Patent Application
20240373662
This application is based on and claims priority under 35 U.S.C. § 119 to Korean Patent Application No. 10-2023-0039290, filed on Mar. 24, 2023, in the Korean Intellectual Property Office, the content of which is herein incorporated by reference in its entirety.
The disclosure relates to a heterocyclic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.
Organic light-emitting devices are self-emissive devices that, as compared with devices in the art, have wide viewing angles, short response times, brightness, reduced driving voltages, and produce full-color images.
In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer that is arranged between the anode and the cathode and includes an emission layer. A hole transport region may be arranged between the anode and the emission layer, and an electron transport region may be arranged between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. The excitons may transition from an excited state to a ground state, thus generating light.
The need remains for novel materials for organic light-emitting devices.
Provided are a heterocyclic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to an aspect of an embodiment, provided is a heterocyclic compound represented by Formula 1:
wherein in Formula 1,
In Formulae 1, 1A, 2A, and 3A,
According to another aspect of the disclosure, an organic light-emitting device includes the heterocyclic compound.
According to another aspect of the disclosure, an electronic apparatus includes the organic light-emitting device.
The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. 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.
An aspect of the disclosure provides a heterocyclic compound represented by Formula 1:
In Formula 1A, one of CY10, CY11, and CY12 may be condensed into Formula 1.
In Formula 1A, X11 and X12 may each independently be O, S, Se, C(R41)(R42), Si(R41)(R42), Ge(R41)(R42), B(R41), P(R41), P(═O)(R41), S(═O)2, or C(═O).
In Formula 1, CY2 may be a group represented by Formula 2A, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R1, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R1:
In Formula 2A, CY21 and CY22 may each independently be a C5-C30 carbocyclic group unsubstituted or substituted with at least one R20 or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R20.
In Formula 2A, X21 and X22 may each independently be O, S, Se, N(R43), C(R43)(R44), Si(R43)(R44), Ge(R43)(R44), B(R43), P(R43), P(═O)(R43), S(═O)2, or C(═O).
In Formula 1, CY3 may be a group represented by Formula 3A, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R1, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R1:
In Formula 3A, CY30 may be a benzene group condensed into Formula 1 and unsubstituted or substituted with at least one R30.
In Formula 3A, CY31 and CY32 may each independently be a C5-C30 carbocyclic group unsubstituted or substituted with at least one R30 or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R30.
In Formula 3A, X31 and X32 may each independently be O, S, Se, N(R45), C(R45)(R46), Si(R45)(R46), Ge(R45)(R46), B(R45), P(R45), P(═O)(R45), S(═O)2, or C(═O).
The heterocyclic compound may include at least one of the group represented by Formula 1A, the group represented by Formula 2A, and the group represented by Formula 3A.
In an embodiment, CY1 may be (i) a first ring, (ii) a second ring, (iii) a condensed cyclic group in which two or more first rings are condensed with each other, (iv) a condensed cyclic group in which two or more second rings are condensed with each other, (v) a condensed cyclic group in which at least one first ring is condensed with at least one second ring, or (vi) the group represented by Formula 1A,
In an embodiment, CY2 may be (i) a first ring, (ii) a second ring, (iii) a condensed cyclic group in which two or more first rings are condensed with each other, (iv) a condensed cyclic group in which two or more second rings are condensed with each other, (v) a condensed cyclic group in which at least one first ring is condensed with at least one second ring, or (vi) the group represented by Formula 2A,
In an embodiment, CY3 may be (i) a first ring, (ii) a second ring, (iii) a condensed cyclic group in which two or more first rings are condensed with each other, (iv) a condensed cyclic group in which two or more second rings are condensed with each other, (v) a condensed cyclic group in which at least one first ring is condensed with at least one second ring, or (vi) the group represented by Formula 3A,
In an embodiment, CY1 may be the group represented by Formula 1A, a C6-C30 aromatic carbocyclic group, or a C1-C30 aromatic heterocyclic group.
In an embodiment, CY2 may be the group represented by Formula 2A, a C6-C30 aromatic carbocyclic group, or a C1-C30 aromatic heterocyclic group.
In an embodiment, CY3 may be the group represented by Formula 3A, a C6-C30 aromatic carbocyclic group, or a C1-C30 aromatic heterocyclic group.
In an embodiment, CY1 may be the group represented by Formula 1A, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, a azabenzothiophene group, a azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.
In an embodiment, CY2 may be the group represented by Formula 2A, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.
In an embodiment, CY3 may be the group represented by Formula 3A, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.
In an embodiment, CY1 may be the group represented by Formula 1A, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, or a phenanthroline group.
In an embodiment, CY2 may be the group represented by Formula 2A, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, or a phenanthroline group.
In an embodiment, CY3 may be the group represented by Formula 3A, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, or a phenanthroline group.
In an embodiment, CY21, CY22, CY31, and CY32 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed, iv) a condensed ring in which at least two second rings are condensed, or v) a condensed ring in which at least one first ring is condensed with at least one second ring,
In an embodiment, CY21, CY22, CY31, and CY32 may each independently be the group represented by Formula 2A, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, a azabenzothiophene group, a azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.
In an embodiment, CY21, CY22, CY31, and CY32 may each independently a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, or a phenanthroline group.
In an embodiment, X11 and X12 may each independently be O, S, or Se.
In an embodiment, X21 and X22 may each independently be O, S, Se, or N(R43).
In an embodiment, X31 and X32 may each independently be O, S, Se, or N(R45).
In an embodiment, the group represented by Formula 1A may be a group represented by Formula 1A-1 or 1A-2:
In an embodiment, the group represented by Formula 2A may be a group represented by Formula 2A-1 or 2A-2:
In an embodiment, the group represented by Formula 3A may be a group represented by Formula 3A-1 or 3A-2:
R1, R10, R20, R30, and R41 to R46 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl 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 C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —B(Q1)(Q2), —P(Q1)(Q2), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2).
In an embodiment, R1, R10, R20, R30, and R41 to R46 may each independently be: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF5, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
In an embodiment, R1, R10, R20, R30, and R41 to R46 may each independently be:
In an embodiment, R2 to R9, R11 to R19, R21 to R29, and R31 and R39 may each independently be hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, a sec-pentyl group, a tert-pentyl group, a neo-pentyl group, a 3-pentyl group, a 3-methyl-2-butyl group, a phenyl group, a biphenyl group, a C1-C20 alkylphenyl group, or a naphthyl group.
In an embodiment, CY1 may be the group represented by Formula 1A.
In an embodiment, CY2 may be the group represented by Formula 2A.
In an embodiment, CY3 may be the group represented by Formula 3A.
In an embodiment, CY1 may be the group represented by Formula 1A, and CY2 may be the group represented by Formula 2A.
In an embodiment, CY1 may be the group represented by Formula 1A, and CY3 may be the group represented by Formula 3A.
In an embodiment, CY2 may be the group represented by Formula 2A, and CY3 may be the group represented by Formula 3A.
In an embodiment, CY1 may be the group represented by Formula 1A, CY2 may be the group represented by Formula 2A, and CY3 may be the group represented by Formula 3A.
In an embodiment, the heterocyclic compound may be represented by one of Formulae 11-1 to 11-7:
In an embodiment, the heterocyclic compound may be represented by one of Formulae 21-1 to 21-7:
In an embodiment, R1, R10, R20, R30, and R41 to R46 may each independently be hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a 2-methylbutyl group, a sec-pentyl group, a tert-pentyl group, a neo-pentyl group, a 3-pentyl group, a 3-methyl-2-butyl group, a phenyl group, a biphenyl group, a C1-C20 alkylphenyl group, or a naphthyl group.
Neighboring two or more of R1, R10, R20, R30, and R41 to R46 may optionally be linked together to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
In an embodiment, neighboring two or more of R2 to R9, R11 to R19, R21 to R29, and R31 and R39 may optionally be linked to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
In an embodiment, the heterocyclic compound may have a symmetrical structure or an asymmetrical structure. “Symmetrical structure” as used herein refers to a linearly symmetrical structure with respect to a symmetry axis.
For example, the heterocyclic compound may have a symmetrical structure with respect to a symmetry axis along the chemical bond connecting N of Formula 1 to CY1, CY2, and/or CY3.
For example, the heterocyclic compound may have an asymmetrical structure.
In the present specification, a substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C2-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, the substituted monovalent non-aromatic condensed heteropolycyclic 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, and the substituted divalent non-aromatic condensed heteropolycyclic group may be:
In the present specification, Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be:
For example, in the present specification, Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be:
In an embodiment, the heterocyclic compound may be one of Compounds 1 to 3, but embodiments are not limited thereto:
The heterocyclic compound represented by Formula 1 may satisfy the aforementioned structure of Formula 1, and may include at least one of the group represented by Formula 1A, the group represented by Formula 2A, and the group represented by 3A. Due to this structure, the heterocyclic compound represented by Formula 1 may have luminescence characteristics, and in particular, may be able to provide deep blue luminescence of a short wavelength.
Although not limited by a certain theory, the heterocyclic compound satisfying the aforementioned structure may have a small difference (ΔEST) between singlet energy and triplet energy and strong spin orbital coupling, and thus the decay time may be reduced. Therefore, when the heterocyclic compound is applied to an organic light-emitting device, a roll-off phenomenon is reduced, and accordingly, the organic light-emitting device can exhibit high luminescence efficiency and a narrow electroluminescence spectrum.
The highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, S1 energy level, T1 energy level in electron volts (eV), and ΔEST of some compounds of the heterocyclic compound represented by Formula 1 were evaluated by using the Gaussian 09 program with the molecular structure optimization obtained by PBE0-based density functional theory (DFT) and results thereof are shown in Table 1.
Referring to Table 1, it is confirmed that the heterocyclic compound represented by Formula 1 has electrical characteristics that are suitable for use as a dopant (e.g., an emitter or a sensitizer) for an electronic device, for example, an organic light-emitting device.
In an embodiment, the full width at half maximum (FWHM) of the emission peak of the emission spectrum or electroluminescence (EL) spectrum of the heterocyclic compound may be 60 nanometers (nm) or less. For example, the FWHM of the emission peak of the emission spectrum or EL spectrum of the heterocyclic compound may be in a range of about 5 nm to about 50 nm, about 7 nm to about 40 nm, or about 10 nm to about 30 nm.
Synthesis methods of the heterocyclic compound represented by Formula 1 may be recognizable by those skilled in the art by referring to Synthesis Examples provided below.
Ways of confirming the structure of the heterocyclic compound represented by Formula 1 are not particularly limited. In an embodiment, the structure of the heterocyclic compound may be confirmed by a known method (e.g., nuclear magnetic resonance spectrometry (NMR), liquid chromatograph-mass spectrometry (LC-MS), etc.).
Another aspect of the disclosure provides an organic light-emitting device including the heterocyclic compound.
In an embodiment, the organic light-emitting device may include: a first electrode; a second electrode; and an organic layer arranged between the first electrode and the second electrode and including an emission layer, wherein
In an embodiment, the emission layer may include the heterocyclic compound.
In an embodiment, the emission layer may further include a host and an emitter, and the emitter may include the heterocyclic compound.
In an embodiment, based on a weight, an amount of the host in the emission layer may be greater than that of the heterocyclic compound in the emission layer.
In an embodiment, the emission layer may further include a sensitizer.
In an embodiment, the sensitizer may include a phosphorescent compound, a delayed fluorescence compound, or any combination thereof.
Details for the aforementioned host, emitter, and sensitizer may be referred to in the descriptions provided herein.
By including the emission layer including the heterocyclic compound represented by Formula 1, the organic light-emitting device may have a relatively narrow FWHM of the emission layer of the EL spectrum and excellent efficiency and lifespan characteristics.
In an embodiment, the heterocyclic compound may serve as a dopant (e.g., an emitter or a sensitizer) in the emission layer, and the emission layer may further include a host (that is, in the emission layer, the amount of the heterocyclic compound represented by Formula 1 may be smaller than that of the host).
In an embodiment, the emission layer may emit blue light. For example, the emission layer may emit blue light having a maximum emission wavelength in a range of about 410 nm to about 490 nm.
The expression “an emission layer includes at least one heterocyclic compound represented by Formula 1” as used herein may include an embodiment in which an emission layer includes identical heterocyclic compounds represented by Formula 1 or an embodiment in which an emission layer includes two or more different heterocyclic compounds represented by Formula 1.
In an embodiment, the emission layer may include, as the heterocyclic compound, only Compound 1. In this embodiment, Compound 1 may be included in the emission layer of the organic light-emitting device. In one or more embodiments, the emission layer may include, as the heterocyclic compound, Compound 1 and Compound 2.
The organic light-emitting device 10 of
The organic layer 15 includes an emission layer, and a hole transport region may be arranged between the first electrode 11 and the emission layer and an electron transport region may be arranged between the emission layer and the second electrode 19.
A substrate may be additionally arranged under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, e.g., a glass substrate or a transparent plastic substrate, each with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and/or water repellency.
The first electrode 11 may be prepared by depositing or sputtering, onto the substrate, a material for forming the first electrode 11. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials with a high work function for easy hole injection.
The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In an embodiment, when the first electrode 11 is a transmissive electrode, the material for forming the first electrode 11 may be selected from indium tin oxide (“ITO”), indium zinc oxide (“IZO”), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but embodiments are not limited thereto. In one or more embodiments, when the first electrode 11 is a semi-transmissive electrode or a reflective electrode, the material for forming the first electrode 11 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combination thereof, but embodiments of the disclosure are not limited thereto.
The first electrode 11 may have a single-layered structure or a multi-layered structure including a plurality of layers.
The emission layer may include the heterocyclic compound.
A thickness of the emission layer may be in a range of about 100 angstroms (Å) to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, excellent luminescence characteristics may be obtained without a substantial increase in driving voltage, e.g., without an increase in driving voltage of greater than about 20%.
In an embodiment, the heterocyclic compound may be a fluorescent emitter.
In an embodiment, the emission layer may further include a host (hereinafter, referred to as ‘Host A’, and Host A is not identical to the heterocyclic compound). Host A may be understood by referring to the description of the host material provided herein, but embodiments are not limited thereto. Host A may be a fluorescent host.
Referring to
Singlet excitons are formed in Host A in the emission layer, and these singlet excitons formed in Host A may be transferred to the fluorescent emitter through Förster energy transfer (or Förster resonance energy transfer (FRET)).
The singlet excitons produced in Host A only accounts for 25%, and thus, 75% of triplet excitons produced in Host A may be fused to one another to be converted into singlet excitons. Thus, efficiency of the organic light-emitting device may be further improved. That is, by using the triplet-triplet fusion (TTF) mechanism, efficiency of the organic light-emitting device may be further improved.
In an embodiment, a ratio of emission components emitted from the heterocyclic compound to the total emission components emitted from the emission layer may be equal to or greater than 80%, for example, equal to or greater than 90%. For example, a ratio of emission components emitted from the heterocyclic compound to the total emission components emitted from the emission layer may be equal to or greater than 95%.
In this regard, the heterocyclic compound may emit fluorescence, and the host may not emit light.
In an embodiment, when the emission layer further includes Host A, in addition to the heterocyclic compound, an amount of the heterocyclic compound may be, based on 100 parts by weight of the emission layer, less than or equal to 50 parts by weight, for example, less than or equal to 30 parts by weight or less, and an amount of Host A in the emission layer may be, based on 100 parts by weight of the emission layer, equal to or greater than 50 parts by weight, for example, equal to or greater than 70 parts by weight. However, embodiments of the disclosure are not limited thereto.
In an embodiment, when the emission layer further includes Host A, in addition to the heterocyclic compound, Host A and the heterocyclic compound may satisfy Condition A:
Here, E(HA)S1 and ES1 may be evaluated by using a Gaussian program according to density functional theory (DFT) method (wherein structure optimization is performed at a degree of B3LYP, and 6-31G(d,p)).
In an embodiment, the heterocyclic compound may be a delayed fluorescence emitter.
In an embodiment, the emission layer may further include a host (hereinafter, referred to as ‘Host B’, and Host B is not identical to the heterocyclic compound). Host B may be understood by referring to the description of the host material provided herein, but embodiments are not limited thereto.
Referring to
25% of singlet excitons produced in Host B of the emission layer may be transferred to a delayed fluorescence emitter through FRET. In addition, 75% of triplet excitons produced in Host B of the emission layer may be transferred to a delayed fluorescence emitter through Dexter energy transfer. Among the transfer, at least a part of the energy of the singlet of the delayed fluorescence emitter may be transferred to the triplet by intersystem crossing (ISC). The energy transferred to the triplet of the delayed fluorescence emitter may undergo reverse intersystem crossing (RISC). Accordingly, by transferring all the singlet excitons and triplet excitons produced in the emission layer to the heterocyclic compound, an organic light-emitting device having improved efficiency may be obtained.
Therefore, a ratio of emission components emitted from the heterocyclic compound to the total emission components emitted from the emission layer may be equal to or greater than 80%, for example, equal to or greater than 90%. For example, a ratio of emission components emitted from the heterocyclic compound to the total emission components emitted from the emission layer may be equal to or greater than 95%.
In this regard, the heterocyclic compound may emit fluorescence and/or delayed fluorescence, and the emission components of the heterocyclic compound are the sum of prompt emission components of the heterocyclic compound and delayed fluorescence components of the heterocyclic compound by the RISC. In addition, Host B may not emit light.
In an embodiment, when the emission layer further includes Host B, in addition to the heterocyclic compound, an amount of the heterocyclic compound may be, based on 100 parts by weight of the emission layer, less than or equal to 50 parts by weight, for example, less than or equal to 30 parts by weight or less, and an amount of Host B in the emission layer may be, based on 100 parts by weight of the emission layer, equal to or greater than 50 parts by weight, for example, equal to or greater than 70 parts by weight. However, embodiments of the disclosure are not limited thereto.
In an embodiment, when the emission layer further includes Host B, in addition to the heterocyclic compound, Host B and the heterocyclic compound may satisfy Condition B:
Here, E(HB)S1 and ES1 may be evaluated by using a Gaussian program according to a density functional theory (DFT) method (wherein structure optimization is performed at a degree of B3LYP, and 6-31G(d,p)).
In an embodiment, the heterocyclic compound may be used as a fluorescence emitter, and the emission layer may include a sensitizer, e.g., a delayed fluorescence sensitizer. In an embodiment, the emission layer may further include a host (hereinafter, referred to as ‘Host C’, and Host C may not be identical to the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter, referred to as ‘Sensitizer A’, and Sensitizer A may not be identical to Host C and the heterocyclic compound). Host C and Sensitizer A may respectively be understood by referring to the descriptions of the host material and the sensitizer material provided herein, but embodiments are not limited thereto.
In an embodiment, a ratio of emission components of the heterocyclic compound to the total emission components emitted from the emission layer may be equal to or greater than 80%, for example, equal to or greater than 90% (or for example, equal to or greater than 95%). For example, the heterocyclic compound may emit fluorescence. In addition, Host C and Sensitizer A may each not emit light.
Referring to
Singlet and triplet excitons may be produced in Host C in the emission layer, and singlet and triplet excitons produced in Host C may be transferred to Sensitizer A and then to the heterocyclic compound through FRET. 25% of singlet excitons produced in Host C may be transferred to Sensitizer A through FRET, and the energy of 75% of triplet excitons produced in Host C may be transferred to singlet and triplet of Sensitizer A. Among the transfer, at least a part of the singlet energy of Sensitizer A may be transferred to the triplet by ISC. The energy transferred to the triplet of Sensitizer A may be transferred to singlet by RISC, and the singlet energy of Sensitizer A may be transferred to the heterocyclic compound by FRET.
Accordingly, by transferring all the singlet excitons and triplet excitons generated in the emission layer to the dopant (e.g., an emitter), the organic light-emitting device having improved efficiency may be obtained. In addition, since the organic light-emitting device may be obtained with significantly reduced energy loss, the lifespan characteristics of the organic light-emitting device may be improved.
Referring to
S1(HC), S1(SA), and S1(HC) may be evaluated according to the DFT method, wherein structure optimization is performed at a degree of B3LYP, and 6-31G(d,p), for example, according to a Gaussian program according to the DFT method.
When Host C, Sensitizer A, and the heterocyclic compound satisfy Condition C-1 and/or C-2, FRET from Sensitizer A to the heterocyclic compound may be facilitated, and accordingly, the organic light-emitting device may have improved luminescence efficiency.
In an embodiment, the heterocyclic compound may be used as a fluorescence emitter, and the emission layer may include a sensitizer, e.g., a photoluminescence sensitizer.
In an embodiment, the emission layer may further include a host (hereinafter, referred to as ‘Host D’, and Host D is not identical to the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter, referred to as ‘Sensitizer B’, and Sensitizer B is not identical to Host D and the heterocyclic compound). Host D and Sensitizer B may respectively be understood by referring to the descriptions of a host material and a sensitizer material described below, but embodiments of the disclosure are not limited thereto.
In an embodiment, a ratio of emission components of the heterocyclic compound to the total emission components emitted from the emission layer may be equal to or greater than 80%, for example, equal to or greater than 90% (or for example, equal to or greater than 95%). For example, the heterocyclic compound may emit fluorescence. In addition, Host D and Sensitizer B may not emit light.
Referring to
75% of triplet excitons produced in Host D of the emission layer may be transferred to Sensitizer B through Dexter energy transfer, and the energy of 25% of singlet excitons produced in Host D may be transferred to singlet and triplet of Sensitizer B. Among the transfer, the energy transferred to singlet of Sensitizer B may be transferred through ISC, and the triplet energy of Sensitizer B may be transferred to the heterocyclic compound through FRET.
Accordingly, by transferring all the singlet excitons and triplet excitons generated in the emission layer to the dopant (e.g., an emitter), the organic light-emitting device having improved efficiency may be obtained. In addition, since an organic light-emitting device may be obtained with significantly reduced energy loss, the lifespan characteristics of the organic light-emitting device may be improved.
In an embodiment, when the emission layer further includes Host D and Sensitizer B, in addition to the heterocyclic compound, Host D and Sensitizer B may satisfy Condition D-1 and/or D-2:
T1(HD), T1(SB), and S1(HC) may be evaluated according to the DFT method, wherein structure optimization is performed at a degree of B3LYP, and 6-31G(d,p), for example, by using a Gaussian program according to the DFT method.
When Host D, Sensitizer B, and the heterocyclic compound satisfy Condition D-1 and/or D-2, FRET from Sensitizer B to the heterocyclic compound may be facilitated, and accordingly, the organic light-emitting device may have improved luminescence efficiency.
In an embodiment, an amount of the sensitizer in the emission layer may be in a range of about 5 weight percent (wt %) to about 50 wt %, or for example, about 10 wt % to about 30 wt %. When the amount is within this range, the energy transfer in the emission layer may be effectively achieved, and accordingly, the organic light-emitting device having high efficiency and long lifespan may be implemented.
In an embodiment, an amount of the heterocyclic compound in the emission layer may be in a range of about 0.01 wt % to about 15 wt %, or for example, about 0.05 wt % to about 3 wt %, but embodiments of the disclosure are not limited thereto.
In an embodiment, the sensitizer and the heterocyclic compound may further satisfy Condition 5:
The decay time of the heterocyclic compound was measured from a time-resolved photoluminescence (TRPL) spectrum at room temperature of a film (hereinafter, referred to as “Film (HC)”) having a thickness of 40 nm formed by vacuum-depositing the host and the heterocyclic compound included in the emission layer on a quartz substrate at a weight ratio of 90:10 at a pressure of 10−7 torr.
In an embodiment, the heterocyclic compound may be used as a delayed fluorescence emitter, and the emission layer may include a sensitizer, e.g., a delayed fluorescence sensitizer.
In an embodiment, the emission layer may further include a host (hereinafter, referred to as ‘Host E’, and Host E is not identical to the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter, referred to as ‘Sensitizer C’, and Sensitizer C is not identical to Host E and the heterocyclic compound). Host E and Sensitizer C may respectively be understood by referring to the descriptions of the host material and the sensitizer material provided herein, but embodiments are not limited thereto.
In an embodiment, a ratio of emission components of the heterocyclic compound to the total emission components emitted from the emission layer may be equal to or greater than 80%, for example, equal to or greater than 90% (or for example, equal to or greater than 95%). For example, the heterocyclic compound may emit fluorescence and/or delayed fluorescence. In addition, Host E and Sensitizer C may not emit light.
In this regard, the heterocyclic compound may emit fluorescence and/or delayed fluorescence, and the emission components of the heterocyclic compound are the sum of prompt emission components of the heterocyclic compound and delayed fluorescence components of the heterocyclic compound by the RISC.
Referring to
25% of singlet excitons produced in Host E in the emission layer may be transferred to a singlet state of Sensitizer C through FRET, and energy of 75% of triplet excitons produced in Host E may be transferred to a triplet state of Sensitizer C, and then singlet energy of Sensitizer C may be transferred to the heterocyclic compound through FRET. Subsequently, the triplet energy of Sensitizer C may be transferred to the heterocyclic compound through Dexter energy transfer. Among the transfer, the energy transferred to triplet of Sensitizer C may be transferred to singlet energy by RISC. In addition, in the case of Sensitizer C, the triplet energy generated in Sensitizer C may be transferred back to Host E (triplet exciton distributing, TED), and then transferred again to the heterocyclic compound to emit light through RISC.
Accordingly, by transferring all the singlet excitons and triplet excitons generated in the emission layer to the dopant (e.g., an emitter), the organic light-emitting device having improved efficiency may be obtained. In addition, since an organic light-emitting device may be obtained with significantly reduced energy loss, the lifespan characteristics of the organic light-emitting device may be improved.
In an embodiment, when the emission layer further includes Host E and Sensitizer C, in addition to the heterocyclic compound, Host E and Sensitizer C may satisfy Condition E-1, E-2, and/or E-3:
S1(HE), S1(SC), S1(HC), T1(SC), and T1(HC) may be evaluated according to the DFT method, wherein structure optimization is performed at a degree of B3LYP, and 6-31G(d,p), for example, by using a Gaussian program according to the DFT method.
When Host E, Sensitizer C, and the heterocyclic compound satisfy Condition E-1, E-2, and/or E-3, Dexter transfer FRET from Sensitizer C to the heterocyclic compound may be facilitated, and accordingly, the organic light-emitting device may have improved luminescence efficiency.
In an embodiment, an amount of Sensitizer C in the emission layer may be in a range of about 5 wt % to about 50 wt %, or for example, about 10 wt % to about 30 wt %. When the amount is within this range, the energy transfer in the emission layer may be effectively achieved, and accordingly, the organic light-emitting device having high efficiency and long lifespan may be implemented.
In an embodiment, an amount of the heterocyclic compound in the emission layer may be in a range of about 0.01 wt % to about 15 wt %, or for example, about 0.05 wt % to about 3 wt %, but embodiments of the disclosure are not limited thereto.
In an embodiment, the host may not include a metal atom.
In an embodiment, the host may include at least one compound selected from a fluorene-containing compound, a carbazole-containing compound, a dibenzofuran-containing compound, a dibenzothiophene-containing compound, an indenocarbazole-containing compound, an indolocarbazole-containing compound, a benzofurocarbazole-containing compound, a benzothienocarbazole-containing compound, an acridine-containing compound, a dihydroacridine-containing compound, a triindolobenzene-containing compound, a pyridine-containing compound, a pyrimidine-containing compound, a triazine-containing compound, a silicon-containing compound, a cyano group-containing compound, a phosphine oxide-containing compound, a sulfoxide-containing compound, and a sulfonyl-containing compound.
For example, the host may be a compound including at least one carbazole ring and at least one cyano group, or a phosphine oxide-containing compound.
In an embodiment, the host may include one kind of host. When the host includes one kind of host, the one kind of host may be selected from a bipolar host, an electron-transporting host, and a hole-transporting host, which will be described later.
In an embodiment, the host may be a mixture of two or more different hosts. For example, the host may be a mixture of an electron-transporting host and a hole-transporting host, a mixture of two types of electron-transporting hosts different from each other, or a mixture of two types of hole-transporting hosts different from each other. The electron-transporting host and the hole-transporting host may be understood by referring to the related description to be presented later.
In an embodiment, the host may include an electron-transporting host including at least one electron-transporting moiety and a hole-transporting host not including an electron-transporting moiety.
The electron-transporting moiety used herein may be selected from a cyano group, a π electron-deficient nitrogen-containing cyclic group, and a group represented by one of the following formulae:
wherein, in the formulae above, *, *′, and *″ each indicate a binding site to a neighboring atom.
In an embodiment, the electron-transporting host in the emission layer may include at least one of a cyano group and a π electron-deficient nitrogen-containing cyclic group.
In an embodiment, the electron-transporting host in the emission layer may include at least one cyano group.
In an embodiment, the electron-transporting host in the emission layer may include at least one cyano group and at least one π electron-deficient nitrogen-containing cyclic group.
In an embodiment, the host may include an electron-transporting host and a hole-transporting host, wherein the electron-transporting host may include at least one π electron-deficient nitrogen-free cyclic group and at least one electron-transporting moiety, and the hole-transporting host may include at least one π electron-deficient nitrogen-free cyclic group and may not include an electron-transporting moiety.
The term “π electron-deficient nitrogen-containing cyclic group” as used herein refers to a cyclic group having at least one *—N═*′ moiety, and for example, may be selected from 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-efficient nitrogen-containing cyclic groups are condensed with each other.
Meanwhile, the π electron-deficient nitrogen-free cyclic group may be selected from a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentacene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a triindolobenzene group, and a condensed cyclic group of two or more π electron-deficient nitrogen-free cyclic groups, but embodiments of the disclosure are not limited thereto.
In an embodiment, when the host includes a mixture of the electron-transporting host and the hole-transporting host, a weight ratio of the electron-transporting host to the hole-transporting host may be selected from a range of about 1:9 to about 9:1, for example, about 2:8 to about 8:2, for example, about 4:6 to about 6:4, and 5:5. When the weight ratio of the electron-transporting host and the hole-transporting host satisfies the ranges above, the hole-and-electron transport balance in the emission layer may be achieved.
The host may include at least one selected from TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, and Compound H51:
In an embodiment, the host may further include a compound represented by Formula 301:
In Formula 301, Ar113 to Ar116 may each independently be:
In Formula 301, g, h, i, and j may each independently be an integer from 0 to 4, and may be, for example, 0, 1, or 2.
In Formula 301, Ar113 to Ar116 may each independently be:
In one or more embodiments, the host may include a compound represented by Formula 302:
In Formula 302, Ar126 and Ar127 may each independently be a C1-C10 alkyl group (for example, a methyl group, an ethyl group, or a propyl group).
In Formula 302, k and l may each independently be an integer from 0 to 4. For example, k and l may be 0, 1, or 2.
In an embodiment, the host may include at least one of Compounds H1 to H26:
In an embodiment, the host may consist of one kind of compound. for example, the one kind of compound may be selected from a first material (the aforementioned hole-transporting host) and a second material (the aforementioned electron-transporting host).
In an embodiment, the host may include two or more different compounds. For example, the host may include two or more different hole-transporting hosts, two or more different electron-transporting hosts, or a combination of at least one hole-transporting host and at least one electron-transporting host.
The emitter may include the heterocyclic compound.
In an embodiment, the sensitizer may include a phosphorescent compound.
In an embodiment, the phosphorescent compound may include an organometallic compound including at least one metal.
In an embodiment, the organometallic compound may include at least one transition metal (M11) and an organic ligand (L11), wherein L11 and M11 may form 1, 2, 3, or 4 cyclometalated rings.
In an embodiment, the organometallic compound may be represented by Formula 101:
M11(L11)n11(L12)n12 Formula 101
In an embodiment, M11 may be platinum (Pt), palladium (Pd), gold (Au), iridium (Ir), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
In an embodiment, the sensitizer may include a delayed fluorescence compound.
In an embodiment, the delayed fluorescence compound may be represented by Formula 101 or 102:
In an embodiment, A21 in Formulae 101 and 102 may be a substituted or unsubstituted π electron-deficient nitrogen-free cyclic group.
Meanwhile, the π electron-deficient nitrogen-free cyclic group may be selected from a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentacene group, a rubicene group, a corogen group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a triindolobenzene group, and a condensed cyclic group of two or more π electron-deficient nitrogen-free cyclic groups, but embodiments of the disclosure are not limited thereto.
In an embodiment, in Formulae 101 and 102, D21 may be selected from: —F, a cyano group, and π electron-deficient nitrogen-containing cyclic group;
In an embodiment, the π electron-deficient nitrogen-free cyclic group is the same as described above.
The term “π electron-deficient nitrogen-containing cyclic group” as used herein refers to a cyclic group having at least one *—N═*′ moiety, and for example, may be selected from 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-efficient nitrogen-containing cyclic groups are condensed with each other.
In an embodiment, an amount of the sensitizer in the organic layer may be greater than an amount of the sensitizer in the organic layer. In an embodiment, a volume ratio of the sensitizer to the emitter may be in a range of about 30:0.1 to about 10:3 or about 10:0.1 to about 20:5. In an embodiment, a weight ratio of the sensitizer to the emitter may be in a range of about 10:0.1 to about 20:5. In one or more embodiment, in the organic layer, a volume ratio of the host to the sensitizer may be in a range of about 60:40 to about 95:5 or about 70:30 to about 90:10. In one or more embodiments, a weight ratio of the host to the sensitizer may be in a range of about 60:40 to about 95:5. When the amounts are satisfied within these ranges, the organic light-emitting device may have improved luminescence efficiency and/or lifespan characteristics.
A substrate may be additionally arranged under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, e.g., a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water repellency.
The first electrode 11 may be produced by depositing or sputtering, onto the substrate, a material for forming the first electrode 11. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials with a high work function for easy hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
The first electrode 11 may have a single-layered structure or a multi-layered structure including a plurality of layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 11 is not limited thereto.
The organic layer 15 is arranged on the first electrode 11.
The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
The hole transport region may be between the first electrode 11 and the emission layer.
The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.
The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, wherein, for each structure, respective layers are sequentially stacked in this stated order from the first electrode 11.
When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, for example, vacuum deposition, spin coating, casting, and/or Langmuir-Blodgett (LB) deposition.
When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10−8 torr to about 10−3 torr, and a deposition rate of about 0.01 angstroms per second to about 100 angstroms per second. However, the deposition conditions are not limited thereto.
When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C. However, the coating conditions are not limited thereto.
The conditions for forming the hole transport layer and the electron blocking layer may be the same as the conditions for forming the hole injection layer.
The hole transport region may include at least one of m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), (polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201, and a compound represented by Formula 202:
In Formula 201, xa and xb may each independently be an integer from 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.
R101 to R108, R111 to R119 and R121 to R124 in Formulae 201 and 202 may each independently be:
R109 in Formula 201 may be:
In an embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments are not limited thereto:
For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include Compounds HT1 to HT20, but embodiments are not limited thereto:
A thickness of the hole transport region may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, a thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The hole transport region may further include, in addition to these materials, a charge-generation material to increase conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
The charge-generation material may be, for example, a p-dopant. The p-dopant may be one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the disclosure are not limited thereto. Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenum oxide; and a cyano group-containing compound, such as Compound HT-D1 or F12, but are not limited thereto:
The hole transport region may include a buffer layer.
Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.
Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary according to a material that is used to form the hole transport layer.
Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be selected from materials for the hole transport region described above and materials for a host to be explained later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be explained later.
When the organic light-emitting device 10 is a full-color organic light-emitting device 10, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light.
When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 part by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the disclosure are not limited thereto.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, excellent luminescence characteristics may be obtained without a substantial increase in driving voltage.
An electron transport region may be located on the emission layer.
The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, and the structure of the electron transport region is not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.
When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq but embodiments of the disclosure are not limited thereto:
A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may further include at least one selected from BCP, Bphen, Alq3, BAlq, TAZ, and NTAZ:
In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25, but are not limited thereto:
A thickness of the electron transport layer may be in the 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 transporting characteristics without a substantial increase in driving voltage.
The electron transport layer may include a metal-containing material in addition to the material as described above.
The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, “LiQ”) or ET-D2:
The electron transport region may include an electron injection layer that promotes the flow of electrons from the second electrode 19 there into.
The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or a combination thereof.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the ranges above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 19 is located on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the second electrode 19. In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
Herein, the organic light-emitting device has been described with reference to
Another aspect of the disclosure provides an electronic apparatus including the organic light-emitting device.
The electronic apparatus may further include a thin-film transistor in addition to the organic light-emitting device as described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the organic light-emitting device.
Another aspect of the disclosure provides a diagnostic composition including the heterocyclic compound represented by Formula 1.
The diagnostic composition may include at least one of the heterocyclic compound represented by Formula 1.
The heterocyclic compound represented by Formula 1 may provide high luminescent efficiency, and thus the diagnostic composition including the heterocyclic compound may have high diagnostic efficiency.
The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
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 non-limiting 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.
Examples of the C1-C60 alkyl group, the C1-C20 alkyl group, and/or the C1-C10 alkyl group are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decyl group, each unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or any combination thereof. For example, Formula 9-33 is a branched C6 alkyl group, for example, a tert-butyl group that is substituted with two methyl groups.
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.
Examples of the C1-C60 alkoxy group, a C1-C20 alkoxy group or C1-C10 alkoxy group are a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy 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 “C3-C10 cycloalkyl group” as used herein may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl(norbornanyl) group, a bicyclo[2.2.2]octyl group, and the like.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom and 1 to 10 carbon atoms, and 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.
Examples of the C1-C10 heterocycloalkyl group are a silolanyl group, a silinanyl group, tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, and a tetrahydrothiophenyl 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 “C2-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one hetero atom selected from N, O, P, Si, and S as a ring-forming atom, 2 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C2-C10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C2-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C2-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 “C7-C60 alkyl aryl group” as used herein refers to a C6-C60 aryl group substituted with at least one C1-C60 alkyl group.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a cyclic aromatic system that has at least one heteroatom selected from N, O, P, Si, 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 carbocyclic aromatic system that has at least one heteroatom selected from N, O, P, and S 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 “C2-C60 alkyl heteroaryl group” as used herein refers to a C1-C60 heteroaryl group substituted with at least one C1-C60 alkyl group.
The term “C6-C60 aryloxy group” as used herein indicates —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group” as used herein indicates —SA103 (wherein A103 is the C6-C60 aryl group).
The term “C1-C60 heteroaryloxy group” as used herein indicates —OA104 (wherein A104 is a C1-C60 heteroaryl group), and the term “C1-C60 heteroarylthio group” as used herein indicates —SA105 (wherein A105 is the C1-C60 heteroaryl group).
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group 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 described above.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 2 to 60 carbon atoms) having two or more rings condensed with each other, a heteroatom selected from N, O, P, Si, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group 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 described above.
The term “C5-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group. Examples of the “C5-C30 carbocyclic group (unsubstituted or substituted with at least one R1a)” as used herein may include an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane(norbornane) group, a bicyclo[2.2.2]octane group, a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, a silole group, and a fluorene group (each unsubstituted or substituted with at least one R1a).
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 selected from N, O, Si, P, and S other than 1 to 30 carbon atoms. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group. Examples of the “C1-C30 heterocyclic group (unsubstituted or substituted with at least one R1a)” as used herein may include a thiophene group, a furan group, a pyrrole group, a silole group, borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group (each unsubstituted or substituted with at least one R1a).
In the present specification, TMS represents *—Si(CH3)3, and TMG represents *—Ge(CH3)3.
Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Example 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 B used was identical to an amount of A used based on molar equivalence.
Compound 1 was synthesized by the method shown in the synthesis scheme below.
An ITO glass substrate was cut to a size of 50 mm×50 mm×0.5 mm, sonicated in acetone, isopropyl alcohol, and pure water, each for 15 minutes, and then cleaned by exposure to UV ozone for 30 minutes.
Then, HAT-CN was deposited on the ITO electrode (anode) on the glass substrate to form a hole injection layer having a thickness of 50 Å, TAPC was deposited on the hole injection layer to form a first hole transport layer having a thickness of 350 Å, TCTA was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 100 Å, and mCP was deposited on the second hole transport layer to form an electron blocking layer having a thickness of 100 Å.
A first host (H25), a second host (H26) and an emitter (Compound 1) were co-deposited on the electron blocking layer to form an emission layer having a thickness of 400 Å. Here, the first host and the second host were mixed at a ratio of 60:40, and the emitter was adjusted to be 3 wt % based on the total weight of the first host, the second host, and the emitter.
PPT was deposited on the emission layer to form a hole blocking layer having a thickness of 100 Å, and then 1,3,5-tris(3-pyridyl-3-phenyl)benzene (“TmPyPB”) and LiF were co-deposited thereon at a weight ratio of 5:5 to form an electron transport layer having a thickness of 300 Å, and then, LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 8 Å, and Al was deposited on the electron injection layer to form a cathode having a thickness of 1,000 Å, thereby completing the manufacture of an organic light-emitting device.
For the organic light-emitting device of Example 1, the driving voltage, full width at half maximum (FWHM), and external quantum efficiency (EQE) were measured by using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). The results are shown in Table 2.
Referring to Table 2, it was confirmed that the organic light-emitting device according to an embodiment had low driving voltage (less than 3.5 volts), narrow FWHM (less than 50 nm), and excellent EQE (greater than 15%).
According to the one or more embodiments, a heterocyclic compound has excellent characteristics in terms of luminescence and charge mobility, and thus an electronic device, e.g., an organic light-emitting device, including the heterocyclic compound may have low driving voltage, high efficiency, and long lifespan characteristics. Thus, due to the use of the heterocyclic compound, a high-quality organic light-emitting device may be implemented.
In addition, due to the inclusion of the organic light-emitting device, an improved quality electronic apparatus may be provided.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2023-0039290 | Mar 2023 | KR | national |
