condensed cyclic compound represented by Formula 1 may be one of Compounds 1 to 24:
wherein D in Compound 22 is deuterium, and
“D=52” in Compound 24 means that all 52 hydrogen atoms in Compound 24 are substituted with deuterium atoms.
In an embodiment, the condensed cyclic compound represented by Formula 1 may emit blue light or cyan light.
In an embodiment, the condensed cyclic compound represented by Formula 1 may have a maximum emission wavelength in a range of about 380 nm to about 500 nm, about 380 nm to about 490 nm, about 380 nm to about 470 nm, about 400 nm to about 500 nm, about 400 nm to about 490 nm, about 400 nm to about 470 nm, about 450 nm to about 500 nm, about 450 nm to about 490 nm, or about 450 nm to about 470 nm.
In an embodiment, the condensed cyclic compound represented by Formula 1 may have a highest occupied molecular orbital (HOMO) energy level of about −6.0 eV or more and a lowest unoccupied molecular orbital (LUMO) energy level of about −2.5 eV or less, and
the HOMO energy level and the LUMO energy level may be values measured a photoelectron spectrometer and a spectrophotometer, respectively.
For example, the HOMO energy level of the condensed cyclic compound represented by Formula 1 may be about −5.8 eV or more and about −5.0 eV or less.
For example, the LUMO energy level of the condensed cyclic compound represented by Formula 1 may be about −3.5 eV or more and about −2.6 eV or less.
In an embodiment, the condensed cyclic compound represented by Formula 1 may have a difference (ΔEST) between a singlet (S1) energy level and a triplet (T1) energy level of about 0.5 eV or less.
For example, the difference ΔEST may be about 0.4 eV or less, about 0.3 eV or less, or about 0.25 eV or less.
In an embodiment, a full width at half maximum (FWHM) in the maximum emission wavelength of the condensed cyclic compound represented by Formula 1 may be about 40 nm or less, about 30 nm or less, or about 25 nm or less in a maximum emission wavelength.
Since the condensed cyclic compound represented by Formula 1 has a rigid intramolecular structure and accordingly suppresses a change in the molecular structure, a narrow emission spectrum may be obtained. In particular, when the condensation directions of the rings including N are the same, such an effect of obtaining a narrow emission spectrum may be increased. In addition, since the compound represented by Formula 1 includes R1 to R5, the difference ΔEST between a singlet excitation energy level and a triplet excitation energy level may be lowered. Accordingly, an organic light-emitting device employing the condensed cyclic compound represented by Formula 1 may have a relatively narrow FWHM of an emission peak in the emission spectrum, leading to high color purity and excellent luminescence efficiency.
Synthesis methods of the condensed cyclic compound represented by Formula 1 may be understood by one of ordinary skill in the art by referring to the Examples below.
Another aspect of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode; and an interlayer arranged between the first electrode and the second electrode and including an emission layer, wherein the interlayer includes at least one condensed cyclic compound.
In an embodiment, the condensed cyclic compound represented by Formula 1 may be included in the emission layer.
In an embodiment, the emission layer may further include a host, and the condensed cyclic compound represented by Formula 1 included in the emission layer may act as a light-emitting dopant. Here, in the emission layer, the amount of the host may be greater than that of the condensed cyclic compound represented by Formula 1.
In one or more embodiments, the emission layer may further include a host and a light-emitting dopant, and the condensed cyclic compound represented by Formula 1 included in the emission layer may act as a sensitizer. Here, in the emission layer, the amount of the host may be greater than the total amount of the light-emitting dopant and the sensitizer. The host will be described in detail later.
When the organic light-emitting device includes the interlayer including the condensed cyclic compound represented by Formula 1, the characteristics of high color purity, a narrow FWHM, and a high external quantum efficiency may be exhibited.
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 act as a dopant, and the emission layer may further include a host (that is, the amount of the condensed cyclic compound represented by Formula 1 may be smaller than that of the host). The emission layer may emit blue light having a maximum emission wavelength of 380 nm or more (for example, 380 nm or more and 500 nm or less).
In one or more embodiments, the condensed cyclic compound included in the emission layer of the organic light-emitting device may act as a delayed fluorescence dopant, so that delayed fluorescence may be emitted from the emission layer.
In one or more embodiments, the emission layer of the organic light-emitting device may further include a host, and the host may be a compound represented by Formula 4:
In Formula 4,
X41 to X56 may each independently be C or N,
L41 may be a single bond, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
R61 to R64 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
n61 to n64 may each independently be an integer from 0 to 4,
R10a may be the same as described in the present specification, and Q1 to Q3 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
In an embodiment, the host may be Compound H-H104, Compound HE6-203, or a combination thereof, but embodiments of the present disclosure are not limited thereto:
The expression “(the interlayer) includes a condensed cyclic compound represented by Formula 1” as used herein may be construed as meaning that “(the interlayer) includes one condensed cyclic compound belonging to the category of Formula 1” or at least two different condensed cyclic compounds belonging to the category of Formula 1.”
In an embodiment, the interlayer may include, as the condensed cyclic compound, only Compound 1. In this regard, Compound 1 may be included in the emission layer of the organic light-emitting device. In one or more embodiments, the interlayer may include, as the condensed cyclic 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 the emission layer), or may exist in different layers (for example, Compound 1 may exist in the emission layer, and Compound 2 may exist in the electron transport region).
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; or 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 interlayer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, wherein 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, 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 “an interlayer” 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 term “sensitizer” as used herein refers to a compound that is included in the interlayer (for example, the emission layer) and delivers excitation energy to a light-emitting dopant compound.
Another aspect of the present disclosure provides an electronic apparatus including the organic light-emitting device.
More details of the electronic apparatus may be the same as described herein. OLED system
An organic light-emitting device according to an embodiment of the present disclosure may include an emission layer including a host and a light-emitting dopant. In the emission layer, and the amount of the host may be greater than that of the condensed cyclic compound.
The host may include at least one of a fluorescent host, a phosphorescent host, or any combination thereof which will be described later. When the host is a mixture of two or more types of host, the host mixture may form an exciplex host.
The host will be described in detail below.
The light-emitting dopant may include the condensed-cyclic compound represented by Formula 1.
An organic light-emitting device according to another embodiment of the present disclosure may include an emission layer including a host, a sensitizer, and a light-emitting dopant. In the emission layer, the amount of the host may be greater than the total amount of the light-emitting dopant and the sensitizer.
The host will be described in detail below.
At least one of the sensitizer and the light-emitting dopant may include the condensed cyclic compound represented by Formula 1.
In an embodiment, the sensitizer may include the condensed cyclic compound represented by Formula 1, but in consideration of the relationship with the light-emitting dopant, the sensitizer may also include a compound having an energy relationship suitable for transferring excited singlet energy and/or excited triplet energy to the light-emitting dopant.
For example, the sensitizer may include the condensed cyclic compound represented by Formula 1, and the light-emitting dopant may include a phosphorescent dopant.
Singlet excitons and triplet excitons of the condensed cyclic compound may respectively be transferred to the excited singlet energy level and the excited triplet energy level of the phosphorescent dopant through a Forster resonance energy transfer (FRET) mechanism and a Dexter energy transfer (DET) mechanism. Here, triplet excitons of the phosphorescent dopant may exhibit phosphorescence emission.
For example, the sensitizer may include the condensed cyclic compound represented by Formula 1, and the light-emitting dopant may include a thermally activated delayed fluorescence (TADF) compound.
The singlet excitons and the triplet excitons of the condensed cyclic compound may respectively be transferred to the excited singlet energy level and the excited triplet energy level of the light-emitting dopant through the FRET and DET mechanisms. Here, triplet excitons of the TADF compound may be converted to singlet excitons by reverse intersystem crossing (RISC), and the accumulated singlet excitons may sequentially transition to a ground state, thereby exhibiting fluorescence.
For example, the sensitizer may include the condensed cyclic compound represented by Formula 1, wherein the condensed cyclic compound may be a TADF compound, and the light-emitting dopant may include a phosphorescent dopant or a TADF compound.
When the condensed cyclic compound is a TADF compound, triplet excitons of the condensed cyclic compound may be converted to singlet excitons by RISC, and at the same time, the energy transfer to the light-emitting dopant by the FRET and DET mechanisms may also occur.
When the sensitizer includes the condensed cyclic compound represented by Formula 1, the triplet-triplet annihilation of the triplet excitons may be suppressed such that the luminescence efficiency of the light-emitting dopant may be improved.
In an embodiment, the light-emitting dopant may include the condensed cyclic compound represented by Formula 1, and the sensitizer may include a TADF compound or an organometallic compound. However, embodiments of the present disclosure are not limited thereto, and any compound capable of transferring excitons to the condensed cyclic compound may be included.
Excitons formed in the sensitizer may be transferred to the light-emitting dopant through the DET mechanism or the FRET mechanism, and the energy of the transferred excitons in the light-emitting dopant may be transitioned to a ground state, and thus light may be emitted.
In this regard, the excitons of the sensitizer may be formed by the host through the FRET mechanism, or by the transfer of excitons generated from the host through the DET mechanism.
In an embodiment, the sensitizer may include a TADF compound.
In addition, the sensitizer may satisfy Expression 1:
ΔEST≤0.3 eV Expression 1
The TADF compound may include singlet excitons and triplet excitons, and regarding the triplet excitons, the triplet excitons may be transferred to the singlet excitons by RISC, and the energy of the singlet excitons accumulated in an excited singlet state may be transferred to the energy of the condensed cyclic compound by the FRET mechanism and/or the DET mechanism.
In one or more embodiments, the sensitizer may include an organometallic compound. For example, the sensitizer may include an organometallic compound including platinum (Pt) as a central metal, but embodiments of the present disclosure are not limited thereto.
The organometallic compound may include singlet excitons and triplet excitons, and regarding the triplet excitons, the energy of the triplet excitons may be transferred to the excited triplet energy of the condensed cyclic compound by the DET mechanism.
The organometallic compound may also satisfy Expression 1 above, and when Expression 1 is satisfied, excitons may respectively be transferred the excited singlet energy level and the excited triplet energy level of the condensed cyclic compound by a mechanism similar to the mechanism applied to the TADF compound, that is, the FRET and/or DET mechanism.
In an embodiment, the excited singlet energy level and the excited triplet energy level of the sensitizer may be lower than the excited singlet energy level and the excited triplet energy level of the host. Thus, the transfer of the excited singlet energy and the excited triplet energy from the host to the sensitizer may easily occur.
In an embodiment, the sensitizer and the light-emitting dopant may each independently include the condensed cyclic compound represented by Formula 1.
As a result, the energy transfer between the sensitizer and the light-emitting dopant may be facilitated by the FRET and DET mechanisms, and accordingly, a high-efficiency organic light-emitting device may be easily manufactured by suppressing the triplet-triplet annihilation.
In general, triplet excitons are known to affect the decrease in lifespan of organic light-emitting devices since they stay in an excited state for a long time. However, due to the use of the condensed cyclic compound of the present disclosure, the time during which the triplet excitons of the sensitizer stays is reduced such that the lifespan of the organic light-emitting device including the condensed cyclic compound may be prolonged.
In an embodiment, the condensed cyclic compound may be a material capable of emitting fluorescence. An emission layer that emits fluorescence may be clearly distinguished from an emission layer of the related art that emits phosphorescence.
For example, the condensed cyclic compound may emit TADF.
The excited singlet and triplet energy levels of the condensed cyclic compound may be lower than the excited singlet and triplet energy levels of the host compound which will be described later. Accordingly, the transfer of the singlet excitons and/or the triplet excitons from the host compound to the condensed cyclic compound may easily Occur.
The condensed cyclic compound may receive singlet excitons and/or triplet excitons from the sensitizer.
In an embodiment, when the sensitizer is a TADF compound, the excited singlet energy level of the condensed cyclic compound may be lower than the excited singlet energy level of the sensitizer, and the condensed cyclic compound may receive singlet excitons from singlet excitons of the sensitizer by the FRET mechanism and/or DET mechanism.
In one or more embodiments, when the sensitizer is an organometallic compound, the excited triplet energy level of the condensed cyclic compound may be lower than the excited triplet energy level of the sensitizer, and the condensed cyclic compound may receive triplet excitons from the sensitizer by the DET mechanism.
In one or more embodiments, when the sensitizer is a TADF compound or an organometallic compound, the condensed cyclic compound may further receive singlet excitons and/or triplet excitons from the host, and the triplet excitons received from the host may be converted to singlet energy of the condensed cyclic compound by RISC.
Due to this mechanism, the triplet-triplet annihilation may be suppressed by reducing the time during which the excitons stay in the excited triplet energy of the condensed cyclic compound, and high-efficiency fluorescence may be realized through the transition of multiple singlet excitons to the ground state.
In the emission layer, the amount of the sensitizer may be in a range of about 5 wt % to about 50 wt %. Within this range, effective energy transfer in the emission layer may be achieved, and accordingly, an organic light-emitting device having high efficiency and a long lifespan may be realized.
In an embodiment, the host, the condensed cyclic compound, and the sensitizer may satisfy Expression 2:
T
1(H)/S1(H)≥T1(S)/S1(S)≥T1(PC)/S1(PC) Expression 2
wherein, in Expression 2,
T1(H) is the lowest excited triplet energy level of the host;
S1(H) is the lowest excited singlet energy level of the host;
T1(CC) is the lowest excited triplet energy level of the condensed cyclic compound;
S1(CC) is the lowest excited singlet energy level of the condensed cyclic compound;
T1(S) is the lowest excited triplet energy level of the sensitizer; and
S1(S) is the lowest excited singlet energy level of the sensitizer.
When the host, the condensed cyclic compound, and the sensitizer further satisfy Condition 2, triplet excitons may be effectively transferred from the emission layer to the condensed cyclic compound, and accordingly, an organic light-emitting device having improved efficiency may be obtained.
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.
The organic light-emitting device 10 of
The organic light-emitting device 10 also includes a hole transport region 3 between the first electrode 2 and the emission layer 4 and an electron transport region 5 between the emission layer 4 and the second electrode 6.
The organic light-emitting device 10 may further include the substrate 1 under the first electrode 2 or above the second electrode 6. For use as the substrate 1, any substrate that is used in organic light-emitting devices of the related art may be used, and for example, a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance, may be used.
The first electrode 2 may be formed by, for example, depositing or sputtering a material for forming the first electrode 2 on the substrate 1. The first electrode 2 may be an anode. The material for forming the first electrode 11 may be a material with a high work function to facilitate hole injection.
The first electrode 2 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 2 is a transmissive electrode, the material for forming the first electrode 2 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but embodiments of the present disclosure are not limited thereto. When the first electrode 2 is a semi-transmissive electrode or a reflective electrode, the material for forming the first electrode 2 may be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof, but embodiments of the present disclosure are not limited thereto.
The first electrode 2 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 2 may have a three-layered structure of ITO/Ag/ITO, but embodiments of the present disclosure are not limited thereto.
An interlayer may be arranged on the first electrode 2.
The interlayer may include: the hole transport region 3; the emission layer 4; and the electron transport region 5.
In the organic light-emitting device 10, the hole transport region 3 may be arranged between the first electrode 2 and the emission layer 4.
The hole transport region 3 may have a single-layered structure or a multi-layered structure.
For example, the hole transport region 3 may consist of a hole injection layer or a hole transport layer, or have a hole injection layer/hole transport layer structure, a hole injection layer/first hole transport layer/second hole transport layer structure, a hole transport layer/interlayer structure, a hole injection layer/hole transport layer/interlayer structure, a hole transport layer/electron blocking layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure. However, embodiments of the present disclosure are not limited thereto.
The hole transport region 3 may include any compound having hole-transporting properties.
For example, the hole transport region 3 may include an amine-based compound.
In an embodiment, the hole transport region 3 may include at least one compound represented by Formulae 201 to 205, but embodiments of the present disclosure are not limited thereto:
wherein, in Formulae 201 to 205,
L201 to L209 may each independently be *—O—*′, *—S—*′, a substituted or unsubstituted C5-C60 carbocyclic group, or a substituted or unsubstituted C1-C60 heterocyclic group,
xa1 to xa9 may each independently be an integer from 0 to 5, and
R201 to R206 may each independently be 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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein two neighboring a group among R201 to R206 may optionally be linked to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.
For example,
L201 to L209 may each independently be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentacene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or a triindolobenzene group, each unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triphenylenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, —Si(Q11)(Q12)(Q13), or any combination thereof,
xa1 to xa9 may each independently be 0, 1, or 2,
R201 to R206 may each independently be 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, a pyridinyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, or a benzothienocarbazolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with —F, 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, a pyridinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), or any combination thereof, and
Q11 to Q13 and Q31 to Q33 may each independently be a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.
In an embodiment, the hole transport region 3 may include a carbazole-containing amine-based compound.
In one or more embodiments, the hole transport region 3 may include a carbazole-containing amine-based compound and a carbazole-free amine-based compound.
The carbazole-containing amine-based compound may be, for example, a compound represented by Formula 201 which include a carbazole group and which further include at least one of a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or any combination thereof.
The carbazole-free amine-based compound may be, for example, a compound represented by Formula 201 which do not include a carbazole group and which include at least one of a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or any combination thereof.
In one or more embodiments, the hole transport region 3 may include at least one compound represented by Formulae 201 and 202.
In one or more embodiments, the hole transport region 3 may include at least one compound represented by Formulae 201-1, 202-1, and 201-2, but embodiments of the present disclosure are not limited thereto:
For example, the hole transport region 3 may include at least one of Compounds HT1 to HT39, but embodiments of the present disclosure are not limited thereto:
In one or more embodiments, hole transport region 3 of the organic light-emitting device 10 may further include a p-dopant. When the hole transport region 3 further includes a p-dopant, the hole transport region 3 may have a structure including a matrix (for example, at least one of compounds represented by Formulae 201 to 205) and a p-dopant included in the matrix. The p-dopant may be uniformly or non-uniformly doped in the hole transport region 3.
In an embodiment, the p-dopant may have a LUMO energy level of about −3.5 eV or less.
The p-dopant may include at least one a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof, but embodiments of the present disclosure are not limited thereto.
In an embodiment, the p-dopant may include at least one of:
a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), or F6-TCNNQ;
a metal oxide, such as tungsten oxide or molybdenum oxide;
1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and
a compound represented by Formula 221,
but embodiments of the present disclosure are not limited thereto:
In Formula 221,
R221 to R223 may each independently be 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 C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein at least one of R221 to R223 may have at least one of a cyano group, —F, —Cl, —Br, —I, a C1-C20 alkyl group substituted with —F, a C1-C20 alkyl group substituted with —Cl, a C1-C20 alkyl group substituted with —Br, and a C1-C20 alkyl group substituted with —I, or any combination thereof.
The hole transport region 3 may have a thickness in a range of about 100 Å to about 10,000 Å, for example, about 400 Å to about 2,000 Å, and the emission layer 4 may have a thickness in a range of about 100 Å to about 3,000 Å, for example, about 300 Å to about 1,000 Å. When the thickness of each of the hole transport region 3 and the emission layer 4 is within these ranges, satisfactory hole transporting characteristics and/or luminescence characteristics may be obtained without a substantial increase in driving voltage.
The emission layer 4 may be a single layer consisting of a single material or a single layer consisting of a plurality of different materials. In addition, the emission layer 4 may have a multi-layered structure including a plurality of layers including different materials.
The emission layer 4 may include the condensed-cyclic compound represented by Formula 1.
The emission layer 4 may have a thickness in a range of about 10 Å to about 1,000 Å, for example, about 100 Å to about 300 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.
In an embodiment, the emission layer 4 of the organic light-emitting device 10 may include, in addition to the condensed cyclic compound represented by Formula 1, an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a chrysene derivative, a dihydrobenzoanthracene derivative, a triphenylene derivative, or any combination thereof.
The emission layer 4 may further include a host, and the light-emitting dopant may include the condensed cyclic compound represented by Formula 1. The host may not include a metal atom.
In an embodiment, the host may include a compound represented by Formula 4.
In an embodiment, the host may include one kind of host. When the host includes one kind of host, the one kind of host may be a bipolar host, an electron-transporting host, or a hole-transporting host, which will be described below.
In one or more embodiments, the host may include a mixture of two or more different hosts. For example, the host may be a mixture of an electron-transporting host and a hole-transporting host, a mixture of two types of electron-transporting hosts different from each other, or a mixture of two types of hole-transporting hosts different from each other. The electron-transporting host and the hole-transporting host will be described in detail below.
In one or more embodiments, the host may include an electron-transporting host which includes at least one electron-transporting moiety and a hole-transporting host which does not include an electron-transporting moiety.
The electron-transporting moiety may be a cyano group, a π electron-deficient nitrogen-containing cyclic group, or a group represented by one of the following formulae:
wherein *, *′, and *″ in the formulae above each indicate a binding site to a neighboring atom.
In one or more embodiments, the electron-transporting host included in the emission layer may include at least one of a cyano group, a π electron-deficient nitrogen-containing cyclic group, or any combination thereof.
In one or more embodiments, the electron-transporting host included in the emission layer may include at least one cyano group.
In one or more embodiments, the electron-transporting host included in the emission layer may include at least one cyano group and at least one π electron deficient nitrogen-containing cyclic group.
In one or more embodiments, the host may include an electron-transporting host and a hole-transporting host, wherein the electron-transporting host may include at least one π electron-deficient nitrogen-free cyclic group and at least one electron-transporting moiety, and the hole-transporting host may include at least one π electron-deficient nitrogen-free cyclic group and may not include an electron-transporting moiety.
The term “π electron-deficient nitrogen-containing cyclic group” as used herein refers to a cyclic group having at least one *—N=*′ moiety, and for example, may be: 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 pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; or a condensed cyclic group in which two or more π electron-efficient nitrogen-containing cyclic a group are condensed with each other.
The π electron-deficient nitrogen-free cyclic group may be: a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentacene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a triindolobenzene group; or a condensed cyclic group in which two or more π electron-deficient nitrogen-free cyclic a group are condensed with each other, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, the electron-transporting host may be a compound represented by Formula E-1, and
the hole-transporting host may be a compound represented by Formula H-1, but embodiments of the present disclosure are not limited thereto:
[Ar301]xb11-[(L301)xb1-R301]xb21
wherein, in Formula E-1,
Ar301 may be a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
xb11 may be 1, 2, or 3,
L301 may be a single bond, a group represented by one of the following formulae, a substituted or unsubstituted C5-C60 carbocyclic group, or a substituted or unsubstituted C1-C60 heterocyclic group, wherein *, *′, and *″ in the following formulae each indicate a binding site to a neighboring atom:
xb1 may be an integer from 1 to 5,
R301 may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C10 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q301)(Q302)(Q303), —N(Q301)(Q302), —B(Q301)(Q302), —C(═O)(Q301), —S(═O)2(Q301), —S(═O)(Q301), —P(═O)(Q301)(Q302), or —P(═S)(Q301)(Q302),
xb21 may be an integer from 1 to 5,
Q301 to Q303 may each independently be a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and
at least one of Conditions 1 to 3 may be satisfied:
Condition 1
at least one of Ar301, L301, R301, or any combination thereof in Formula E-1 each independently includes a π electron-deficient nitrogen-containing cyclic group;
Condition 2
L301 in Formula E-1 is a group represented by one of the following formulae; and
Condition 3
R301 in Formula E-1 is a cyano group, —S(═O)2(Q301), —S(═O)(Q301), —P(═O)(Q301)(Q302), or —P(═S)(Q301)(Q302),
Ar401-(L401)xd1-(Ar402)xd11 Formula H-1
wherein, in Formulae H-1, 11, and 12,
L401 may be:
a single bond; or
a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentacene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, and a triindolobenzene group, each unsubstituted or substituted with at least one deuterium, a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triphenylenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, or —Si(Q401)(Q402)(Q403),
xd1 may be an integer from 1 to 10, wherein, when xd1 is 2 or more, two or more of L401(s) may be identical to or different from each other,
Ar401 may be a group represented by Formulae 11 or 12,
Ar402 may be:
a group represented by Formulae 11 or 12, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group; or
a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group, each substituted with at least one deuterium, a hydroxyl 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, or any combination thereof,
xd11 may be an integer from 1 to 10, wherein, when xd11 is 2 or more, two or more of Ar402(s) may be identical to each other or different from each other,
CY401 and CY402 may each independently be a benzene group, a naphthalene group, a fluorene group, a carbazole group, a benzocarbazole group, an indolocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a benzonaphthofuran group, a benzonaphthothiophene group, or a benzonaphthosilole group,
A21 may be a single bond, O, S, N(R51), C(R51)(R52), or Si(R51)(R52),
A22 may be a single bond, O, S, N(R53), C(R53)(R54), or Si(R53)(R54),
at least one of A21, A22, or any combination thereof in Formula 12 may not be a single bond,
R51 to R54, R60, and R70 may each independently be:
hydrogen, deuterium, a hydroxyl 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 C1-C20 alkyl group, or a C1-C20 alkoxy group;
a C1-C20 alkyl group or a C1-C20 alkoxy group, each substituted with at least one deuterium, a hydroxyl 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 phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof;
a π electron-deficient nitrogen-free cyclic group (for example, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group);
a π electron-deficient nitrogen-free cyclic group (for example, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group) substituted with at least one deuterium, a hydroxyl 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, or any combination thereof; or
—Si(Q404)(Q405)(Q406),
e1 and e2 may each independently be an integer from 0 to 10,
Q401 to Q406 may each independently be hydrogen, deuterium, a hydroxyl 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 phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group, and
* indicates a binding site to a neighboring atom.
In an embodiment, in Formula E-1, Ar301 and L301 may each independently be a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene 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 pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof,
at least one of L301(s) in the number of xb1 may each independently be 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 pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, or any combination thereof, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof, and
R301 may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing tetraphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), and
Q31 to Q33 may each independently be a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, but embodiments of the present disclosure are not limited thereto.
In one or more embodiments,
Ar301 may be: a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32); and
a group represented by one of Formulae 5-1 to 5-3 and 6-1 to 6-33, and
L301 may be a group represented by one of Formulae 5-1 to 5-3 and 6-1 to 6-33:
In Formulae 5-1 to 5-3 and 6-1 to 6-33,
Z1 may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, a cyano-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), d4 may be 0, 1, 2, 3, or 4, d3 may be 0, 1, 2, or 3, d2 may be 0, 1, or 2,
* and *′ each indicate a binding site to a neighboring atom, and
Q31 to Q33 may respectively be the same as described herein.
In one or more embodiments, L301 may be a group represented by one of Formulae 5-2, 5-3, and 6-8 to 6-33.
In one or more embodiments, R301 may be a cyano group or a group represented by one of Formula 7-1 to 7-18, and at least one of Ar402(s) in the number of xd11 may be a group represented by one of Formulae 7-1 to 7-18, but embodiments of the present disclosure are not limited thereto:
In Formulae 7-1 to 7-18,
xb41 to xb44 may each be 0, 1, or 2, wherein xb41 in Formula 7-10 is not 0, the sum of xb41 and xb42 in Formulae 7-11 to 7-13 is not 0, the sum of xb41, xb42, and xb43 in Formulae 7-14 to 7-16 is not 0, the sum of xb41, xb42, xb43, and xb44 in Formulae 7-17 and 7-18 is not 0, and * indicates a binding site to a neighboring atom.
In an embodiment, two or more of Ar301(s) in Formula E-1 may be identical to or different from each other, two or more of L301(s) in Formula E-1 may be identical to or different from each other, two or more of L401(s) in Formula H-1 may be identical to or different from each other, and two or more Ar402(s) in Formula H-1 may be identical to or different from each other.
In an embodiment, the electron-transporting host may include i) at least one of a cyano group, a pyrimidine group, a pyrazine group, a triazine group, or any combination thereof, and ii) a triphenylene group, and the hole-transporting host may include a carbazole group.
In one or more embodiments, the electron-transporting host may include at least one cyano group.
The electron-transporting host may be, for example, compounds of a group HE1 to HE7 and Compound HE6-203, but embodiments of the present disclosure are not limited thereto:
In an embodiment, the hole-transporting host may be one of Compounds H-H1 to H-H104, but embodiments of the present disclosure are not limited thereto:
In an embodiment, the bipolar host may be Group HEH1, but embodiments of the present disclosure are not limited thereto:
wherein, in Compounds 1 to 432,
Ph refers to a phenyl group.
When the host is a mixture of the electron-transporting host and the hole-transporting host, a weight ratio of the electron-transporting host and the hole-transporting host may be in a range of about 1:9 to 9:1, for example, about 2:8 to 8:2, for example, about 4:6 to 6:4, and for example, about 5:5. When the weight ratio of the electron transport host and the hole transport host is satisfied with these ranges, the hole-and-electron transport balance in the emission layer may be achieved.
In one or more embodiments, the host may include at least one of bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 3,3′-di(9H-carbazol-9-yl)-1,1′-biphenyl (Mcbp), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF), tris(4-carbazoyl-9-ylphenyl)amine (TCTA), Alq3, poly(n-vinylcarbazole) (PVK), 3-tert-butyl-9,10-di(2-naphthyl)anthracene (TBADN), (dystyryl allylene), 4,54′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis (naphthalen-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis (triphenylsilyl)benzene (UGH2), (hexaphenyl)cyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF), TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compounds H50 to H52, or any combination thereof:
In one or more embodiments, the host may further include a compound represented by Formula 301:
wherein, in Formula 301, Ar111 and Ar112 may each independently be:
a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; or
a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group, each substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or any combination thereof.
In Formula 301, Ar113 to Ar116 may each independently be:
a C1-C10 alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group; or
a phenyl group, a naphthyl group, a phenanthrenyl group, or a pyrenyl group, each substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or any combination thereof.
In Formula 301, g, h, i, and j may each independently be an integer from 0 to 4, and for example, may each independently be 0, 1, or 2.
In Formula 301, Ar113 to Ar116 may each independently be:
a C1-C10 alkyl group substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group, or any combination thereof;
a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl, a phenanthrenyl group, or a fluorenyl group;
a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, or a fluorenyl group, each substituted with at least one of 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, or any combination thereof; or
but embodiments of the present disclosure are not limited thereto.
In one or more embodiments, the host may include a compound represented by Formula 302:
wherein, in Formula 302, Ar122 to Ar125 may each independently be the same as described in connection with Ar113 in Formula 301.
In Formula 302, Ar126 and Ar127 may each independently be a C1-C10 alkyl group (for example, a methyl group, an ethyl group, or a propyl group).
In Formula 302, k and l may each independently be an integer from 0 to 4. For example, k and l may each independently be 0, 1, or 2.
When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer 4 may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In an embodiment, based on a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer 4 may emit white light, and various modifications are possible.
When the emission layer 4 includes a host and a light-emitting dopant, an amount of the light-emitting dopant may be generally in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
A thickness of the emission layer 4 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 4 is within these ranges, excellent luminescence characteristics may be obtained without a substantial increase in driving voltage.
In an embodiment, the light-emitting dopant may include the condensed cyclic compound represented by Formula 1.
In one or more embodiments, the light-emitting dopant may include 1,4-bis[2-(3-N-ethylcarbazolyl)-vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4′-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl)phenyl)-N-phenylbenzeneamine (N-BDAVBi), 2,5,8,11-tetra-t-butylperylene (TBP), or any combination thereof.
In an embodiment, the sensitizer may include the condensed cyclic compound represented by Formula 1.
In one or more embodiments, the sensitizer may include an organic metallic compound including at least one metal of a Period 1 transition metal, Period 2 transition metal, Period 3 transition metal, or a combination thereof of the Periodic Table of Elements.
In one or more embodiments, the sensitizer may include: at least one metal (M11) of a Period 1 transition metal, Period 2 transition metal, Period 3 transition metal, or any combination thereof of the Periodic Table of Elements; and an organic ligand (L1), wherein L1 and M11 may form 1, 2, 3, or 4 cyclometallated rings.
In one or more embodiments, the sensitizer may include an organometallic compound represented by Formula 101:
M11(L1)n1(L2)n2 Formula 101
wherein, in Formula 101,
M11 may be a Period 1 transition metal, a Period 2 transition metal, or a Period 3 transition metal of the Periodic Table of Elements,
L1 may be an organic ligand represented by one of Formulae 10-1 to 10-4,
L2 may be a monodentate ligand or a bidentate ligand,
n1 may be 1, and
n2 may be 0, 1, or 2,
wherein, in Formulae 10-1 to 10-4,
A1 to A4 may each independently be a substituted or unsubstituted C5-C30 carbocyclic group, a substituted or unsubstituted C1-C30 heterocyclic group, or a non-cyclic group,
Y11 to Y14 may each independently be a chemical bond, O, S, N(R91), B(R91), P(R91), or C(R91)(R92),
T1 to T4 may each independently be a single bond, a double bond, *—N(R93)—*′, *—*—B(R93)—*′, *—C(R93)(R94)—*′, *—Si(R93)(R94)—*′, *—Ge(R93)(R94)—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R93)=*′, *═C(R93)—*′, *—C(R93)═C(R94)—*′, *—C(═S)—*′, or *—C≡C—*′,
a substituent of the substituted C5-C30 carbocyclic group, a substituent of substituted C1-C30 heterocyclic group, and R91 to R94 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 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), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2), wherein each of the substituent of the substituted C5-C30 carbocyclic group and the substituent of substituted C1-C30 heterocyclic group is not hydrogen,
*1, *2, *3, and *4 each indicate a binding site to M11, and
Q1 to Q3 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkylaryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, or a C6-C60 aryl group, or a C6-C60 aryl group that is substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof.
In one or more embodiments, the sensitizer may be one of groups I to VI, but embodiments of the present disclosure are not limited thereto:
a compound represented by Formula A:
(L101)n101-M101-(L102)m101 Formula A
wherein, in Formula A, L101, n101, M101, L102, and m101 may respectively be the same as described in connection with Tables 1 to 3:
In Tables 1 to 3, LM1 to LM243 may respectively be understood by referring to Formulae 11-1 to 11-3 and Tables 4 to 6:
In Tables 4 to 6, X1 to X10 and Y1 to Y18 may respectively be the same as described herein, and Ph in the tables refers to a phenyl group:
In one or more embodiments, the sensitizer may be a TADF emitter that satisfies Condition 7:
ΔEST≤0.3 eV Condition 7
wherein, in Condition 7,
ΔEST is the difference between a excitation singlet energy level and a excitation triplet energy level of the sensitizer.
In one or more embodiments, the sensitizer may include a TADF emitter represented by Formula 401 or 402:
wherein, in Formulae 401 and 402,
A21 may be an acceptor group,
D21 may be a donor group,
m21 may be 1, 2, or 3, and n21 may be 1, 2, or 3,
the sum of n21 and m21 in Formula 401 may be 6 or less, and the sum of n21 and m21 in Formula 402 may be 5 or less,
R21 may 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 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 alkylaryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 alkylheteroaryl group, a substituted or unsubstituted C2-C60 heteroaryl alkyl 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), or —P(═S)(Q1)(Q2), wherein a plurality of R21(s) may optionally be linked together to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, and
Q1 to Q3 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkylaryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof, or a C6-C60 aryl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof.
For example, A21 in Formulae 401 and 402 may be a substituted or unsubstituted π electron-deficient nitrogen-free cyclic group.
In an embodiment, the π electron-deficient nitrogen-free cyclic group may be: a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentacene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a triindolobenzene group; or a condensed cyclic group in which two or more π electron-deficient nitrogen-free cyclic a group are condensed with each other, but embodiments of the present disclosure are not limited thereto.
For example, D21 in Formulae 401 and 402 may be: —F, a cyano group, or an π-electron deficient nitrogen-containing cyclic group;
a C1-C60 alkyl group, an π-electron deficient nitrogen-containing cyclic group, or an π electron-deficient nitrogen-free cyclic group, each substituted with at least one —F, a cyano group, or any combination thereof; or
an π-electron deficient nitrogen-containing cyclic group, each substituted with at least one deuterium, a C1-C60 alkyl group, an π-electron deficient nitrogen-containing cyclic group, an π electron-deficient nitrogen-free cyclic group, or any combination thereof.
In detail, the π electron-deficient nitrogen-free cyclic group may be the same as described herein.
The term “π electron-deficient nitrogen-containing cyclic group” as used herein refers to a cyclic group having at least one *—N=*′ moiety, and, for example, may be: 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 pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, and a benzimidazolobenzimidazole group; or a condensed cyclic group in which two or more π electron-efficient nitrogen-containing cyclic a group are condensed with each other.
In one or more embodiments, the sensitizer may be A group VII to XI, but embodiments of the present disclosure are not limited thereto:
Next, the electron transport region 5 is arranged on the emission layer 4.
In the organic light-emitting device 10, the electron transport region 5 may be arranged between the emission layer 4 and the second electrode 6.
The electron transport region 5 may have a single-layered structure or a multi-layered structure.
For example, the electron transport region 5 may consist of an electron transport layer, or may have an electron transport layer/electron injection layer structure, a buffer layer/electron transport layer structure, a hole blocking layer/electron transport layer structure, a buffer layer/electron transport layer/electron injection layer structure, or a hole blocking layer/electron transport layer/electron injection layer structure, but embodiments of the present disclosure are not limited thereto. The electron transport region 5 may further include an electron control layer.
The electron transport region 5 may include an electron-transporting material known in the art.
The electron transport region 5 (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-deficient nitrogen-containing C1-C60 cyclic group. The π electron-deficient nitrogen-containing C1-C60 cyclic group may be the same as described herein.
In an embodiment, the electron transport region 5 may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21 Formula 601
wherein, in Formula 601,
Ar601 and L601 may each independently be a substituted or unsubstituted C5-C60 carbocyclic group unsubstituted or substituted with at least one R601a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R601a,
xe11 may be 1, 2, or 3,
xe1 may be an integer from 0 to 5,
R601a and R601 may each independently be 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(Q601)(Q602)(Q603), —C(═O)(Q601), —S(═O)2(Q601), or —P(═O)(Q601)(Q602),
Q601 to Q603 may each independently be a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and
xe21 may be an integer from 1 to 5.
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 C1-C60 cyclic group.
In an embodiment, Ar601 and L601 in Formula 601 may each independently be a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole 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, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q31)(Q32)(Q33), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof, and
Q31 to Q33 may each independently be a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.
When xe11 in Formula 601 is 2 or more, two or more of Ar601(s) may be linked to each other via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be an anthracene group.
In an embodiment, the compound represented by Formula 601 may be represented by Formula 601-1:
wherein, in Formula 601-1,
X614 may be N or C(R614), X615 may be N or C(R615), X616 may be N or C(R616), and at least one of X614 to X616 may be N,
L611 to L613 may each independently be the same as described in connection with L601,
xe611 to xe613 may each independently be the same as described in connection with xe1,
R611 to R613 may each independently be the same as described in connection with R601, and
R614 to R616 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.
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: a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl 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, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, or an azacarbazolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl 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, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, or any combination thereof; or
—S(═O)2(Q601) or —P(═O)(Q601)(Q602), and
Q601 and Q602 may respectively be the same as described herein.
In an embodiment, the electron transport region 5 may include at least one compound of Compounds ET1 to ET36 and HE6-203, but embodiments of the present disclosure are not limited thereto:
In one or more embodiments, the electron transport region 5 may include at least one of 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), NTAZ, or any combination thereof:
A thicknesses of each of the buffer layer, the hole blocking layer, and the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thickness of the buffer layer, the hole blocking layer, or the electron control layer is 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, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
In one or more embodiments, the electron transport region 5 (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 of an alkali metal complex, an alkaline earth-metal complex, or a combination thereof. The alkali metal complex may include a Li ion, a Na ion, a K ion, a Rb ion, a Cs ion, or any combination thereof, and the alkaline earth-metal complex may include a Be ion, a Mg ion, a Ca ion, a Sr ion, a Ba ion, or any combination thereof. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be 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, or a cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or ET-D2:
The electron transport region 5 may include an electron injection layer that facilitates the injection of electrons from the second electrode 6. The electron injection layer may directly contact the second electrode 6.
The electron injection layer may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
The alkali metal may be Li, Na, K, Rb, or 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 of the present disclosure are not limited thereto.
The alkaline earth metal may be Mg, Ca, Sr, or Ba.
The rare earth metal may be Sc, Y, Ce, Tb, Yb, or Gd.
The alkali metal compound, the alkaline earth-metal compound, and the rare earth metal compound may be an oxide or a halide (for example, fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth-metal, or the rare earth metal.
The alkali metal compound may be an alkali metal oxide, such as Li2O, Cs2O, or K2O, or an alkali metal halide, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI. In an embodiment, the alkali metal compound may be LiF, Li2O, NaF, LiI, NaI, CsI, or KI, but embodiments of the present disclosure are not limited thereto.
The alkaline earth metal compound may be an alkaline earth metal oxide, 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 BaO, SrO, and CaO, but embodiments of the present disclosure are not limited thereto.
The rare earth metal compound may be YbF3, ScF3, ScO3, Y2O3, Ce2O3, GdF3, or TbF3. In an embodiment, the rare earth metal compound may be YbF3, ScF3, TbF3, YbI3, ScI3, or TbI3, but embodiments of the present disclosure are not limited thereto.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include an ion of alkali metal, alkaline earth-metal, and rare earth metal as described above, and a ligand coordinated with a metal ion of the alkali metal complex, the alkaline earth-metal complex, or the rare earth metal complex may be hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
The electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 6 may be arranged on the electron transport region 5. The second electrode 6 may be a cathode which is an electron injection electrode, and in this regard, a material for forming the second electrode 6 may be a metal, an alloy, an electrically conductive compound, and a combination thereof, each having a relatively low work function.
The second electrode 6 may include at least one of lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, IZO, or any combination thereof, but embodiments of the present disclosure are not limited thereto. The second electrode 6 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 6 may have a single-layered structure having a single layer or a multi-layered structure including a plurality of layers.
A thickness of the second electrode 6 may be about 100 Å or more and about 10,000 Å or less, but embodiments of the present disclosure are not limited thereto.
In addition, a sealing layer may be further arranged on the second electrode 6. The sealing layer is not particularly limited, and for example, may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4, N4, N4′, N4′-tetra(phenyl-4-yl)biphenyl-4,4′-diamine (TPD15), 4,4′,4″-tris(carbazol-9-yl)-triphenylamine (TCTA), N,N′-bis(naphthalene-1-yl), or any combination thereof.
Hereinbefore, the organic light-emitting device has been described with reference to
Another aspect of the present disclosure provides a diagnostic composition including at least one condensed cyclic compound represented by Formula 1.
Since the condensed cyclic compound represented by Formula 1 provides high luminescence efficiency, the diagnostic composition including the at least one condensed cyclic compound may have high diagnostic efficiency.
The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
Another aspect of the present disclosure provides an electronic apparatus including the organic light-emitting device.
In an embodiment, the electronic device may further include a thin-film transistor, and the thin-film transistor may include a source electrode and a drain electrode, wherein the first electrode of the organic light-emitting device may be electrically connected to at least one of the source electrode and the drain electrode of the thin-film transistor.
In an embodiment, the electronic device may be applied in various fields such as, a diagnostic kit, a biosensor, a biomarker, a display, and a lighting device.
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 are 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” used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof are 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 are 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 are 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 are 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 saturated monocyclic group having at least one heteroatom of N, O, P, Si, B, Se, Ge, Te, S, or a combination thereof as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof are 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 are 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 heteroatom N, O, P, Si, B, Se, Ge, Te, S, or a combination thereof 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 are 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 are 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 “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system that has at least one heteroatom of N, O, P, Si, B, Se, Ge, Te, S, or a 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, Ge, Te, S, or a 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 C6-C60 heteroaryl group and the C6-C60 heteroarylene group each include two or more rings, the two or more rings may be fused to each other.
The term “C6-C60 aryloxy group” as used herein refers to —OA102 (where A102 is the C6-C60 aryl group), the term “C6-C60 arylthio group” as used herein refers to —SA103 (where A103 is the C6-C60 aryl group), and the term “C6-C60 arylalkyl group” as used herein refers to —(CR2)nA104 (where A104 is the C6-C60 aryl group, R is H or a C1-C10 alkyl group, and n is an integer from 1 to 10).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group are 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 described above.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 2 to 60 carbon atoms) having two or more rings condensed with each other, a heteroatom N, O, P, Si, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group are 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 described above.
The term “C5-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group. When the C5-C30 carbocyclic group is an unsaturated cyclic group, the unsaturated cyclic group can be aromatic or non-aromatic.
The term “C1-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one of heteroatom N, O, Si, P, B, Se, Ge, Te, S, or a combination thereof other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group. When the C1-C30 heterocyclic group is an unsaturated cyclic group, the unsaturated cyclic group can be aromatic or non-aromatic.
In an embodiment, the π electron-deficient nitrogen-containing C1-C60 cyclic group may be 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 pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, a benzoisoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an acridine group, or a pyridopyrazine group.
For example, the π electron-rich C3-C60 cyclic group may be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, a furan group, a thiophene group, an isoindole group, an indole group, an indene group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphthopyrrole group, a naphthofuran group, a naphthothiophene group, a naphthosilole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a triindolobenzene group, a pyrrolophenanthrene group, a furanophenanthrene group, a thienophenanthrene group, a benzonaphthofuran group, a benzonaphthothiophene group, an (indolo)phenanthrene group, a (benzofuran)phenanthrene group, or a (benzothieno)phenanthrene group.
For example, the C5-C60 cyclic group may 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, an indene group, a fluorene group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.
For example, the C1-C60 heterocyclic group may be a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a borole group, phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-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 pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole 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, or a benzothiadiazole group.
The term “a π electron-deficient nitrogen-containing C1-C60 cyclic group, a π electron-rich C3-C60 cyclic group, a C5-C60 cyclic group, and a C1-C60 heterocyclic group” may be part of a condensed cycle or may be a monovalent, a divalent, a trivalent, a tetravalent, a pentavalent, or a hexavalent group, depending on the formula structure.
At least one substituent of the substituted π electron-deficient nitrogen-containing C1-C60 cyclic group, the substituted π electron-rich C3-C60 cyclic group, the substituted C5-C30 carbocyclic group, the substituted C2-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 C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C6-C60 aryl alkyl 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:
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, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group,
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with at least one 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, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C6-C60 aryl alkyl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q16), —B(Q16)(Q17), —P(═O)(Q18)(Q19), or any combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C6-C60 aryl alkyl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one 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, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C6-C60 aryl alkyl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), or any combination thereof; or
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37), or —P(═O)(Q38)(Q39), and
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C6-C60 aryl alkyl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.
For example, Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 as used herein may each independently be:
—CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2, or
an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a phenyl group, or any combination thereof.
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.
The term “room temperature” as used herein refers to a temperature of about 25° C.
The terms “a biphenyl group, a terphenyl group, and a tetraphenyl group” as used herein respectively refer to monovalent a group in which two, three, or four phenyl a group which are linked together via a single bond.
The terms “a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, and a cyano-containing tetraphenyl group” as used herein respectively refer to a phenyl group, a biphenyl group, a terphenyl group, and a tetraphenyl group, each of which is substituted with at least one cyano group. In “a cyano-containing phenyl group, a cyano-containing biphenyl group, a cyano-containing terphenyl group, and a cyano-containing tetraphenyl group”, a cyano group may be substituted to any position of the corresponding group, and “the cyano-containing phenyl group, the cyano-containing biphenyl group, the cyano-containing terphenyl group, and the cyano-containing tetraphenyl group” may further include substituents other than a cyano group. For example, a phenyl group substituted with a cyano group and a phenyl group substituted with a cyano group and a methyl group may all belong to “a cyano-containing phenyl group”.
The term “R10a” as used herein may be:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C2-C60 heteroarylalkyl group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, or a C2-C60 heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32).
In the present specification, Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 aryl alkyl group, or a C2-C60 heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
In the present specification, * and *′, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.
Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Examples and Examples. However, the organic light-emitting device is not limited thereto. The wording “‘B’ was used instead of ‘A’” as 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.
In a three-neck flask under argon atmosphere, 3,6-dibromocarbazole (1 eq. 61.5 mmol, 20 g), diphenylamine (2.2 eq. 135.4 mmol, 22.9 g), tris(dibenzylideneacetone)dipalladium (1.23 mmol, 1.1 g), tri-tert-butylphosphonium-tetrafluoroborate (6.15 mmol, 1.79 g), and THF (125 ml) were added and stirred. Then, lithium bis(trimethylsilyl)amide (1 M tetrahydrofuran solution, 203 mmol, 203 ml) was added to the resultant mixture and stirred at 65° C. for 6 hours. The temperature of the reaction solution was lowered to room temperature, and H2O (about 500 ml) was added thereto and stirred. The resultant reaction solution was filtered, and the solid thus obtained was purified by silica gel column chromatography, so as to obtain Intermediate 1-1.
In a three-neck flask under argon atmosphere, Intermediate 1-1 (2.05 eq. 19.83 mmol, 9.95 g), 1, 5-dibromo-2, 4-difluorobenzene (1 eq. 9.67 mmol, 2.63 g), K2CO3 (2.4 eq. 23.22 mmol, 3.21 g), and N—N-dimethylformamide (50 ml) were added and stirred at 120° C. for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and H2O (100 ml) and methanol (MeOH) (100 ml) were added thereto and stirred. The solid obtained by filtering the resultant reaction solution was purified by silica gel column chromatography and then subjected to recrystallization using toluene and hexane, so as to obtain Intermediate 1-2.
In a three-neck flask under argon atmosphere, Intermediate 1-2 (1 eq. 6.23 mmol, 7.69 g), palladium acetate (30 mol %, 1.87 mmol, 0.42 g), triphenylphosphine (0.7 eq. 4.36 mmol, 1.14 g), K2CO3 (10 eq. 62.3 mmol, 8.604 g), benzyltriethylammonium chloride (2 eq. 12.45 mmol, 2.836 g), and N, N-dimethylacetamide (500 ml) were added and stirred at 160° C. for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and H2O (200 ml) and methanol (MeOH) (200 ml) were added thereto and stirred. The solid obtained by filtering the resultant reaction solution was purified by silica gel column chromatography and then subjected to recrystallization using toluene and hexane, so as to obtain Compound 1.
Compound 1 was dissolved in tetrahydrofuran at a concentration of 0.1 wt %, and mass spectrometry was performed thereon by using a LC-MS measurement apparatus 1260 Infinity-4 Quadrupole 6100MS (manufactured by Agilent technologies, Inc.). Results thereof were as follows.
LC-MS: 1074 ([M+H]+).
Compound 2 was obtained in the same manner as in Synthesis Example 1, except that 3-methyl-N-phenylaniline was used instead of diphenylamine in the synthesis of Intermediate 1-1.
Results of mass spectrometry performed on the obtained compound were as follows: LC-MS: 1130 ([M+H]+).
Compound 3 was obtained in the same manner as in Synthesis Example 1, except that 2,4-dimethyl-N-phenylaniline was used instead of diphenylamine in the synthesis of Intermediate 1-1.
Results of mass spectrometry performed on the obtained compound were as follows: LC-MS: 1186 ([M+H]+).
In a three-neck flask under argon atmosphere, aniline (1 eq. 53.69 mmol, 5.0 g), 2-bromo-m-xylene (1 eq. 53.69 mmol, 9.94 g), tris(dibenzylideneacetone)dipalladium (0.54 mmol, 0.49 g), tri-tert-butyl phosphonium-tetrafluoroborate (2.15 mmol, 0.62 g), sodium tert-butoxide (tert-BuONa) (1.5 eq. 80.53 mmol, 7.74 g), and toluene (270 ml) were added and stirred at 120° C. for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature and filtered using Celite. The filtrate was concentrated and purified by silica gel column chromatography, so as to obtain Intermediate 4-1.
Compound 4 was obtained in the same manner as in Synthesis Example 1, except that Intermediate 4-1 was used instead of diphenylamine in the synthesis of Intermediate 1-1.
Results of mass spectrometry performed on the obtained compound were as follows: LC-MS: 1186 ([M+H]+).
In a three-neck flask under argon atmosphere, 3,6-diiodinecarbazole (1 eq. 23.87 mmol, 10.0 g), di-tert-butylcarbonate (1.3 eq. 31.03 mmol, 6.77 g), 4-dimethylaminopyridine (4.77 mmol, 0.583 g), and THF (40 ml) were added and heated at 80° C. for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature and then concentrated. Afterwards, the concentrated reaction product was washed using methanol (MeOH), so as to obtain Intermediate 5-1.
In a three-neck flask under argon atmosphere, Intermediate 5-1 (1 eq. 1.93 mmol, 1.0 g), 3-fluorodiphenylamine (2 eq. 3.85 mmol, 0.72 g), tris(dibenzylideneacetone)dipalladium (0.08 mmol, 0.071 g), tri-tert-butylphosphonium.tetrafluoroborate (0.15 mmol, 0.045 g), sodium-tert-butoxide (tert-BuONa) (3 eq. 5.78 mmol, 0.56 g), and toluene (3.9 ml) were added and stirred at 120° C. for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature and filtered using Celite. The filtrate was then concentrated, and THF (5 ml) and hydrochloric acid (20 ml) were added thereto and stirred at 60° C. for 8 hours. After completion of the reaction, the resulting reaction solution was neutralized with an aqueous NaHCO3 solution, and an extraction process was performed thereon using toluene. Next, the organic layer thus obtained was dried with anhydrous magnesium sulfate, concentrated, and purified by silica gel column chromatography. The resultant product was then subjected to recrystallization using methanol (MeOH), so as to obtain Intermediate 5-2.
Compound 5 was obtained in the same manner as in Synthesis Example 1, except that Intermediate 5-2 was used instead of Intermediate 1-1 in the synthesis of Intermediate 1-2.
Results of mass spectrometry performed on the obtained compound were as follows: LC-MS: 1146 ([M+H]+)
Regarding compounds other than the compounds synthesized according to Synthesis Examples 1 to 5, synthesis methods may be easily understood to those skilled in the art by referring to the synthesis pathways and raw materials described above.
For the compounds synthesized according to Synthesis Examples 1 to 5 and Compounds A to C as comparative compounds, S1 energy level (s-S1, eV), T1 energy level (s-T1, eV), and s-ΔEST were evaluated using the DFT method of the Gaussian program with the structure optimization at the B3LYP/6-31G(d,p) level, and results thereof are shown in Table 7.
To measure HOMO and LUMO energy levels of the compounds synthesized according to Synthesis Examples 1 to 5 and Compounds A to C as comparative compounds, the compounds were respectively prepared as solids.
(1) Preparation of Test Sample for Measurement
1) A sample solution containing each compound in an amount of 4 parts by weight based on 100 parts by weight of methyl benzoate as a solvent was prepared.
2) The sample solution prepared in Section 1) was coated on each of an ITO substrate and a quartz substrate by a spin-coating method to form a coating film having a dry film thickness of 50 nm. The formed coating film was heated under vacuum of 10−1 Pa or lower at 120° C. for 1 hour. Then, under vacuum of 10−1 Pa or lower, the resulting coating film was cooled to room temperature to form a thin-film layer (also referred to as a thin-film sample).
(2) Measurement of HOMO Energy Level
A HOMO energy level of the thin-film sample was measured using a photoelectron spectrometer AC-3 (manufactured by Riken Keiki Co., Ltd.) in the atmosphere. Results of the measurement are shown in Table 8.
(3) Measurement of LUMO Energy Level
An energy gap value (Eg) at an absorption edge of an ultraviolet visible absorption spectrum of the thin-film sample was measured using a spectrophotometer U-3900 (manufactured by Hitachi High Tech Corp.), and then a LUMO energy level was calculated according to Equation 2. Results of the calculation were shown in Table 8.
LUMO=HOMO+Eg Equation 2
To measure PL of the compounds synthesized according to Synthesis Examples 1 to 5 and Compounds A to C as comparative compounds, the compounds were respectively dissolved in toluene to prepare a 1×10−5 M solution for each compound. A permeability cell with 4 sides having a length of 1 cm each was filled with the prepared solution, and PL of each cell was measured at room temperature using a spectrophotofluorometer F7000 (manufactured by Hitachi High Tech Corp.). From the measured PL spectrum, a peak wavelength and its full width at half maximum (FWHM) at which luminescence intensity was halved were calculated. Results of the calculation were shown in Table 8.
To measure S1 energy level, T1 energy level, and ΔEST of the compounds synthesized according to Synthesis Examples 1 to 5 and Compounds A to C as comparative compounds, the compounds were respectively prepared as solids.
1) Each of the compounds and polymethyl methacrylate (PMMA) were dissolved in toluene to mix PMMA and each compound at a weight ratio of 99.5:0.5 (PMMA solution: compound solution), so as to prepare a sample solution containing 5 wt % of toluene.
2) The sample solution prepared in Section (1) was spin-coated on an ITO substrate and a quartz substrate by using a spin coater MS-B100 (manufactured by Mikasa Corporation) to form a spin-coating film having a dry film thickness of 500 nm. Subsequently, the formed spin-coating film was heated at 120° C. for 1 hour to prepare a thin-film sample.
(2) Measurement of S1 Energy Level, T1 Energy Level, and ΔEST
A fluorescence spectrum and a phosphorescence spectrum of the thin-film sample were measured at 77 K using a spectrophotofluorometer F7000 (manufactured by Hitachi High Tech Corp.). Then, a singlet (S1) energy level was calculated from the measured fluorescence spectrum, and a triplet (T1) energy level was calculated from the measured phosphorescence spectrum. In addition, ΔEST was calculated according to Equation 3, and results thereof were shown in Table 8.
ΔEST=S1−T1 Equation 3
To measure PLQY of the compounds synthesized according to Synthesis Examples 1 to 5 and Compounds A and B as comparative compounds, each of the compounds shown in Table 8 and mCP as a host compound were co-deposited at a weight ratio of 1 wt % with respect to the host compound on a quartz substrate at a vacuum pressure of 10−5 Pa, so as to prepare a thin film having a thickness of 50 nm. Then, PLQY of the thin film for each compound was measured using a C11347-01 Quantaurus-QY absolute PLQY measurement meter (manufactured by Hamamatsu Photonics Co., Ltd.). For the measurement, an excitation wavelength was scanned and measured at intervals of 10 nm from 300 nm to 400 nm, and then an excitation wavelength region in which an absorption value of the compound was an excitation light intensity ratio of 10% or more was selected. Here, the highest value in the selected excitation wavelength region was set as the PLQY value. Results of the evaluation were shown in Table 8.
Referring to Table 8, it was confirmed that the condensed cyclic compound of the present disclosure exhibited luminescence having a narrow spectrum width with a wavelength region of blue light as a peak wavelength, so that blue luminescence with high color purity was identified. It was also confirmed that the condensed cyclic compound of the present invention had small ΔEST, so that luminescence with high efficiency was identified.
A glass substrate on which an ITO stripe was formed to a thickness of 150 nm was formed.
Subsequently, poly(3,4-ethylene dioxythiophene)/poly(4-styrene sulfonate)(PEDOT/PSS) (manufactured by Sigma-Aldrich) was spin-coated on the ITO electrode (anode) of the glass substrate to form a hole injection layer having a thickness of 30 nm.
A solvent including HTP1 (weight average molecular weight Mw=400,000, PDI (Mw/Mn)=2.7) in an amount of 3 parts by weight based on 100 parts by weight of anisole was prepared first, and a solution including AD1 in an amount of 0.6 parts by weight based on 100 parts by weight of the solvent was prepared. Then, the prepared solution was spin-coated on the hole injection layer to form a coating film having a thickness of 125 nm. The formed coating film was heated under vacuum of 10−1 Pa or lower at 230° C. for 1 hour, and cooled to room temperature under vacuum of 10−1 Pa or lower to form a hole transport layer.
H-H104 was deposited on the hole transport layer to form an electron blocking layer having a thickness of 10 nm.
Compound 1, H-H104, and HE6-203 were co-deposited on the electron blocking layer at a ratio of 1.5 wt %:39.4 wt %:59.1 wt % to form an emission layer having a thickness of 40 nm.
HE6-203 was deposited on the emission layer to form a hole blocking layer having a thickness of 10 nm.
LiQ and KLET-03 (available from Chemi-Pro Co., Ltd.) were co-deposited on the hole blocking layer at a weight ratio of 2:8 to form an electron transport layer having a thickness of 20 nm.
Next, LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 3.5 nm.
Aluminum (Al) was deposited on the electron injection layer to form a second electrode (cathode) having a thickness of 100 nm, and in a glove box under nitrogen atmosphere with a moisture concentration of 1 ppm or less and an oxygen concentration of 1 ppm or less, a glass sealing tube with a desiccant and an ultraviolet curable resin were used to seal the second electrode, thereby completing the manufacture of an organic light-emitting device.
In HTP1, n is an integer from 1 or more.
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that, in forming an emission layer, compounds shown in Table 9 were used respectively.
For each of the organic light-emitting devices manufactured according to Examples 1 and 2 and Comparative Example 1, CIEx, CIEy, emission peak wavelength, FWHM, and relative value (%) of a maximum external quantum efficiency (Max EQE) were evaluated, and results were shown in Table 9. As evaluation apparatuses, a current-voltmeter (Keithley 2400) and a luminance meter (Hamamatsu Photonics, PMA12) were used. From the measurement results, the current value and the EQE (%) were calculated. In addition, a wavelength having the maximum value in the EQE graph for the wavelength was defined as an emission peak wavelength (nm), and a wavelength width corresponding to the half of the emission peak wavelength was defined as FWHM (nm). Here, Max EQE refers to an EQE value at a current density of 0.1 (mA/m2) as calculated from the area of the organic light-emitting device during current driving.
A glass substrate on which an ITO stripe was formed to a thickness of 150 nm was formed.
Subsequently, F6-TCNNQ was deposited on the ITO electrode (anode) of the glass substrate to form a hole injection layer having a thickness of 10 nm.
HT1 was deposited on the hole injection layer to form a hole transport layer having a thickness of a 125 nm.
H-H104 was deposited on the hole transport layer to form an electron blocking layer having a thickness of 10 nm.
Compound 1, H-H104, and HE6-203 were co-deposited on the electron blocking layer at a ratio of 1.5 wt %:39.4 wt %:59.1 wt % to form an emission layer having a thickness of 40 nm.
HE6-203 was deposited on the emission layer to form a hole blocking layer having a thickness of 10 nm.
ET17 and LiQ were co-deposited at a weight ratio of 5:5 on the emission layer to form an electron transport layer having a thickness of 36 nm.
Next, LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 3.5 nm.
Al was deposited on the electron injection layer to form a second electrode (cathode) having a thickness of 100 nm, and in a glove box under nitrogen atmosphere with a moisture concentration of 1 ppm or less and an oxygen concentration of 1 ppm or less, a glass sealing tube with a desiccant and an ultraviolet curable resin were used to seal the second electrode, thereby completing the manufacture of an organic light-emitting device.
For the organic light-emitting device manufactured according to Example 3, CIEx, CIEy, emission peak wavelength, FWHM, and relative value (%) of Max EQE were evaluated, and results were shown in Table 10.
Referring to Tables 9 and 10, it was confirmed that, as compared to the organic light-emitting device of Comparative Example 1, the organic light-emitting devices of Examples 1 to 3 exhibited luminescence having a narrow spectrum width with a blue wavelength region as a peak wavelength, so that blue luminescence with high color purity and excellent external quantum efficiency were identified.
As described above, according to the one or more embodiments, a condensed cyclic compound may be used in manufacturing a light-emitting device having high color purity and excellent luminescence efficiency, and such a light-emitting device may be used in manufacturing a high-quality electronic apparatus having excellent luminescence efficiency.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.
| Number | Date | Country | Kind |
|---|---|---|---|
| 2020-216557 | Dec 2020 | JP | national |
| 10-2021-0087429 | Jul 2021 | KR | national |
