ORGANIC LIGHT-EMITTING DEVICE

Abstract
Provided is an organic light-emitting device including a host, a cooling dopant, and a sensitizer.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the priority to and the benefit of Korean Patent Application Nos. 10-2019-0037245, filed on Mar. 29, 2019, and 10-2020-0027986, filed on Mar. 5, 2020, in the Korean Intellectual Property Office, the contents of which are incorporated herein in their entirety by reference.


BACKGROUND
1. Field

The present disclosure relates to an organic light-emitting device including an emission layer which includes a host, a cooling dopant, and a sensitizer.


2. Description of Related Art

Organic light-emitting devices are self-emission devices that produce full-color images, and also have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed, compared to devices in the art.


In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be between the anode and the emission layer, and an electron transport region may be 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. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.


SUMMARY

Provided is an organic light-emitting device including an emission layer which includes a host, a cooling dopant, and a sensitizer.


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, an organic light-emitting device includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein


the organic layer may include an emission layer;


the emission layer may include a host, a cooling dopant, and a sensitizer, wherein


the cooling dopant and the sensitizer satisfy Conditions 1 and 2, and


the sensitizer may include platinum (Pt):






T
decay(CD)<Tdecay(S)  Condition 1






T
decay(CD)<1.5 μs  Condition 2


wherein, in Conditions 1 and 2,


Tdecay(CD) is a decay time of the cooling dopant, and


Tdecay(S) is a decay time of the sensitizer.


Another aspect provides an organic light-emitting device including: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein


the organic layer may include an emission layer;


the emission layer may include a host, a cooling dopant, and a sensitizer, wherein


the cooling dopant and the sensitizer satisfy Conditions 1 and 2, and


the sensitizer may include a thermally activated delayed fluorescence emitter, and


the thermally activated delayed fluorescence emitter does not include a metal:






T
decay(CD)<Tdecay(S)  Condition 1






T
decay(CD)<1.5 μs  Condition 2


wherein, in Conditions 1 and 2,


Tdecay(CD) is a decay time of the cooling dopant, and


Tdecay(S) is a decay time of the sensitizer.


According to an aspect of another embodiment, an organic light-emitting device includes: a first electrode; a second electrode; m emission units between the first electrode and the second electrode and including at least one emission layer; and


m−1 charge generating layers between neighboring two emission units of the m emission units and including an n-type charge generating layer and a p-type charge generating layer,


m may be an integer of 2 or more,


the maximum emission wavelength of light emitted from at least one emission unit of the m emission units may be different from the maximum emission wavelength of light emitted from at least one emission unit of the remaining emission units,


the emission layer may include a host, a cooling dopant, and a sensitizer, wherein


the cooling dopant and the sensitizer satisfy Conditions 1 and 2, and


the sensitizer may include Pt.


According to an aspect of another embodiment, an organic light-emitting device includes: a first electrode; a second electrode; m emission units between the first electrode and the second electrode and including at least one emission layer; and


m−1 charge generating layers between neighboring two emission units of the m emission units and including an n-type charge generating layer and a p-type charge generating layer,


m may be an integer of 2 or more,


the maximum emission wavelength of light emitted from at least one emission unit of the m emission units may be different from the maximum emission wavelength of light emitted from at least one emission unit of the remaining emission units,


the emission layer may include a host, a cooling dopant, and a sensitizer, wherein


the cooling dopant and the sensitizer satisfy Conditions 1 and 2, and


the sensitizer may include a thermally activated delayed fluorescence emitter, and


thermally activated delayed fluorescence emitter does not include metal.


According to an aspect of an embodiment, an organic light-emitting device includes: a first electrode; a second electrode; and m emission layers between the first electrode and the second electrode, wherein


m may be an integer of 2 or more,


the maximum emission wavelength of light emitted from at least one emission layer of the m emission layers may be different from the maximum emission wavelength of light emitted from at least one emission layer of the remaining emission layers,


the emission layer may include a host, a cooling dopant, and a sensitizer, wherein


the cooling dopant and the sensitizer satisfy Conditions 1 and 2, and


the sensitizer may include Pt.


According to an aspect of an embodiment, an organic light-emitting device includes: a first electrode; a second electrode; and m emission layers between the first electrode and the second electrode, wherein


m may be an integer of 2 or more,


the maximum emission wavelength of light emitted from at least one emission layer of the m emission layers may be different from the maximum emission wavelength of light emitted from at least one emission layer of the remaining emission layers,


the emission layer may include a host, a cooling dopant, and a sensitizer, wherein


the cooling dopant and the sensitizer satisfy Conditions 1 and 2, and


the sensitizer may include a thermally activated delayed fluorescence emitter, and


thermally activated delayed fluorescence emitter does not include metal.





BRIEF DESCRIPTION OF THE DRAWING

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:



FIG. 1 shows a schematic cross-sectional view of an organic light-emitting device according to an embodiment;



FIGS. 2A to 2C each show a diagram schematically illustrating energy transfer in an emission layer of an organic light-emitting device according to an embodiment;



FIG. 3 is a schematic cross-sectional view of an organic light-emitting device according to another embodiment; and



FIG. 4 is a schematic cross-sectional view of an organic light-emitting device according to another embodiment;



FIG. 5 is a graph of luminance versus external quantum efficiency of the organic light-emitting devices manufactured according to Example 3 and Comparative Example 3P; and



FIG. 6 is a graph of relative luminance versus relative lifespan of the organic light-emitting devices manufactured according to Example 3 and Example 3P.





DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.


It will be understood that when an element is referred to as being “on” another element, it can be directly on the other element or intervening elements may be present therebetween In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present


It will be understood that, although the terms “first,” “second,” “third” etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section Thus, “a first element,” “component,” “region,” “layer” or “section” discussed below could be termed a second element, component, region, layer or section without departing from the teachings herein.


The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, “a,” “an,” “the,” and “at least one” do not denote a limitation of quantity, and are intended to cover both the singular and plural, unless the context clearly indicates otherwise. For example, “an element” has the same meaning as “at least one element,” unless the context clearly indicates otherwise.


“Or” means “and/or.” As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.


Furthermore, relative terms, such as “lower” or “bottom” and “upper” or “top,” may be used herein to describe one element's relationship to another element as illustrated in the 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.


Description of FIGS. 1 and 2


FIG. 1 is a schematic view of an organic light-emitting device 10 according to an embodiment. Hereinafter, a structure and a manufacturing method of an organic light-emitting device according to an example of the present disclosure will be described with reference to FIG. 1.


The organic light-emitting device 10 of FIG. 1 includes a first electrode 11, a second electrode 19 facing the first electrode 11, and an organic layer 10A between the first electrode 11 and the second electrode 19.


The organic layer 10A includes an emission layer 15, a hole transport region 12 may be located between the first electrode 11 and the emission layer 15, and an electron transport region 17 may be located between the emission layer 15 and the second electrodes 19.


A substrate may be additionally located under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in organic light-emitting devices available in the art may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.


First Electrode 11

In one or more embodiments, the first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be materials with a high work function to facilitate hole injection.


The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 11 is a transmissive electrode, a material for forming a first electrode may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combinations thereof, but embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflectable electrode, a material for forming a first electrode may be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combinations thereof, but embodiments of the present disclosure are not limited thereto.


The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers.


Emission Layer 15

The emission layer 15 may include a host, a cooling dopant, and a sensitizer.


The emission layer may emit fluorescent light. That is, the cooling dopant may be a material that may emit fluorescent light. The emission layer 15, which emits the fluorescent light, is clearly distinguished from an emission layer of the related art that emits phosphorescent light.


In an embodiment, the emission layer may include a host, a cooling dopant, and a sensitizer,


the cooling dopant and the sensitizer satisfy Conditions 1 and 2, and


the sensitizer may include Pt:






T
decay(CD)<Tdecay(S)  Condition 1






T
decay(CD)<1.5 μs  Condition 2


wherein, in Conditions 1 and 2,


Tdecay(CD) is a decay time of the cooling dopant, and


Tdecay(S) is a decay time of the sensitizer.


The decay time of the cooling dopant is calculated from a time-resolved photoluminescence (TRPL) at room temperature with respect to a 40 nm-thickness film (hereinafter referred to as “Film (CD)”) obtained by vacuum-codepositing the host and the dopant comprised in the emission layer at the weight ratio of 90:10 on a quartz substrate at the vacuum pressure of 10−7 torr.


The decay time of the sensitizer is calculated from TRPL at room temperature with respect to a 40 nm-thickness film (hereinafter referred to as “Film (S)”) obtained by vacuum-codepositing the host and the sensitizer comprised in the emission layer at the weight ratio of 90:10 on a quartz substrate at the vacuum pressure of 10−7 torr.


The detailed evaluation method of the decay time of each of the cooling dopant and the sensitizer may be understood by referring to the following examples.


In general, it is known that since triplet excitons remain long in an excited state, they influence the decrease in the lifespan of organic light-emitting devices. However, according to the present disclosure, the cooling dopant is used to reduce the time during which the triplet excitons of the sensitizer remains in the excited state. Accordingly, an organic light-emitting device including the cooling dopant may have a prolonged lifespan.


In one or more embodiments, the more triplet excitons the sensitizer has, the more excess energy is accumulated in the sensitizer, resulting in more hot excitons. That is, the amount of triplet excitons of the sensitizer is proportional to the amount of hot excitons. The hot excitons break down various chemical bonds of a compound included in an emission layer and/or a compound existing at the interface of the emission layer and other layers to degrade the compound. Accordingly, the lifespan of organic light-emitting devices may be reduced. However, according to the present disclosure, by using cooling dopants, the triplet excitons of the sensitizer can be quickly converted to singlet excitons of the cooling dopant, ultimately reducing the amount of hot excitons and increasing the lifespan of an organic light-emitting.


In this regard, “hot excitons” may be generated or increased by exciton-exciton annihilation due to an increase in the density of excitons in an emission layer, exciton-charge annihilation due to the charge imbalance in an emission layer, and/or radical ion pairs due to the delivery of electrons between a host and dopant.


In order to quickly convert triplet excitons of the sensitizer to singlet excitons of the cooling dopant, Condition 1 should be satisfied.


In addition, since the cooling dopant emits fluorescent light, a high color purity organic light-emitting device can be provided, and in particular, since Condition 2 is satisfied, so that the singlet excitons of the cooling dopant excited state at room temperature can be rapidly transferred, and thus, the single state of the cooling dopant in the excited state may not be accumulated, and the lifespan of an organic light-emitting device may be increased.


In addition, when Condition 3 is further satisfied, the transition from the triplet excitons of the sensitizer to the singlet excitons of the cooling dopant may occur more smoothly. Accordingly, the lifespan of an organic light-emitting device may be further prolonged:






T
decay(CD)/Tdecay(S)<0.5  Condition 3


wherein, in Condition 3,


Tdecay(CD) is a decay time of the cooling dopant, and


Tdecay(S) is a decay time of the sensitizer.


In one or more embodiments, the organic light-emitting device may further satisfy Condition 4:





BDE(S)−T1(S)<3.0 eV  Condition 4


wherein, in Condition 4,


BDE (S) is the bond dissociation energy level of the sensitizer, and


T1 (S) is the lowest excitation triplet energy level of the sensitizer.


Ultimately, the organic light-emitting device may have the target level of lifespan by satisfying Condition 5 below:






R(Hex)/e10<15  Condition 5


wherein, in Condition 5,


R (Hex) is the production rate of hot excitons.


In this regard, R (Hex) was subjected to the photochemical stability of the organic light-emitting device (photochemical stability), and then calculated through the Gaussian 09 program according to Equation C below.






R(Hex)=a×Tdecay(Se−(BDE(S)-T1(S))  Equation C


wherein, in Equation C,


a is an arbitrary constant,


Tdecay(S) is a decay time of the sensitizer,


BDE (S) is the bond dissociation energy level of the sensitizer, and


T1 (S) is the lowest excitation triplet energy level of the sensitizer.


The hot-exciton production rate is estimated to be proportional to (decay time)×e-(BDE-T1), and in order to obtain the target level of the lifespan of the organic light-emitting device, (hot-exciton production rate)/e10 should be less than 15.


In this regard, the degradation analysis (PCS) of organic light-emitting devices was calculated according to the following Equation P:






PCS (%)=I2/I1×100  Equation P


wherein, in Equation P,


I1, with respect to a film formed by depositing a compound of which PCS is to be measured, is a maximum light intensity obtained from the PL spectrum which is evaluated at room temperature under Ar atmosphere where outside air is blocked immediately after the formation of the film by using a He—Cd laser (excitation wavelength=325 nanometers, laser power density=100 mW/cm2) of KIMMON-KOHA Inc., and


I2, with respect to a film formed by depositing a compound of which PCS is to be measured, is a maximum light intensity obtained from the PL spectrum which is evaluated at room temperature under Ar atmosphere where outside air is blocked, by exposing the film to light of the He—Cd laser (excitation wavelength=325 nanometers and laser power density=100 mW/cm2) of KIMMON-KOHA Inc., which is a pumping laser which has been used to evaluate I1, for 3 hours, and then, using He—Cd laser of KIMMON-KOHA Inc. (excitation wavelength=325 nanometers). In the case of the sensitizer, reverse intersystem crossing (RISC) and/or intersystem crossing (ISC) actively occur, which allows excitons generated at the host to be delivered to the cooling dopant.


Specifically, the general energy transfer of an organic light-emitting device (type I) according to an embodiment will be described with reference to FIG. 2A.


Singlet and triplet excitons are formed at the host in the emission layer, and the singlet and triplet excitons formed at the host are transferred to the sensitizer and then to the cooling dopant through Förster energy transfer (FRET). At this time, in order to embody the high efficiency and long lifespan of the organic light-emitting device, it is necessary to control the hot excitons generated in the emission layer, which requires optimization of energy transfer.


Specifically, the general energy transfer of an organic light-emitting device (type I) according to an embodiment will be described with reference to FIG. 2B. This is the case when the sensitizer is a thermally activated delayed fluorescence (TADF) emitter satisfying the condition of ΔEST≤0.3 eV.


The singlet excitons formed at the host, which is 25% of the total excitons, are transferred to the sensitizer through FRET, and the energy of triplet excitons formed at the host, which is 75% of the total excitons, is transferred to the singlet and triplet of the sensitizer, among which the energy delivered to triplet is subjected to RISC into singlet, and then, the singlet energy of the sensitizer is transferred to the cooling dopant through FRET.


Specifically, the general energy transfer of an organic light-emitting device (type II) according to an embodiment will be described with reference to FIG. 2C. In this case, the sensitizer is an organic metallic compound including Pt.


The triplet excitons formed at the host, which is 75% of the total excitons, are transferred to the sensitizer through Dexter energy transfer, and the energy of singlet excitons formed at the host, which is 25% of the total excitons, is transferred to the singlet and triplet of the sensitizer, among which the energy delivered to singlet is subjected to ISC into triplet, and then, the triplet energy of the sensitizer is transferred to the cooling dopant through FRET.


Accordingly, by transferring all the singlet excitons and triplet excitons generated in the emission layer to the dopant, an organic light-emitting device having improved efficiency can be obtained. In addition, since an organic light-emitting device can be obtained with significantly reduced energy loss, the lifespan characteristics of the organic light-emitting device can be improved.


The amount of the sensitizer in the emission layer may be from about 5 wt % to about 50 wt %. Within these ranges, it is possible to achieve effective energy transfer in the emission layer, and accordingly, an organic light-emitting device having high efficiency and long lifespan can be obtained.


In one or more embodiments, the host, the cooling dopant, and the sensitizer may further satisfy Condition 6:






T
1(H)≥T1(S)≥S1(CD)  Condition 6


wherein, in Condition 6,


T1(H) is the lowest excitation triplet energy level of the host,


S1(CD) is the lowest excitation singlet energy level of the cooling dopant, and


T1(S) is the lowest excitation triplet energy level of the sensitizer.


When the host, the cooling dopant, and the sensitizer each satisfy Equation 3, triplet excitons may be effectively transferred from the emission layer to the cooling dopant, and thus, an organic light-emitting device having improved efficiency may be obtained.


The emission layer may consist of the host, the cooling dopant, and the sensitizer. That is, the emission layer may not further include materials other than the host, the cooling dopant, and the sensitizer.


A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.


Host in Emission Layer 15

The host may include no metal atoms.


In one or more embodiments, the host may include one kind of host. When the host includes one host, the one host may be an amphiprotic host, an electron transport host, a hole transport host, or any combination thereof which will be described later.


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 transport host and a hole transport host, a mixture of two types of electron transport hosts different from each other, or a mixture of two types of hole transport hosts different from each other. The electron transport host and the hole transport host may be understood by referring to the related description to be presented later.


In one or more embodiments, the host may include an electron transport host including at least one electron transport moiety, a hole transport host that is free of an electron transport moiety, or a combination thereof.


The electron transport moiety used herein may be a cyano group, a π electron-deficient nitrogen-containing cyclic group, a group represented by one of the following Formulae, or a combination thereof:




embedded image


In the formulae, *, *′, and *″ are each binding sites to neighboring atoms.


In one or more embodiments, the electron transport host of the emission layer 15 may include at least one of a cyano group, a π electron-deficient nitrogen-containing cyclic group, or a combination thereof.


In one or more embodiments, the electron transport host in the emission layer 15 may include at least one cyano group.


In one or more embodiments, the electron transport host in the emission layer 15 may include at least one cyano group, at least one π electron deficient nitrogen-containing cyclic group, or a combination thereof.


In one or more embodiments, the host may include an electron transport host and a hole transport host, wherein the electron transport host may include at least one π electron-deficient nitrogen-free cyclic group, at least one electron transport moiety, or a combination thereof and the hole transport host may include at least one π electron-deficient nitrogen-free cyclic group and may not include an electron transport moiety.


The term “π electron-deficient nitrogen-containing cyclic group” used herein refers to a cyclic group having at least one *—N═*′ moiety, and for example, 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; and a condensed cyclic group in which two or more π electron-deficient nitrogen-containing cyclic groups.


Meanwhile, 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, 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 of two or more π electron-deficient nitrogen-free cyclic groups, but embodiments of the present disclosure are not limited thereto.


In one or more embodiments, the electron transport host may be compounds represented by Formula E-1, and


the hole transport host may be compounds represented by Formula H-1, but embodiments of the present disclosure are not limited thereto:





[Ar301]xb11-[(L301)xb1-R301]xb21  Formula E-1


wherein, in Formula E-1,


Ar301 may be a substituted or unsubstituted C5-C60 carbocyclic group, a substituted or unsubstituted C1-C60 heterocyclic group, or a combination thereof,


x11 may be 1, 2, or 3,


L301 may each independently be a single bond, a group represented by the following formula, a substituted or unsubstituted C5-C60 carbocyclic group, or a substituted or unsubstituted C1-C60 heterocyclic group, and *, *′ and *″ in the following formulae are each a binding site to a neighboring atom,




embedded image


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-C60 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 are 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 Condition 1 to Condition 3 is satisfied:


Condition 1


Ar301, L301, and R301 in Formula E-1 may each independently include a π electron-deficient nitrogen-containing cyclic group.


Condition 2


L301 in Formula E-1 is a group represented by the following groups:




embedded image


Condition 3


R301 in Formula E-1 may be a cyano group, —S(═O)2(Q301), —S(═O)(Q301), —P(═O)(Q301)(Q302), or —P(═S)(Q301)(Q302).




embedded image


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, 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 coronene 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 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, —Si(Q401)(Q402)(Q403), or any combination thereof;


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 Formula 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, and 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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, or a triphenylenyl group;


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 is a single bond, O, S, N(R51), C(R51)(R52), or Si(R51)(R52),


A22 is a single bond, O, S, N(R53), C(R53)(R54), or Si(R53)(R54),


at least one A21, A22, or a combination thereof in Formula 12 is not a single bond,


R51 to R54, R60, and R70 are each independently:


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), 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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, or a biphenyl group; 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 one or more embodiments, Ar301 and L301 in Formula E-1 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), or —P(═O)(Q31)(Q32),


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, 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), or —P(═O)(Q31)(Q32), 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),


wherein 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); or


a group represented by one of Formulae 5-1 to 5-3 and Formulae 6-1 to 6-33, and


L301 may be a group represented by one of Formulae 5-1 to 5-3 and Formulae 6-1 to 6-33:




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wherein, 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


* and *′ each indicate a binding site to a neighboring atom.


Q31 to Q33 are the same as described in the present specification.


In one or more embodiments, L301 may be a group represented by 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:




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wherein, 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.


Two or more Ar301(S) in Formula E-1 may be identical to or different from each other, two or more L301(S) may be identical to or different from each other, two or more 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 one or more embodiments, the electron transport host includes 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 transport host may include a carbazole group.


In one or more embodiments, the electron transport host may include at least one cyano group.


The electron transport host may be, for example, a group of HE1 to HE7, but embodiments of the present disclosure are not limited thereto:


Group HE1




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Group HE2




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Group HE3




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Group HE4




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Group HE5




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Group HE6




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Group HE7




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In one or more embodiments, the hole transport host may be Compounds H-H1 to H-H103, but embodiments of the present disclosure are not limited thereto:




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In one or more embodiments, the amphiprotic host may be of group HEH1, but embodiments of the present disclosure are not limited thereto:


Group HEH1




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wherein, in Compounds 1 to 432,


Ph may be a phenyl group.


When the host is a mixture of an electron transport host and a hole transport host, the weight ratio of the electron transport host and hole transport host may be 1:9 to 9:1, for example, 2:8 to 8:2, for example, 4:6 to 6:4, for example, 5:5. When the weight ratio of the electron transport host and the hole transport host satisfies the above-described ranges, the hole-and-electron transport balance in the emission layer 15 may be made.


Cooling Dopant in Emission Layer 15

Since the cooling dopant emits fluorescent light, organic light-emitting devices according to an embodiment of the present disclosure are clearly distinguished from organic light-emitting devices containing compounds that emit phosphorescent light.


The cooling dopant satisfies Condition 2, as described above.


The maximum emission wavelength of the emission spectrum of the cooling dopant may be about 400 nm or more and about 550 nm or less. For example, the maximum emission wavelength of the emission spectrum of the cooling dopant may be about 400 nm or more and about 495 nm or less, or about 450 nm or more and about 495 nm or less, but embodiments of the present disclosure are not limited thereto. In other words, the cooling dopant may emit blue light. The “maximum emission wavelength” refers to a wavelength at which the emission intensity is the greatest, and may also be referred to as “a peak emission wavelength”.


In an embodiment, the cooling dopant may not include metal atoms.


In an embodiment, the cooling dopant may be a condensed polycyclic compound, a styryl-based compound, or any combination thereof.


For example, the cooling dopant may include one of a naphthalene-containing core, a fluorene-containing core, a spiro-bifluorene-containing core, a benzofluorene-containing core, a dibenzofluorene-containing core, a phenanthrene-containing core, an anthracene-containing core, a fluoranthene-containing core, a triphenylene-containing core, a pyrene-containing core, a chrysene-containing core, a naphthacene-containing core, a picene-containing core, a perylene-containing core, a pentaphene-containing core, an indenoanthracene-containing core, a tetracene-containing core, a bisanthracene-containing core, or a core represented by one of Formulae 501-1 to 501-18, but embodiments of the present disclosure are not limited thereto:




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In one or more embodiments, the cooling dopant may be a styryl-amine-based compound, a styryl-carbazole-based compound, or any combination thereof but embodiments of the present disclosure are not limited thereto.


In one or more embodiments, the cooling dopant may be compounds represented by Formula 501:




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In Formula 501,


Ar501 may be:


a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene 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 tetracene group, a bisanthracene group, or a group represented by one of Formulae 501-1 to 501-18; or


a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene 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 indenoanthracene group, a tetracene group, a bisanthracene group, or a group represented by one of Formulae 501-1 to 501-18, each substituted with at least one deuterium, —F, —C, —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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q501)(Q502)(Q503), or any combination thereof (wherein Q501 to Q503 may each independently be hydrogen, C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof);


L501 to L503 may each independently be a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,


R501 to R508 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 pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, a triazinyl group, a dibenzofuranyl group, or a dibenzothiophenyl group; or


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 pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each substituted with at least one 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, 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 pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, or a dibenzothiophenyl group,


xd1 to xd3 may each independently be 0, 1, 2, or 3, and


xd4 may be 0, 1, 2, 3, 4, 5, or 6.


For example, in Formula 501,


Ar501 may be:


a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene 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 tetracene group, a bisanthracene group, or a group represented by one of Formulae 501-1 to 501-18; or


a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene 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 tetracene group, a bisanthracene group, or a group represented by Formula 501-1 to 501-18, each substituted with at least one 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, 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 dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, —Si(Q501)(Q502)(Q503), or any combination thereof (Q501 to Q503 may each independently be hydrogen, C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group),


L501 to L503 are the same as described in connection with L21,


xd1 to xd3 may each independently be 0, 1, or 2, and


xd4 may be 0, 1, 2, or 3, but embodiments of the present disclosure are not limited thereto.


In one or more embodiments, the cooling dopant may include a compound represented by one of Formulae 502-1 to 502-5:




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wherein, in Formulae 502-1 to 502-5,


X51 may be N or C-[(L501)xd1-R501], X52 may be N or C-[(L502)xd2-R502], X53 may be N or C-[(L503)xd3-R503], X54 may be N or C-[(L504)xd4-R504], X55 may be N or C-[(L505)xd5-R505], X56 may be N or C-[(L506)xd6-R506], Xs; may be N or C-[(L507)xd7-R507], and X58 may be N or C-[(L508)xd8-R508],


L501 to L508 are each the same as described in connection with L501 in Formula 501,


xd1 to xd8 are each the same as described in connection with xd1 in Formula 501,


R501 to R508 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, or 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 pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, a triazinyl group, a dibenzofuranyl group, or a dibenzothiophenyl group; or


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 pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each substituted with at least one 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, 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 pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof,


xd11 and xd12 may each independently be an integer from 0 to 5, and


two of R501 to R504 may optionally be linked together to form a saturated or unsaturated ring, and


two of R505 to R508 may optionally be linked together to form a saturated or unsaturated ring.


The cooling dopant may include, for example, at least one of the following compounds FD(1) to FD(16) and FD1 to FD18:




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The amount of the cooling dopant in the emission layer may be from about 0.01 wt % to about 15 wt %, but embodiments of the present disclosure are not limited thereto.


Sensitizer in Emission Layer 15

The sensitizer may include Pt. In one or more embodiments, the sensitizer may be an organic metallic compound containing Pt.


In one or more embodiments, the sensitizer may include Pt and an organic ligand (L11), and L11 and Pt may form 1, 2, 3, or 4 cyclometalated rings.


In an embodiment, the sensitizer may include an organometallic compound represented by Formula 101:





Pt(L11)n11(L12)n12  Formula 101


wherein, in Formula 101,


L11 is a ligand represented by one of Formulae 1-1 to 1-4;


L12 may be a monodentate ligand or a bidentate ligand;


n11 may be 1,


n12 may be 0, 1, or 2;




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wherein, in Formulae 1-1 to 1-4,


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)—*″, *—P(R93)—*″, *—C(R93)(R94)—*′, *—Si(R93)(R94)—*″, *—Ge(R93)(R94)—*″, *—S—*′, *—Se—*′, *—O—*″, *—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 a group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 Pt, and


Q1 to Q3 may each independently 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 alkyl aryl 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, and a C6-C60 aryl group, and a C6-C60 aryl group that is substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, or a C6-C60 aryl group.


In one or more embodiments, the sensitizer may be of Groups I to VI, but embodiments of the present disclosure are not limited thereto:


Group I



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Group II



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Group III



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Group V includes a compound represented by Formula A below:





(L101)n101-M101-(L102)m101.  Formula A


L101, n101, M101, L102, and m101 in Formula A are the same as shown in Table 1:
















TABLE 1







Compound








name
L101
n101
M101
L102
m101









BD263
LM11
2
Pt

0



BD264
LM13
2
Pt

0



BD265
LM15
2
Pt

0



BD266
LM45
2
Pt

0



BD267
LM47
2
Pt

0



BD268
LM49
2
Pt

0



BD269
LM98
2
Pt

0



BD270
LM100
2
Pt

0



BD271
LM102
2
Pt

0



BD272
LM132
2
Pt

0



BD273
LM134
2
Pt

0



BD274
LM136
2
Pt

0



BD275
LM151
2
Pt

0



BD276
LM153
2
Pt

0



BD277
LM158
2
Pt

0



BD278
LM180
2
Pt

0



BD279
LM182
2
Pt

0



BD280
LM187
2
Pt

0



BD281
LM201
2
Pt

0



BD282
LM206
2
Pt

0



BD283
LM211
2
Pt

0



BD284
LM233
2
Pt

0



BD285
LM235
2
Pt

0



BD286
LM240
2
Pt

0



BD287
LFM5
2
Pt

0



BD288
LFM6
2
Pt

0



BD289
LFM7
2
Pt

0



BD290
LFP5
2
Pt

0



BD291
LFP6
2
Pt

0



BD292
LFP7
2
Pt

0



BD293
LM47
1
Pt
AN1
1



BD294
LM47
1
Pt
AN2
1



BD295
LM47
1
Pt
AN3
1



BD296
LM47
1
Pt
AN4
1



BD297
LM47
1
Pt
AN5
1










LM11, LM13, LM15, LM45, LM47, LM49, LM98, LM100, LM102, LM132, LM134, LM136, LM151, LM153, LM158, LM180, LM182, LM187, LM201, LM206, LM211, LM233, LM235, LM240, LFM5, LFM6, LFM7, LFP5, LFP6, and LFP7 in Table 1 may be understood by referring to Formulae 1-1 to 1-3 and Tables 2 to 4:




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TABLE 2







Formula 1-1

















Ligand name
R11
R12
R13
R14
R15
R16
R17
R18
R19
R20





LM11
Y3
D
Y11
D
Y3
D
D
D
D
D


LM13
Y3
D
Y11
D
Y3
D
Y3
D
D
D


LM15
Y3
D
Y11
D
Y3
D
Y12
D
D
D


LM45
Y3
D
Y12
D
Y3
D
D
D
D
D


LM47
Y3
D
Y12
D
Y3
D
Y3
D
D
D


LM49
Y3
D
Y12
D
Y3
D
Y12
D
D
D


LM98
Y10
D
Y13
D
Y10
D
D
D
D
D


LM100
Y10
D
Y13
D
Y10
D
Y3
D
D
D


LM102
Y10
D
Y13
D
Y10
D
Y12
D
D
D


LM132
Y10
D
Y14
D
Y10
D
D
D
D
D


LM134
Y10
D
Y14
D
Y10
D
Y3
D
D
D


LM136
Y10
D
Y14
D
Y10
D
Y12
D
D
D


LM151
Y3
D
Y15
D
Y3
D
D
D
D
D


LM153
Y3
D
Y15
D
Y3
D
Y3
D
D
D


LM158
Y3
D
Y15
D
Y3
D
Y12
D
D
D


LM180
Y10
D
Y15
D
Y10
D
D
D
D
D


LM182
Y10
D
Y15
D
Y10
D
Y3
D
D
D


LM187
Y10
D
Y15
D
Y10
D
Y12
D
D
D


LM201
Y3
Y15
D
D
Y3
D
D
D
D
D


LM206
Y3
Y15
D
D
Y3
D
Y3
D
D
D


LM211
Y3
Y15
D
D
Y3
D
Y12
D
D
D


LM233
Y10
Y15
D
D
Y10
D
D
D
D
D


LM235
Y10
Y15
D
D
Y10
D
Y3
D
D
D


LM240
Y10
Y15
D
D
Y10
D
Y12
D
D
D
















TABLE 3







Formula 1-2




















Ligand name
R11
X11
R101
R102
R103
R104
R14
R15
R16
R17
R18
R19
R20





LFM5
Y10
O
D
D
D
D
D
Y10
D
D
D
D
D


LFM6
Y10
O
D
D
D
D
D
Y10
D
Y3
D
D
D


LFM7
Y10
O
D
D
D
D
D
Y10
D
Y12
D
D
D
















TABLE 4







Formula 1-3




















Ligand name
R11
X11
R101
R102
R103
R104
R14
R15
R16
R17
R18
R19
R20





LFP5
Y10
O
D
D
D
D
D
Y10
D
D
D
D
D


LFP6
Y10
O
D
D
D
D
D
Y10
D
Y3
D
D
D


LFP7
Y10
O
D
D
D
D
D
Y10
D
Y12
D
D
D









X1 to X10 and Y1 to Y18 in Tables 2 to 4 are the same as below, and Ph in the tables refers to a phenyl group:




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Group VI



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In one or more embodiments, the sensitizer may be a thermally activated delayed fluorescence emitter. Thermally activated delayed fluorescence emitter may not include metal. In one or more embodiments, thermally activated delayed fluorescence emitter may satisfy Condition 7:





ΔEST≤0.3 eV  Condition 7


wherein, in Condition 7,


ΔEST is the difference between the lowest excitation singlet energy level and the lowest excitation triplet energy level of the sensitizer.


In one or more embodiments, the sensitizer may include a thermally activated delayed fluorescence emitter represented by Formula 201 or 202:




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In Formulae 201 and 202,


A21 is an acceptor group,


D21 is 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 201 may be 6 or less, and the sum of n21 and m21 in Formula 202 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), a plurality of R21 may optionally be linked together to form a substituted unsubstituted C5-C30 carbocyclic group or a substituted unsubstituted C1-C30 heterocyclic group,


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 alkyl aryl 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, and 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.


For example, A21 in Formula 201 and 202 may be a substituted unsubstituted π electron-deficient nitrogen-free cyclic group.


In one or more embodiments, 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, 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 coronene 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 of two or more π electron-deficient nitrogen-free cyclic groups, but embodiments of the present disclosure are not limited thereto.


For example, D21 in Formulae 201 and 202 may be: —F, a cyano group, and an π-electron deficient nitrogen-containing cyclic group;


a C1-C60 alkyl group, a π-electron deficient nitrogen-containing cyclic group, or a π electron-deficient nitrogen-free cyclic group, each substituted with at least one —F, a cyano group, or any combination thereof; or


a π-electron deficient nitrogen-containing cyclic group, substituted with at least one deuterium, a C1-C60 alkyl group, an π-electron deficient nitrogen-containing cyclic group, a π electron-deficient nitrogen-free cyclic group, or any combination thereof.


In one or more embodiments, the π electron-deficient nitrogen-free cyclic group is the same as described above.


The term “π electron-deficient nitrogen-containing cyclic group” 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; and a condensed cyclic group in which two or more π electron-deficient nitrogen-containing cyclic groups are condensed with each other.


In one or more embodiments, the sensitizer may be of Groups VII to XI, but embodiments of the present disclosure are not limited thereto:


Group VII



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Group VIII



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Group IX



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Group X



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Group XI



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Hole Transport Region 12

The hole transport region 12 may be located between the first electrode 11 and the emission layer 15 of the organic light-emitting device 10.


The hole transport region 12 may have a single-layered structure or a multi-layered structure.


For example, the hole transport region 12 may have a hole injection layer, a hole transport layer, 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/middle layer structure, a hole injection layer/hole transport layer/middle layer structure, a hole transport layer/electron blocking layer or hole injection layer/hole transport layer/electron blocking layer structure, but embodiments of the present disclosure are not limited thereto.


The hole transport region 12 may include any compound having hole transport properties.


For example, the hole transport region 12 may include an amine-based compound.


In one or more embodiments, the hole transport region 1 may include at least one of a compound represented by one of Formulae 201 to 205, but embodiments of the present disclosure are not limited thereto:




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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 xa 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 neighboring two groups of 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 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 coronene 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 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(Q11)(Q12)(Q13),


xa1 to xa9 may each independently be 0, 1, or 2, and


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 indeno carbazolyl 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,


wherein 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 one or more embodiments, the hole transport region 12 may include a carbazole-containing amine-based compound.


In one or more embodiments, the hole transport region 12 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 including a carbazole group and further including 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 does 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 a combination thereof.


In one or more embodiments, the hole transport region 12 may include at least one compounds represented by Formulae 201 or 202.


In one or more embodiments, the hole transport region 12 may include at least one compounds represented by Formulae 201-1, 202-1, 201-2, or a combination thereof, but embodiments of the present disclosure are not limited thereto:




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In Formulae 201-1, 202-1, and 201-2, L201 to L203, L205, xa1 to xa3, xa5, R201 and R202 are the same as described herein, and R211 to R213 are each independently 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 phenyl group substituted with a C1-C10 alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a dimethylfluorenyl group, a diphenyla fluorenyl group, a triphenylenyl 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, or a pyridinyl group.


For example, the hole transport region 12 may include at least one Compounds HT1 to HT39, but embodiments of the present disclosure are not limited thereto.




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In one or more embodiments, hole transport region 12 of the organic light-emitting device 10 may further include a p-dopant. When the hole transport region 12 further includes a p-dopant, the hole transport region 12 may have 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 12.


In one or more embodiments, the LUMO energy level of the p-dopant may be −3.5 eV or less.


The p-dopant may include at least one of a quinone derivative, a metal oxide, or a cyano-containing compound, but embodiments of the present disclosure are not limited thereto.


In one or more embodiments, the p-dopant may include at least one:


a quinone derivative, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), F6-TCNNQ, or any combination thereof;


a metal oxide, such as tungsten oxide or molybdenum oxide;


1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); or


a compound represented by Formula 221 below,


or any combination thereof,


but embodiments of the present disclosure are not limited thereto:




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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, and at least one R221 to R223 may have at least one 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, a C1-C20 alkyl group substituted with —I, or any combination thereof.


The hole transport region 12 may have a thickness of about 100 Å to about 10000 Å, for example, about 400 Å to about 2000 Å, and the emission layer 15 may have a thickness of about 100 Å to about 3000 Å, for example, about 300 Å to about 1000 Å. When the thickness of each of the hole transport region 12 and the emission layer 15 is within these ranges described above, satisfactory hole transportation characteristics and/or luminescent characteristics may be obtained without a substantial increase in driving voltage.


[Electron Transport Region 17]


The electron transport region 17 is placed between the emission layer 15 and the second electrode 19 of the organic light-emitting device 10.


The electron transport region 17 may have a single-layered structure or a multi-layered structure.


For example, the electron transport region 17 may have an electron transport layer, an electron transport layer/electron injection layer structure, a buffer layer/electron transport layer structure, 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 17 may further include an electron control layer.


The electron transport region 17 may include known electron transport materials.


The electron transport region (for example, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-deficient nitrogen-containing cyclic group. The π electron-deficient nitrogen-containing cyclic group is the same as described above.


For example, the electron transport region may include a compound represented by Formula 601 below:





Ar601]xe11-[(L601)xe1-R601]xe21.  Formula 601


In Formula 601,


Ar601 and L601 may each independently be a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,


xe11 may be 1, 2, or 3,


xe1 may be an integer from 0 to 5, R601 may 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 one or more embodiments, 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 cyclic group.


In one or more embodiments, ring 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, and 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 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, —Si(Q31)(Q32)(Q33), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), wherein 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 Ar601(s) may be linked to each other via a single bond.


In one or more embodiments, Ar601 in Formula 601 may be an anthracene group.


In one or more embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:




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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 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, and 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 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 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; or


—S(═O)2(Q601) and —P(═O)(Q601)(Q602),


wherein Q601 and Q602 are the same as described above.


The electron transport region may include at least one of Compounds ET1 to ET36, but embodiments of the present disclosure are not limited thereto:




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In one or more embodiments, the electron transport region may include at least one 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:




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Thicknesses 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 thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are 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 the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.


The electron transport region 17 (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 alkali metal complex, 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, or a Cs ion, and the alkaline earth-metal complex may include a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may 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 (lithium quinolate, LiQ) or ET-D2:




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The electron transport region 17 may include an electron injection layer that facilitates injection of electrons from the second electrode 19. The electron injection layer may directly contact the second electrode 19.


The electron injection layer may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.


The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof.


The alkali metal may be Li, Na, K, Rb, or Cs. In one or more embodiments, 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 oxides and halides (for example, fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth-metal, and the rare earth metal.


The alkali metal compound may be 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 one or more embodiments, 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 bean alkaline earth-metal oxide, such as BaO, SrO, CaO, BaxSr1-xO (0×1), or BaxCa1-xO (0×1). In one or more embodiments, the alkaline earth-metal compound may be BaO, SrO, or CaO, but embodiments of the present disclosure are not limited thereto.


The rare earth metal compound may be YbF3, ScF3, ScO3, Sc2O3, Y2O3, Ce2O3, GdF3, or TbF3. In one or more embodiments, 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 an alkali metal, an alkaline earth-metal, and a rare earth metal as described above, and a ligand coordinated with the metal ion of the alkali metal complex, the alkaline earth-metal complex, or the rare earth metal complex that 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, or cyclopentadiene, but embodiments of the present disclosure are not limited thereto.


The electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.


A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.


Second Electrode 19

The second electrode 19 is located on the organic layer 10A having such a structure. The second electrode 19 may be a cathode which is an electron injection electrode, and in this regard, a material for forming the second electrode 19 may be a metal, an alloy, an electrically conductive compound, or a combination thereof, which may have a relatively low work function.


The second electrode 19 may include at least one 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 19 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.


The second electrode 19 may have a single-layered structure having a single layer or a multi-layered structure including two or more layers.


Hereinbefore, the organic light-emitting device has been described with reference to FIGURE, but embodiments of the present disclosure are not limited thereto.


Description of FIG. 3


FIG. 3 is a schematic cross-sectional view of an organic light-emitting device 100 according to another embodiment.


The organic light-emitting device 100 of FIG. 3 includes a first electrode 110, a second electrode 190 facing the first electrode 110, and a first emission unit 151 and a second emission unit 152 between the first electrode 110 and the second electrode 190. A charge generating layer 141 is located between the first emission unit 151 and the second emission unit 152, and the charge generating layer 141 may include an n-type charge generating layer 141-N and a p-type charge generating layer 141-P. The charge generating layer 141 is a layer that generates charge and supplies the charge to neighboring emission units, and any known material may be used therefor.


The first emission unit 151 may include a first emission layer 151-EM, and the second emission unit 152 may include a second emission layer 152-EM. The maximum emission wavelength of light emitted from the first emission unit 151 may be different from the maximum emission wavelength of light emitted from the second emission unit 152. For example, the mixed light of the light emitted from the first emission unit 151 and the light emitted from the second emission unit 152 may be white light, but embodiments of the present disclosure are not limited thereto.


The hole transport region 120 is located between the first emission unit 151 and the first electrode 110, and the second emission unit 152 may include the first hole transport region 121 located on the side of the first electrode 110.


An electron transport region 170 is located between the second emission unit 152 and the second electrode 190, and the first emission unit 151 may include a first electron transport region 171 located between the charge generating layer 141 and the first emission layer 151-EM.


The first emission layer 151-EM may include a host, a cooling dopant, and a sensitizer, and the cooling dopant and the sensitizer may satisfy Conditions 1 and 2.


The second emission layer 152-EM may include a host, a cooling dopant, and a sensitizer, and the cooling dopant and the sensitizer may satisfy Conditions 1 and 2.


The first electrode 110 and the second electrode 190 illustrated in FIG. 3 may be the same as described in connection with the first electrode 11 and the second electrode 19 illustrated in FIG. 1.


The first emission layer 151-EM and the second emission layer 152-EM illustrated in FIG. 3 are each the same as described in connection with the emission layer 15 illustrated in FIG. 1.


The hole transport region 120 and the first hole transport region 121 illustrated in FIG. 3 are each the same as described in connection with the hole transport region 12 illustrated in FIG. 1.


The electron transport region 170 and the first electron transport region 171 illustrated in FIG. 3 are each the same as described in connection with the electron transport region 17 illustrated in FIG. 1.


As described above, referring to FIG. 3, an organic light-emitting device in which each of the first emission unit 151 and the second emission unit 152 includes an emission layer including a host, a cooling dopant, and a sensitizer, has been described. However, the organic light-emitting device may have various other forms. For example, one of the first emission unit 151 and the second emission unit 152 of the organic light-emitting device 100 of FIG. 3 may be replaced with any known emission unit, or may include three or more emission units.


Description of FIG. 4


FIG. 4 is a schematic cross-sectional view of an organic light-emitting device 200 according to another embodiment.


The organic light-emitting device 200 includes a first electrode 210, a second electrode 290 facing the first electrode 210, and a first emission layer 251 and a second emission layer 252 which are stacked between the first electrode 210 and the second electrode 290.


The maximum emission wavelength of light emitted from the first emission layer 251 may be different from the maximum emission wavelength of light emitted from the second emission layer 252. For example, the mixed light of the light emitted from the first emission layer 251 and the light emitted from the second emission layer 252 may be white light, but embodiments of the present disclosure are not limited thereto.


In one or more embodiments, a hole transport region 220 may be located between the first emission layer 251 and the first electrode 210, and an electron transport region 270 may be located between the second emission layer 252 and the second electrode 290.


The first emission layer 251 may include a host, a cooling dopant, and a sensitizer, and the cooling dopant and the sensitizer may satisfy Conditions 1 and 2.


The second emission layer 252 may include a host, a cooling dopant, and a sensitizer, and the cooling dopant and the sensitizer may satisfy Conditions 1 and 2.


The first electrode 210, the hole transport region 220, and the second electrode 290 illustrated in FIG. 4 are respectively the same as described in connection with the first electrode 11, the hole transport region 12, and the second electrode 19 illustrated in FIG. 1.


The first emission layer 251 and the second emission layer 252 illustrated in FIG. 4 are each the same as described in connection with the emission layer 15 illustrated in FIG. 1.


The electron transport region 270 illustrated in FIG. 4 may be the same as described in connection with the electron transport region 17 in FIG. 1.


As described above, referring to FIG. 4, an organic light-emitting device, in which each of the first emission layer 251 and the second emission layer 252 includes a host, a cooling dopant, and a sensitizer, has been described. However, the organic light-emitting device may have various other forms. For example, one of the first emission layer 251 and the second emission layer 252 of the organic light-emitting device 200 of FIG. 4 may be replaced with any known emission layer, or an interlayer may be additionally located between neighboring emission layers.


Explanation of Terms

The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.


The term “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 include a methoxy group, an ethoxy group, and an isopropyloxy group.


The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.


The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethynyl group, and a propynyl group. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.


The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.


The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having at least one N, O, P, Si, B, Se, Ge, S, or any combination thereof as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkyl group.


The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.


The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one N, O, P, Si, B, Se, Ge, S, or any combination thereof as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.


The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.


The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heterocarbocyclic aromatic system that has at least one N, O, P, Si, B, Se, Ge, S, or any combination thereof as a ring-forming atom, and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one N, O, P, Si, B, Se, Ge, S, or any combination thereof as a ring-forming atom, and 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C6-C60 heteroaryl group and the C6-C60 heteroarylene group each include two or more rings, the rings may be fused to each other.


The term “C6-C60 aryloxy group” as used herein refers to —OA102 (wherein A102 is the C6-C60 aryl group), and a C6-C60 arylthio group used herein refers to —SA103 (wherein A103 is the C6-C60 aryl group).


The term “monovalent non-aromatic condensed polycyclic group” used herein refers to a monovalent group in which two or more rings are condensed with each other, only carbon is used as a ring-forming atom (for example, the number of carbon atoms may be 8 to 60) and the whole molecule is a non-aromaticity group. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.


The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group having two or more rings condensed to each other, N, O, P, Si, B, Se, Ge, S, or any combination thereof other than carbon atoms (for example, having 1 to 60 carbon atoms), as a ring-forming atom, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.


The term “C5-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, and may be a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group, depending on the formula structure.


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 heteroatom N, O, Si, P, B, Ge, Se, S, or any combination thereof other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group, and may be a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group, depending on the formula structure.


At least one substituent of the substituted C5-C60 carbocyclic group, the substituted C1-C60 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 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 of 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —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 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 of deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 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),


wherein 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 aryl group substituted with at least one a C1-C60 alkyl group, and 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.


The term “room temperature” used herein refers to a temperature of about 25° C.


The terms “a biphenyl group, a terphenyl group, and a tetraphenyl group” used herein respectively refer to monovalent groups in which two, three, or four phenyl groups 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” 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.”


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’” 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.


EXAMPLES
Evaluation Example 1: Decay Time Measurement

On the quartz substrate, compounds of Tables 5 to 7 were vacuum-codeposited at a vacuum pressure of 10−7 torr at a weight ratio of Tables 5 to 7 to manufacture films, each having a thickness of 40 nm. With respect to each of the films, the PL spectrum was evaluated at room temperature by using FluoTime 300 of PicoQuant Inc. and PLS340, which is a pumping source of PicoQuant Inc., (excitation wavelength=340 nm, and spectrum width=20 nm). In detail, the wavelength of the main peak of the spectrum obtained for each film was identified, and the number of photons emitted from the respective sample at the wavelength of the main peak by photon pulses (pulse width=500 μs) applied by the PLS340 to the respective film was repeatedly measured based on time-correlated single photon counting (TCSPC), to obtain a TRPL curve which can be subjected to fitting. Two or more exponential decay functions, obtained therefrom, were subjected to fitting to calculate a decay time with respect to each film. In this regard, the same measurement was performed for the same measurement time as used to obtain the TRPL curve in the dark condition (The light low pulse signal incident to the predetermined film was blocked) to obtain a background signal curve which was then subjected to fitting. The resultant was used as a baseline.


At this time, in the case of the film of Table 5, the function used for fitting is the same as Equation A below, and the largest value among the Taus obtained therefrom was taken. For the films of Tables 6 and 7 below, Tau was obtained by Equation B using the amplitude values (A1, A2, A3, etc.) and Tau values (Tau1, Tau2, Tau3, etc.) obtained by fitting:










f


(
t
)


=




i
=
1

n




A
i



exp


(


-
t

/

T

decay
,
i



)








Equation





A






Tau
=


(




i
=
1

n




A
i

×

Tau
i



)

÷

(




i
=
1

n



A
i


)






Equation





B


















TABLE 5









Decay



Film No.
Film composition (weight ratio)
time(μs)




















SP002ND
H-H1:H-E1:SP002 (45:45:10)
2.393



SP003ND
H-H1:H-E1:SP003 (45:45:10)
2.703



SP004ND
H-H1:H-E1:SP004 (45:45:10)
4.924



SP005ND
H-H1:H-E1:SP005 (45:45:10)
2.866



SP006ND
H-H1:H-E1:SP006 (45:45:10)
1.836



SP007ND
H-H1:H-E1:SP007 (45:45:10)
2.223



ST001ND
H-H1:H-E1:ST001 (45:45:10)
1.13



ST002ND
H-H1:H-E1:ST002 (45:45:10)
2.69



















TABLE 6







Decay


Film No.
Film composition (weight ratio)
time(μs)

















SP002D
H-H1:H-E1:SP002:FD11 (42.75:42.75:9.5:5)
0.363


SP003D
H-H1:H-E1:SP003:FD11 (42.75:42.75:9.5:5)
0.378


SP004D
H-H1:H-E1:SP004:FD11 (42.75:42.75:9.5:5)
0.269


SP005D
H-H1:H-E1:SP005:FD11 (42.75:42.75:9.5:5)
0.398


SP006D1
H-H1:H-E1:SP006:FD11 (42.75:42.75:9.5:5)
0.307


SP006D2
H-H1:H-E1:SP006:FD5 (42.75:42.75:9.5:5)
0.634


SP007D1
H-H1:H-E1:SP007:FD11 (42.75:42.75:9.5:5)
0.413


SP007D2
H-H1:H-E1:SP007:FD5 (42.75:42.75:9.5:5)
0.749


ST001D1
H-H1:H-E1:ST001:FD11 (42.75:42.75:9.5:5)
0.012


ST001D2
H-H1:H-E1:ST001:FD5 (42.75:42.75:9.5:5)
0.09


ST002D1
H-H1:H-E1:ST002:FD11 (42.75:42.75:9.5:5)
0.719


ST002D2
H-H1:H-E1:ST002:FD5 (42.75:42.75:9.5:5)
0.673




















TABLE 7









Decay



Film No.
Film composition (weight ratio)
time(μs)









FD001
H-H1:H-E1:FD11 (47.5:47.5:5)
0.027



FD002
H-H1:H-E1:FD5 (47.5:47.5:5)
0.069












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Example 1

An ITO glass substrate was cut to a size of 50 mm×50 mm×0.5 mm and then, sonicated in acetone isopropyl alcohol and pure water, each for 15 minutes, and then, washed by exposure to UV ozone for 30 minutes.


Then, F6-TCNNQ was deposited on the ITO electrode (anode) of the glass substrate to form a hole injection layer having a thickness of 100 Å, and HT1 was deposited on the hole injection layer to form a hole transport layer having a thickness of 1260 Å, thereby completing a hole transport region.


Compound H-H1 (first host), H-E1 (second host), Compound SP002(sensitizer) (in this case, the weight ratio of the first host, the second host and the sensitizer was 45:45:10) and FD11 (cooling dopant)(in this case, the cooling dopant was 5 wt % based on the total weight of the first host, the second host, the sensitizer, and the cooling dopant) were co-deposited on the hole transport region to form an emission layer having a thickness of 400 Å thickness.


Compound ET17 and Liq were co-deposited at the weight ratio of 5:5 on the emission layer to form an electron transport layer having a thickness of 360 Å thickness, and then, LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 5 Å thickness, and Al was deposited on the electron injection layer to a thickness of 800 Å, thereby completing of an organic light-emitting device.


Examples 2 to 12

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that the sensitizers and the cooling dopants shown in Table 8 were used in forming an emission layer.














TABLE 8







First
Second

Cooling



host
host
Sensitizer
dopant






















Example 1
H-H1
H-E1
SP002
FD11



Example 2
H-H1
H-E1
SP003
FD11



Example 3
H-H1
H-E1
SP004
FD11



Example 4
H-H1
H-E1
SP005
FD11



Example 5
H-H1
H-E1
SP006
FD11



Example 6
H-H1
H-E1
SP006
FD11



Example 7
H-H1
H-E1
SP007
FD11



Example 8
H-H1
H-E1
SP007
FD5



Example 9
H-H1
H-E1
ST001
FD11



Example 10
H-H1
H-E1
ST001
FD5



Example 11
H-H1
H-E1
ST002
FD11



Example 12
H-H1
H-E1
ST002
FD5










Comparative Example 1F and 2F

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that, in forming an emission layer, a sensitizer was not used and the first host, the second host, and the cooling dopant were used as shown in Table 9.














TABLE 9










Weight ratio






(first host:second



First
Second
Cooling
host:cooling



host
host
dopant
dopant)




















Comparative
H-H1
H-E1
FD11
47.5:47.5:5


Example 1F


Comparative
H-H1
H-E1
FD5
47.5:47.5:5


Example 2F









Comparative Examples 1P to 6P

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that, in forming an emission layer, a cooling dopant was not used and the first host, the second host, and the sensitizer were used as shown in Table 10.














TABLE 10










Weight ratio



First
Second

(first host:second



host
host
Sensitizer
host:sensitizer)




















Comparative
H-H1
H-E1
SP002
45:45:10


Example 1P


Comparative
H-H1
H-E1
SP003
45:45:10


Example 2P


Comparative
H-H1
H-E1
SP004
45:45:10


Example 3P


Comparative
H-H1
H-E1
SP005
45:45:10


Example 4P


Comparative
H-H1
H-E1
SP006
45:45:10


Example 5P


Comparative
H-H1
H-E1
SP007
45:45:10


Example 6P









Comparative Examples 1T and 2T

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that, in forming an emission layer, a cooling dopant was not used and the first host, the second host, and the sensitizer were used as shown in Table 11.














TABLE 11










Weight ratio



First
Second

(first host:second



host
host
Sensitizer
host:sensitizer)




















Comparative
H-H1
H-E1
ST001
45:45:10


Example 1T


Comparative
H-H1
H-E1
ST002
45:45:10


Example 2T









Evaluation Example 2: OLED Lifespan and External Quantum Efficiency Measurements

The external quantum efficiency (EQE) and lifespan of each of organic light-emitting devices manufactured according to Examples 1 to 12 were evaluated, and then, the results are calculated as a relative value (%), and results thereof are shown in Table 12. As an evaluation apparatus, a luminance meter (Minolta Cs-1000A) was used. The lifespan (T95) was determined by evaluating the time taken for 100% of initial luminance to be 95% thereof under the same luminance measurement conditions.


In addition, after measuring the lifespan and EQE of Example 3, Comparative Example 3P, 1F, and 2F, the relative value (%) was calculated based on the value of Comparative Example 1F and the results are shown in Table 13, and FIGS. 5 and 6.
















TABLE 12







First host
Second host
Sensitizer
Cooling dopant
Lifespan (%)
EQE (%)






















Example 1
H-H1
H-E1
SP002
FD11
688
181


Example 2
H-H1
H-E1
SP003
FD11
234
142


Example 3
H-H1
H-E1
SP004
FD11
296
121


Example 4
H-H1
H-E1
SP005
FD11
100
100


Example 5
H-H1
H-E1
SP006
FD11
1051
134


Example 6
H-H1
H-E1
SP006
FD11
340
102


Example 7
H-H1
H-E1
SP007
FD11
1355
144


Example 8
H-H1
H-E1
SP007
FD5
487
124


Example 9
H-H1
H-E1
ST001
FD11
43
65


Example 10
H-H1
H-E1
ST001
FD5
24
86


Example 11
H-H1
H-E1
ST002
FD11
232
129


Example 12
H-H1
H-E1
ST002
FD5
140
162









Referring to Table 12, it can be seen that the organic light-emitting device of Example 1 to 12 has long life span and high efficiency.
















TABLE 13







First host
Second host
Sensitizer
Cooling dopant
Lifespan (%)
EQE (%)






















Example 3
H-H1
H-E1
SP004
FD11
296
121


Comparative Example 3P
H-H1
H-E1
SP004

13
86


Comparative Example 1F
H-H1
H-E1

FD11
66
31









Referring to Table 13, and FIGS. 5 and 6, it can be seen that the organic light-emitting device of Example 3 has a long lifespan and high EQE compared to a phosphorescent organic light-emitting device (Comparative Example 3P) and a fluorescent organic light-emitting device (Comparative Example 1F).


Evaluation Example 3: Calculation of OLED Lifespan Increase

For Examples 1 to 12 and Comparative Examples 1F and 2F, the time (T95) taken for 100% of the initial luminance to be decreased to 95% thereof at 6000 nits was measured. Then, the lifespan increase of Example 1 to 12 was calculated using the following equation L and the results are shown in Table 14.





Lifespan increase of device A={T95 of device A}/{T95 of device B}  Equation L













TABLE 14









Lifespan Increase of



Device A
Device B
Device A




















Example 1
Comparative Example 1F
5.8



Example 2
Comparative Example 1F
4.6



Example 3
Comparative Example 1F
22.3



Example 4
Comparative Example 1F
9.74



Example 5
Comparative Example 1F
5.70



Example 6
Comparative Example 1F
1.84



Example 7
Comparative Example 1F
4.17



Example 8
Comparative Example 2F
1.5



Example 9
Comparative Example 1F
11.3



Example 10
Comparative Example 2F
6.14



Example 11
Comparative Example 1F
5.74



Example 12
Comparative Example 2F
3.46










Referring to the Table 14, it can be seen that the organic light-emitting devices of Examples 1 to 12 have a significant improvement in lifespan compared to the fluorescent organic light-emitting devices of Comparative Examples 1F and 2F which do not include the sensitizer.


Evaluation Example 4: Calculation of OLED EQE Increase

For Examples 1 to 12, Comparative Examples 1P to 6P, and Comparative Examples 1T and 2T, external quantum efficiency (EQE) was measured. Then, the lifespan increase of Example 1 to 12 was calculated using the following equation E and the results are shown in Table 15.





EQE increment of device C={EQE of device C}/{EQE of device D}  Equation E













TABLE 15









EQE increment of



Device C
Device D
device C




















Example 1
Comparative Example 1P
5.78



Example 2
Comparative Example 2P
4.52



Example 3
Comparative Example 3P
3.85



Example 4
Comparative Example 4P
3.19



Example 5
Comparative Example 5P
4.26



Example 6
Comparative Example 5P
1.66



Example 7
Comparative Example 6P
4.60



Example 8
Comparative Example 6P
2.02



Example 9
Comparative Example 1T
2.07



Example 10
Comparative Example 1T
1.40



Example 11
Comparative Example 2T
4.11



Example 12
Comparative Example 2T
2.62










Referring to the Table 15, it can be seen that the organic light-emitting devices of Examples 1 to 12 show a significant improvement in lifespan compared to Comparative Examples 1P to 6P which do not include a cooling dopant, phosphorescence of 1T, and 2T, or TADF organic light-emitting devices.


The organic light-emitting device may have a long lifespan.


It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.

Claims
  • 1. An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode;the organic layer comprises an emission layer;the emission layer comprises a host, a cooling dopant, and a sensitizer, whereinthe cooling dopant and the sensitizer satisfy Conditions 1 and 2, andthe sensitizer comprises platinum (Pt): Tdecay(CD)<Tdecay(S)  Condition 1Tdecay(CD)<1.5 μs  Condition 2wherein, in Conditions 1 and 2,Tdecay(CD) is a decay time of the cooling dopant, andTdecay(S) is a decay time of the sensitizer.
  • 2. An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode;the organic layer comprises an emission layer;the emission layer comprises a host, a cooling dopant, and a sensitizer, whereinthe cooling dopant and the sensitizer satisfy Conditions 1 and 2, andthe sensitizer comprises a thermally activated delayed fluorescence emitter, andthe thermally activated delayed fluorescence emitter does not comprise a metal: Tdecay(CD)<Tdecay(S)  Condition 1Tdecay(CD)<1.5 μs  Condition 2wherein, in Conditions 1 and 2,Tdecay(CD) is a decay time of the cooling dopant, andTdecay(S) is a decay time of the sensitizer.
  • 3. The organic light-emitting device of claim 1, wherein the organic light-emitting device further satisfies Condition 3: Tdecay(CD)/Tdecay(S)<0.5  Condition 3wherein, in Condition 3,Tdecay(CD) is a decay time of the cooling dopant, andTdecay(S) is a decay time of the sensitizer.
  • 4. The organic light-emitting device of claim 1, wherein the organic light-emitting device further satisfies Condition 4: BDE(S)−T1(S)<3.0 eV  Condition 4wherein, in Condition 4,BDE (S) is a bond dissociation energy level of the sensitizer, andT1 (S) is a lowest excitation triplet energy level of the sensitizer.
  • 5. The organic light-emitting device of claim 1, wherein the organic light-emitting device further satisfies Condition 5: R(Hex)/e10<15  Condition 5wherein, in Condition 5,R (Hex) is a production rate of hot excitons.
  • 6. The organic light-emitting device of claim 1, wherein the host, the dopant, and the sensitizer further satisfy Condition 6: T1(H)≥T1(S)≥S1(CD)  Condition 6wherein, in Condition 6,T1(H) is a lowest excitation triplet energy level of the host,T1(S) is a lowest excitation triplet energy level of the sensitizer, andS1(CD) is a lowest excitation singlet energy level of the cooling dopant.
  • 7. The organic light-emitting device of claim 1, wherein the emission layer consists of the host, the cooling dopant, and the sensitizer.
  • 8. The organic light-emitting device of claim 1, wherein the host comprises an amphiprotic host, an electron transport host, a hole transport host, or a combination thereof,the electron transport host comprises at least one electron transport moiety,the hole transport host does not comprise an electron transport moiety,the electron transport moiety is a cyano group, a π electron-deficient nitrogen-containing cyclic group, a group represented by one of the following Formulae, or a combination thereof:
  • 9. The organometallic compound of claim 8, wherein the electron transport host comprises at least one π electron-deficient nitrogen-free cyclic group and at least one electron transport moiety,the hole transport host comprises at least one π electron-deficient nitrogen-free cyclic group, and does not comprise an electron transport moiety, andthe electron transport moiety is a cyano group or an π-electron deficient nitrogen-containing cyclic group.
  • 10. The organic light-emitting device of claim 9, wherein the π electron-deficient nitrogen-containing cyclic group is: 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 of two or more π electron-deficient nitrogen-containing cyclic groups,the π electron-deficient nitrogen-free cyclic group is a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, 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 of two or more π electron-deficient nitrogen-free cyclic groups.
  • 11. The organometallic compound of claim 8, wherein the electron transport host comprises 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, andthe hole transport host comprises a carbazole group.
  • 12. The organic light-emitting device of claim 1, wherein the maximum emission wavelength of the emission spectrum of the cooling dopant is about 400 nm or more and about 550 nm or less.
  • 13. The organic light-emitting device of claim 1, wherein the cooling dopant does not comprise a metal atom.
  • 14. The organic light-emitting device of claim 1, wherein the cooling dopant comprises one of a naphthalene-containing core, a fluorene-containing core, a spiro-bifluorene-containing core, a benzofluorene-containing core, a dibenzofluorene-containing core, a phenanthrene-containing core, an anthracene-containing core, a fluoranthene-containing core, a triphenylene-containing core, a pyrene-containing core, a chrysene-containing core, a naphthacene-containing core, a picene-containing core, a perylene-containing core, a pentaphene-containing core, an indenoanthracene-containing core, a tetracene-containing core, a bisanthracene-containing core, or a core represented by one of Formulae 501-1 to 501-18:
  • 15. The organic light-emitting device of claim 1, wherein the organic layer comprises the organometallic compound represented by Formula 101: Pt(L11)n11(L12)n12  Formula 101wherein, in Formula 101,L11 is a ligand represented by one of Formulae 1-1 to 1-4;L12 is a monodentate ligand or a bidentate ligand;n11 is 1,n12 is 0, 1, or 2;
  • 16. The organic light-emitting device of claim 2, wherein the sensitizer satisfies Condition 7: ΔEST≤0.3 eV  Condition 7wherein, in Condition 7,ΔEST is a difference between the lowest excitation singlet energy level and a lowest excitation triplet energy level of the sensitizer.
  • 17. The organic light-emitting device of claim 2, wherein the sensitizer is represented by Formula 201 or 202:
  • 18. The organic light-emitting device of claim 17, wherein A21 is a substituted unsubstituted π electron-deficient nitrogen-free cyclic group;D21 is: —F, a cyano group, or a n-electron deficient nitrogen-containing cyclic group;a C1-C60 alkyl group, a n-electron deficient nitrogen-containing cyclic group, or a π electron-deficient nitrogen-free cyclic group, each substituted with at least one —F, a cyano group, or a combination thereof; ora π-electron deficient nitrogen-containing cyclic group substituted with at least one deuterium, a C1-C60 alkyl group, a π-electron deficient nitrogen-containing cyclic group, a π electron-deficient nitrogen-free cyclic group, or any combination thereof;wherein:the π electron-deficient nitrogen-free cyclic group is a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, 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 coronene 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 of two or more π electron-deficient nitrogen-free cyclic groups, andthe π electron-deficient nitrogen-containing cyclic group is a cyclic group having at least one *—N═*′ moiety, and is 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, a benzimidazolobenzimidazole group; or a condensed cyclic group of two or more π electron-deficient nitrogen-containing cyclic groups.
  • 19. An organic light-emitting device comprising: a first electrode; a second electrode; m emission units located between the first electrode and the second electrode and comprising at least one emission layer; andm−1 charge generating layers between neighboring two emission units of the m emission units and comprising an n-type charge generating layer and a p-type charge generating layer,m is an integer of 2 or more,a maximum emission wavelength of light emitted from at least one emission unit of the m emission units is different from a maximum emission wavelength of light emitted from at least one emission unit of the remaining emission units,the emission layer comprises a host, a cooling dopant, and a sensitizer, whereinthe cooling dopant and the sensitizer satisfy Conditions 1 and 2, andthe sensitizer comprises platinum (Pt): Tdecay(CD)<Tdecay(S)  Condition 1Tdecay(CD)<1.5 μs  Condition 2wherein, in Conditions 1 and 2,Tdecay(CD) is a decay time of the cooling dopant, andTdecay(S) is a decay time of the sensitizer.
  • 20. An organic light-emitting device comprising: a first electrode; a second electrode; m emission units located between the first electrode and the second electrode and comprising at least one emission layer; andm−1 charge generating layers between neighboring two emission units of the m emission units and comprising an n-type charge generating layer and a p-type charge generating layer,m is an integer of 2 or more,a maximum emission wavelength of light emitted from at least one emission unit of the m emission units is different from a maximum emission wavelength of light emitted from at least one emission unit of the remaining emission units,the emission layer comprises a host, a cooling dopant, and a sensitizer, whereinthe cooling dopant and the sensitizer satisfy Conditions 1 and 2, andthe sensitizer comprises a thermally activated delayed fluorescence emitter, andthe thermally activated delayed fluorescence emitter does not comprise a metal: Tdecay(CD)<Tdecay(S)  Condition 1Tdecay(CD)<1.5 μs  Condition 2wherein, in Conditions 1 and 2,Tdecay(CD) is a decay time of the cooling dopant, andTdecay(S) is a decay time of the sensitizer.
  • 21. An organic light-emitting device comprising: a first electrode; a second electrode; and m emission layers between the first electrode and the second electrode,m is an integer of 2 or more,a maximum emission wavelength of light emitted from at least one emission layer of the m emission layers is different from the maximum emission wavelength of light emitted from at least one emission layer of the remaining emission layers,a emission layer comprises a host, a cooling dopant, and a sensitizer, whereinthe cooling dopant and the sensitizer satisfy Conditions 1 and 2, andthe sensitizer comprises platinum (Pt): Tdecay(CD)<Tdecay(S)  Condition 1Tdecay(CD)<1.5 μs  Condition 2wherein, in Conditions 1 and 2,Tdecay(CD) is a decay time of the cooling dopant, andTdecay(S) is a decay time of the sensitizer.
  • 22. An organic light-emitting device comprising: a first electrode; a second electrode; and m emission layers between the first electrode and the second electrode,m is an integer of 2 or more,a maximum emission wavelength of light emitted from at least one emission layer of the m emission layers is different from a maximum emission wavelength of light emitted from at least one emission layer of the remaining emission layers,the emission layer comprises a host, a cooling dopant, and a sensitizer, whereinthe cooling dopant and the sensitizer satisfy Conditions 1 and 2, andthe sensitizer comprises a thermally activated delayed fluorescence emitter, andthe thermally activated delayed fluorescence emitter does not comprise a metal: Tdecay(CD)<Tdecay(S)  Condition 1Tdecay(CD)<1.5 μs  Condition 2wherein, in Conditions 1 and 2,Tdecay(CD) is a decay time of the cooling dopant, andTdecay(S) is a decay time of the sensitizer.
Priority Claims (2)
Number Date Country Kind
10-2019-0037245 Mar 2019 KR national
10-2020-0027986 Mar 2020 KR national