Patent Application
20240116955
This application claims priority under 35 U.S.C. § 119 to Korean Patent Application No. 10-2022-0108725, filed on Aug. 29, 2022, in the Korean Intellectual Property Office, the disclosure of which is incorporated by reference herein in its entirety.
The disclosure relates to a heterocyclic compound, an organic light-emitting device including the same, and a diagnostic composition including the heterocyclic compound.
Organic light-emitting devices are self-emissive devices, which have improved characteristics in terms of viewing angles, response time, luminance, driving voltage, and response speed, and produce full-color images.
An organic light-emitting device may include an anode, a cathode, and an organic layer that is located between the anode and the cathode and includes an emission layer. A hole transport region may be arranged between the anode and the emission layer, and an electron transport region may be arranged between the emission layer and the cathode. Holes provided from the anode move toward the emission layer through the hole transport region, and electrons provided from the cathode move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transition from an excited state to the ground state to thereby generate light.
Provided are a heterocyclic compound, an organic light-emitting device including the same, and a diagnostic composition including the heterocyclic compound.
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 one or more embodiments, there is provided a heterocyclic compound represented by Formula 1
In Formulae 1 and 2,
According to one or more embodiments, an organic light-emitting device includes the heterocyclic compound.
According to one or more embodiments, a diagnostic composition includes the heterocyclic compound.
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.
A heterocyclic compound according to an embodiment is represented by Formula 1:
In an embodiment, Y1 may be B, N, or P.
For example, Y1 may be B.
In Formula 1, X1 and X2 may each independently be a single bond, O, S, Se, N[(CY5)—Ar2], N(R1), C(R1)(R2), Si(R1)(R2), Ge(R1)(R2), B(R1), P(R1), P(═O)(R1), S(═O)2, or C(═O).
In an embodiment, X1 and X2 may each independently be a single bond, O, S, Se, N[(CY5)—Ar2], N(R1), C(R1)(R2), or Si(R1)(R2).
In Formula 1, k1 may be 0 or 1. When k1 is 0, CY1 and CY3 are not linked to each other via X1.
In Formula 1, k2 may be 0 or 1. When k2 is 0, CY1 and CY2 are not linked to each other via X2.
In Formula 1, the sum of k1 and k2 may be greater than or equal to 1.
For example, at least one of k1 and k2 may be 1.
In Formula 1, CY1 to CY3 may each independently a C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
In an embodiment, CY1 to CY3 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) a condensed ring in which at least one first ring is condensed with at least one second ring.
The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazasilole group, and
In an embodiment, CY1 to CY3 may each independently be a C6-C30 aromatic carbocyclic group or a C1-C30 aromatic heterocyclic group.
In an embodiment, CY1 to CY3 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 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, adamantane group, a norbornane group, or a norbornene group.
In an embodiment, CY1 to CY3 may each independently be a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, or a quinazoline group.
In Formula 1, CY4 and CY5 may each independently be a C5-C30 carbocyclic group that is unsubstituted or substituted with at least one R40 or a C1-C30 heterocyclic group that is unsubstituted or substituted with at least one R40.
In an embodiment, CY4 and CY5 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a 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, CY4 and CY5 may each independently be a benzene group, a naphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, or a quinazoline group, each unsubstituted or substituted with at least one R40.
In an embodiment, CY4 and CY5 may each independently be a benzene group that is unsubstituted or substituted with at least one R40.
In an embodiment, CY4 and CY5 may each independently be of Formulae 4-1 to 4-3:
In Formula 1, Ar1 and Ar2 may each independently be a group represented by Formula 2.
In Formula 2, L1 may be a single bond, a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.
In an embodiment, L1 may be a single bond.
In Formula 2, a1 may be 1, 2, or 3.
In an embodiment, a1 may be 1.
In Formula 2, CY10 may be a C3-C10 non-aromatic carbocyclic group or a C1-C10 non-aromatic heterocyclic group.
In an embodiment, CY10 may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, or a cycloheptene group.
In Formula 2, * may indicate a binding site to a neighboring atom.
In an embodiment, Ar1 and Ar2 may each independently be a group represented by Formula 2A or 2B.
In an embodiment, Ar1 and Ar2 may each independently be a group represented by one of Formulae 5-1 to 5-4:
In an embodiment, Ar1 and Ar2 may each independently be a group represented by one of Formulae 5-11 to 5-26:
In an embodiment, Ar1 and Ar2 may have the same structure.
In an embodiment, Ar1 and Ar2 may have different structures.
In Formula 1, R1, R2, R10, R20, R30, and R40 may each independently be a group represented by Formula 2, 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 C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkylaryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkylheteroaryl 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), —P(═S)(Q1)(Q2), or a group represented by Formula 3.
In Formula 2, R50 and R60 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 C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkylaryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkylheteroaryl 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), —P(═S)(Q1)(Q2), or a group represented by Formula 3:
In Formula 3, X31 may be a single bond, O, S, N(R301), or C(R301)(R302).
In Formula 3, k31 may be 0 or 1.
In Formula 3, CY31 and CY32 may each independently be a C5-C30 carbocyclic group or a C1-C30 heterocyclic group.
In an embodiment, CY31 and CY32 may each independently be a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzosilole group.
In Formula 3, L30 may be a single bond, a substituted or unsubstituted C5-C30 carbocyclic group, or a substituted or unsubstituted C1-C30 heterocyclic group.
In Formula 3, a30 may be 0, 1, 2, or 3.
In an embodiment, a30 may be 0 or 1.
In Formula 3, R301, R302, R310, and R320 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 carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkylaryl 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 alkylheteroaryl 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, R301, R302, R310, and R320 may each independently be:
In an embodiment, R301, R302, R310, and R320 may each independently be
In Formula 3, b310 and b320 may each independently be 1, 2, 3, 4, 5, 6, 7, or 8.
In an embodiment, R1, R2, R10, R20, R30, and R40 may each independently be: a group represented by Formula 2, a group represented by Formula 3, 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;
—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), —P(═S)(Q1)(Q2), or any combination thereof.
In an embodiment, R50 and R60 may each independently be: a group represented by Formula 3, 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, R2, R10, R20, R30, and R40 may each independently be:
In an embodiment, R50 and R60 may each independently be:
In an embodiment, at least one instance of R10 may be a group represented by Formula 3.
In an embodiment, at least one instance of R20 may be a group represented by Formula 3.
In an embodiment, at least one instance of R30 may be a group represented by Formula 3.
In an embodiment, at least one instance of R10, at least one instance of R20, and at least one instance of R30 may be a group represented by Formula 3. In an embodiment, one of R30 may be a group represented by Formula 3.
In Formulae 1 and 2, b10, b20, b30, b40, and b60 may each independently be 1, 2, 3, 4, 5, 6, 7, or 8.
In Formula 2, b50 may be 1, 2, or 3.
In an embodiment, a group represented by Formula 3 may be a group represented by one of Formulae 3-1 to 3-3:
In an embodiment, the heterocyclic compound may be represented by Formula 1A or 1B:
In an embodiment, the heterocyclic compound may be represented by one of Formulae 11-1 to 11-9:
In an embodiment, at least one of R11 to R14 may be a group represented by Formula 3.
In an embodiment, at least one of R21 to R24 may be a group represented by Formula 3.
In an embodiment, at least one of R31 to R33 may be a group represented by Formula 3.
In an embodiment, at least one of R11 to R14, at least one of R21 to R24, and at least one of R31 to R33 may be a group represented by Formula 3.
In an embodiment, the heterocyclic compound may have a symmetric structure or an asymmetric structure.
For example, the heterocyclic compound may have a symmetric structure.
As another example, the heterocyclic compound may have an asymmetric structure.
As used herein, “a symmetric structure” means that when is drawn down the middle of the structure (i.e., through the B and center of the CY3 ring Formula I), each side is the same. For example, Compound 1 has a symmetric structure, whereas Compound 25 has an asymmetric structure.
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 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:
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid or a salt thereof; a sulfonic acid or a salt thereof; a phosphoric acid or a salt thereof; a C1-C60 alkyl group that is unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C10 cycloalkyl group; a C1-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C1-C10 heterocycloalkenyl group; a C6-C60 aryl group that is unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
For example, 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 at least one of Compounds 1 to 792, but embodiments are not limited thereto:
The heterocyclic compound represented by Formula 1 satisfies the structure of Formula 1 described above, and includes a structure in which a group represented by Formula 2 is substituted in ring CY4 of Formula 1. Due to this structure, the heterocyclic compound represented by Formula 1 has excellent luminescent characteristics, and in particular, may implement deep blue light emission having a short wavelength.
Although not limited by a particular theory, the heterocyclic compound that satisfies the structure as described above may have high oscillator strength (f), and thus, when the heterocyclic compound is applied to an electronic device, efficiency of the electronic device may increase. In addition, since the heterocyclic compound includes a substituent having a bulky structure represented by Formula 2 as described above, the heterocyclic compound may have a high S1 energy level and a high photoalignment. Accordingly, when the heterocyclic compound is used as a luminescent material, Dexter energy transfer is suppressed and excellent lifespan characteristics may be exhibited.
Therefore, an electronic device, for example, an organic light-emitting device, including the heterocyclic compound represented by Formula 1 may have high efficiency and long lifespan.
The highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, S1 energy level, T1 energy level, and oscillator strength (f) of some of the heterocyclic compounds represented by Formula 1 were evaluated using the Gaussian 09 program with the molecular structure optimization obtained by B3LYP-based density functional theory (DFT), and results thereof are shown in Table 1.
From the Table 1, it may be seen that the heterocyclic compound represented by Formula 1 has electric characteristics suitable for use as a dopant (for example, an emitter or a sensitizer) in an electronic device, for example, an organic light-emitting device. For example, the heterocyclic compound has a deeper HOMO value and a significantly higher f value, as compared to Compounds A to D as comparative compounds.
In an embodiment, a full width at half maximum (FWHM) of an emission peak of an emission spectrum or an electroluminescence (EL) spectrum of the heterocyclic compound may be 60 nm or less. For example, an FWHM of an emission peak of an emission spectrum or an EL spectrum of the heterocyclic compound may be 5 nm to 50 nm, 7 nm to 40 nm, or 10 nm to 30 nm.
Synthesis method of the heterocyclic compound represented by Formula 1 may be recognized by those skilled in the art with reference to the following Synthesis Examples.
A method of identifying a structure of the heterocyclic compound represented by Formula 1 is not particularly limited. In an embodiment, the structure of the heterocyclic compound may be identified by a known method (for example, nuclear magnetic resonance (NMR) or liquid chromatography-mass spectrometry (LC-MS)).
According to one or more embodiments, an organic light-emitting device includes 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, and the organic layer may include the heterocyclic compound represented by Formula 1.
In an embodiment, the emission layer may include the heterocyclic compound.
In an embodiment, the emission layer may include a host and an emitter, and the emitter may include the heterocyclic compound.
In an embodiment, in the emission layer, an amount of the host may be greater than an amount of the heterocyclic compound based on the weight.
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.
The host, the emitter, and the sensitizer are each the same as described in the present specification.
Since the organic light-emitting device includes the emission layer including the heterocyclic compound represented by Formula 1 as described above, the organic light-emitting device may have a relatively narrow FWHM of an emission peak of an EL spectrum, excellent efficiency, and excellent lifespan characteristics.
In an embodiment, the heterocyclic compound may act as a dopant (for example, an emitter or a sensitizer) in the emission layer, and the emission layer may further include a host (in other words, in the emission layer, an amount of the heterocyclic compound represented by Formula 1 may be less than an amount 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 of about 410 nm to about 490 nm.
The wording “(emission layer) includes at least one heterocyclic compound” as used herein may be to mean that the (emission layer) may include one kind of heterocyclic compound represented by Formula 1 or two or more different kinds of heterocyclic compounds, each represented by Formula 1.
For example, the emission layer may include, as the heterocyclic compound, only Compound 1. In this regard, Compound 1 may be included in the emission layer of the organic light-emitting device. In an embodiment, the emission layer may include, as the heterocyclic compound, Compound 1 and Compound 2.
In
The organic layer 15 includes an emission layer, 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 disposed 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. When the first electrode 11 is a transmissive electrode, a material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof, but embodiments are not limited thereto. In some embodiments, when the first electrode 11 is a semi-transmissive electrode or a reflective electrode, as a material for forming the first electrode 11, at least one of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof may be used, but embodiments are not limited thereto.
The first electrode 11 may have a single-layered structure or a multilayer 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 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within the range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
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 may not be identical to the heterocyclic compound). Host A may be understood by referring to the description of a host material described below, 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 the singlet excitons formed in Host A are transferred to a fluorescent emitter through Förster energy transfer (or, Förster resonance energy transfer (FRET)).
A proportion of the singlet excitons formed in Host A may be only 25%, and thus, 75% of triplet excitons formed in Host A may be fused to each other to be converted into singlet excitons. Thus, efficiency of the organic light-emitting device may be further improved. In other words, the efficiency of the organic light-emitting device may be further improved using a triplet-triplet fusion (TTF) mechanism.
In an embodiment, among total emission components emitted from the emission layer, a proportion of emission components emitted from the heterocyclic compound may be greater than or equal to 80%, for example, greater than or equal to 90%. For example, among total emission components emitted from the emission layer, a proportion of emission components emitted from the heterocyclic compound may be greater than or equal to 95%.
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 about 50 parts by weight or less, for example, about 30 parts by weight or less, about 10 parts by weight or less, or about 1 part by weight to about 5 parts by weight, based on 100 parts by weight of the emission layer, and an amount of Host A in the emission layer may be about 50 parts by weight or greater, for example, about 70 parts by weight or greater, about 90 parts by weight or greater, or about 95 part by weight to about 99 parts by weight, based on 100 parts by weight of the emission layer, but embodiments 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:
E(HA)S1>ES1 Condition A
Here, E(HA)S1 and ES1 are evaluated using the DFT method of the Gaussian program, wherein structure optimization is performed at B3LYP/6-31G(d,p) level.
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 a host material described below, but embodiments are not limited thereto.
Referring to
25% of singlet excitons formed in Host B in the emission layer are transferred to a delayed fluorescence emitter through FRET. In addition, 75% of triplet excitons formed in Host B in the emission layer are transferred to a delayed fluorescence emitter through Dexter energy transfer. At least a portion of energy of a singlet state of the delayed fluorescence emitter may be transferred to a triplet state by intersystem crossing (ISC). The energy transferred to the triplet state of the delayed fluorescence emitter may be transferred to the singlet state by reverse intersystem crossing (RISC). Accordingly, by transferring all the singlet excitons and triplet excitons generated in the emission layer to the heterocyclic compound, the organic light-emitting device having improved efficiency may be obtained.
Therefore, in an embodiment, among total emission components emitted from the emission layer, a proportion of emission components emitted from the heterocyclic compound may be greater than or equal to 80%, for example, greater than or equal to 90%. For example, among total emission components emitted from the emission layer, a proportion of emission components emitted from the heterocyclic compound may be greater than or equal to 95%.
Here, the heterocyclic compound may emit fluorescence and/or delayed fluorescence, and the emission components of the heterocyclic compound may be a total of prompt emission components of the heterocyclic compound and delayed fluorescence components by RISC of the heterocyclic compound. 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 about 50 parts by weight or less, for example, about 30 parts by weight or less, based on 100 parts by weight of the emission layer, and an amount of Host B in the emission layer may be about 50 parts by weight or greater, for example, about 70 parts by weight or greater, based on 100 parts by weight of the emission layer, but embodiments 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:
E(HB)S1>ES1 Condition B
Here, E(HB)S1 and ES1 are evaluated using the DFT method of the Gaussian program, wherein structure optimization is performed at B3LYP/6-31G(d,p) level.
In an embodiment, the heterocyclic compound may be used as a fluorescent emitter, and the emission layer may further include a sensitizer, for example, a delayed fluorescence sensitizer. In an embodiment, the emission layer may further include a host (hereinafter, referred to as ‘Host C’, and Host C is not identical to the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter, referred to as ‘Sensitizer A’, and Sensitizer A is not identical to Host C and the heterocyclic compound). Host C and Sensitizer A may respectively be understood by referring to the descriptions of a host material and a sensitizer material described below, but embodiments are not limited thereto.
In an embodiment, among total emission components emitted from the emission layer, a proportion of emission components of the heterocyclic compound may be greater than or equal to 80%, for example, greater than or equal to 90% (or for example, greater than or equal to 95%). For example, the heterocyclic compound may emit fluorescence. In addition, Host C and Sensitizer A may not each emit light.
Referring to
Singlet and triplet excitons are formed in Host C in the emission layer, and the singlet and triplet excitons formed in Host C may be transferred to Sensitizer A and then to the heterocyclic compound through FRET. 25% of the singlet excitons are formed in Host C and are transferred to Sensitizer A through FRET, and 75% of the triplet excitons are formed in Host C and energy thereof is transferred to a singlet state and triplet state of Sensitizer A. At least a portion of energy of the singlet state of Sensitizer A may be transferred to the triplet state by ISC. The energy transferred to the triplet state of Sensitizer A is transferred to the singlet state by RISC, and then, the singlet state energy of Sensitizer A is transferred to the heterocyclic compound through FRET.
Accordingly, by transferring all the singlet excitons and triplet excitons generated in the emission layer to a dopant (for example, an emitter), the organic light-emitting device having improved efficiency may be obtained. In addition, since the organic light-emitting device with significantly reduced energy loss may be obtained, lifespan characteristics of the organic light-emitting device may be improved.
Referring to
S
1(HC)≥S1(SA) Condition C-1
S
1(SA)≥S1(HC) Condition C-2
S1(HC), S1(SA), and S1(HC) are evaluated using the DFT method of the Gaussian program, wherein structure optimization is performed at B3LYP/6-31G(d,p) level.
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 emission efficiency.
In an embodiment, the heterocyclic compound may be used as a fluorescent emitter, and the emission layer may further include a sensitizer, for example, a phosphorescent 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 are not limited thereto.
In an embodiment, among total emission components emitted from the emission layer, a proportion of emission components of the heterocyclic compound may be greater than or equal to 80%, for example, greater than or equal to 90% (or for example, greater than or equal to 95%). For example, the heterocyclic compound may emit fluorescence. In addition, Host D and Sensitizer B may not each emit light.
Referring to
75% of triplet excitons are formed in Host D in the emission layer and are transferred to Sensitizer B through Dexter energy transfer, and 25% of singlet excitons are formed in Host D and energy thereof is transferred to a singlet state and triplet state of Sensitizer B. The energy transferred to the singlet state of Sensitizer B is transferred to the triplet state by ISC, and then, the triplet energy of Sensitizer B is transferred to the heterocyclic compound through FRET.
Accordingly, by transferring all the singlet excitons and triplet excitons generated in the emission layer to a dopant (for example, an emitter), the organic light-emitting device having improved efficiency may be obtained. In addition, since the organic light-emitting device with significantly reduced energy loss may be obtained, 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, Sensitizer B, and the heterocyclic compound may satisfy Condition D-1 and/or D-2:
T
1(HD)≥T1(SB) Condition D-1
T
1(SB)≥S1(HC) Condition D-2
T1(HD), T1(SB), and S1(HC) are evaluated using the DFT method of the Gaussian program, wherein structure optimization is performed at B3LYP/6-31G(d,p) level.
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 emission efficiency.
In an embodiment, an amount of Sensitizer B in the emission layer may be about 5 wt % to about 50 wt %, for example, about 10 wt % to about 30 wt %. When the amount is within the range described above, effective energy transfer in the emission layer may be achieved. Thus, the organic light-emitting device may have high efficiency and long lifespan.
In an embodiment, an amount of the heterocyclic compound in the emission layer may be about 0.01 wt % to about 15 wt %, for example, about 0.05 wt % to about 3 wt %, but embodiments are not limited thereto.
In an embodiment, the heterocyclic compound may further satisfy Condition 5:
0 μs<Tdecay(HC)<5 μs Condition 5
The decay time of the heterocyclic compound is a value calculated from a time-resolved photoluminescence (TRPL) spectrum at room temperature of a film (hereinafter, referred to as “Film (HC)”) having a thickness of about 40 nm, which is obtained by vacuum-codepositing the host and the heterocyclic compound included in the emission layer on a quartz substrate at a weight ratio of 90:10 at a vacuum pressure of 10−7 torr.
In an embodiment, the heterocyclic compound may be used as a delayed fluorescence emitter, and the emission layer may further include a sensitizer, for example, 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 a 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 description of a host material and a sensitizer material described below, but embodiments are not limited thereto.
In an embodiment, among total emission components emitted from the emission layer, a proportion of emission components of the heterocyclic compound may be greater than or equal to about 80%, for example, greater than or equal to about 90% (or for example, greater than or equal to about 95%). For example, the heterocyclic compound may emit fluorescence and/or delayed fluorescence. In addition, Host E and Sensitizer C may not each emit light.
Here, the heterocyclic compound emits fluorescence and/or delayed fluorescence, and the emission components of the heterocyclic compound are a total of prompt emission components of the heterocyclic compound and delayed fluorescence components of the heterocyclic compound by RISC.
Referring to
25% of singlet excitons are formed in Host E in the emission layer and are transferred to a singlet of Sensitizer C through FRET, and 75% of triplet excitons are formed in Host E and energy thereof is transferred to a triplet of Sensitizer C. Then, the singlet energy of Sensitizer C is transferred to the heterocyclic compound through FRET, and the triplet energy of Sensitizer C is transferred to the heterocyclic compound through Dexter energy transfer. The energy transferred to the triplet of Sensitizer C may be transferred to the singlet by RISC. In addition, in the case of Sensitizer C, the energy of the triplet state formed in Sensitizer C is reversely transferred to Host E (triplet exciton distributing (TED)), and then transferred 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 a dopant (for example, an emitter), the organic light-emitting device having improved efficiency may be obtained. In addition, since the organic light-emitting device with significantly reduced energy loss is obtained, 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, Sensitizer C, and the heterocyclic compound may satisfy Condition E-1, E-2, and/or E-3:
S
1(HE)≥S1(SC) Condition E-1
S
1(SC)≥S1(HC) Condition E-2
T
1(SC)≥T1(HC) Condition E-3
S1(HE), S1(SC), S1(HC), T1(SC), and T1(HC) are evaluated using the DFT method of the Gaussian program, wherein structure optimization is performed at B3LYP/6-31G(d,p) level.
When Host E, Sensitizer C, and the heterocyclic compound satisfy Condition E-1, E-2, and/or E-3, Dexter energy transfer and FRET from Sensitizer C to the heterocyclic compound may be facilitated, and accordingly, the organic light-emitting device may have improved emission efficiency.
In an embodiment, an amount of Sensitizer C in the emission layer may be about 5 wt % to about 50 wt %, for example, about 10 wt % to about 30 wt %. When the amount is within the range described above, effective energy transfer in the emission layer may be achieved. Thus, the organic light-emitting device may have high efficiency and long lifespan.
In an embodiment, an amount of the heterocyclic compound in the emission layer may be about 0.01 wt % to about 15 wt %, for example, about 0.05 wt % to about 3 wt %, but embodiments 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 of 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, a sulfonyl-containing compound, or any combination thereof.
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 consist of one kind of host. When the host consists of one kind of host, the one kind of host may be a bipolar host, an electron-transporting host, or a hole-transporting host, which will be described later.
In an embodiment, the host may be a mixture of two or more different kinds of hosts. For example, the host may be a mixture of an electron-transporting host and a hole-transporting host, a mixture of two different kinds of electron-transporting hosts, or a mixture of two different kinds of hole-transporting hosts. The electron-transporting host and the hole-transporting host may respectively be the same as those described below.
In an embodiment, the host may include an electron-transporting host including at least one electron-transporting moiety and a hole-transporting host that does not include an electron-transporting moiety.
The electron-transporting moiety used herein may be a cyano group, a π electron-deficient nitrogen-containing cyclic group, a group represented by one of the following Formulae, or a combination thereof:
In an embodiment, the electron-transporting host in the emission layer may include at least one of a cyano group, a π electron-deficient nitrogen-containing cyclic group, or a combination thereof.
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” 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 ring in which two or more π electron-deficient nitrogen-containing cyclic groups are condensed with each other.
Meanwhile, the π electron-deficient nitrogen-free cyclic group may be: a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, 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, a condensed ring in which two or more π electron-deficient nitrogen-free cyclic groups are condensed with each other, or any combination thereof, but embodiments are not limited thereto.
In an embodiment, when the host is a mixture of an electron-transporting host and a hole-transporting host, then then a weight ratio of the electron-transporting host and the hole-transporting host may be 1:9 to 9:1, for example, 2:8 to 8:2, for example, 4:6 to 6:4, for example, 5:5. When the weight ratio of the electron-transporting host and the hole-transporting host satisfies the range described above, then a balance of hole and electron transport in the emission layer may be achieved.
The host may include at least one of TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, or any combination thereof:
In an embodiment, the host may further include a compound represented by Formula 301:
Ar113 to Ar116 in Formula 301 may each independently be:
The designations g, h, i, and j in Formula 301 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 an embodiment, the host may include a compound represented by Formula 302:
Ar122 to Ar125 in Formula 302 are the same as described in detail in connection with Ar113 in Formula 301.
Ar126 and Ar127 in Formula 302 may each independently be a C1-C10 alkyl group (for example, a methyl group, an ethyl group, or a propyl group).
The designations k and l in Formula 302 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 H25:
In an embodiment, the host may consist of one kind of compound. For example, the one kind of compound may be a first material (hole-transporting host), a second material (electron-transporting host) as described above, or any combination thereof.
In an embodiment, the host may include two or more kinds of compounds. For example, the host may include two or more different kinds of hole-transporting hosts, or two or more different kinds of electron-transporting hosts, or a combination of at least one hole-transporting host and at least one electron-transporting host.
The emitter includes 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 one cyclometalated ring, two cyclometalated rings, three cyclometalated rings, or four cyclometalated rings.
In an embodiment, the organometallic compound may be represented by Formula 101:
M
11(L11)n11(L12)n12. Formula 101
In an embodiment, the transition metal may be platinum (Pt), palladium (Pd), gold (Au), iridium (Ir), osmium (Os), titanium (T1), 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, in Formulae 101 and 102, A21 may be a substituted or unsubstituted π electron-deficient nitrogen-free cyclic group.
In detail, the π electron-deficient nitrogen-free cyclic group may be: a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or a triindolobenzene group; or a condensed ring in which two or more π electron-deficient nitrogen-free cyclic groups are condensed with each other, but embodiments are not limited thereto.
For example, in Formulae 101 and 102, D21 may be: —F, a cyano group, or a π electron-deficient nitrogen-containing cyclic group;
In detail, the π electron-deficient nitrogen-free cyclic group is the same as described above.
In detail, the π electron-deficient nitrogen-containing cyclic group refers to a cyclic group having at least one *—N=*′ moiety, and, for example, may be: an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, or a benzimidazolobenzimidazole group; or a condensed ring in which two or more π electron-deficient nitrogen-containing cyclic groups are condensed with each other.
In an embodiment, in the organic layer, an amount of the sensitizer may be greater than an amount of the emitter. For example, a volume ratio of the sensitizer and the emitter may be about 30:0.1 to about 10:3, or about 10:0.1 to about 20:5. As another example, a weight ratio of the sensitizer and the emitter may be about 10:0.1 to about 20:5. Meanwhile, a volume ratio of the host and the sensitizer in the organic layer may be about 60:40 to about 95:5 or about 70:30 to about 90:10. Alternatively, a weight ratio of the host and the sensitizer may be about 60:40 to about 95:5. When the amount is within the range described above, the organic light-emitting device may have improved emission efficiency and/or lifespan characteristics.
A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. For use as the substrate, any substrate that is used in organic light-emitting devices available in the art may be used, and for example, a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance, may be used.
The first electrode 11 may be formed by depositing or sputtering, for example, 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 a material 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). Alternatively, 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 multilayer structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but embodiments are not limited thereto.
The organic layer 15 is disposed above the first electrode 11.
The organic layer 15 may include a hole transport region, an emission layer, or 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. Alternatively, the hole transport region may have a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/electron blocking layer structure, or a hole injection layer/a first hole transport layer/a second hole transport layer/an 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 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 condition may vary according to a compound used as a material to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition condition 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 Å/sec to about 100 Å/sec. However, the deposition condition are not limited thereto.
When the hole injection layer is formed by spin coating, the coating condition may vary according to a compound used as a material to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the coating condition may include a coating speed of about 2,000 rpm to about 5,000 rpm, and a heat treatment temperature of about 80° C. to about 200° C. for removing a solvent after coating. However, the coating condition 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, a compound represented by Formula 202, or any combination thereof:
In Formula 201, xa and xb may each independently be an integer from 0 to 5, or may each independently be or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.
In Formulae 201 and 202, R101 to R108, R111 to R119, and R121 to R124 may each independently be:
In Formula 201, R109 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 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 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 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 as described above, 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 for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
The charge-generation material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments are not limited thereto. For example, examples of the p-dopant are: a quinone derivative, such as tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenum oxide; or a cyano group-containing compound, such as Compound HT-D1 or F12, but embodiments are not limited thereto:
The hole transport region may include a buffer layer.
The buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of the organic light-emitting device may be improved.
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 described above. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, examples of a material for the electron blocking layer may include mCP described below.
Then, an emission layer may be formed on the hole transport region using vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition condition and the coating condition may vary according to a compound used as a material to form the emission layer, but the deposition condition and the coating condition may be similar to those applied in forming the hole injection layer.
When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. Alternatively, the emission layer has a structure in which a red emission layer, a green emission layer, and/or a blue emission layer are stacked, and thus, may emit white light, and various modifications may be made.
When the emission layer includes a host and a dopant, an amount of the dopant may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments are not limited thereto.
A thickness of the emission layer may be 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 the range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
Next, an electron transport region may be disposed above 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, but embodiments are not limited thereto. The electron transport layer may have a single-layered structure or a multilayer 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, BAlq, or any combination thereof, but embodiments are not limited thereto:
A thickness of the hole blocking layer may be 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 the range as described above, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.
The electron transport layer may include at least one of BCP, Bphen, Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
Alternatively, the electron transport layer may include at least one of Compounds ET1 to ET25, but embodiments are not limited thereto:
A thickness of the electron transport layer may be 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 as described above, satisfactory electron transporting characteristics may be obtained 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:
In addition, the electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 19 thereinto.
The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or a combination thereof.
A thickness of the electron injection layer may be about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range as described above, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 19 is disposed above the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may include a 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. Alternatively, a transmissive formed using ITO or IZO may be used as the second electrode 19 in order to manufacture a top-emission type light-emitting device,
Hereinbefore, the organic light-emitting device has been described with reference to
According to one or more embodiments, there is provided 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 active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to one of the first electrode and the second electrode of the organic light-emitting device.
According to one or more embodiments, there is provided a diagnostic composition including the heterocyclic compound represented by Formula 1.
The diagnostic composition may include at least one heterocyclic compound represented by Formula 1.
The heterocyclic compound represented by Formula 1 provides high emission efficiency, and accordingly, 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 C1-C60 alkyl group as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The 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 as used herein may include 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, or a tert-decyl group. 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 C1-C60 alkoxy group used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C6 alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropoxy group.
Examples of the C1-C60 alkoxy group, the C1-C20 alkoxy group, or the C1-C10 alkoxy group as used herein may include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group.
The C2-C60 alkenyl group as used herein has a structure including 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 C2-C60 alkenylene group as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
The C2-C60 alkynyl group as used herein has a structure including 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 C2-C60 alkynylene group as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
The C3-C10 cycloalkyl group as used herein refers to a monovalent saturated hydrocarbon cyclic 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 C3-C10 cycloalkylene group as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
The 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 group (norbornanyl group), a bicyclo[2.2.2]octyl group, and the like.
The C1-C10 heterocycloalkyl group as used herein refers to a monovalent saturated cyclic group having at least one heteroatom, for example, N, O, P, S1, B, Ti, S, Se, Te, Ge, or any combination thereof as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof include a tetrahydrofuranyl group and a tetrahydrothiophenyl group.
The 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 as used herein may include a silolanyl group, a silinanyl group, a tetrahydrofuranyl group, a tetrahydro-2H-pyranyl group, and a tetrahydrothiophenyl group.
The C3-C10 cycloalkenyl group as used herein refers to a monovalent cyclic group that has 3 to 10 carbon atoms, at least one carbon-carbon double bond in its ring, and no aromaticity, and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The C3-C10 cycloalkenylene group as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
The C1-C10 heterocycloalkenyl group as used herein refers to a monovalent cyclic group that has at least one hetero atom, for example, N, O, P, S1, B, Ti, S, Se, Te, Ge, or any combination thereof as a ring-forming atom, 2 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C1-C10 heterocycloalkenyl group include a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group. The C2-C10 heterocycloalkenylene group as used herein refers to a divalent group having the same structure as the C1-C10 heterocycloalkenyl group.
The 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 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 two or more rings may be fused to each other.
The C7-C60 alkylaryl group as used herein refers to a C6-C60 aryl group that is substituted with at least one C1-C60 alkyl group.
The C1-C60 heteroaryl group as used herein refers to a monovalent group having a cyclic aromatic system that has at least one heteroatom, for example, N, O, P, S1, B, Ti, S, Se, Te, Ge, or any combination thereof as a ring-forming atom, and 1 to 60 carbon atoms. The C1-C60 heteroarylene group as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom, for example, N, O, P, S1, B, Ti, S, Se, Te, Ge, or any combination thereof as a ring-forming atom, and 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C6-C60 heteroaryl group and the C6-C60 heteroarylene group each include two or more rings, the two or more rings may be fused to each other.
The C2-C60 alkylheteroaryl group as used herein refers to a C1-C60 heteroaryl group that is substituted with at least one C1-C60 alkyl group.
The C6-C60 aryloxy group as used herein indicates —OA102 (wherein A102 is the C6-C60 aryl group), and the C6-C60 arylthio group as used herein indicates —SA103 (wherein A103 is the C6-C60 aryl group).
The C1-C60 heteroaryloxy group used herein indicates —OA104 (wherein A104 is a C1-C60 heteroaryl group), and the C1-C60 heteroarylthio group indicates —SA105 (wherein A105 is the C1-C6 heteroaryl group).
The monovalent non-aromatic condensed polycyclic group as used herein refers to a monovalent group having two or more rings condensed with each other, only carbon atoms (for example, having 8 to 60 carbon atoms) as ring-forming atoms, and no aromaticity in its molecular structure when considered as a whole. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The divalent non-aromatic condensed polycyclic group as used herein refers to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.
The monovalent non-aromatic condensed heteropolycyclic group as used herein refers to a monovalent group having two or more rings condensed with each other, a heteroatom, for example, N, O, P, S1, B, Ti, S, Se, Te, Ge, or any combination thereof, other than carbon atoms (for example, having 2 to 60 carbon atoms), as a ring-forming atom, and no aromaticity in its molecular structure when considered as a whole. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The divalent non-aromatic condensed heteropolycyclic group as used herein refers to a divalent group having the same structure as a monovalent non-aromatic condensed heteropolycyclic group.
The 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 (that is unsubstituted or substituted with at least one R1a)” 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 group (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 C1-C30 heterocyclic group as used herein refers to a saturated or unsaturated cyclic group having at least one heteroatom, for example, N, O, S1, P, B, Ti, S, Se, Te, Ge, or any combination thereof, other than 1 to 30 carbon atoms, as a ring-forming atom. The C1-C30 heterocyclic group may be a monocyclic group or a polycyclic group. Examples of the “C1-C30 heterocyclic group (that is unsubstituted or substituted with at least one R1a)” may include a thiophene group, a furan group, a pyrrole group, a silole group, a 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 isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group (each unsubstituted or substituted with at least one R1a).
Herein, TMS represents *—S1(CH3)3, and TMG represents *—Ge(CH3)3.
As used herein, the number of carbons in each group that is substituted (e.g., C1-C60) excludes the number of carbons in the substituent. For example, a C1-C60 alkyl group can be substituted with a C1-C60 alkyl group. The total number of carbons included in the C1-C60 alkyl group substituted with the C1-C60 alkyl group is not limited to 60 carbons. In addition, more than one C1-C60 alkyl substituent may be present on the C1-C60 alkyl group. This definition is not limited to the C1-C60 alkyl group and applies to all substituted groups that recite a carbon range.
At least one substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkyl aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkyl heteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:
Hereinafter, a compound and an organic light-emitting device according to an embodiment are described in detail with reference to Synthesis Examples and Examples. However, the disclosure is not limited to the following 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 based on molar equivalence.
Under nitrogen, 9-(3,4,5-trichlorophenyl)-9H-carbazole (3 g, 8.65 mmol), 3′,5′-di-tert-butyl-N-(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl)-[1,1′-biphenyl]-3-amine (9.69 g, 17.31 mmol), Pd2(dba)3 (0.79 g, 0.86 mmol), S-phos (0.710 g, 1.73 mmol), and Nat-OBu (2.91 g, 30.28 mmol) were added to 300 ml of xylene and refluxed for 30 minutes, and then a saturated ammonium chloride solution was used to terminate the reaction. An organic layer was extracted using ethyl acetate and then dried using MgSO4. The dried organic layer was concentrated in vacuo to remove a solvent therefrom, followed by purification through column chromatography using methylene chloride (MC):hexane (1:3), to thereby obtain 10 g of Compound 1-1 which was a white solid.
LCMS (m/z) calculated: 1361.63 g/mol, found: [M+] 1359.81 g/mol
Under nitrogen, Compound 1-1 (5 g, 3.6 mmol) was dissolved in 90 ml of t-butylbenzene, the mixture was cooled to −78° C., t-BuLi (6.2 ml, 8.99 mmol) was added thereto, and then the mixture was stirred at 60° C. for 1 hour and 30 minutes. The mixture was cooled to 0° C., boron tribromide (0.69 ml, 7.20 mmol) was added thereto, and then the mixture was stirred at room temperature for an hour and 30 minutes. The mixture was cooled to 0° C., N,N-diisopropylethyl amine (1.22 ml, 7.20 mmol) was added thereto, the mixture was heated at 120° C. for 4 hours, and then a sodium acetate solution (1.0 M in water) was used to terminate the reaction. An organic layer was extracted and dried using MgSO4. The dried organic layer was concentrated in vacuo to remove a solvent therefrom, followed by purification through column chromatography using MC:hexane (1:4), to thereby obtain 1 g of Compound 1 which was a solid. (yield: 25%)
LCMS (m/z) calculated: 1334.694 g/mol, found: [M+] 1333.74 g/mol.
An ITO glass substrate was cut to a size of 50 mm×50 mm×0.5 mm and then, sonicated in acetone isopropyl alcohol and pure water, each for 15 minutes, and then, 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 100 Å, NPB was deposited on the hole injection layer to form a first hole transport layer having a thickness of 500 Å, TCTA was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 50 Å, and mCP was deposited on the second hole transport layer to form an electron blocking layer having a thickness of 50 Å.
A first host (H16), a second host (H25), and an emitter (Compound 1) were co-deposited on the electron blocking layer to form an emission layer having a thickness of 400 Å. In this regard, the first host and the second host were mixed at a weight 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.
DBFPO was deposited on the emission layer to form a hole blocking layer having a thickness of 100 Å, and DBFPO and LiQ were co-deposited thereon at a weight ratio of 5:5 to form an electron transport layer having a thickness of 300 Å, LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and then 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.
Organic light-emitting devices were manufactured in the same manner as in Example 1, except that compounds shown in Table 2 were each used instead of the emitter in forming the emission layer.
The lifespan T95 (at 1,200 cd/m2, hr), FWHM (nm) of EL spectrum, and external quantum efficiency (EQE, %) of the organic light-emitting devices manufactured in Example 1 and Comparative Examples 1 and 2 were measured and evaluated using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). The lifespan T95 (at 1,200 cd/m2, hr) is a time taken for the luminance of the organic light-emitting devices to reduce from initial luminance of 100% to 95% thereof. The results are shown in Table 2.
From Table 2, it could be seen that the organic light-emitting device according to an embodiment had excellent emission efficiency, FWHM, and lifespan characteristics. In addition, it could be seen that the organic light-emitting device of Example 1 had higher external quantum efficiency, narrower FWHM, and significantly longer lifespan than those of the organic light-emitting devices of Comparative Examples 1 and 2.
According to the one or more embodiments, a heterocyclic compound has excellent luminescent characteristics and charge mobility characteristics, and thus, an electronic device, for example, an organic light-emitting device, including the heterocyclic compound may have low driving voltage, high efficiency, and long lifespan characteristics. Therefore, a high-quality organic light-emitting device may be implemented using the heterocyclic compound.
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 |
|---|---|---|---|
| 10-2022-0108725 | Aug 2022 | KR | national |
