Patent Grant
11944008
This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0054778, filed on May 7, 2020, in the Korean Intellectual Property Office, the entire content of which is hereby incorporated by reference.
One or more embodiments of the present disclosure relate to a heterocyclic compound and a light-emitting device including the heterocyclic compound.
Organic light-emitting devices (OLEDs) are self-emission devices which have wide viewing angles, high contrast ratios, short response times, and excellent brightness, driving voltage, and response speed characteristics, and produce full-color images.
OLEDs may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to produce excitons. These excitons transit (e.g., transition or relax) from an excited state to a ground state to thereby generate light.
One or more embodiments of the present disclosure include a condensed cyclic compound and an organic light-emitting device having including the same.
Additional aspects of embodiments will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one or more embodiments, a heterocyclic compound may be represented by Formula 1:
According to one or more embodiments, an organic light-emitting device may include a first electrode, a second electrode facing the first electrode, and an organic layer between the first electrode and the second electrode and including an emission layer, and the organic light-emitting device may include at least one of the heterocyclic compound.
The above and other aspects and features of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
Reference will now be made in more 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 of embodiments of the present description. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression “at least one of a, b or c” indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.
As the present disclosure allows for various changes and numerous embodiments, example embodiments will be illustrated in the drawings and described in more detail in the written description. Effects, features, and a method of achieving the subject matter of the present disclosure will be readily apparent to those of ordinary skill in the art by referring to example embodiments of the present disclosure with reference to the attached drawings. The subject matter of the present disclosure may, however, be embodied in many different forms and should not be construed as being limited to the embodiments set forth herein.
Hereinafter, the subject matter of the present disclosure will be described in more detail by explaining example embodiments of the present disclosure with reference to the attached drawings. Like reference numerals in the drawings denote like elements, and thus, duplicative description thereof will not be repeated.
In the embodiments described in the present specification, an expression used in the singular encompasses the expression of the plural, unless it has a clearly different meaning in the context.
In the present specification, it is to be understood that the terms such as “including,” “having,” and “comprising” are intended to indicate the existence of the features or components disclosed in the specification, and are not intended to preclude the possibility that one or more other features or components may exist or may be added.
It will be understood that when a layer, region, or component is referred to as being “on” or “onto” another layer, region, or component, it may be directly or indirectly formed over the other layer, region, or component. That is, for example, intervening layers, regions, or components may be present.
Sizes of components in the drawings may be exaggerated for convenience of explanation. In other words, because sizes and thicknesses of components in the drawings may be arbitrarily illustrated for convenience of explanation, the following embodiments are not limited thereto.
The term “organic layer” as used herein refers to a single and/or a plurality of layers between a first electrode and a second electrode in an organic light-emitting device. A material included in the “organic layer” is not limited to an organic material. For example, the organic layer may include an inorganic material.
As used herein, the expression that “(an organic layer) includes a compound represented by Formula 1” may be construed as meaning that “(the organic layer) may include one compound represented by Formula 1 or at least two different compounds represented by Formula 1.”
A heterocyclic compound may be represented by Formula 1:
In Formula 1, L1 may be selected from groups represented by Formulae 2A to 2F.
The heterocyclic compound may satisfy condition (i) or condition (ii) when a1 in Formula 1 is 1:
In Formula 1, n1 indicates the number of Ar(s), and n1 may be an integer from 1 to 10. When n1 is greater than 1, the plurality of Ar's may each bond to L1 by way of the respective L31.
In an embodiment, n1 may be 1 or 2, but the present disclosure is not limited thereto.
In some embodiments, X1 may be selected from O, S, N(R28), C(R28)(R29), and Si(R28)(R29).
In some embodiments, L31 may be selected from a single bond, a substituted or unsubstituted C5-C60 carbocyclic group, and a substituted or unsubstituted C1-C60 heterocyclic group.
In some embodiments, a31 may be an integer from 1 to 5.
In some embodiments, R1, R21 to R29, R31, and R32 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —S(═O)2(Q1), and —P(═O)(Q1)(Q2).
In some embodiments, c1 may be an integer from 0 to 5, where, when c1 is greater than 1, the plurality of R1's may each bond directly to L1, c21, c23, c26, c31, and c32 may each independently be an integer from 1 to 4, c22, c24, c25, c21′, and c23′ may each independently be an integer from 1 to 3, and c27 may be 1 or 2.
In some embodiments, 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 C2-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
In Formulae 2A to 2F and 3, *, *′, and *″ each indicate a binding site to an adjacent atom.
In Formulae 2A to 2F, X1 may be selected from O, S, N(R28), C(R28)(R29), and Si(R28)(R29).
In an embodiment, X1 may be selected from O, N(R28), C(R28)(R29), and Si(R28)(R29).
In an embodiment, in Formula 1, L1 may be selected from groups represented by Formulae 2A-1 to 2A-3, 2B-1, 2C-1 to 2C-4, 2D-1, 2E-1 to 2E-50, and 2F-1 to 2F-10. When a1 is 1, condition (iii) or condition (iv) may be satisfied:
In an embodiment, in Formula 1, L1 may be selected from groups represented by Formulae 2AA-1 to 2AA-7, 2BB-1, 2CC-1 to 2CC-4, 2DD-1, 2EE-1 to 2EE-8, and 2FF-1. When a1 is 1, condition (v) or condition (vi) may be satisfied:
In an embodiment, in Formula 1, a group represented by *-[L1]a1-*′ may be selected from groups represented by *-L11-*′, *-L11-L12-*′, *-L11-L12-L13-*′, and *-L11-L12-L13-L14-*′, and L11 to L14 may each independently be selected from groups represented Formulae 2A to 2F. When *-[L1]a1-*′ is *-L11-*′, condition (vii) or condition (viii) may be satisfied:
In one or more embodiments, a group represented by *-[L1]a1-*′ may be selected from groups represented by *-L11-*′, *-L11-L12-*′, and *-L11-L12-L13-L14-*′, L11 to L14 may each independently be selected from groups represented by Formulae 2A to 2F, and n1 may be 1 or 2. When *-[L1]a1-*′ is *-L11-*′, condition (vii) or condition (viii) may be satisfied.
In Formula 3, L31 may be selected from a single bond, a substituted or unsubstituted C5-C60 carbocyclic group, and a substituted or unsubstituted C1-C60 heterocyclic group.
In some embodiments, L31 may be selected from a single bond, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group; and
In an embodiment, L31 may be a single bond, and a31 may be 1.
In Formula 1, R1, R21 to R29, R31, and R32 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an am idino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —S(═O)2(Q1), and —P(═O)(Q1)(Q2).
In some embodiments, R1 may be selected from a C1-C20 alkyl group, a C1-C20 alkyl group substituted with at least one phenyl group, and a C1-C20 alkoxy group;
In one or more embodiments, in Formula 1, R1 may be selected from a C1-C20 alkyl group, a C1-C20 alkyl group substituted with at least one phenyl group, a C1-C20 alkoxy group, groups represented by Formulae 5-1 to 5-51, —Si(Q1)(Q2)(Q3), and —N(Q1)(Q2):
* indicates a binding site to an adjacent atom.
In one or more embodiments, in Formula 1, R1 may be selected from groups represented by Formulae 6-1 to 6-151:
In an embodiment, in Formulae 2A to 2F and 3, R21 to R29, R31, and R32 may each independently be selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
In one or more embodiments, in Formulae 2A to 2F, R21 to R29, R31, and R32 may each independently be selected from: hydrogen, deuterium, a phenyl group, a biphenyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl group, —Si(Q1)(Q2)(Q3), and —N(Q1)(Q2); and
In an embodiment, in Formula 3, R31 and R32 may each be hydrogen.
In Formulae 2A to 2F and 3, c21, c23, c26, c31, and c32 may each independently be an integer from 1 to 4, c22, c24, c25, c21′, and c23′ may each independently be an integer from 1 to 3, and c27 may be 1 or 2.
The heterocyclic compound according to one or more embodiments may be represented by any one of Formulae 1-1 to 1-10:
In an embodiment, in Formulae 1-1 to 1-3, i) L11 may be selected from groups represented by Formulae 2C-1 to 2C-4, 2D-1, 2E-1 to 2E-50, and 2F-1 to 2F-10, or ii) L11 may be selected from groups represented by Formulae 2A-1 to 2A-3 and 3B-1, c1 may be an integer from 1 to 5, and R1 may not be a substituted or unsubstituted pyridinyl group.
In one or more embodiments, in Formulae 1-1 to 1-3, i) L11 may be selected from groups represented by Formulae 2CC-1 to 2CC-4, 2DD-1, 2EE-1 to 2EE-8, and 2FF-1, or ii) L11 may be selected from groups represented by Formulae 2AA-1 to 2AA-7 and 2BB-1, c1 may be an integer from 1 to 5, and R1 may not be a substituted or unsubstituted pyridinyl group.
In an embodiment, in Formulae 1-4 to 1-10, L11 to L14 may each independently be selected from groups represented by Formulae 2A-1 to 2A-3, 2B-1, 2C-1 to 2C-4, 2D-1, 2E-1 to 2E-50, and 2F-1.
In one or more embodiments, in Formulae 1-4 to 1-10, L11 to L14 may each independently be selected from groups represented by Formulae 2AA-1 to 2AA-7, 2BB-1, 2CC-1 to 2CC-4, 2DD-1, 2EE-1 to 2EE-8, and 2FF-1.
In the present specification, 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 C2-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
In an embodiment, the heterocyclic compound represented by Formula 1 may be selected from Compounds 1 to 85:
The heterocyclic compound represented by Formula 1 may include at least one group represented by Formula 3. The group represented by Formula 3 may have a high glass transition temperature by including a structure in which adamantane, which is relatively large and has relatively high rigidity, is condensed at a carbon-9 position of 9,9-dihydroacridine. Accordingly, the heterocyclic compound may have improved thermal stability. In addition, as the heterocyclic compound may have a bulky substituent in the molecule thereof, intermolecular interaction may be reduced due to the relatively large steric hindrance of the bulky substituent, and accordingly, the heterocyclic compound may have a relatively high triplet energy level. Thus, when the heterocyclic compound is applied to an organic light-emitting device, diffusion of triplet excitons generated from the emission layer to an organic layer close to the emission layer, e.g., a hole transport layer or an electron transport layer, may be prevented or reduced, thereby improving luminescence efficiency of the organic light-emitting device. Therefore, the organic light-emitting device may have excellent luminescence characteristics.
Further, as the heterocyclic compound has a relatively high triplet energy level, the heterocyclic compound may be suitable for use as a host material of a blue dopant.
In Formula 1, L1 group may be selected from groups represented by Formulae 2A to 2F in which may not include an electron-deficient moiety. The heterocyclic compound may have a structure including an adamantyl-acridine moiety, e.g., a strong electron-donor group and an electron-donating linker L1, thereby improving hole injection characteristics. Accordingly, when the heterocyclic compound is applied to an organic light-emitting device, the driving voltage may be lowered, and charge balance characteristics may be improved, thereby improving luminescence efficiency.
In addition, as various heterorings and substituents are introduced to L1 and R1 in the heterocyclic compound, controlling energy level and steric hindrance effects of the compound may be facilitated, and the triplet energy of the heterocyclic compound may be well-maintained, and thus, the heterocyclic compound may be used as a phosphorescence and TADF host material.
Therefore, an electronic device, e.g., an organic light-emitting device, including the heterocyclic compound represented by Formula 1 may have a low driving voltage, high efficiency, and high maximum quantum efficiency.
Methods of synthesizing the heterocyclic compound represented by Formula 1 should be readily apparent to those of ordinary skill in the art by referring to the Examples described herein.
At least one heterocyclic compound represented by Formula 1 may be included between a pair of electrodes in an organic light-emitting device. In some embodiments, the heterocyclic compound may be included in at least one selected from a hole transport region, an electron transport region, and an emission layer. In some embodiments, the heterocyclic compound represented by Formula 1 may be used as a material for forming a capping layer, which is on outer sides of a pair of electrodes in an organic light-emitting device.
Accordingly, there is provided an organic light-emitting device including a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, and the organic light-emitting device may include at least one heterocyclic compound represented by Formula 1.
In an embodiment, the organic layer in the organic light-emitting device may include the at least one heterocyclic compound represented by Formula 1.
As used herein, the expression that “(an organic layer) includes at least one heterocylic compound” may be construed as meaning that “(the organic layer) may include one heterocylic compound of Formula 1 or at least two different heterocylic compounds of Formula 1.”
For example, the organic layer may include Compound 1 only as the heterocylic compound. In this embodiment, Compound 1 may be included in the emission layer of the organic light-emitting device. In some embodiments, the organic layer may include Compounds 1 and 2 as the heterocyclic compounds. In this embodiment, Compounds 1 and 2 may be included in the same layer (for example, both Compounds 1 and 2 may be included in an emission layer) or in different layers (for example, Compound 1 may be included in an emission layer, and Compound 2 may be included in an hole transport layer).
In some embodiments, a first electrode of the organic light-emitting device may be an anode,
In an embodiment, the heterocyclic compound may be included in the organic layer of the organic light-emitting device.
In an embodiment, the heterocyclic compound may be included in the emission layer of the organic light-emitting device.
In an embodiment, the emission layer may include a host and a dopant, a content (e.g., an amount) of a host in the emission layer may be greater than a content (e.g., an amount) of a dopant in the emission layer, and the host may include the heterocyclic compound.
In some embodiments, the dopant in the emission layer may include a phosphorescent dopant or a fluorescent dopant. The fluorescent dopant may include a thermally activated delayed fluorescent (TADF) dopant.
In some embodiments, the dopant may be a phosphorescent dopant, and the phosphorescent dopant may include an organometallic complex represented by Formula 401:
The heterocyclic compound has a high triplet energy level, and thus, the heterocyclic compound may be suitable for use as a blue host. In some embodiments, the heterocyclic compound may be a blue phosphorescent host or a blue fluorescent host.
In one or more embodiments, a dopant in the emission layer may include the heterocyclic compound. A content (e.g., an amount) of the dopant in the emission layer may be in a range of about 0.1 parts to about 50 parts by weight, based on 100 parts by weight of the emission layer.
In an embodiment, an emission layer including the heterocyclic compound may emit blue light. The blue light may have a maximum emission wavelength in a range of about 390 nanometers (nm) to about 440 nm.
In an embodiment, a hole transport region of the organic light-emitting device may include a charge generating material. In an embodiment, the charge generating material may include a p-dopant of which the lowest unoccupied molecular orbital (LUMO) energy level may be about −3.5 electron volts (eV) or lower.
In an embodiment, the organic light-emitting device may further include a metal-containing material in the electron transport region thereof.
In some embodiments, the electron transport region may further 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 a combination thereof.
Description of
Hereinafter, the structure of the organic light-emitting device 10 according to an embodiment and a method of manufacturing an organic light-emitting device according to an embodiment will be described in connection with
First Electrode 110
In
The first electrode 110 may be formed by depositing or sputtering, onto the substrate, a material for forming the first electrode 110. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be selected from materials having a high work function that facilitate hole injection.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combinations thereof, but the present disclosure is not limited thereto. In some embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, as a material for forming the first electrode 110, at least one of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combination thereof may be used, but the present disclosure is not limited thereto.
The first electrode 110 may have a single-layered structure, or a multi-layered structure including two or more layers. In some embodiments, the first electrode 110 may have a triple-layered structure of ITO/Ag/ITO, but the present disclosure is not limited thereto.
Organic Layer 150
The organic layer 150 may be on the first electrode 110. The organic layer 150 may include an emission layer.
The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190.
Hole Transport Region in Organic Layer 150
The hole transport region may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.
For example, the hole transport region may have a single-layered structure including a single layer including a plurality of different materials or a multi-layered structure, e.g., a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein layers of each structure are sequentially stacked on the first electrode 110 in each stated order, but the present disclosure is not limited thereto.
The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, a spiro-TPD, a spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, and a compound represented by Formula 202:
In some embodiments, in Formula 202, R201 and R202 may optionally be bound via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R203 and R204 may optionally be bound via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.
In some embodiments, in Formulae 201 and 202,
In one or more embodiments, xa1 to xa4 may each independently be 0, 1, or 2.
In one or more embodiments, xa5 may be 1, 2, 3, or 4.
In one or more embodiments, R201 to R204 and Q201 may each independently be selected from: a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group; and
In one or more embodiments, in Formula 201, at least one of R201 to R203 may be selected from:
In one or more embodiments, in Formula 202, i) R201 and R202 may be bound via a single bond, and/or ii) R203 and R204 may be bound via a single bond.
In one or more embodiments, in Formula 202, at least one of R201 to R204 may be selected from:
The compound represented by Formula 201 may be represented by Formula 201-1:
In some embodiments, the compound represented by Formula 201 may be represented by Formula 201-2, but the present disclosure is not limited thereto:
In some embodiments, the compound represented by Formula 201 may be represented by Formula 201-2(1), but the present disclosure is not limited thereto:
The compound represented by Formula 201 may be represented by Formula 201A:
In some embodiments, the compound represented by Formula 201 may be represented by Formula 201A(1), but the present disclosure is not limited thereto:
In some embodiments, the compound represented by Formula 201 may be represented by Formula 201A-1, but the present disclosure is not limited thereto:
In some embodiments, the compound represented by Formula 202 may be represented by Formula 202-1:
In one or more embodiments, the compound represented by Formula 202 may be represented by Formula 202-1(1):
In some embodiments, the compound represented by Formula 202 may be represented by Formula 202A:
In some embodiments, the compound represented by Formula 202 may be represented by Formula 202A-1:
In Formulae 201-1, 201-2, 201-2(1), 201A, 201A(1), 201A-1, 202-1, 202-1(1), 202A, and 202A-1,
The hole transport region may include at least one compound selected from Compounds HT1 to HT48, but the present disclosure is not limited thereto:
The thickness of the hole transport region may be in a range of about 100 (Angstroms) Å to about 10,000 Å, and in some embodiments, about 100 Å to about 1,000 Å. When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and in some embodiments, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, and in some embodiments, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of the foregoing ranges, excellent hole transport characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer. The electron blocking layer may reduce or eliminate the flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may include the aforementioned materials.
p-Dopant
The hole transport region may include a charge generating material as well as the aforementioned materials, to improve conductive properties (e.g., electrical conductivity) of the hole transport region. The charge generating material may be substantially homogeneously or non-homogeneously dispersed in the hole transport region.
The charge generating material may include, for example, a p-dopant.
In some embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be −3.5 eV or less.
The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but the present disclosure is not limited thereto.
In some embodiments, the p-dopant may include:
When the organic light-emitting device 10 is a full color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure. The stacked structure may include two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer. The two or more layers may be in direct contact (e.g., physical contact) with each other. In some embodiments, the two or more layers may be separated (e.g., spaced apart) from each other. In one or more embodiments, the emission layer may include two or more materials. The two or more materials may include a red light-emitting material, a green light-emitting material, or a blue light-emitting material. The two or more materials may be mixed with each other in a single layer. The two or more materials mixed with each other in the single layer may emit white light.
The emission layer may include a host and a luminescent material. The luminescent material may include at least one selected from a phosphorescent dopant, a fluorescent dopant, and a quantum dot.
The amount of the dopant in the emission layer may be, in general, in a range of about 0.01 parts to about 15 parts by weight based on 100 parts by weight of the host, but the present disclosure is not limited thereto.
The thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 200 Å to about 600 Å. When the thickness of the emission layer is within any of the foregoing ranges, improved luminescence characteristics may be obtained without a substantial increase in driving voltage.
Host in Emission Layer
The host may include the heterocyclic compound represented by Formula 1.
In some embodiments, the host may further include a compound represented by Formula 301:
[Ar601]xe11-[(L601)xe1-R601]xe21 Formula 301
In some embodiments, in Formula 301, Ar301 may be selected from:
When xb11 in Formula 301 is 2 or greater, at least two Ar301(s) may be bound via a single bond.
In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or 301-2:
In some embodiments, in Formulae 301, 301-1, and 301-2, L301 to L304 may each independently be selected from:
In some embodiments, in Formulae 301, 301-1, and 301-2, R301 to R304 may each independently be selected from:
In some embodiments, the host may include an alkaline earth metal complex and/or zinc (Zn) complex. For example, the host may include a beryllium (Be) complex, e.g., Compound H55, a magnesium (Mg) complex, and/or a zinc (Zn) complex.
The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55, but the present disclosure is not limited thereto:
Phosphorescent Dopant Included in Emission Layer of Organic Layer 150
The phosphorescent dopant may include an organometallic complex represented by Formula 401:
In some embodiments, in Formula 402, A401 and A402 may each independently be selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group, and a dibenzothiophene group.
In one or more embodiments, in Formula 402, i) X401 may be nitrogen, and X402 may be carbon, or ii) X401 and X402 may each be nitrogen.
In an embodiment, in Formula 402, R401 and R402 may each independently be selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
In one or more embodiments, when xc1 in Formula 401 is 2 or greater, two A401(s) of at least two L401(s) may optionally be linked via X407 as a linking group; or two A402(s) may optionally be linked via X408 as a linking group (see Compounds PD1 to PD4 and PD7). X407 and X408 may each independently be selected from a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q413)-*′, *—C(Q413)(Q414)-*′, and *—C(Q413)=C(Q414)-*′, wherein Q413 and Q414 may each independently be hydrogen, deuterium, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, but the present disclosure is not limited thereto.
In some embodiments, the phosphorescent dopant may include, for example, at least one selected from Compounds PD1 to PD25, but the present disclosure is not limited thereto:
Fluorescent Dopant in Emission Layer
The fluorescent dopant may include an arylamine compound or a styrylamine compound.
In some embodiments, the fluorescent dopant may include a compound represented by Formula 501:
Ar501 may be selected from a substituted or unsubstituted C5-C60 carbocyclic group and a substituted or unsubstituted C1-C60 heterocyclic group,
In some embodiments, in Formula 501, Ar501 may be selected from:
In an embodiment, in Formula 501, L501 and L503 may each independently be selected from:
In an embodiment, in Formula 501, R501 and R502 may each independently be selected from:
In one or more embodiments, xd4 in Formula 501 may be 2, but the present disclosure is not limited thereto.
In some embodiments, the fluorescent dopant may be selected from Compounds FD1 to FD22:
In some embodiments, the fluorescent dopant may be selected from the following compounds, but the present disclosure is not limited thereto:
Quantum Dot
The emission layer included in the organic light-emitting device of the present disclosure may include a quantum dot material.
The quantum dot is a particle having a crystal structure of several to tens of nanometers in size. The quantum dot may include hundreds to thousands of atoms.
Because the quantum dot is very small in size, quantum confinement effect may occur. The quantum confinement is a phenomenon in which a band gap of an object becomes larger when the object becomes smaller than a nanometer size. Accordingly, when light of a wavelength having an energy larger than a band gap of the quantum dot is incident on the quantum dot, the quantum dot is excited by absorbing the light, emits light of a set or specific wavelength, and falls to the ground state. In this case, the wavelength of the emitted light may have a value corresponding to the band gap.
A core of the quantum dot may include a II-VI compound, a III-VI compound, a III-V compound, a IV-VI compound, a Group IV element or compound, a1-Ill-VI compound, or a combination thereof.
The II-VI compound may be selected from a binary compound selected from the group consisting of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and a mixture thereof; a ternary compound selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and a mixture thereof; and a quaternary compound selected from the group consisting of CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and a mixture thereof.
The III-VI compound may include a binary compound such as In2S3 or In2Se3; a ternary compound such as InGaS3 or InGaSe3; or any combination thereof.
The III-V compound may be selected from a binary compound selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AIP, AlAs, AlSb, InN, InP, InAs, InSb and a mixture thereof; a ternary compound selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP, and a mixture thereof; and a quaternary compound selected from the group consisting of GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and a mixture thereof. The III-V semiconductor compound may further include a Group II metal (e.g., InZnP).
The IV-VI compound may be selected from a binary compound selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and a mixture thereof; a ternary compound selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and a mixture thereof; and a quaternary compound selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and a mixture thereof. The Group IV element may be selected from the group consisting of Si, Ge, and a mixture thereof. The IV compound may be a binary compound selected from the group consisting of SiC, SiGe, and a mixture thereof.
In this embodiment, the binary compound, the ternary compound, or the quaternary compound may be present in particles at a uniform (e.g., substantially uniform) concentration or in the same particle by being partially divided into different concentrations. In addition, one quantum dot may have a core-shell structure surrounding another quantum dot. An interface between a core and a shell may have a concentration gradient where a concentration of elements present in the shell decreases toward the core.
In some embodiments, the quantum dot may have a core-shell structure including a core including the nanocrystals described above and a shell surrounding the core. The shell of the quantum dot may serve as a protective layer for preventing or reducing chemical denaturation of the core to maintain semiconductor characteristics and/or as a charging layer for imparting electrophoretic characteristics to the quantum dot. The shell may be monolayer or multilayer. An interface between a core and a shell may have a concentration gradient where a concentration of elements present in the shell decreases toward the core. Examples of the shell of the quantum dot include metal or nonmetal oxide, a semiconductor compound, or a combination thereof.
In some embodiments, the metal or nonmetal oxide may be a binary compound such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, or NiO or a ternary compound such as MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4, but the present disclosure is not limited thereto.
In addition, the semiconductor compound may be CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, or AlSb, but the present disclosure is not limited thereto.
The quantum dot may have a full width of half maximum (FWHM) of an emission wavelength spectrum of about 45 nm or less, about 40 nm or less, or about 30 nm or less. When the FWHM of the emission wavelength spectrum of the quantum dot is within this range, color purity or color reproducibility may be improved. In addition, because light emitted through the quantum dot is emitted in all directions, an optical viewing angle may be improved.
In addition, the form of the quantum dot may be a form generally used in the art and is not particularly limited. The quantum dot may be a spherical form, a pyramidal form, a multi-armed form, or a cubic nanoparticle, a nanotube, a nanowire, a nanofiber, a nano-plate particle, or the like.
The quantum dot may control color of emitted light according to the particle size. Accordingly, the quantum dot may have various suitable emission colors such as blue, red, or green.
Electron Transport Region in Organic Layer 150
The electron transport region may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure each having a plurality of layers, each having a plurality of different materials.
The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but the present disclosure is not limited thereto.
In some embodiments, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein layers of each structure are sequentially stacked on the emission layer in each stated order, but the present disclosure is not limited thereto.
The electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound including at least one 7 electron-depleted nitrogen-containing ring.
The term “7 electron-depleted nitrogen-containing ring,” as used herein, refers to a C1-C60 heterocyclic group having at least one *—N═*′ moiety as a ring-forming moiety.
For example, the “7 electron-depleted nitrogen-containing ring” may be i) a 5-membered to 7-membered heteromonocyclic group having at least one *—N═*′ moiety, ii) a heteropolycyclic group in which at least two 5-membered to 7-membered heteromonocyclic groups, each having at least one *—N═*′ moiety, are condensed (e.g., combined together), or iii) a heteropolycyclic group in which at least one of a 5-membered to 7-membered heteromonocyclic group, each having at least one *—N═*′ moiety, is condensed with (e.g., combined with) at least one C5-C60 carbocyclic group.
Examples of the π electron-depleted nitrogen-containing ring may include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, benzoisothiazole, benzoxazole, benzoisoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole, but the present disclosure is not limited thereto.
In some embodiments, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21 Formula 601
Ar601 may be selected from a substituted or unsubstituted C5-C60 carbocyclic group and a substituted or unsubstituted C1-C60 heterocyclic group,
In some embodiments, at least one selected from Ar601(s) in the number of xe11 and R601 (S) in the number of xe21 may include the π electron-depleted nitrogen-containing ring.
In some embodiments, in Formula 601, Ar601 may be selected from:
When xe11 in Formula 601 is 2 or greater, at least two Ar601(s) may be bound via a single bond.
In one or more embodiments, Ar601 in Formula 601 may be an anthracene group.
In some embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:
In some embodiments, in Formulae 601 and 601-1, L601 and L611 to L613 may each independently be selected from:
In one or more embodiments, in Formulae 601 and 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
In one or more embodiments, in Formulae 601 and 601-1, R601 and R611 to R613 may each independently be selected from:
The electron transport region may include at least one compound selected from Compounds ET1 to ET36, but the present disclosure is not limited thereto:
In some embodiments, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ:
The thicknesses of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, and in some embodiments, about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer or the electron control layer are within any of the foregoing ranges, excellent hole blocking characteristics or excellent electron controlling characteristics may be obtained without a substantial increase in driving voltage.
The thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within any of the foregoing ranges, excellent electron transport characteristics may be obtained without a substantial increase in driving voltage.
The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from a lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, and a cesium (Cs) ion. The alkaline earth metal complex may include a metal ion selected from a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium (Sr) ion, and a barium (Ba) ion. Each ligand coordinated with the metal ion of the alkali metal complex and the alkaline earth metal complex may independently be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the present disclosure is not limited thereto.
For example, the metal-containing material may include a Li complex. The Li complex may include, e.g., Compound ET-D1 (LiQ) or Compound ET-D2:
The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may be in direct contact (e.g., physical contact) with the second electrode 190.
The electron injection layer may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers, each 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 a combination thereof.
The alkali metal may be selected from Li, Na, K, Rb, and Cs. In some embodiments, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the present disclosure is not limited thereto.
The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.
The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may each independently be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodines) of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively.
The alkali metal compound may be selected from alkali metal oxides, such as Li2O, Cs2O, or K2O, and alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, or RbI. In some embodiments, the alkali metal compound may be selected from LiF, Li2O, NaF, LiI, NaI, CsI, and KI, but the present disclosure is not limited thereto.
The alkaline earth-metal compound may be selected from alkaline earth-metal compounds, such as BaO, SrO, CaO, BaxSr1-xO (wherein 0<x<1), and BaxCa1-xO (wherein 0<x<1). In some embodiments, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the present disclosure is not limited thereto.
The rare earth metal compound may be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, and TbF3. In some embodiments, the rare earth metal compound may be selected from YbF3, ScF3, TbF3, YbI3, ScI3, and TbI3, but the present disclosure is not limited thereto.
The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may each include ions of the above-described alkali metal, alkaline earth metal, and rare earth metal. Each ligand coordinated with the metal ion of the alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may independently be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the present disclosure is not limited thereto.
The electron injection layer may include (e.g., 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 a combination thereof, as described above. In some embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal compound, the alkaline earth metal compound, the rare earth metal compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or a combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
The thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and in some embodiments, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within any of the foregoing ranges, excellent electron injection characteristics may be obtained without a substantial increase in driving voltage.
Second Electrode 190
The second electrode 190 may be on the organic layer 150. In an embodiment, the second electrode 190 may be a cathode that is an electron injection electrode. In this embodiment, a material for forming the second electrode 190 may be a material having a low work function, for example, a metal, an alloy, an electrically conductive compound, or a combination thereof.
The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), silver-magnesium (Ag—Mg), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, and IZO, but the present disclosure is not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
The second electrode 190 may have a single-layered structure, or a multi-layered structure including two or more layers.
Description of
Referring to
The first electrode 110, the organic layer 150, and the second electrode 190 illustrated in
In the organic light-emitting devices 20 and 40, light emitted from the emission layer in the organic layer 150 may pass through the first electrode 110 (which may be a semi-transmissive electrode or a transmissive electrode) and through the first capping layer 210 to the outside. In the organic light-emitting devices 30 and 40, light emitted from the emission layer in the organic layer 150 may pass through the second electrode 190 (which may be a semi-transmissive electrode or a transmissive electrode) and through the second capping layer 220 to the outside.
The first capping layer 210 and the second capping layer 220 may improve the external luminescence efficiency based on the principle of constructive interference.
The first capping layer 210 and the second capping layer 220 may each independently have a refractive index of 1.6 or greater at a wavelength of 589 nm.
The first capping layer 210 and the second capping layer 220 may each independently be a capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.
At least one of the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In some embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include an amine-based compound.
In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include a compound represented by Formula 201 or a compound represented by 202.
In one or more embodiments, at least one of the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from Compounds HT28 to HT33 and Compound CP1 to CP5, but the present disclosure is not limited thereto:
Hereinbefore, the organic light-emitting device has been described with reference to
Electronic Apparatus
The organic light-emitting device may be included in various suitable electronic apparatuses. In some embodiments, an electronic apparatus including the organic light-emitting device may be an emission apparatus or an authentication apparatus.
The electronic apparatus (e.g., an emission apparatus) may further include, in addition to the organic light-emitting device, i) a color filter, ii) a color-conversion layer, or iii) a color filter and a color-conversion layer. The color filter and/or the color-conversion layer may be on at least one traveling direction of light emitted from the organic light-emitting device. For example, light emitted from the organic light-emitting device may be blue light or white light. The organic light-emitting device may be understood by referring to the description of the organic light-emitting device provided herein. In some embodiments, the color-conversion layer may include a quantum dot. The quantum dot may be, for example, the quantum dot described herein.
The electronic apparatus may include a first substrate. The first substrate may include a plurality of sub-pixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the plurality of sub-pixel areas, and the color-conversion layer may include a plurality of color-conversion areas respectively corresponding to the plurality of sub-pixel areas.
A pixel defining film may be located between the plurality of sub-pixel areas to define each sub-pixel area.
The color filter may further include a plurality of color filter areas and light-blocking patterns between the plurality of color filter areas, and the color-conversion layer may further include a plurality of color-conversion areas and light-blocking patterns between the plurality of color-conversion areas.
The plurality of color filter areas (or a plurality of color-conversion areas) may include: a first area emitting first color light; a second area emitting second color light; and/or a third area emitting third color light, and the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths. In some embodiments, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In some embodiments, the plurality of color filter areas (or the plurality of color-conversion areas) may each include a quantum dot. In some embodiments, the first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include a quantum dot. The quantum dot may be understood by referring to the description of the quantum dot provided herein. The first area, the second area, and/or the third area may each further include an emitter.
In some embodiments, the organic light-emitting device may emit first light, the first area may absorb the first light to emit 1-1 color light (e.g., a first first color light), the second area may absorb the first light to emit 2-1 color light (e.g., a second first color light), and the third area may absorb the first light to emit 3-1 color light (e.g., a third first color light). In this embodiment, the 1-1 color light (e.g., the first first color light), the 2-1 color light (e.g., the second first color light), and the 3-1 color light (e.g., the third first color light) may each have a different maximum emission wavelength. In some embodiments, the first light may be blue light, the 1-1 color light (e.g., the first first color light) may be red light, the 2-1 color light (e.g., the second first color light) may be green light, and the 3-1 light (e.g., the third first color light) may be blue light.
The electronic apparatus may further include a thin-film transistor, in addition to the organic light-emitting device. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein one of the source electrode and the drain electrode may be electrically coupled to one of the first electrode and the second electrode of the organic light-emitting device.
The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.
The activation layer may include a crystalline silicon, an amorphous silicon, an organic semiconductor, and/or an oxide semiconductor.
The electronic apparatus may further include a sealing portion for sealing the organic light-emitting device. The sealing portion may be located between the color filter and/or the color-conversion layer and the organic light-emitting device. The sealing portion may allow light to pass to the outside from the organic light-emitting device and prevent or reduce permeation of air and moisture into the organic light-emitting device at the same time. The sealing portion may be a sealing substrate including a transparent glass and/or a plastic substrate. The sealing portion may be a thin-film encapsulating layer including at least one of an organic layer and/or an inorganic layer. When the sealing portion is a thin film encapsulating layer, the electronic apparatus may be flexible.
In addition to the color filter and/or the color-conversion layer, various suitable functional layers may be on the sealing portion depending on the use of an electronic apparatus. Examples of the functional layer may include a touch screen layer, a polarization layer, and/or the like. The touch screen layer may be a resistive touch screen layer, a capacitive touch screen layer, and/or an infrared beam touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that identifies an individual according biometric information (e.g., a fingertip, a pupil, and/or the like).
The authentication apparatus may further include a biometric information collecting unit, in addition to the organic light-emitting device described above.
The electronic apparatus may be applicable in various suitable displays, an optical source, lighting, a personal computer (e.g., a mobile personal computer), a cellphone, a digital camera, an electronic note, an electronic dictionary, an electronic game console, a medical device (e.g., an electronic thermometer, a blood pressure meter, a glucometer, a pulse measuring device, a pulse wave measuring device, an electrocardiograph recorder, an ultrasonic diagnosis device, and/or an endoscope display device), a fish finder, various suitable measurement devices, gauges (e.g., gauges of an automobile, an airplane, and/or a ship), and/or a projector.
The layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region may be formed in a set or specific region by using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser printing, and/or laser-induced thermal imaging.
When the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are each formed by vacuum deposition, the vacuum deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C. at a vacuum degree in a range of about 10−8 torr to about 10−3 torr, and at a deposition rate in a range of about 0.01 Angstroms per second (Å/sec) to about 100 Å/sec, depending on the material to be included in each layer and the structure of each layer to be formed.
When the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are each formed by spin coating, the spin coating may be performed at a coating rate of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and at a heat treatment temperature of about 80° C. to about 200° C., depending on the material to be included in each layer and the structure of each layer to be formed.
General Definitions of Substituents
The term “C1-C60 alkyl group,” as used herein, refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Examples thereof include a methyl group, an ethyl group, a propyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. The term “C1-C60 alkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group,” as used herein, refers to a hydrocarbon group having at least one carbon-carbon double bond at a main chain (e.g., in the middle) or at a terminal end (e.g., the terminus) of the C2-C60 alkyl group. 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 substantially the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group,” as used herein, refers to a hydrocarbon group having at least one carbon-carbon triple bond at a main chain (e.g., in the middle) or at a terminal end (e.g., the terminus) of the C2-C60 alkyl group. 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 substantially the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group,” as used herein, refers to a monovalent group represented by —OA101 (wherein A101 is a C1-C1 alkyl group). Examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C3-C10 cycloalkyl group,” as used herein, refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms. 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 substantially the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group,” as used herein, refers to a monovalent monocyclic group including at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms. Examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group,” as used herein, refers to a divalent group having substantially 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 double bond in its ring, and is not aromatic. 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 substantially the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group,” as used herein, refers to a monovalent monocyclic group including at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolylgroup, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkyl group.
The term “C6-C60 aryl group,” as used herein, refers to a monovalent group having a carbocyclic aromatic system having 6 to 6 carbon atoms. 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 fluorenyl group, 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 independently include two or more rings, the respective rings may be fused (e.g., combined together).
The term “C1-C60 heteroaryl group,” as used herein, refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S 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 heterocyclic aromatic system having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group include a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each independently include two or more rings, the respective rings may be fused (e.g., combined together).
The term “C6-C60 aryloxy group,” as used herein, is represented by —OA102 (wherein A102 is the C6-C60 aryl group). The term “C6-C60 arylthio group,” as used herein, is represented by —SA103 (wherein A103 is the C6-C60 aryl group).
The term “monovalent non-aromatic condensed polycyclic group,” as used herein, refers to a monovalent group that has two or more rings condensed (e.g., combined together) and only carbon atoms as ring forming atoms (e.g., 8 to 60 carbon atoms), wherein the entire molecular structure is non-aromatic. Examples of the monovalent non-aromatic condensed polycyclic group may include an adamantyl group. The term “divalent non-aromatic condensed polycyclic group,” as used herein, refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group,” as used herein, refers to a monovalent group that has two or more condensed rings and at least one heteroatom selected from N, O, Si, P, and S, in addition to carbon atoms (e.g., 1 to 60 carbon atoms), as a ring-forming atom, wherein the entire molecular structure is non-aromatic. Examples of the monovalent non-aromatic condensed heteropolycyclic group may include an azaadamantyl group. The term “divalent non-aromatic condensed heteropolycyclic group,” as used herein, refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
The term “C5-C60 carbocyclic group,” as used herein, refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms only as ring-forming atoms. The C5-C60 carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The term “C5-C60 carbocyclic group,” as used herein, refers to a ring (e.g., a benzene group), a monovalent group (e.g., a phenyl group), or a divalent group (e.g., a phenylene group). Also, depending on the number of substituents connected to the C5-C60 carbocyclic group, the C5-C60 carbocyclic group may be a trivalent group or a quadrivalent group.
The term “C1-C60 heterocyclic group,” as used herein, refers to a group having substantially the same structure as the C5-C60 carbocyclic group, except that at least one heteroatom selected from N, O, Si, P, and S is used as a ring-forming atom, in addition to carbon atoms (e.g., 1 to 60 carbon atoms).
In the present specification, at least one of substituents of the substituted C5-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, the substituted C3-C10 cycloalkylene group, the substituted C1-C10 heterocycloalkylene group, the substituted C3-C10 cycloalkenylene group, the substituted C1-C10 heterocycloalkenylene group, the substituted C6-C60 arylene group, the substituted C1-C60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
“Ph,” as used herein, represents a phenyl group, “Me,” as used herein, represents a methyl group, “Et,” as used herein, represents an ethyl group, “ter-Bu” or “But,” as used herein, represents a tert-butyl group, and “OMe,” as used herein, represents a methoxy group.
The term “biphenyl group,” as used herein, refers to a phenyl group substituted with at least one phenyl group. The “biphenyl group” belongs to “a substituted phenyl group” having a “C6-C60 aryl group” as a substituent.
The term “terphenyl group,” as used herein, refers to a phenyl group substituted with at least one phenyl group. The “terphenyl group” belongs to “a substituted phenyl group” having a “C6-C60 aryl group substituted with a C6-C60 aryl group” as a substituent.
The symbols * and *′, as used herein, unless defined otherwise, refer to a binding site to an adjacent atom in a corresponding formula.
Hereinafter, compounds and an organic light-emitting device according to one or more embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of B used was identical to an amount of A used in terms of molar equivalents.
Synthesis of Intermediate 8-1
9H-carbazole (CAS no. 86-74-8) was reacted with 1-bromo-2-fluorobenzene (CAS no. 1072-85-1) in the presence of a Pd catalyst, thereby obtaining Intermediate 8-1. Intermediate 8-1 was subjected to liquid chromatography-mass spectrometry (LC-MS) to identify the M+1 peak value thereof.
C18H12BrN: M+1 322.11
Synthesis of Intermediate 8-2
Intermediate 8-1 was reacted with n-BuLi and then with trimethyl borate to obtain Intermediate 8-2. Intermediate 8-2 was subjected to LC-MS to identify the M+1 peak value thereof.
C18H14BNO2: M+1 288.01
Synthesis of Intermediate 8-3
Bromo-9H-carbazole (CAS no. 1592-95-6), potassium hydroxide, and 4-toluene sulfonyl chloride were reacted together, thereby obtaining Intermediate 8-3. Intermediate 8-3 was subjected to LC-MS to identify the M+1 peak value thereof. C19H14BrNO2S: M+1 399.87
1-4. Synthesis of Intermediate 8-4
Intermediate 8-3 was reacted with Intermediate 66-3 in the presence of a Pd catalyst, thereby obtaining Intermediate 8-4. Intermediate 8-4 was subjected to LC-MS to identify the M+1 peak value thereof.
C41H36N2O2S: M+1 621.13
1-5. Synthesis of Intermediate 8-5
Intermediate 8-4 was reacted with sodium hydroxide, thereby obtaining Intermediate 8-5. Intermediate 8-5 was subjected to LC-MS to identify the M+1 peak value thereof.
C34H30N2: M+1 467.25
1-6. Synthesis of Intermediate 8-6
Intermediate 8-5 was reacted with 1-bromo-3-iodobenzene (CAS no. 591-18-4) in the presence of a Cu catalyst, thereby obtaining Intermediate 8-6. Intermediate 8-6 was subjected to LC-MS to identify the M+1 peak value thereof.
C40H33BrN2: M+1 621.33
1-7. Synthesis of Compound 8
4 grams (g) of Intermediate 8-6, 1.9 g of Intermediate 8-2, 1.3 g of potassium carbonate, 0.37 g of tetrakis(triphenyl phosphine)palladium (0), 20 milliliters (mL) of tetrahydrofuran, and 5 mL of water were added to a reaction vessel and refluxed for 24 hours. Once the reaction was believed to be complete, the reaction solution was subjected to extraction using ethyl acetate, and the resulting organic layer was dried using magnesium sulfate. Then, the solvent was removed therefrom. The residue obtained by removing the solvent was separated and purified using silica gel column chromatography, thereby obtaining 3.8 g of Compound 8 (yield: 76%). Compound 8 was identified using LC-MS and 1H-nuclear magnetic resonance (NMR).
3 g of bromodibenzofuran (CAS no. 86-76-0), 5.9 g of Intermediate 8-5, 1.8 g of sodium tert-butoxide, 0.46 g of tris(dibenzylideneacetone)dipalladium (0), 0.4 mL of tri-tert-butylphosphine, and 60 mL of toluene were added to a reaction vessel and refluxed for 24 hours. Once the reaction was believed to be complete, the reaction solution was subjected to extraction using ethyl acetate, and the resulting organic layer was dried using magnesium sulfate. Then, the solvent was removed therefrom. The residue obtained by removing the solvent was separated and purified using silica gel column chromatography, thereby obtaining 10.8 g of Compound 29 (yield: 85%). Compound 29 was identified using LC-MS and 1H-NMR.
10.1 g of Compound 34 was synthesized in substantially the same manner as in Synthesis of Compound 29, except that 2-bromodibenzothiophene (CAS no. 22439-61-8) was used instead of 2-bromodibenzofuran (CAS no. 86-76-0) (yield: 82%). Compound 34 was identified using LC-MS and 1H-NMR.
8.7 g of Compound 38 was synthesized in substantially the same manner as in Synthesis of Compound 29, except that 3-bromo-9-phenyl-9H-carbazole (CAS no. 1153-85-1) was used instead of 3-bromodibenzofuran (CAS no. 86-76-0) (yield: 80%). Compound 38 was identified using LC-MS and 1H-NMR.
5-1. Synthesis of Intermediate 40-1
Intermediate 8-5 was reacted with 1-bromo-2-fluorobenzene (CAS no. 1072-85-1) in the presence of a Pd catalyst, thereby obtaining Intermediate 40-1. Intermediate 40-1 was subjected to LC-MS to identify the M+1 peak value thereof.
C40H33BrN2: M+1 621.24
5-2. Synthesis of Compound 40
5.5 grams (g) of Intermediate 40-1, 3.4 g of (3-(triphenylsilyl)phenyl)boronic acid, 1.7 g of potassium carbonate, 0.46 g of tetrakis(triphenyl phosphine)palladium (0), 25 mL of 1,4-dioxane, and 6 mL of water were added to a reaction vessel and refluxed for 24 hours. Once the reaction was believed to be complete, the reaction solution was subjected to extraction using ethyl acetate, and the resulting organic layer was dried using magnesium sulfate. Then, the solvent was removed therefrom. The residue obtained by removing the solvent was separated and purified using silica gel column chromatography, thereby obtaining 4.8 g of Compound 40 (yield: 68%). Compound 40 was identified using LC-MS and 1H-NMR.
7.5 g of Compound 44 was synthesized in substantially the same manner as in Synthesis of Compound 29, except that (3-bromophenyl)triphenyl silane (CAS no. 185626-73-7) was used instead of 2-bromodibenzofuran (CAS no. 86-76-0) (yield: 78%). Compound 44 was identified using LC-MS and 1H-NMR.
7.3 g of Compound 59 was synthesized in substantially the same manner as in Synthesis of Compound 29, except that 3-bromo-9,9-diphenyl-9H-fluorene (CAS no. 1547491-70-2) was used instead of 2-bromodibenzofuran (CAS no. 86-76-0) (yield: 75%). Compound 59 was identified using LC-MS and 1H-NMR.
8-1. Synthesis of Intermediate 66-1
2-bromo-N-phenylaniline (CAS no. 61613-22-7), 4-(dimethylamino)pyridine (4-DMAP), and dineopentyl dicarbonate (CAS no. 24424-99-5) were reacted to obtain Intermediate 66-1. Intermediate 66-1 was subjected to LC-MS to identify the M+1 peak value thereof.
C17H18BrNO2: M+1 348.15
8-2. Synthesis of Intermediate 66-2
Intermediate 66-1 was reacted with n-BuLi and then with 2-adamantane-one (CAS no. 700-58-3) to obtain Intermediate 66-2. Intermediate 66-2 was subjected to LC-MS to identify the M+1 peak value thereof.
C27H33NO3: M+1 420.21
8-3. Synthesis of Intermediate 66-3
Intermediate 66-2, acetic acid, and hydrochloric acid were reacted together to obtain Intermediate 66-3. Intermediate 66-3 was subjected to LC-MS to identify the M+1 peak value thereof.
C22H23N: M+1 302.31
8-4. Synthesis of Intermediate 66-4
9H-carbazole (CAS no. 86-74-8) was reacted with 2-bromo-1-fluoro-3-iodobenzene (CAS no. 851368-08-6) in the presence of a Pd catalyst to obtain Intermediate 66-4. Intermediate 66-4 was subjected to LC-MS to identify the M+1 peak value thereof.
C18H11BrIN: M+1 447.97
8-5. Synthesis of Intermediate 66-5
Intermediate 66-3 was reacted with Intermediate 66-4 in the presence of a Cu catalyst, thereby obtaining Intermediate 66-6. Intermediate 66-5 was subjected to LC-MS to identify the M+1 peak value thereof.
C40H33BrN2: M+1 620.24
8-6. Synthesis of Compound 66
3.5 g of Compound 66 was synthesized in substantially the same manner as in Synthesis of Compound 40, except that Intermediate 66-5 was used instead of Intermediate 40-1 (yield: 50%). Compound 66 was identified using LC-MS and 1H-NMR.
Compounds synthesized in Synthesis Examples 1 to 8 were identified by 1H NMR and LC-MS. The results thereof are shown in Table 1.
Methods of synthesizing compounds other than compounds shown in Table 1 may be readily understood by those skilled in the art by referring to the synthesis pathways and raw materials described above.
1H NMR (CDCl3, 400 MHz)
An ITO substrate having a thickness of 1,200 Å was used as a first electrode (anode). The ITO substrate was sonicated for 5 minutes each using isopropyl alcohol and distilled water, and then irradiated with ultraviolet rays for 30 minutes and exposure to ozone for washing. The washed ITO substrate was mounted in a vacuum-deposition apparatus.
N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB) was vacuum-deposited on the ITO substrate prepared by washing to form a hole injection layer having a thickness of 300 Å. mCP was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 200 Å.
Subsequently, Compound 8 (as a host) and Ir(pmp)3 (as a dopant) were co-deposited on the hole transport layer to a weight ratio of 92:8 to form an emission layer having a thickness of 250 Å.
Then, 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ) was deposited on the emission layer to form an electron transport layer having a thickness of 200 Å. LiF was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer. Al was vacuum-deposited on the electron injection layer to a thickness of 100 Å to form a second electrode (cathode), thereby forming an LiF/Al electrode. HT28 was vacuum-deposited on the cathode to form a capping layer having a thickness of 700 Å, thereby completing the manufacture of an organic light-emitting device.
Materials used in preparation of the organic light-emitting device may be represented by the following formula:
Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 2 were respectively used in the formation of the emission layer.
Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that Compounds C1 to C3 were respectively used in the formation of the emission layer.
To evaluate characteristics of the organic light-emitting devices manufactured in Examples 1 to 8 and Comparative Examples 1 to 3, the driving voltage, current efficiency, and maximum quantum efficiency of the organic light-emitting devices at a current density of 10 milliamperes per square centimeter (mA/cm2) were measured. The driving voltage and the current density of the organic light-emitting devices were measured using a source meter (Keithley Instrument, 2400 series). The maximum quantum efficiency of the organic light-emitting devices were measured using Hamamatsu Absolute PL Quantum Yield Measurement System C9920-2-12. In evaluation of the maximum quantum efficiency, luminance/current density was measured using a luminance meter with calibration of wavelength sensitivity, and the maximum external quantum efficiency was calculated on the assumption of the angular luminance distribution (Lambertian) assuming a complete diffusion reflecting surface. The evaluation results of the organic light-emitting devices are shown in Table 2.
As shown in the results of Table 2, the organic light-emitting devices of Examples 1 to 8 were found to have a low driving voltage and a high maximum quantum efficiency, as compared with the organic light-emitting device of Comparative Examples 1 to 3.
As apparent from the foregoing description, an organic light-emitting device including the heterocyclic compound may have a low driving voltage, high efficiency, and high maximum quantum efficiency.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the following claims, and equivalents thereof.
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| 109438350 | Mar 2019 | CN |
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