Heterocyclic compounds, organic light-emitting device including the heterocyclic compounds, and electronic device including the organic light-emitting device

Abstract

Provided are a heterocyclic compound, an organic light-emitting device including the heterocyclic compound, and an electronic device including the organic light-emitting device, the heterocyclic compound being represented by Formula 1 and Formula 2, wherein, in Formula 1 and Formula 2, each group and parameter can be understood by referring to the detailed description.

Description

[0001] Cross-reference to related applications

[0002] This application claims priority to Japanese Patent Application No. 2020-216562, filed on December 25, 2020, with the Japan Patent Office, and Korean Patent Application No. 10-2021-0053758, filed on April 26, 2021, with the Korean Intellectual Property Office, the entire disclosure of which is incorporated herein by reference. Technical Field

[0003] This disclosure relates to heterocyclic compounds, organic light-emitting devices including said heterocyclic compounds, and electronic devices including said organic light-emitting devices. Background Technology

[0004] Organic light-emitting devices (OLEDs) are self-emitting devices that, compared to conventional devices, offer a wide viewing angle, high contrast, short response time, and excellent brightness, driving voltage, and response speed characteristics, while also producing full-color images.

[0005] An OLED comprises an anode, a cathode, and an organic layer between the anode and cathode, including an emitter layer. A hole transport region is located between the anode and the emitter layer, and an electron transport region is located between the emitter layer and the cathode. Holes supplied from the anode can move towards the emitter layer through the hole transport region, and electrons supplied from the cathode can move towards the emitter layer through the electron transport region. Holes and electrons recombine in the emitter layer to generate excitons. Excitons can transition from an excited state to the ground state, thereby producing light. Summary of the Invention

[0006] One or more embodiments relate to heterocyclic compounds, organic light-emitting devices comprising said heterocyclic compounds, and electronic devices comprising said organic light-emitting devices, and more particularly, to heterocyclic compounds that can improve the luminous efficiency of organic light-emitting devices, said heterocyclic compounds having a narrow emission spectral width and improved color purity and emitting blue light.

[0007] Other 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 embodiments presented in this disclosure.

[0008] According to one embodiment, the heterocyclic compound is represented by Formula 1 and (plus) Formula 2:

[0009] Formula 1

[0010]

[0011] Formula 2

[0012]

[0013] Among them, in equations 1 and 2,

[0014] Ar1-Ar5 are each independently an aromatic hydrocarbon ring having 6 or more and 14 or fewer cyclic atoms, or a heteroaromatic ring having 5 or more and 14 or fewer cyclic atoms.

[0015] R1-R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted halocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted heteroarylalkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heteroarylthio group, or a substituted or unsubstituted amino group.

[0016] n1 is 0, 1, 2, 3, 4, 5, or 6.

[0017] n2 and n5 are each independently 0, 1, 2, 3, 4, 5, 6, 7, or 8.

[0018] n3 and n4 are each independently 0, 1, 2, 3, 4, 5, 6, or 7.

[0019] When n1 is 2 or greater, two or more R1s can be the same or different from each other.

[0020] When n² is 2 or greater, two or more R² can be the same or different from each other.

[0021] When n3 is 2 or greater, two or more R3s can be the same or different from each other.

[0022] When n4 is 2 or greater, two or more R4s can be the same or different from each other.

[0023] When n5 is 2 or greater, two or more R5s can be the same or different from each other, and

[0024] In Formula 2, * represents a binding site with a cyclic atom of Ar1 in Formula 1, a cyclic atom of Ar2 in Formula 1, or a cyclic atom of Ar3 in Formula 1, or a combination thereof.

[0025] In Formulas 1 and 2, two or more adjacent groups of R1, R2, R3, R4, or R5 are optionally connected to each other to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0026] According to another embodiment, the organic light-emitting device includes a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, including an emission layer, and the organic light-emitting device includes the heterocyclic compound.

[0027] According to another embodiment, the electronic device includes the organic light-emitting device. Attached Figure Description

[0028] The above and other aspects, features, and advantages of certain embodiments of this disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, wherein:

[0029] Figure 1 A schematic cross-sectional view illustrating an organic light-emitting device according to an exemplary embodiment;

[0030] Figure 2 A schematic cross-sectional view illustrating an organic light-emitting device according to another exemplary embodiment;

[0031] Figure 3 A schematic cross-sectional view illustrating an organic light-emitting device according to yet another exemplary embodiment;

[0032] Figures 4A-4E Each is a schematic diagram illustrating the energy levels of an organic light-emitting device according to an exemplary embodiment;

[0033] Figure 5 To demonstrate the effect of compound 1 obtained in synthesis example 4 1 The H-NMR spectrum; and

[0034] Figure 6 To demonstrate the effect of compound 23 obtained in synthesis example 4 1 The 1H-NMR spectrum. Detailed Implementation

[0035] The embodiments will now be described, examples of which are shown in the accompanying drawings, wherein the same reference numerals always refer to the same elements. In this respect, the embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below only by reference to the accompanying drawings to illustrate aspects. As used herein, the term "and / or" includes any and all combinations of one or more of the associated enumerated items. Expressions such as "at least one of" modify the entire list of elements when preceding or following it, without modifying any individual element of the list.

[0036] It will be understood that when an element is referred to as being "on" another element, it may be directly on said other element or there may be intermediate elements between them. Conversely, when an element is referred to as being "directly on" another element, there are no intermediate elements.

[0037] 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 parts, these elements, components, regions, layers, and / or parts should not be limited by these terms. These terms are used only to distinguish one element, component, region, layer, or part from another. Therefore, without departing from the teachings herein, the “first element,” “component,” “region,” “layer,” or “part” discussed below may be referred to as a second element, component, region, layer, or part.

[0038] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, “a”, “the”, and “at least one” do not indicate a limitation of quantity and are intended to cover both the singular and the plural unless the context clearly indicates otherwise. For example, “(a) element” has the same meaning as “at least one element” unless the context clearly indicates otherwise.

[0039] "Or" means "and / or". As used herein, "and / or" includes any and all combinations of one or more of the associated listed items. It will be further understood that the terms "comprising" or "including", when used in this specification, indicate the presence of the stated features, areas, integrals, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more additional features, areas, integrals, steps, operations, elements, components, and / or collections thereof.

[0040] Furthermore, relative terms such as “lower” or “bottom” and “upper” or “top” may be used herein to describe the relationship between one element and another element as shown in the figures. It will be understood that, in addition to the orientation shown in the figures, relative terms are also intended to cover different orientations of the device. For example, if the device in one of the figures is flipped, the element described as being on the “lower” side of another element will be oriented on the “upper” side of said other element. Thus, depending on the specific orientation of the figure, the exemplary term “lower” can cover both “lower” and “upper” orientations. Similarly, if the device in one of the figures is flipped, the element described as being “below” or “under” other elements will be oriented “above” said other elements. Thus, the exemplary terms “below” or “under” can cover both “above” and “below” orientations.

[0041] As used herein, “about” or “approximately” includes the stated value and means within an acceptable range of deviation from the specific value, as determined by a person skilled in the art taking into account the measurement in question and the errors associated with the measurement of the specific quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations relative to the stated value, or within ±10% or 5%.

[0042] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It will be further understood that terms, such as those defined in common dictionaries, should be interpreted as having the same meaning as they have in the context of this disclosure and the relevant field, and will not be interpreted in an idealized or overly formal sense unless clearly defined herein.

[0043] Exemplary embodiments are described herein with reference to cross-sectional views that serve as schematic representations of idealized embodiments. Thus, deviations from the shapes shown in the figures will be anticipated as a result of, for example, manufacturing techniques and / or tolerances. Therefore, the embodiments described herein should not be construed as limited to the specific shapes of the regions illustrated herein, but rather include deviations in shape caused, for example, by manufacturing processes. For example, regions illustrated or described as flat may typically have rough and / or non-linear characteristics. Furthermore, sharp corners in the figures may be rounded. Therefore, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shapes of the regions nor to limit the scope of the claims.

[0044] Unless otherwise defined, measurements of operational and physical properties may be performed at room temperature (about 20°C or higher and about 25°C or lower) and at a relative humidity (RH) of about 40% or higher and about 50% or lower.

[0045] The term “X and Y can be independent of each other” as used in this article can be understood as X and Y being the same or different from each other.

[0046] As used herein, the term "cycle-derived group" refers to a group obtained by removing hydrogen atoms that are bonded to cyclic atoms in a ring structure.

[0047] Heterocyclic compounds

[0048] The heterocyclic compound can be represented by Formula 1 and Formula 2:

[0049] Formula 1

[0050]

[0051] Formula 2

[0052]

[0053] Among them, in equations 1 and 2,

[0054] Ar1-Ar5 can each independently be an aromatic hydrocarbon ring having 6 or more and 14 or fewer cyclic atoms, or a heteroaromatic ring having 5 or more and 14 or fewer cyclic atoms.

[0055] R1-R5 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkylalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted cycloalkenylalkyl group, a substituted or unsubstituted heterocyclic alkyl group, a substituted or unsubstituted heterocyclic alkylalkyl group, a substituted or unsubstituted heterocyclic alkenyl group, or a substituted or unsubstituted haloalkyl group. Substituted or unsubstituted halocycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted cycloalkoxy, substituted or unsubstituted alkylthio, substituted or unsubstituted cycloalkoxy, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted heteroarylthio, or substituted or unsubstituted amino.

[0056] n1 can be 0, 1, 2, 3, 4, 5, or 6.

[0057] n2 and n5 can each be independently 0, 1, 2, 3, 4, 5, 6, 7, or 8.

[0058] n3 and n4 can each be independently 0, 1, 2, 3, 4, 5, 6, or 7.

[0059] When n1 is 2 or greater, two or more R1s can be the same or different from each other.

[0060] When n² is 2 or greater, two or more R² can be the same or different from each other.

[0061] When n3 is 2 or greater, two or more R3s can be the same or different from each other.

[0062] When n4 is 2 or greater, two or more R4s can be the same or different from each other.

[0063] When n5 is 2 or greater, two or more R5s can be the same or different from each other, and

[0064] In Formula 2, * represents a binding site with a cyclic atom of Ar1 in Formula 1, a cyclic atom of Ar2 in Formula 1, a cyclic atom of Ar3 in Formula 1, or a combination thereof.

[0065] In Formulas 1 and 2, two or more adjacent groups of R1, R2, R3, R4, or R5 are optionally connected to each other to form substituted or unsubstituted C5-C. 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0066] In Equations 1 and 2, when each of n1-n5 is 0, R1-R5 corresponding to n1-n5 may not exist, and the rings including R1-R5 may not be replaced by R1-R5, but instead are bonded to the rings by hydrogen atoms.

[0067] The heterocyclic compound may include one structure of Formula 1 and one, two, or three structures of Formula 2. When the heterocyclic compound includes two or three structures of Formula 2, the two or three structures of Formula 2 may be the same as or different from each other. For example, Formula 2 may be combined with Formula 1 as follows:

[0068] 1. When the heterocyclic compound comprises a structure of Formula 2,

[0069] Equation (1-1)2 can be combined only with the cyclic atoms of Ar1 in Equation 1.

[0070] Equation 2 (1-2) can be combined only with the cyclic atoms of Ar2 in Equation 1, or

[0071] Equation (1-3)2 can be combined only with the cyclic atoms of Ar3 in Equation 1.

[0072] 2. When the heterocyclic compound comprises two structures of formula 2,

[0073] (2-1) One structure of Formula 2 can be incorporated into the cyclic atom of Ar1 in Formula 1, and another structure of Formula 2 can be incorporated into the cyclic atom of Ar2 in Formula 1.

[0074] (2-2) One structure of Formula 2 can be incorporated into the cyclic atom of Ar1 in Formula 1, and another structure of Formula 2 can be incorporated into the cyclic atom of Ar3 in Formula 1.

[0075] (2-3) One structure of Formula 2 can be incorporated into the cyclic atom of Ar2 in Formula 1, and another structure of Formula 2 can be incorporated into the cyclic atom of Ar3 in Formula 1.

[0076] (2-4) One structure of Formula 2 can be incorporated into the cyclic atom of Ar1 in Formula 1, and another structure of Formula 2 can be incorporated into the cyclic atom of Ar1 in Formula 1.

[0077] (2-5) One structure of Formula 2 can be incorporated into the cyclic atom of Ar2 in Formula 1, and another structure of Formula 2 can be incorporated into the cyclic atom of Ar2 in Formula 1, or

[0078] (2-6) One structure of Formula 2 can be incorporated into the cyclic atom of Ar3 in Formula 1, and another structure of Formula 2 can be incorporated into the cyclic atom of Ar3 in Formula 1.

[0079] 3. When the heterocyclic compound comprises three structures of formula 2,

[0080] (3-1) One structure of Formula 2 can be combined with the cyclic atom of Ar1 in Formula 1, another structure of Formula 2 can be combined with the cyclic atom of Ar2 in Formula 1, and yet another structure of Formula 2 can be combined with the cyclic atom of Ar3 in Formula 1.

[0081] In some embodiments, the heterocyclic compound may be in the form of (1-1).

[0082] In some embodiments, the heterocyclic compound represented by Formulas 1 and 2 may be represented by one of Formulas 1-1 to 1-4. When the heterocyclic compound is represented by one of Formulas 1-1 to 1-4, the heterocyclic compound may have a narrower blue emission spectrum and higher color purity. Therefore, organic light-emitting devices comprising the heterocyclic compound may have improved luminous efficiency.

[0083] Equation 1-1

[0084]

[0085] Formula 1-2

[0086]

[0087] Formula 1-3

[0088]

[0089] Formula 1-4

[0090]

[0091] Among them, in equations 1-1 to 1-4,

[0092] Ar1-Ar5, R1-R5, and n1-n5 can each be understood by referring to the descriptions of Ar1-Ar5, R1-R5, and n1-n5 provided herein.

[0093] Ar1-Ar5 in Formulas 1, 2, and 1-1 to 1-4 can each independently be an aromatic hydrocarbon ring having 6 or more and 14 or fewer cyclic atoms, or a heteroaromatic ring having 5 or more and 14 or fewer cyclic atoms.

[0094] R1-R5 in Formulas 1, 2, and 1-1 to 1-4 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkylalkyl group, a substituted or unsubstituted cycloalkenylalkyl group, a substituted or unsubstituted heterocyclic alkyl group, a substituted or unsubstituted heterocyclic alkylalkyl group, a substituted or unsubstituted heterocyclic alkenyl group, or a substituted or unsubstituted halogen. Alkyl, substituted or unsubstituted halocycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted cycloalkoxy, substituted or unsubstituted alkylthio, substituted or unsubstituted cycloalkoxy, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted heteroarylthio, or substituted or unsubstituted amino.

[0095] In Formulas 1, 2, and 1-1 to 1-4, the aromatic hydrocarbon ring may be a single ring or a fused ring composed of two or more rings. The number of cyclic atoms in the aromatic hydrocarbon ring may be 6 or more and 14 or fewer, 6 or more and 10 or fewer, or 6. For example, the aromatic hydrocarbon ring may be a benzene ring, a naphthalene ring, an anthracene ring, or a phenanthrene ring. In some embodiments, the aromatic hydrocarbon ring may be a benzene ring.

[0096] In Formulas 1, 2, and 1-1 to 1-4, the heteroaromatic ring may be a single ring or a fused ring composed of two or more rings. The heteroaromatic ring may include at least one heteroatom (e.g., N, O, P, S, or Si) as a cyclic atom, and other cyclic atoms may be C. The heteroatom may be N, O, or S. In some embodiments, the heteroatom may be N. The number of cyclic atoms in the heteroaromatic ring may be 5 or more and 14 or fewer, 5 or more and 13 or fewer, 5 or more and 12 or fewer, or 5 or more and 10 or fewer. The number of heteroatoms in the heteroaromatic ring may be 1 or more and 3 or fewer, 1 or more and 2 or fewer, or 1. For example, the heteroaromatic ring may be a furan ring, a benzofuran ring, an isobenzofuran ring, a pyrrole ring, an indole ring, an isoindole ring, a thiophene ring, a benzothiophene ring, a benzo(c)thiophene ring, a selenophene ring, a benzoselenophene ring, a benzo(c)selenophene ring, an imidazole ring, a benzimidazole ring, a purine ring, a pyrazole ring, or an indazole ring. azole ring, benzo[a] azole ring, iso- azole ring, benzyl isocyanate The heteroaromatic ring may be an azole ring, a thiazole ring, a benzothiazole ring, a pyridine ring, a quinoline ring, an isoquinoline ring, a pyrazine ring, a quinoxaline ring, an acridine ring, a pyrimidine ring, a quinazoline ring, a pyridazine ring, a cyclophosphine ring, a 1,2,3-triazine ring, a 1,2,4-triazine ring, a 1,3,5-triazine ring, a dibenzofuran ring, or a dibenzothiophene ring. For example, the heteroaromatic ring may be a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring.

[0097] In some embodiments, Ar1-Ar5 in Formulas 1, 2, and 1-1 to 1-4 may each be independently a benzene ring, a naphthyl ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring.

[0098] In some embodiments, Ar1-Ar5 in Formulas 1, 2, and 1-1 to 1-4 may each be independently a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring.

[0099] In some embodiments, Ar1-Ar5 in Formulas 1, 2, and 1-1 to 1-4 may each be a benzene ring simultaneously.

[0100] As used herein, the term "alkyl" refers to a straight-chain or branched monovalent aliphatic hydrocarbon group. As used herein, the term "cycloalkyl" refers to a monovalent cyclic group of a saturated hydrocarbon. Examples of alkyl and cycloalkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, or adamantyl.

[0101] As used herein, the term "alkenyl" refers to a hydrocarbon group formed by including at least one carbon-carbon double bond at the middle or end of an alkyl group, and examples include vinyl, propenyl, and butenyl.

[0102] As used herein, the term "cycloalkenyl" refers to a monovalent monocyclic group having at least one carbon-carbon double bond in its ring and not being aromatic, and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl.

[0103] As used herein, the term "alkynyl" refers to a hydrocarbon group formed by including at least one carbon-carbon triple bond at the middle or end of an alkyl group, and examples of such groups include ethynyl and propynyl.

[0104] As used herein, the term "cycloalkylalkyl" refers to a monovalent saturated hydrocarbon cyclic group attached to an alkylene group. As used herein, "alkylene" refers to a divalent group having the same structure as an alkyl group. Non-limiting examples of cycloalkylalkyl groups include -CH2-cyclopropyl.

[0105] As used herein, the term "heterocyclic alkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom as a cyclic atom. Non-limiting examples include tetrahydrofuranyl and tetrahydrothiophenyl.

[0106] As used herein, the term "heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom as a cyclizing atom in its ring and having at least one carbon-carbon double bond. C1-C 10 Examples of heterocyclic alkenyl groups are 2,3-dihydrofuranyl and 2,3-dihydrothiophenyl.

[0107] As used herein, the term "heterocyclic alkyl group" refers to a monovalent saturated monocyclic group having at least one heteroatom as a cyclizing atom and attached to an alkylene group. Non-limiting examples include -CH2-tetrahydrofuranyl.

[0108] As used herein, the term "haloalkyl" refers to a halogen-substituted alkylene group. The alkyl group may be in a straight-chain or branched form. There is no particular limitation on the number of carbon atoms in the haloalkyl group, and it may be one or more and 20 or fewer, or for example, 10 or fewer, or 4 or fewer. In Formulas 1, 2, and 1-1 to 1-4, the term "halocycloalkyl" refers to a halogen-substituted monovalent cycloalkyl group. The halocycloalkyl group may be substituted with a straight-chain or branched alkyl group. There is no particular limitation on the number of carbon atoms in the halocycloalkyl group, and it may be three or more and 10 or fewer, or for example, 8 or fewer, or 6 or fewer. There is no particular limitation on examples of haloalkyl and halocycloalkyl groups. At least one hydrogen atom in the alkyl and cycloalkyl groups may be replaced by a halogen atom. The halogen atom may be a fluorine atom, a chlorine atom, a bromine atom, and / or an iodine atom. In some embodiments, examples of alkyl halogens include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, iodomethyl, diiodomethyl, triiodomethyl, fluoroethyl, chloroethyl, bromoethyl, and iodoethyl.

[0109] As used herein, the term "alkoxy" refers to the compound formed by -OA 101 (where A) 101 An alkoxy group is a monovalent group represented by an alkyl group. The alkyl group may be in a straight-chain or branched form. The number of carbon atoms in the alkoxy group is not particularly limited and may be one or more, and 20 or fewer, or for example, 10 or fewer, or 4 or fewer. As used herein, the term "cycloalkoxy" refers to a group consisting of -OA... 102 (where A) 102The cycloalkoxy group is a monovalent group represented by a cycloalkyl group. A cycloalkoxy group may be substituted with a straight-chain or branched alkyl group. There is no particular limitation on the number of carbon atoms in the cycloalkoxy group, and it may be 3 or more and 10 or fewer, or for example, 8 or fewer or 6 or fewer. There are no particular limitations on the examples of alkoxy and cycloalkoxy groups. Examples of alkoxy and cycloalkoxy groups may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, isobutoxy, 2-ethylbutoxy, 3,3-dimethylbutoxy, n-pentoxy, isopentoxy, neopentoxy, tert-pentoxy, cyclopentoxy, 1-methylpentoxy, 3-methylpentoxy, 2-ethylpentoxy, 4-methyl-2-pentoxy, n-hexoxy, 1-methylhexoxy, 2-ethylhexoxy, 2-butylhexoxy, cyclohexoxy, 4-methylcyclohexoxy, 4-tert-butylcyclohexoxy, n-heptoxy, 1-methylheptoxy, 2,2-dimethylheptoxy, 2-ethylheptoxy, 2-butylheptoxy, n-octoxy, tert-octoxy, 2-ethyloctoxy, 2-butyloctoxy, 2-hexyloctoxy, 3,7-dimethyloctoxy, cyclooctoxy, n-nonoxy, n-decoxy, and adamantoxy.

[0110] As used herein, the term "alkylthio" refers to the group consisting of -SA 110 (where A) 110 A monovalent group represented by an alkyl group. The alkyl group may be in a straight-chain or branched form. The number of carbon atoms in the alkylthio group is not particularly limited and may be one or more, and 20 or fewer, or for example, 10 or fewer, or 4 or fewer. As used herein, the term "cycloalkylthio" refers to a group consisting of -SA 111 (where A) 111 The cycloalkyl group is a monovalent group represented by a cycloalkyl group. The cycloalkyl thio group may be replaced by a straight-chain or branched alkyl group. There is no particular limitation on the number of carbon atoms in the cycloalkyl thio group and it may be 3 or more and 10 or fewer, or for example 8 or fewer or 6 or fewer.

[0111] As used herein, the term "aryl" refers to a group derived from a hydrocarbon ring that is partially or entirely aromatic. When an aryl group comprises a hydrocarbon ring that is partially or entirely aromatic, the hydrocarbon ring may be linked by a single bond or be fused. When an aryl group comprises a hydrocarbon ring that is partially or entirely aromatic, multiple hydrocarbon rings may share a single atom. The number of carbon atoms in an aryl group is not particularly limited and may be 6 or more and 30 or fewer, 6 or more and 12 or fewer, or 6 or fewer. Examples of aryl groups are not particularly limited. Examples of aryl groups include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, anthracene, tetraphenyl, pentylenyl, hexenyl, benzo[9,10]phenanthryl, pyrene, benzofluorenyl, and In some embodiments, the aryl group may be phenyl.

[0112] As used herein, the term "arylalkyl" refers to a monovalent aryl group attached to an alkylene group. Non-limiting examples of arylalkyl groups include -CH2-phenyl.

[0113] As used herein, the term "heteroaryl" refers to a group derived from a heterocyclic ring that is partially or entirely aromatic. When a heteroaryl group comprises a partially or entirely aromatic heterocyclic ring, the heterocyclic ring may be linked by a single bond or be fused. When a heteroaryl group comprises a partially or entirely aromatic heterocyclic ring, multiple heterocyclic rings may share a single atom. There are no particular limitations on the heteroatoms included in a heteroaryl group. For example, a heteroaryl group may include at least one heteroatom (e.g., N, O, P, S, Si, Se, or Ge) as a cyclizing atom and include 3 to 30 carbon atoms. There are no particular limitations on the number of cyclizing atoms in a heteroaryl group. The number of cyclizing atoms may be 5 or more and 30 or fewer, 5 or more and 14 or fewer, or 5 or more and 13 or fewer. There are no particular limitations on the number of heteroatoms in a heteroaryl group. The number of heteroatoms may be 1 or more and 3 or fewer, 1 or more and 2 or fewer, or 1. Examples of heteroaryl groups include thienyl, furanyl, pyrroleyl, imidazolyl, and thiazolyl. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Triazolyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phenyl Azinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzocarbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzothiaphenyl, dibenzothiaphenyl, thienothiaphenyl, benzofuranyl, phenanthrolinel, thiazolyl, iso azole group, Diazolyl, thiadiazolyl, phenothiazinyl, dibenzothiophenolyl, dibenzofuranyl, and xanthoneyl.

[0114] As used herein, the term "heteroarylalkyl" refers to a monovalent heteroaryl group attached to an alkylene group. Non-limiting examples of heteroarylalkyl groups include -CH2-pyridyl.

[0115] As used herein, the term "aryloxy group" refers to the group consisting of -OA 104 (where A) 104The aryl group is a monovalent group represented by an aryl group. There is no particular limitation on the number of carbon atoms in the aryl group, and it can be 6 or more and 30 or fewer, 6 or more and 12 or fewer, or 6 or fewer. Examples of aryl groups include phenyloxy, biphenyloxy, triphenyloxy, naphthyloxy, fluorenyloxy, anthraceneyloxy, tetraphenyloxy, penfenyloxy, benzo[9,10]phenanthreneoxy, pyreneoxy, benzo[9,10]fluorenyloxy, and... Oxykji.

[0116] As used herein, the term "arylthio" refers to a group consisting of -SA 105 (where A) 105 The aryl thioyl group is a monovalent group. The number of carbon atoms in the aryl thioyl group is not particularly limited and can be 6 or more and 30 or fewer, 6 or more and 12 or fewer, or 6 or fewer. Examples of aryl thioyl groups are not particularly limited. Aryl thioyl groups can be phenylthioyl, biphenylthioyl, triphenylthioyl, naphthioyl, fluorenylthio, anthraceneylthio, tetraphenylthio, pentylenylthio, benzo[9,10]phenanthreneylthio, pyreneylthio, benzofluorenylthio, etc. Thio group, or a combination thereof.

[0117] As used herein, the term "heteroaryloxy" refers to a compound formed by -OA 106 (where A) 106 A heteroaryl group (represented by a heteroaryl group) is a monovalent group. There are no particular limitations on the heteroatoms included in a heteroaryl group. For example, a heteroaryl group may include at least one heteroatom (e.g., N, O, P, S, Si, Se, or Ge) as a cyclizing atom and include 3-30 carbon atoms. There are no particular limitations on the number of cyclizing atoms in a heteroaryl group. The number of cyclizing atoms may be 5 or more and 30 or less, 5 or more and 14 or less, or 5 or more and 13 or less. There are no particular limitations on the number of heteroatoms in a heteroaryl group. The number of heteroatoms may be 1 or more and 3 or less, 1 or more and 2 or less, or 1. There are no particular limitations on examples of heteroaryl groups. Examples of heteroaryl groups include thienyloxy, furanyloxy, pyrroleyloxy, imidazolyloxy, thiazolyloxy, and others. azoleoxy Diazolyloxy, Triazolyloxy, Pyridyloxy, Bipyridyloxy, Pyrimidinyloxy, Triazinyloxy, Triazolyloxy, Acridineyloxy, Pyridazinyloxy, Quinolinyloxy, Quinazolinyloxy, Quinoxalinyloxy, Phenyl Phthalomethazinyloxy, pyridopyrimidinyloxy, pyridopyrazinyloxy, pyrazinopyrazinyloxy, isoquinolinyloxy, indolyloxy, carbazoleyloxy, benzocarbazoleyloxy, benzo[] Azoxyl, benzimidazolyloxy, benzothiazolyloxy, benzothiaphenyloxy, dibenzothiaphenyloxy, thienothiaphenyloxy, benzofuranyloxy, phenanthrolineloxy, thiazolyloxy, iso azoleoxy Diazolyloxy, thiadiazolyloxy, phenthiazinyloxy, dibenzothiopyrrolyloxy, dibenzofuranyloxy, and xanthoneyloxy.

[0118] In Formulas 1, 2, and 1-1 to 1-4, the term "heteroarylthio" refers to the group consisting of -SA 107 (where A) 107 This is a monovalent group represented by a heteroaryl group. There are no particular limitations on the heteroatoms included in a heteroaryl thio group. For example, a heteroaryl thio group may include at least one heteroatom (e.g., N, O, P, S, Si, Se, or Ge) as a cyclic atom and include 3-30 carbon atoms. There are no particular limitations on the number of cyclic atoms in a heteroaryl thio group, and it may be 5 or more and 30 or fewer, 5 or more and 14 or fewer, or 5 or more and 13 or fewer. There are no particular limitations on the number of heteroatoms in a heteroaryl thio group. The number of heteroatoms may be 1 or more and 3 or fewer, 1 or more and 2 or fewer, or 1. Examples of heteroaryl thio groups are not particularly limited and include thiophene thio, furanyl thio, pyrrole thio, imidazolyl thio, thiazolyl thio, etc. azole thio, Diazolylthio, Triazolylthio, Pyridylthio, Bipyridylthio, Pyrimidylthio, Triazinylthio, Triazolylthio, Acridineylthio, Pyridazinylthio, Quinolinylthio, Quinazolinylthio, Quinoxalinylthio, Phenoyl Phthalothio, Phthalothio, Pyridopyrimidinylthio, Pyridopyrazinylthio, Pyrazopyrazinylthio, Isoquinolineylthio, Indoleylthio, Carbazoleylthio, Benzocarbazoleylthio, Benzo Azolylthio, benzimidazolylthio, benzothiazolylthio, benzothiopheneylthio, dibenzothiopheneylthio, thienenothiopheneylthio, benzofuranylthio, phenanthrolinelthio, thiazolylthio, iso azole thio, Diazolylthio, thiadiazolylthio, phenothiazinylthio, dibenzothiopyrroleylthio, dibenzofuranylthio, and xanthoneylthio.

[0119] In Formulas 1, 2, and 1-1 to 1-4, the halogen atom is not particularly limited. For example, the halogen atom may be a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. In some embodiments, the halogen atom may be a fluorine atom.

[0120] In formulas 1, 2, and 1-1 to 1-4, the amino group may be -NH2 or a monosubstituted amino group represented by -NHR or a disubstituted amino group represented by -NRR′, wherein R and R′ may each be an organic group independently. R and R′ may not be particularly limited. For example, R and R′ may each be a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl, and R and R′ may be the same as or different from each other.

[0121] The alkyl, alkenyl, and alkynyl groups in R and R′ can each be in a straight-chain, branched, or cyclic form, or for example, a straight-chain form. The number of carbon atoms in the alkyl, alkenyl, and alkynyl groups is not particularly limited and can be one or more and 20 or fewer, or for example, 10 or fewer, or 4 or fewer. Examples of the alkyl group are not particularly limited, and the alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, or adamantyl. The alkenyl group is not particularly limited. The alkenyl group may be vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, or 1-ethyl-2-propenyl. The alkynyl group is not particularly limited. The alkynyl group may be 2-butynyl, 3-pentyl, hexynyl, heptyynyl, octyynyl, or decanynyl.

[0122] The aryl groups in R and R′ can be understood by referring to the descriptions of aryl groups provided herein. In some embodiments, the aryl groups in R and R′ may be monovalent groups derived from an aromatic hydrocarbon ring having six or more cyclic atoms. Furthermore, the aromatic hydrocarbon ring having six or more cyclic atoms can be understood by referring to the descriptions of aromatic hydrocarbon rings provided herein.

[0123] The heteroaryl groups in R and R′ can be understood by referring to the descriptions of heteroaryl groups provided herein. In some embodiments, the heteroaryl groups in R and R′ may be monovalent groups derived from a heteroaromatic ring having five or more cyclic atoms. Furthermore, the heteroaromatic ring having five or more cyclic atoms can be understood by referring to the descriptions of heteroaromatic rings provided herein.

[0124] In some embodiments, the amino group may be a disubstituted amino group represented by -NRR′. R and R′ may each be independently aryl or heteroaryl. Examples of amino groups are not particularly limited. Examples of amino groups may include N,N-diarylamino, N,N-diheteroarylamino, or N-aryl-N-heteroarylamino. Furthermore, R and R′ may each be independently a monovalent group derived from an aromatic hydrocarbon ring having 6 or more and 30 or fewer cyclic atoms, or from a heteroaromatic ring having 5 or more and 30 or fewer cyclic atoms. In particular, R and R′ may each be independently a monovalent group derived from an aromatic hydrocarbon ring having 6 or more and 30 or fewer cyclic atoms. The aromatic hydrocarbon ring and the heteroaromatic ring can be understood respectively by referring to the description of aromatic hydrocarbon rings and heteroaromatic rings provided herein. In some embodiments, the amino group may be N,N-diphenylamino.

[0125] In formulas 1, 2, and 1-1 to 1-4, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocycloalkyl, heterocycloalkylalkyl, haloalkyl, halocycloalkyl, alkoxy, cycloalkoxy, alkylthio, cycloalkylthio, aryl, arylalkyl, heteroaryl, heteroarylalkyl, aryloxy, heteroaryloxy, arylthio, heteroarylthio, and amino groups may each be substituted. Substituents are not particularly limited, and may be, for example, alkyl, cycloalkyl, alkenyl, alkynyl, deuterium, halogen, cyano, alkoxy, alkylthio, silyl, germanyl, halogen-substituted alkyl, and deuterium-substituted alkyl. In some embodiments, the substituent may be a fluorine atom or an alkyl group; for example, the substituent may be methyl, tert-butyl, or a fluorine atom. In formulas 1, 2, and 1-1 to 1-4, the amino group may be a monosubstituted amino group or a disubstituted amino group, and the substituents bonded to the alkyl, alkenyl, or alkynyl group forming the amino group may be, for example, a deuterium atom, a halogen atom, or a cyano group. In formulas 1, 2, and 1-1 to 1-4, the amino group may be a monosubstituted amino group or a disubstituted amino group, and the groups bonded to the N atom of the monosubstituted and disubstituted amino groups include aryl and / or heteroaryl groups. The aryl and / or heteroaryl groups bonded to the N atom of the monosubstituted and disubstituted amino groups may be substituted by at least one substituent. Substituents may include, for example, alkyl, cycloalkyl, alkenyl, alkynyl, deuterium atom, halogen atom, cyano, alkoxy, alkylthio, silyl, germanyl, halogen-substituted alkyl, and deuterium-substituted alkyl. In some embodiments, the substituents may be fluorine atoms or alkyl groups, such as methyl, tert-butyl, or fluorine atoms, or, for example, methyl or fluorine atoms. Furthermore, the substituents, including alkyl, alkenyl, alkynyl, halogen atoms, and alkyl groups substituted with deuterium atoms, can be understood by referring to the descriptions of alkyl, alkenyl, alkynyl, halogen atoms, and alkyl groups substituted with deuterium atoms provided herein.

[0126] In some embodiments, the alkyl group may not be substituted with an alkyl group, and the haloalkyl group may not be further substituted with an alkyl group and / or a halogen atom.

[0127] In some embodiments, in formulas 1, 2, and 1-1 to 1-4, R1-R5 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a straight-chain or branched unsubstituted alkyl group having one or more and 20 or fewer carbon atoms, a straight-chain or branched unsubstituted alkenyl group having two or more and 20 or fewer carbon atoms, a straight-chain or branched unsubstituted alkynyl group having two or more and 20 or fewer carbon atoms, a substituted or unsubstituted cycloalkyl group having three or more and 10 or fewer carbon atoms, or a substituted or unsubstituted cycloalkyl group having four or more and 10 or fewer carbon atoms. Cycloalkylalkyl with fewer carbon atoms, substituted or unsubstituted cycloalkenyl with 3 or more and 10 or fewer carbon atoms, substituted or unsubstituted cycloalkenylalkyl with 4 or more and 10 or fewer carbon atoms, substituted or unsubstituted heterocyclic alkyl with 2 or more and 10 or fewer carbon atoms, substituted or unsubstituted heterocyclic alkylalkyl with 3 or more and 10 or fewer carbon atoms, unsubstituted straight-chain or branched haloalkyl with 1 or more and 20 or fewer carbon atoms, substituted or unsubstituted with 3 or more and 10 or fewer carbon atoms Halogenated cycloalkyl, straight-chain or branched unsubstituted alkoxy group having one or more and 20 or fewer carbon atoms, substituted or unsubstituted cycloalkoxy group having three or more and 10 or fewer carbon atoms, substituted or unsubstituted alkylthio group having one or more and 20 or fewer carbon atoms, substituted or unsubstituted cycloalkoxy group having three or more and 10 or fewer carbon atoms, substituted or unsubstituted aryl group having six or more and 30 or fewer carbon atoms, substituted or unsubstituted arylalkyl group having seven or more and 30 or fewer carbon atoms, substituted or unsubstituted The following are substituted aryloxy groups having 6 or more and 30 or fewer carbon atoms, substituted or unsubstituted arylthio groups having 6 or more and 30 or fewer carbon atoms, substituted or unsubstituted heteroaryl groups having 3 or more and 30 or fewer carbon atoms, substituted or unsubstituted heteroarylalkyl groups having 4 or more and 30 or fewer carbon atoms, substituted or unsubstituted heteroaryloxy groups having 3 or more and 30 or fewer carbon atoms, substituted or unsubstituted heteroarylthio groups having 3 or more and 30 or fewer carbon atoms, or disubstituted amino groups represented by -NRR′, and

[0128] R and R′ can each be a monovalent group derived independently from an aromatic hydrocarbon ring having 6 or more and 30 or fewer cyclic atoms, or a monovalent group derived from a heteroaromatic ring having 5 or more and 30 or fewer cyclic atoms.

[0129] In some embodiments, in formulas 1, 2, and 1-1 to 1-4, R1-R5 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a straight-chain or branched unsubstituted alkyl group having one or more and 20 or fewer carbon atoms, a substituted or unsubstituted cycloalkyl group having three or more and 10 or fewer carbon atoms, or a substituted or unsubstituted aryl group having six or more and 30 or fewer carbon atoms.

[0130] In some embodiments, in formulas 1, 2, and 1-1 to 1-4, R1-R5 may each independently be a hydrogen atom, a deuterium atom, -F, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by any one of formulas 9-1 to 9-39, a group represented by any one of formulas 9-1 to 9-39 wherein at least one hydrogen atom is replaced by a deuterium atom, a group represented by any one of formulas 9-1 to 9-39 wherein at least one hydrogen atom is replaced by -F, or a group represented by formulas 10-12 to 10-13. A group represented by one of the following formulas: 0; a group represented by one of the following formulas: 10⁻¹² to 10⁻¹³⁰, wherein at least one hydrogen atom is replaced by a deuterium atom; a group represented by one of the following formulas: 10⁻¹² to 10⁻¹³⁰, wherein at least one hydrogen atom is replaced by a deuterium atom; or a group represented by one of the following formulas: 10⁻³⁵⁹ to 10⁻³⁸⁰, wherein at least one hydrogen atom is replaced by a deuterium atom; or a group represented by one of the following formulas: 10⁻³⁵⁹ to 10⁻³⁸⁰, wherein at least one hydrogen atom is replaced by a deuterium atom; or a group represented by one of the following formulas: 10⁻³⁵⁹ to 10⁻³⁸⁰, wherein at least one hydrogen atom is replaced by a deuterium atom.

[0131]

[0132]

[0133]

[0134]

[0135]

[0136] In equations 9-1 to 9-39, 10-12 to 10-130, and 10-359 to 10-380,

[0137] * indicates a binding site with an adjacent atom, "Ph" represents phenyl, "TMS" represents trimethylsilyl, and "TMG" represents trimethylgermanyl.

[0138] "A group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen atom is replaced by deuterium" can be, for example, a group represented by one of formulas 9-501 to 9-514:

[0139]

[0140] "A group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen atom is replaced by -F" can be, for example, a group represented by one of formulas 9-701 to 710:

[0141]

[0142] "A group in which at least one hydrogen atom is replaced by deuterium, represented by one of formulas 10-12 to 10-130" can be, for example, a group represented by one of formulas 10-505 to 10-576:

[0143]

[0144]

[0145]

[0146] "A group represented by one of formulas 10-1 to 10-130, wherein at least one hydrogen atom is replaced by -F" can be, for example, a group represented by one of formulas 10-601 to 10-617:

[0147]

[0148] In some embodiments, in formulas 1, 2, and 1-1 to 1-4, R1-R5 may each be independently a fluorine atom, methyl, tert-butyl, phenyl, tert-butylphenyl, or 2,4,6-trimethylphenyl.

[0149] In some implementations, equation 1 may be represented by equation 1A, and equation 2 may be represented by equation 2A:

[0150] Formula 1A

[0151]

[0152] Formula 2A

[0153]

[0154] Among them, in equations 1A and 2A,

[0155] Ar1-Ar5, R1-R5, and n1-n5 can each be understood by referring to the descriptions of Ar1-Ar5, R1-R5, and n1-n5 provided herein.

[0156] In Formula 2A, * indicates a binding site with a cyclic atom of Ar1 in Formula 1A, a cyclic atom of Ar2 in Formula 1A, a cyclic atom of Ar3 in Formula 1A, or a combination thereof.

[0157] X 11 -X17 and X 21 -X 25 Each can be independently a carbon atom, and

[0158] X 11 and X 12 The key between X 13 and X 14 The key between X 14 and X 15 The key between X 16 and X 17 The key between X 21 and X 22 The key between X 22 and X 23 The key between, and X 24 and X 25 The bonds between them can be either single or double bonds.

[0159] For example, in formulas 1A and 2A, Ar1-Ar5 can each independently be a benzene ring, a naphthyl ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring.

[0160] In some embodiments, Ar1-Ar5 in Formulas 1A and 2A may each be independently a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring.

[0161] In some embodiments, Ar1-Ar5 in Formulas 1A and 2A may simultaneously be benzene rings.

[0162] In equations 1A and 2A, when Ar1-Ar5 are each independently a 6-membered ring,

[0163] Ar1 in Equation 1A can be represented by Equation 3-1.

[0164] Ar2 in Equation 1A can be represented by Equation 3-2.

[0165] Ar3 in Equation 1A can be represented by Equation 3-3.

[0166] Ar4 in Equation 2A can be represented by Equation 3-4, and

[0167] Ar5 in Equation 2A can be represented by Equation 3-5:

[0168]

[0169] Among them, in equations 3-1 to 3-5,

[0170] Y 11 It can be C(R) 101 ) or N, Y 12 It can be C(R) 102 ) or N, Y13 It can be C(R) 103 ) or N, Y 14 It can be C(R) 104 ) or N, Y 15 It can be C(R) 105 ) or N, Y 16 It can be C(R) 106 ) or N, Y 17 It can be C(R) 107 ) or N, Y 18 It can be C(R) 108 ) or N, Z 11 It can be C(R) 111 ) or N, Z 12 It can be C(R) 112 ) or N, Z 13 It can be C(R) 113 ) or N, Y 21 It can be C(R) 201 ) or N, Y 22 It can be C(R) 202 ) or N, Y 23 It can be C(R) 203 ) or N, Y 24 It can be C(R) 204 ) or N, Z 21 It can be C(R) 211 ) or N, Z 22 It can be C(R) 212 ) or N, and Z 23 It can be C(R) 213 ) or N,

[0171] The * in Equation 2A is combined with the * selected from Y in Equation 1A. 11 -Y 18 and Z 11 -Z 13 The two, and

[0172] R 101 -R 108 R 111 -R 113 R 201 -R 204 and R 211 -R 213Each of these can be a binding site with * in Formula 2A, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted halocycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted cycloalkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heteroarylthio group, or a substituted or unsubstituted amino group.

[0173] In some implementations, in equations 3-1 to 3-5, X 11 -X 17 X 21 -X 25 Y 11 -Y 18 Y 21 -Y 24 Z 11 -Z 13 and Z 21 -Z 23 Each can be an independent carbon atom.

[0174] In some embodiments, the heterocyclic compounds represented by Formula 1 and Formula 2 may be represented by one of Formulas 1-11 to 1-13, 1-21 to 1-23, 1-31, and 1-41:

[0175] Formula 1-11

[0176]

[0177] Formula 1-12

[0178]

[0179] Formula 1-13

[0180]

[0181] Formula 1-21

[0182]

[0183] Formula 1-22

[0184]

[0185] Formula 1-23

[0186]

[0187] Formula 1-31

[0188]

[0189] Formula 1-41

[0190]

[0191] Among them, in equations 1-11 to 1-13, 1-21 to 1-23, 1-31, and 1-41,

[0192] X 11 -X 17 and X 21 -X 25 Each is an independent carbon atom.

[0193] Y 11 It can be C(R) 101 ) or N, Y 12 It can be C(R) 102 ) or N, Y 13 It can be C(R) 103 ) or N, Y 14 It can be C(R) 104 ) or N, Y 15 It can be C(R) 105 ) or N, Y 16 It can be C(R) 106 ) or N, Y 17 It can be C(R) 107 ) or N, Y 18 It can be C(R) 108 ) or N, Z 11 It can be C(R) 111 ) or N, Z 12 It can be C(R) 112 ) or N, Z 13 It can be C(R) 113 ) or N, Y 21 It can be C(R) 201 ) or N, Y 22 It can be C(R) 202 ) or N, Y 23 It can be C(R) 203 ) or N, Y 24 It can be C(R) 204 ) or N, Z 21 It can be C(R) 211 ) or N, Z 22 It can be C(R) 212 ) or N, and Z 23 It can be C(R) 213 ) or N, and

[0194] R 101 -R 108 R 111 -R 113 R 201-R 204 and R 211 -R 213 Each can be understood by referring to the description of R1 provided in this article.

[0195] In some embodiments, the heterocyclic compound may be selected from compounds 1 to 27, but the embodiments are not limited thereto:

[0196]

[0197]

[0198]

[0199] In compounds 16 and 17, "Ph" indicates an unsubstituted phenyl group.

[0200] In some embodiments, the heterocyclic compound may be selected from compounds 1 to 3.

[0201] Various compounds are being considered as luminescent materials for organic light-emitting devices. In particular, heterocyclic compounds containing heteroatoms are being considered as materials that emit blue light. Furthermore, materials emitting delayed fluorescence have recently been studied from the viewpoint of improving the efficiency of organic light-emitting devices that use not only singlet excitons but also triplet excitons.

[0202] Typically, it has a relatively small ΔE ST The compounds with this value can emit thermally activated (activated) delayed fluorescence (TADF). However, even the heterocyclic compounds of the present invention have a ΔE value of... ST The values ​​are relatively large; for example, the heterocyclic compound can satisfy conditions 1-4, the heterocyclic compound can also emit TADF, and the organic light-emitting device including the heterocyclic compound can have improved efficiency.

[0203] Condition 1

[0204] ΔE ST >ΔE ST2 +ΔE' TT

[0205] Condition 2

[0206] 0eV<ΔE ST2 +ΔE' TT ≤1.0eV

[0207] Condition 3

[0208] 0eV<ΔE' TT ≤0.15eV

[0209] Condition 4

[0210] ΔE ST2 >0eV

[0211] Among them, in conditions 1-4,

[0212] ΔE ST This represents the difference between the lowest excited singlet energy level calculated based on the S1 equilibrium structure of the heterocyclic compound and the lowest excited triplet energy level calculated based on the T1 equilibrium structure of the heterocyclic compound.

[0213] ΔE ST2 This represents the difference between the lowest excited singlet state energy level calculated based on the S1 equilibrium structure of the heterocyclic compound and the second low-excited triplet state energy level calculated based on the T2 equilibrium structure of the heterocyclic compound, and...

[0214] ΔE′ TT This represents the difference between the second low-excited triplet energy level calculated using the T2 equilibrium structure of the heterocyclic compound and the lowest excited triplet energy level calculated using the T2 equilibrium structure of the heterocyclic compound.

[0215] Furthermore, by using the heterocyclic compound as a sensitizer, the energy transferred to the triplet state can undergo reverse intersystem crossing (RISC) to the singlet state. Then, the singlet state energy of the heterocyclic compound can be... Energy is transferred to the dopant. Therefore, the organic light-emitting device can simultaneously have improved efficiency and lifetime.

[0216] In some embodiments, the heterocyclic compound may satisfy condition 5:

[0217] Condition 5

[0218] ΔE ST2 ≤0.1eV

[0219] Among them, in condition 5,

[0220] ΔE ST2 This represents the difference between the lowest excited singlet state energy level calculated based on the S1 equilibrium structure of the heterocyclic compound and the second low-excited triplet state energy level calculated based on the T2 equilibrium structure of the heterocyclic compound.

[0221] In some embodiments, the heterocyclic compound may satisfy condition 6:

[0222] Condition 6

[0223] ΔE ST >0.2eV

[0224] Among them, in condition 6,

[0225] ΔE STThis represents the difference between the lowest excited singlet energy level calculated using the S1 equilibrium structure of the heterocyclic compound and the lowest excited triplet energy level calculated using the T1 equilibrium structure of the heterocyclic compound.

[0226] That is, the heterocyclic compound according to one or more embodiments, even in ΔE ST TADF can also be emitted at a voltage greater than 0.2 eV.

[0227] Because the heterocyclic compound has a rigid structure in which aromatic or heteroaromatic rings are fused, structural relaxation in the excited state can be suppressed. As a result, the heterocyclic compound can have a narrow blue emission spectral width and improved color purity.

[0228] The highest occupied molecular orbital (HOMO) energy level of the heterocyclic compound according to one or more embodiments is not particularly limited and can be about -6.5 eV or higher, or for example, about -6.3 eV or higher. When the HOMO energy level is in this range, the organic light-emitting device can have a low driving voltage. Furthermore, from the viewpoint of consistency with the energy map of other conventional materials forming the emission layer and stability in the atmosphere, the HOMO energy level of the heterocyclic compound according to the embodiments can be about -5.0 eV or lower.

[0229] The lowest unoccupied molecular orbital (LUMO) energy level of the heterocyclic compound according to one or more embodiments is not particularly limited and may be about -2.5 eV or lower, or for example, about -2.6 eV or lower. When the LUMO energy level is in this range, the organic light-emitting device may have a low driving voltage. Furthermore, from the viewpoint of consistency with the energy maps of other conventional materials forming the emitting layer, the LUMO energy level of the heterocyclic compound according to the embodiments may be about -4.0 eV or higher.

[0230] Specifically, the HOMO level can be measured and / or calculated using an atmospheric photoelectron spectrometer, and the LUMO level can be measured and / or calculated using both an atmospheric photoelectron spectrometer and a spectrophotometer. The measurement and / or calculation methods are described in the embodiments.

[0231] The peak wavelength in the photoluminescence (PL) spectrum of the heterocyclic compound according to the embodiments is not particularly limited and may be about 430 nanometers (nm) or greater. In some embodiments, the peak wavelength may be about 435 nm or greater, about 440 nm or greater, about 450 nm or greater, about 460 nm or greater, about 500 nm or greater, about 490 nm or greater, or about 480 nm or greater. When the peak wavelength is within any of these ranges, the heterocyclic compound according to the embodiments may be more suitable for blue light emission.

[0232] Heterocyclic compounds according to one or more embodiments may have a small half-width (FWHM) of the peak having the PL peak wavelength. In some embodiments, the FWHM may be about 45 nm or less, about 40 nm or less, about 35 nm or less, about 30 nm or less, about 25 nm or less, about 20 nm or less, or about 15 nm or less. When the FWHM is within any of these ranges, the heterocyclic compounds according to the embodiments may have further improved color purity.

[0233] The peak wavelength in the PL spectrum and the FWHM of the peak possessing the PL peak wavelength can be measured and / or calculated using a fluorescence spectrophotometer. The measurement and / or calculation methods are described in the examples.

[0234] ΔE of heterocyclic compounds according to one or more embodiments ST This is the value obtained by subtracting the triplet energy (T1) of the phosphorescence spectrum from the singlet energy (S1) of the fluorescence spectrum. Singlet energy S1, triplet energy T1, and ΔE ST The measurements and / or calculations can be performed by measuring the fluorescence and phosphorescence spectra at 77 K using a fluorescence spectrophotometer. The measurement and / or calculation methods are described in the examples.

[0235] The method for synthesizing the heterocyclic compound according to one or more embodiments is not particularly limited and can be synthesized according to known synthetic methods. In particular, it can be synthesized according to or in consideration of the methods described in the examples. For example, in the methods described in the examples, the heterocyclic compound according to one or more embodiments can be synthesized by, for example, by changing the starting materials and reaction conditions, adding or excluding some processes, or appropriately combining it with other known synthetic methods.

[0236] There are no particular limitations on the methods used to confirm the structure of heterocyclic compounds according to one or more embodiments. Nitrogen-containing heterocyclic compounds according to one or more embodiments can be confirmed by known methods such as NMR or LC-MS.

[0237] Figure 1-3 Description

[0238] In the following text, refer to Figure 1-3 The embodiments of the organic light-emitting device 10 will be described in detail.

[0239] Figure 1 This is a schematic diagram of an organic light-emitting device according to an exemplary embodiment. The organic light-emitting device 10 according to the embodiment may include a substrate 1, a first electrode 2, a hole transport region 3, an emission layer 4, an electron transport region 5, and a second electrode 6, which are stacked sequentially in the stated order.

[0240] Figure 2This is a schematic diagram of an organic light-emitting device according to another exemplary embodiment. The organic light-emitting device 10 according to the embodiment may include a substrate 1, a first electrode 2, a hole transport region 3, an emission layer 4, an electron transport region 5, and a second electrode 6. For example... Figure 2 As shown, the hole transport region 3 may include a hole injection layer 31 and a hole transport layer 32, which are stacked sequentially in the stated order. Furthermore, as... Figure 2 As shown, the electron transport region 5 may include an electron transport layer 52 and an electron injection layer 51, which are stacked sequentially in the stated order.

[0241] Figure 3 This is a schematic diagram of an organic light-emitting device according to yet another exemplary embodiment. The organic light-emitting device 10 according to the embodiment may include a substrate 1, a first electrode 2, a hole transport region 3, an emission layer 4, an electron transport region 5, and a second electrode 6. For example... Figure 3 As shown, the hole transport region 3 may include a hole injection layer 31, a hole transport layer 32, and an electron blocking layer 33, which are stacked sequentially in the stated order. Furthermore, as... Figure 3 As shown, the electron transport region 5 may include a hole blocking layer 53, an electron transport layer 52, and an electron injection layer 51, which are stacked sequentially in the stated order.

[0242] One implementation may include, for example, an organic electroluminescent device, which includes a first electrode, a second electrode, and one or more emitting layers. The second electrode may be located on the first electrode.

[0243] In this specification, "on" may apply not only to the case of "just on" another part, but also to the case where there may be another part in between. Similarly, when a part, such as a layer, film, region, plate, etc., is described as "below" or "under" another part, it may include the case of "just below" another part as well as the case where there may be another part in between.

[0244] In this specification, "arrangement" may include a situation where one of the parts is arranged not only on the upper part but also on the lower part.

[0245] The organic light-emitting device 10 may include a heterocyclic compound according to one or more embodiments. For example, the heterocyclic compound according to one or more embodiments may be included in an organic layer between the first electrode 2 and the second electrode 6. In some embodiments, the heterocyclic compound may be included in the emitting layer 4.

[0246] The following describes embodiments in which the emission layer comprises a heterocyclic compound according to one or more embodiments.

[0247] Launch layer 4

[0248] The emitting layer 4 can emit light through fluorescence or phosphorescence.

[0249] The emission layer 4 can be a single layer comprising a single material or a single layer comprising multiple different materials. Furthermore, the emission layer 4 can have a multilayer structure comprising multiple layers comprising a single material or multiple different materials.

[0250] In the emission layer 4, the heterocyclic compound may be used alone or in combination of two or more of them.

[0251] In some embodiments, the emitting layer 4 may further include a host; in other words, the emitting layer 4 may include the host and the heterocyclic compound, which may be different from each other. The host may not emit light, and the heterocyclic compound may emit light. That is, the heterocyclic compound may be a dopant.

[0252] In some embodiments, the emitting layer 4 may further include a host and a dopant; in other words, the emitting layer 4 may include the host, the dopant, and the heterocyclic compound, wherein the host, the dopant, and the heterocyclic compound may be different from each other. In this embodiment, the host and the heterocyclic compound may each not emit light, and the dopant may emit light.

[0253] In the embodiments, the body and the dopant will be described in more detail.

[0254] The emitter layer 4 may include known host materials and known dopant materials.

[0255] For example, the main body may include at least one of the following: bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4′-bis(carbazole-9-yl)biphenyl (CBP), 3,3′-bis(carbazole-9-yl)biphenyl (mCBP), 1,3-bis(carbazole-9-yl)benzene (mCP), 2,8-bis(diphenylphospho)dibenzo[b,d]furan (PPF), 4,4′,4"-tris(N-carbazole)triphenylamine (TCTA), 1,3,5-tris(N-phenyl-benzimidazol-2-yl)benzene (TPBi), tris(8-hydroxyquinoline)aluminum (Alq3), poly(N-vinylcarbazole) (PVK), 9,10-bis(naphthalene)anthracene (ADN), 3-tert-butyl 9,10-bis(naphthyl-2-yl)anthracene (TBADN), distyrylarylene (DSA), 4,4′-bis(9-carbazole)-2,2′-dimethylbiphenyl (dmCBP), 4,5′-bis(9-carbazole)-2,2′-dimethylbiphenyl (CDBP), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), and 2,8-bis(diphenylphospho)dibenzofuran (PPF), or any combination thereof.

[0256] For example, the dopant may include styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4′-[(di-p-tolylamino)styrene]benzene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi)), perylene or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene or its derivatives (e.g., 1,1-bipyrene, 1,4-dipyrenebenzene, or 1,4-bis(N,N-diphenylamino) The following are examples of compounds: pyrene, rubrene or a derivative thereof, coumarin or a derivative thereof, 4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) or a derivative thereof, iridium complexes such as bis[2-(4,6-difluorophenyl)pyridine]pyridinecarboxylic acid iridium(III) (FIrpic), bis(1-phenylisoquinoline)(acetylacetone) iridium(III) (Ir(piq)2(acac)), tris(2-phenylpyridine) iridium(III) (Ir(ppy)3), or tris(2-(3-p-xylyl)phenyl)pyridine iridium(III) (dopant), osmium complexes, or platinum complexes, but the embodiments are not limited thereto.

[0257] When the emitter layer comprises the body and the dopant, the amount of the dopant may be selected from about 0.01 parts by weight to about 15 parts by weight, based on about 100 parts by weight of the body, but the implementation is not limited thereto.

[0258] The thickness of the emitter layer is not particularly limited and can be in the range of about 1 nm to about 100 nm, or for example, about 10 nm to about 70 nm.

[0259] There is no particular limitation on the emission wavelength of the organic light-emitting device. However, the organic light-emitting device may emit light having a peak in the wavelength region of about 430 nm or larger and about 500 nm or smaller, about 435 nm or larger to about 490 nm or smaller, about 440 nm or larger to about 480 nm or smaller, or about 450 nm or larger to about 470 nm or smaller.

[0260] The emission spectrum of the organic light-emitting device may have an FWHM of about 45 nm or less, about 40 nm or less, about 35 nm or less, about 30 nm or less, about 25 nm or less, or about 0 nm or greater.

[0261] First Implementation Method - Figure 4A Description

[0262] In a first embodiment, the heterocyclic compound may be a fluorescent emitter. According to the first embodiment, the emitting layer may further include a host (hereinafter referred to as "host A," and host A may not be the same as the heterocyclic compound). Host A can be understood by referring to the description of the host material provided herein, but the embodiments are not limited thereto. Host A may be a fluorescent host.

[0263] According to Figure 4A The general energy transfer of the first embodiment is explained.

[0264] Singlet excitons can be generated by host A in the emitter layer, and the singlet excitons generated by host A can be transmitted through... Energy transfer (FRET) is transferred to the fluorescent emitter.

[0265] The proportion of singlet excitons generated by host A can be 25%, and therefore, 75% of the triplet excitons generated by host A can fuse with each other to be converted into singlet excitons. Therefore, the efficiency of the organic light-emitting device can be further improved. That is, by utilizing the triplet-triplet fusion (TTF) mechanism, the efficiency of the organic light-emitting device can be further improved.

[0266] According to a first embodiment, the ratio of the emission component emitted from the heterocyclic compound to the total emission component emitted from the emission layer can be about 80% or more, for example, about 90% or more. In some embodiments, the ratio of the emission component emitted from the heterocyclic compound to the total emission component emitted from the emission layer can be about 95% or more.

[0267] The heterocyclic compound may emit fluorescence, while the host may not emit light.

[0268] In a first embodiment, when the emission layer further includes a body A in addition to the heterocyclic compound, the content 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 the content of body A in the emission layer may be about 50 parts by weight or more, for example, about 70 parts by weight or more, but the embodiment is not limited thereto.

[0269] In the first embodiment, when the emitter layer further includes a host A in addition to the heterocyclic compound, host A and the heterocyclic compound can satisfy condition A:

[0270] Condition A

[0271] E(H A ) S1 >E S1

[0272] Among them, in condition A,

[0273] E(H A ) S1 Represents the lowest excited singlet state energy level of subject A, and

[0274] E S1 This represents the lowest excited singlet state energy level of the heterocyclic compound.

[0275] Here, E(H) A ) S1 and E S1 The results can be evaluated using the Gaussian procedure based on density functional theory (DFT) methods (where structural optimization is performed at the B3LYP and 6-31G(d,p) levels).

[0276] Second Implementation Method - Figure 4B Description

[0277] In a second embodiment, the heterocyclic compound may be a delayed fluorescence emitter. According to the second embodiment, the emitting layer may further include a host (hereinafter referred to as "host B," and host B may not be the same as the heterocyclic compound). Host B can be understood by referring to the description of the host material provided herein, but the embodiments are not limited thereto.

[0278] According to Figure 4B The general energy transfer of the second embodiment is explained.

[0279] 25% of the singlet excitons generated by host B in the emitter layer can be transferred to the delayed fluorescent emitter via FRET. Furthermore, 75% of the triplet excitons generated by host B in the emitter layer can be transferred to the delayed fluorescent emitter via Dexter energy transfer. The energy of the triplet state transferred to the delayed fluorescent emitter can undergo RISC to singlet state. Therefore, both singlet and triplet excitons generated by the emitter layer can be transferred to the heterocyclic compound. Thus, the organic light-emitting device can have improved efficiency.

[0280] According to a second embodiment, the ratio of the emission component emitted from the heterocyclic compound to the total emission component emitted from the emission layer can be about 80% or more, for example, about 90% or more. In some embodiments, the ratio of the emission component emitted from the heterocyclic compound to the total emission component emitted from the emission layer can be about 95% or more.

[0281] Here, the heterocyclic compound may emit fluorescence and / or delayed fluorescence, and the emission component of the heterocyclic compound may be the sum of the instantaneous emission component of the heterocyclic compound and the delayed fluorescence component of the heterocyclic compound via RISC. Furthermore, the host B may not emit light.

[0282] In a second embodiment, when the emission layer further includes a body B in addition to the heterocyclic compound, the content 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 the content of the body B in the emission layer may be about 50 parts by weight or more, for example, about 70 parts by weight or more, but the embodiments are not limited thereto.

[0283] In the second embodiment, when the emitter layer further includes a host B in addition to the heterocyclic compound, the host B and the heterocyclic compound can satisfy condition B:

[0284] Condition B

[0285] E(H B ) S1 >E S1

[0286] Among them, in condition B,

[0287] E(H B ) S1 Represents the lowest excited singlet state energy level of subject B, and

[0288] E S1 This represents the lowest excited singlet state energy level of the heterocyclic compound.

[0289] Here, E(H) B ) S1 and E S1 The results can be evaluated using the Gaussian procedure based on density functional theory (DFT) methods (where structural optimization is performed at the B3LYP and 6-31G(d,p) levels).

[0290] Third and Fourth Embodiments

[0291] Third implementation method - Figure 4C Description

[0292] In a third embodiment, the heterocyclic compound may be used as a fluorescent emitter, and the emission layer may include a sensitizer, such as a delayed fluorescence sensitizer. In a third embodiment, the emission layer may further include a host (hereinafter, the host may be referred to as "host C," and host C may not be the same as the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter, the sensitizer may be referred to as "sensitizer A," and sensitizer A may not be the same as host C and the heterocyclic compound). Host C can be understood by referring to the description of the host material provided herein, and sensitizer A may be a conventional sensitizer material in the art, such as a delayed fluorescence sensitizer, but the embodiments are not limited thereto.

[0293] In a third embodiment, the ratio of the emission component of the heterocyclic compound to the total emission component emitted from the emission layer may be about 80% or greater, for example, about 90% or greater (or for example, about 95% or greater). For example, the heterocyclic compound may emit fluorescence. Furthermore, the host C and the sensitizer A may each not emit light.

[0294] According to Figure 4C The general energy transfer of the third embodiment is explained.

[0295] Singlet and triplet excitons can be generated from host C in the emitter layer, and these excitons can be transferred to sensitizer A via FRET, and then to the heterocyclic compound. 25% of the singlet excitons generated by host C can be transferred to sensitizer A via FRET, and 75% of the energy of the triplet excitons generated by host C can be transferred to the singlet and triplet states of sensitizer A. The energy of the triplet state transferred to sensitizer A can undergo RISC to the singlet state, and then the singlet state energy of sensitizer A can be transferred to the heterocyclic compound via FRET.

[0296] Therefore, singlet and triplet excitons generated by the emitter layer can be transferred to the dopant. Consequently, the organic light-emitting device (OLED) can have improved efficiency. Furthermore, the energy loss of the OLED can be significantly reduced. Therefore, the OLED can have improved lifetime characteristics.

[0297] In the third embodiment, when the emission layer further comprises a host C and a sensitizer A in addition to the heterocyclic compound, the host C and the sensitizer A may satisfy conditions C-1 and / or C-2:

[0298] Condition C-1

[0299] S1(H C )≥S1(S A )

[0300] Condition C-2

[0301] S1(S A )≥S1(HC)

[0302] Among them, in conditions C-1 and C-2,

[0303] S1(H C ) represents the lowest excited singlet state energy level of the host C.

[0304] S1(S A ) represents the lowest excited singlet state energy level of sensitizer A, and

[0305] S1(HC) represents the lowest excited singlet state energy level of the heterocyclic compound.

[0306] S1(H C ), S1(S A S1(HC) can be evaluated, for example, according to the Gaussian procedure, based on a DFT method that performs structural optimization at the levels of B3LYP and 6-31G(d,p).

[0307] When the host C, sensitizer A, and the heterocyclic compound satisfy conditions C-1 and / or C-2, FRET from sensitizer A to the heterocyclic compound can be promoted, and therefore, the organic light-emitting device can have improved luminous efficiency.

[0308] Fourth Implementation Method - Figure 4D Description

[0309] In a fourth embodiment, the heterocyclic compound may be used as a fluorescent emitter, and the emitting layer may include a sensitizer, such as a phosphorescent sensitizer. In a fourth embodiment, the emitting layer may further include a host (hereinafter, the host may be referred to as "host D," and host D may not be the same as the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter, the sensitizer may be referred to as "sensitizer B," and sensitizer B may not be the same as host D and the heterocyclic compound). Host D can be understood by referring to the description of the host material provided herein, and sensitizer B may be a conventional sensitizer material in the art, such as a phosphorescent sensitizer material, but the embodiments are not limited thereto.

[0310] In the fourth embodiment, the ratio of the emission component of the heterocyclic compound to the total emission component emitted from the emission layer may be about 80% or greater, for example, about 90% or greater (or, for example, about 95% or greater). For example, the heterocyclic compound may emit fluorescence. Furthermore, the host D and the sensitizer B may each be non-emitting.

[0311] According to Figure 4D The general energy transfer of the fourth implementation method is explained.

[0312] 75% of the triplet excitons generated by the host D in the emitter layer can be transferred to the sensitizer B via Dexter energy transfer, and 25% of the energy of the singlet excitons generated by the host D can be transferred to the singlet and triplet states of the sensitizer B. The energy transferred to the singlet state of the sensitizer B can pass through ISC to the triplet state, and then the triplet state energy of the sensitizer B can be transferred to the heterocyclic compound via FRET.

[0313] Therefore, singlet and triplet excitons generated by the emitter layer can be transferred to the dopant. Consequently, the organic light-emitting device (OLED) can have improved efficiency. Furthermore, the energy loss of the OLED can be significantly reduced. Therefore, the OLED can have improved lifetime characteristics.

[0314] In the third embodiment, when the emission layer further comprises, in addition to the heterocyclic compound, a host D and a sensitizer B, the host D and the sensitizer B may satisfy conditions D-1 and / or D-2:

[0315] Condition D-1

[0316] T1(H D )≥T1(S B )

[0317] Condition D-2

[0318] T1(S B )≥S1(HC)

[0319] Among them, in conditions D-1 and D-2,

[0320] T1(H D () represents the lowest excited triplet energy level of the main body D.

[0321] T1(S B ) represents the lowest excited triplet energy level of sensitizer B, and

[0322] S1(HC) represents the lowest excited singlet state energy level of the heterocyclic compound.

[0323] T1(H D ), T1(S B S1(HC) can be evaluated according to the DFT method (where structural optimization is performed at the levels of B3LYP and 6-31G(d,p)) for example, according to the Gaussian procedure.

[0324] When the host D, sensitizer B, and the heterocyclic compound satisfy conditions D-1 and / or D-2, FRET from sensitizer B to the heterocyclic compound can be promoted, and therefore, the organic light-emitting device can have improved luminous efficiency.

[0325] In the third and fourth embodiments, the content of the sensitizer in the emitting layer can be in the range of about 5% by weight to about 50% by weight, or for example, about 10% by weight to about 30% by weight. When the content is within this range, energy transfer in the emitting layer can occur efficiently. Therefore, the organic light-emitting device can have high efficiency and long lifetime.

[0326] In the third and fourth embodiments, the content of the heterocyclic compound in the emission layer may be in the range of about 0.01% by weight to about 15% by weight, or for example about 0.05% by weight to about 3% by weight, but the embodiments are not limited thereto.

[0327] In the third and fourth embodiments, the heterocyclic compound may further satisfy condition 7:

[0328] Condition 7

[0329] 0μs <T 衰减 (HC) < 5 μs

[0330] Among them, in condition 7,

[0331] T 衰减 (HC) represents the decay time of the heterocyclic compound.

[0332] The decay time of the heterocyclic compound is determined by measuring 10... -7 The time-resolved photoluminescence (TRPL) spectra of a 40 nm thick film (hereinafter referred to as "film (HC)") formed by vacuum deposition of the host and heterocyclic compound included in the emission layer onto a quartz substrate at a weight ratio of 90:10 under vacuum pressure were measured at room temperature.

[0333] Fifth Implementation Method - Figure 4E Description

[0334] In a fifth embodiment, the heterocyclic compound may be used as a delayed fluorescence emitter, and the emission layer may include a sensitizer, such as a delayed fluorescence sensitizer. In a fifth embodiment, the emission layer may further include a host (hereinafter, the host may be referred to as "host E," and host E may not be the same as the heterocyclic compound and the sensitizer) and a sensitizer (hereinafter, the sensitizer may be referred to as "sensitizer C," and sensitizer C may not be the same as host E and the heterocyclic compound). Host E can be understood by referring to the description of the host material provided herein, and sensitizer C may be a conventional sensitizer material in the art, such as a delayed fluorescence sensitizer, but the embodiments are not limited thereto.

[0335] In a fifth embodiment, the ratio of the emission component of the heterocyclic compound to the total emission component emitted from the emission layer may be about 80% or greater, for example 90% or greater (or for example 95% or greater). In some embodiments, the heterocyclic compound may emit fluorescence and / or delayed fluorescence. Furthermore, the host E and the sensitizer C may each be non-emitting.

[0336] Here, the heterocyclic compound may emit fluorescence and / or delayed fluorescence, and the emission component of the heterocyclic compound may be the sum of the instantaneous emission component of the heterocyclic compound and the delayed fluorescence component of the heterocyclic compound via RISC.

[0337] According to Figure 4E The general energy transfer of the fifth implementation method is explained.

[0338] 25% of the singlet excitons generated by the host E in the emitter layer can be transferred to the singlet state of the sensitizer C via FRET, and 75% of the energy of the triplet excitons generated by the host E can be transferred to the triplet state of the sensitizer C. The singlet state energy of the sensitizer C can then be transferred to the heterocyclic compound via FRET. Subsequently, the triplet state energy of the sensitizer C can be transferred to the heterocyclic compound via Dexter energy transfer. The energy transferred to the triplet state of the sensitizer C can undergo RISC to the singlet state. Further, in the case of sensitizer C, the energy of the triplet excitons generated by the sensitizer C can undergo a reverse transfer to the host E and then to the heterocyclic compound, thereby being emitted via reverse intersystem transfer.

[0339] Therefore, singlet and triplet excitons generated by the emitter layer can be transferred to the dopant. Consequently, the organic light-emitting device (OLED) can have improved efficiency. Furthermore, the energy loss of the OLED can be significantly reduced. Therefore, the OLED can have improved lifetime characteristics.

[0340] In the fifth embodiment, when the emission layer further comprises a host E and a sensitizer C in addition to the heterocyclic compound, the host E and the sensitizer C may satisfy conditions E-1, E-2, and / or E-3:

[0341] Condition E-1

[0342] S1(H E )≥S1(S C )

[0343] Condition E-2

[0344] S1(S C )≥S1(HC)

[0345] Condition E-3

[0346] T1(S C )≥T1(HC

[0347] Among them, in conditions E-1, E-2, and E-3,

[0348] S1(H E () represents the lowest excited singlet state energy level of the subject E.

[0349] S1(S C () represents the lowest excited singlet state energy level of sensitizer C.

[0350] S1(HC) represents the lowest excited singlet state energy level of the heterocyclic compound.

[0351] T1(S C) represents the lowest excited triplet energy level of sensitizer C, and

[0352] T1(HC) represents the lowest excited triplet energy level of the heterocyclic compound.

[0353] S1(H E ), S1(S C S1(HC), T1(S) C T1(HC) can be evaluated according to the DFT method (where structural optimization is performed at the levels of B3LYP and 6-31G(d,p)) for example, according to the Gaussian evaluation.

[0354] When the host E, the sensitizer C, and the heterocyclic compound satisfy conditions E-1, E-2, and / or E-3, the transfer of FRET from the sensitizer C to the heterocyclic compound by Dexter can be promoted, and therefore, the organic light-emitting device can have improved luminous efficiency.

[0355] In the fifth embodiment, the content of sensitizer C in the emitting layer can be in the range of about 5% to about 50% by weight, or for example, about 10% to about 30% by weight. When the content is within this range, energy transfer in the emitting layer can occur efficiently. Therefore, the organic light-emitting device can have high efficiency and long lifetime.

[0356] In the fifth embodiment, the content of the heterocyclic compound in the emission layer may be in the range of about 0.01% by weight to about 15% by weight, or for example about 0.05% by weight to about 3% by weight, but the embodiments are not limited thereto.

[0357] The following text will describe in detail the regions and layers other than emission layer 4.

[0358] Substrate 1

[0359] The organic light-emitting device 10 may include a substrate 1. The substrate 1 may be any suitable substrate commonly used in organic light-emitting devices. For example, the substrate 1 may be a glass substrate, a silicon substrate, or a transparent plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance, but the embodiments are not limited thereto.

[0360] First electrode 2

[0361] The first electrode 2 may be formed on the substrate 1. The first electrode 2 may be an anode and is formed of a material with a relatively high work function selected from metals, alloys, conductive compounds, and combinations thereof to facilitate hole injection. The first electrode 2 may be a pixel electrode. The first electrode 2 may be a reflective electrode, a transmissive electrode, or a transmissive electrode. There are no particular limitations on the material used to form the first electrode 2, and when the first electrode 2 is a transparent electrode, it may be, for example, indium tin oxide (ITO), zinc tin oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc., which have excellent transparency and conductivity. When the first electrode 2 is a transmissive or reflective electrode, it may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, In, LiF / Ca, LiF / Al, Mo, Ti, or mixtures thereof (e.g., a mixture of Ag and Mg or a mixture of Mg and In).

[0362] The first electrode 2 may be a single layer comprising a single material or a single layer comprising multiple different materials. In some embodiments, the first electrode 2 may have a multilayer structure comprising multiple layers containing multiple different materials.

[0363] The thickness of the first electrode 2 is not particularly limited and can be about 10 nm or more and about 1,000 nm or less, or about 100 nm or more and about 300 nm or less.

[0364] Hole transport region 3

[0365] Hole transport region 3 can be set on the first electrode 2.

[0366] The hole transport region 3 may include at least one of the following: a hole injection layer 31, a hole transport layer 32, an electron blocking layer 33, a hole buffer layer (not shown), or any combination thereof.

[0367] The hole transport region 3 may be a single layer comprising a single material or a single layer comprising multiple different materials. In some embodiments, the hole transport region 3 may have a multilayer structure comprising multiple layers containing multiple different materials.

[0368] The hole transport region 3 may include a hole-only injection layer 31 or a hole-only transport layer 32. In some embodiments, the hole transport region 3 may be a single layer comprising a hole injection material and / or a hole transport material. The hole transport region 3 may have a hole injection layer / hole transport layer structure, a hole injection layer / hole buffer layer structure, a hole injection layer / hole transport layer / hole buffer layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the layers of each structure are stacked sequentially on the first electrode 2 in the order stated therein.

[0369] There are no particular limitations on the layers forming the hole injection layer 31 and other layers included in the hole transport region 3, and they may include known hole injection materials and / or hole transport materials. The hole injection material and / or the hole transport material may include at least one of the following: triphenylamine containing poly(ether ketone) (TPAPEK), tetra(pentafluorophenyl)borate 4-isopropyl-4′-methyldiphenyliodonium (PPBI), dipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN), N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine (… DNTPD), phthalocyanine compounds such as copper phthalocyanine, 4,4′,4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), 4,4′,4"-tris(diphenylamino)triphenylamine (TDATA), 4,4′,4"-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxy) Thiophene / poly(4-sulfonated styrene) (PEDOT / PSS), polyaniline / 10-camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-sulfonated styrene) (PANI / PSS), 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), carbazole derivatives such as N-phenylcarbazole or polyvinylcarbazole, fluorene-based derivatives, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), 4,4′,4" Tris(N-carbazolyl)triphenylamine (TCTA), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), N,N,N′,N′-tetra(3-methylphenyl)-3,3′-dimethylbenzidine (HMTPD), 1,3-bis(carbazol-9-yl)phenyl (mCP), poly(9,9-dioctyl-fluorene-co-N-(4-butylphenyl)-diphenylamine) (TFB), compound HTP1, compound AD1, compound P-1, compound FA-14, or any combination thereof:

[0370]

[0371] (n is an integer of 1 or greater)

[0372]

[0373] (n is an integer of 1 or greater)

[0374]

[0375] In addition to the aforementioned materials, the hole transport region 3 may also include a charge-generating material to improve the electrical conductivity of the hole transport region. The charge-generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region 3.

[0376] The charge-generating material is not particularly limited and may be, for example, a p-doper. Examples of p-dopers include quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and compounds containing a cyano group, but the embodiments are not limited thereto.

[0377] The hole buffer layer (not shown) can improve luminous efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emitting layer 4. There are no particular limitations on the material used to form the hole buffer layer (not shown), and known hole buffer layer materials can be used, such as compounds that may be included in the hole transport region 3.

[0378] The electron blocking layer 33 prevents electrons from being injected from the electron transport region 5 into the hole transport region 3. There are no particular limitations on the material used to form the electron blocking layer 33, and known electron blocking layer materials can be used, such as compounds that can be included in the hole transport region 3.

[0379] The thickness of the hole transport region 3 is not particularly limited and can be about 1 nm or larger and about 1,000 nm or smaller, or for example, about 10 nm or larger and about 500 nm or smaller. Furthermore, the thickness of the hole injection layer 31 is not particularly limited and can be about 3 nm or larger and about 100 nm or smaller. Furthermore, the thickness of the hole transport layer 32 is not particularly limited and can be about 3 nm or larger and about 100 nm or smaller. Furthermore, the thickness of the electron blocking layer 33 is not particularly limited and can be about 1 nm or larger and about 100 nm or smaller. Furthermore, the thickness of the hole buffer layer (not shown) is not particularly limited, as long as the hole buffer layer does not adversely affect the function of the organic light-emitting device. When the thicknesses of the hole transport region 3, hole injection layer 31, hole transport layer 32, or electron blocking layer 33 are within these ranges, excellent hole transport characteristics can be obtained without a significant increase in driving voltage.

[0380] Launch layer 4

[0381] Hole transport region 3 may be disposed on transmission layer 4. Transmission layer 4 can be understood by referring to the description of transmission layer 4 described above.

[0382] Electronic transmission area 5

[0383] The electron transport region 5 may be disposed on the emission layer 4. The electron transport region 5 may include at least one of the following: a hole blocking layer 53, an electron transport layer 52, an electron injection layer 51, or any combination thereof.

[0384] The electron transport region 5 may be a single layer comprising a single material or a single layer comprising multiple different materials. In some embodiments, the electron transport region 5 may have a multilayer structure comprising multiple layers containing multiple different materials.

[0385] The electron transport region 5 may include an electron transport layer 52 or an electron injection layer 51. In some embodiments, the electron transport region 5 may be a single layer comprising an electron injection material and / or an electron transport material. In some embodiments, the electron transport region 5 may include an electron transport layer / electron injection layer structure or a hole blocking layer / electron transport layer / electron injection layer structure, which are sequentially stacked on the emitter layer 4.

[0386] The electron injection layer 51 is not particularly limited and may include, for example, known electron injection materials. For example, the electron injection layer material may include Yb, lithium compounds such as lithium (8-hydroxyquinoline) (Liq) and lithium fluoride (LiF), sodium chloride (NaCl), cesium fluoride (CsF), rubidium fluoride (RbCl), lithium oxide (Li2O), or barium oxide (BaO).

[0387] In some embodiments, the electron injection layer 51 may include the electron transport material and an insulating organometallic salt. The metal salt is not particularly limited and may be, for example, a material having a band gap of about 4 eV or higher. The organometallic salt may include, for example, metal acetate, metal benzoate, metal acetylacetone, or metal stearate.

[0388] The electron transport layer 52 is not particularly limited and may include, for example, known electron transport materials. The electron transport material may be, for example, tris(8-hydroxyquinoline)aluminum (Alq3), Balq, 1,3,5-tris[(3-pyridyl)-benzene-3-yl]benzene, bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 1,3,5-tris[(3-pyridyl)-benzene-3-yl]benzene, 2,4,6-tris(3′-(pyridyl-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl-phenyl)-9,10- Dinaphthylanthracene, 3-(4-phenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphth-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(N-phenyl-benzimidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4- Diazole (tBu-PBD), KLET-01, KLET-02, KLET-03, KLET-10, or KLET-M1 (available from Chemipro Kasei).

[0389] The hole blocking layer 53 prevents holes from being injected from the hole transport region 3 into the electron transport region 5. There are no particular limitations on the materials included in the hole blocking layer 53, and known hole blocking materials can be used. The hole blocking layer 53 can be, for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), etc.

[0390] The thickness of the electron transport region 5 is not particularly limited and can be about 0.1 nm or greater and about 210 nm or less, or for example, about 100 nm or greater and about 150 nm or less. The thickness of the electron transport layer 52 is not particularly limited and can be about 10 nm or greater and about 100 nm or less, or for example, about 15 nm or greater and about 50 nm or less. The thickness of the hole blocking layer 53 is not particularly limited and can be about 10 nm or greater and about 100 nm or less, or for example, about 15 nm or greater and about 50 nm or less. The thickness of the electron injection layer 51 is not particularly limited and can be about 0.1 nm or greater and about 10 nm or less, or for example, about 0.3 nm or greater and about 9 nm or less. When the thickness of the electron injection layer 51 is within any of these ranges, excellent electron injection characteristics can be obtained without a significant increase in driving voltage. When the thicknesses of the electron transport region 5, the electron injection layer 51, the electron transport layer 52, or the hole blocking layer 53 are within these ranges, excellent hole transport characteristics can be obtained without a significant increase in driving voltage.

[0391] Second electrode 6

[0392] The second electrode 6 may be formed on the electron injection layer 51. The second electrode 6 may be a cathode and formed of a material selected from metals, alloys, or conductive compounds having a relatively low work function to facilitate electron injection. The second electrode 6 may be a conventional electrode. The second electrode 6 may be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. The second electrode 6 may have a monolayer structure or a multilayer structure comprising multiple layers. There are no particular limitations on the materials used to form the second electrode 6, and for example, when the second electrode 6 is a transparent electrode, it may include transparent metal oxides such as ITO, IZO, ZnO, or ITZO. When the second electrode 6 is a semi-transparent or reflective electrode, it may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, In, LiF / Ca, LiF / Al, Mo, Ti, or mixtures thereof (e.g., a mixture of Ag and Mg or a mixture of Mg and In).

[0393] The second electrode 6 may be a single layer comprising a single material or a single layer comprising multiple different materials. In some embodiments, the second electrode 6 may have a multilayer structure comprising multiple layers containing multiple different materials.

[0394] Furthermore, the thickness of the second electrode 6 is not particularly limited and can be about 10 nm or larger and about 1,000 nm or lower.

[0395] The second electrode 6 can be further connected to an auxiliary electrode (not shown). When the second electrode 6 is connected to the auxiliary electrode, the resistance of the second electrode 6 can be further reduced.

[0396] Furthermore, an encapsulation layer (not shown) may be present on the second electrode 6. The encapsulation layer (not shown) may be, for example, α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4′,N4′-tetra(phenyl-4-yl)biphenyl-4,4′-diamine (TPD15), TCTA, or N,N′-bis(naphthyl-1-yl).

[0397] Furthermore, the stacking structure of the organic light-emitting device 10 according to the embodiments is not limited to the previous description. The organic light-emitting device 10 according to the embodiments may have different stacking structures known in the art. For example, the organic light-emitting device 10 may not include at least one selected from the hole injection layer 31, the hole transport layer 32, the electron transport layer 52, and the electron injection layer 51, or may further include additional layers. In some embodiments, the layers of the organic light-emitting device 10 may be formed as a single layer or as multiple layers.

[0398] There are no particular limitations on the methods for forming the layers of the organic light-emitting device 10 according to one or more embodiments. For example, vacuum deposition, solution coating, laser printing, Langmuir-Broguet (LB) method, or laser-induced thermal imaging (LITI) can be used to form the layers.

[0399] The solution coating may include spin coating, casting, microgravure coating, gravure coating, bar coating, roller coating, wire rod coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, or inkjet printing.

[0400] The solvents used in the solution coating may include toluene, xylene, diethyl ether, chloroform, ethyl acetate, dichloromethane, tetrahydrofuran, acetone, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, anisole, hexamethyl phosphate triamide, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, dioxane, cyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, methyl ethyl ketone, cyclohexanone, butyl acetate, ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol, 1,2-hexanediol, methanol, ethanol, propanol, isopropanol, cyclohexanol, N-methyl-2-pyrrolidone, or any combination thereof. However, there are no particular limitations on the solvents used. Any suitable solvent that can dissolve the materials used to form the layers can be used.

[0401] Considering factors such as coatability, the concentration of the solution may be about 0.1% by weight (wt%) or more and 10% by weight or less, and more particularly about 0.5% by weight or more and 5% by weight or less, but the implementation is not limited thereto.

[0402] The vacuum deposition can be performed at a deposition temperature in the range of about 100°C to about 500°C, at a temperature of about 10... -8 To-10 -3 The deposition is carried out under vacuum pressure within the range of Torr and at deposition rates in the range of about 0.01 nm / s to about 10 nm / s, although the conditions may vary depending on the compound used and the desired structure and thermal properties of the layer.

[0403] In some embodiments, the first electrode 2 may be the anode, and the second electrode 6 may be the cathode.

[0404] For example, the first electrode 2 may be an anode, the second electrode 6 may be a cathode, and the organic layer may include an emission layer 4 between the first electrode 2 and the second electrode 6 and may further include a hole transport region 3 between the first electrode 2 and the emission layer 4 and an electron transport region 5 between the emission layer 4 and the second electrode 6. The hole transport region 3 may include at least one of the following: a hole injection layer 31, a hole transport layer 32, a hole buffer layer, an electron blocking layer 33, or any combination thereof. The electron transport region 5 may include at least one of the following: a hole blocking layer 53, an electron transport layer 52, an electron injection layer 51, or any combination thereof.

[0405] In some embodiments, the first electrode 2 may be a cathode, and the second electrode 6 may be an anode.

[0406] As mentioned above, Figure 1-3 Organic light-emitting device 10 has been described, but the implementation is not limited thereto.

[0407] The following will describe in detail an example in which the heterocyclic compound is included in the emission layer 4.

[0408] electronic devices

[0409] The organic light-emitting device can be included in a variety of electronic devices.

[0410] In addition to the organic light-emitting device, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein one of the source electrode and the drain electrode is electrically connected to one of the first electrode and the second electrode of the organic light-emitting device.

[0411] The organic light-emitting device according to the embodiments will be described in more detail below with reference to synthetic examples and embodiments; however, this disclosure is not limited thereto. The phrase "using B instead of A" used in describing synthetic examples means using an equimolar amount of B instead of A.

[0412] Example

[0413] Mass (mass spectrometry) analysis

[0414] The compound was dissolved in tetrahydrofuran (THF) at a concentration of 0.1% by weight and mass spectrometry was performed using an LC-MS instrument 1260 Infinity-4 Quadrupole 6100MS (available from Agilent Technologies).

[0415] NMR spectroscopy measurement

[0416] The compound was dissolved using deuterated THF (THF-d8), and the concentrations of the compound were measured at room temperature using an Avance III (300 MHz, Bruker). 1 H-NMR spectrum.

[0417] Example 1

[0418] Synthesis Example 1: Synthesis of Intermediate (11)

[0419]

[0420] 21 g (89 mmol) of m-dibromobenzene (10), 17.4 g (187 mmol) of aniline, 21.4 g (223 mmol) of sodium tert-butoxide (NaOtBu), 815 mg (0.89 mmol) of tris(dibenzylacetone)palladium (0) (Pd2(dba)3), and 1.66 g (2.67 mmol) of (±) 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) were added to a 1 L 3-necked flask, followed by the addition of 300 mL of toluene and heating under reflux for 3 h in a nitrogen atmosphere. After cooling to room temperature, the reaction solution was passed through a Florida silica gel and a silica gel pad, and the solvent was distilled off. The resulting residue was purified by column chromatography (eluent: hexane-ethyl acetate) to obtain intermediate (11) (yield: 7.5 g, 32%).

[0421] Synthesis Example 2: Synthesis of Intermediate (13)

[0422]

[0423] 1.56 g (6.0 mmol) of intermediate (11), 5.8 g (18 mmol) of dimethyl 2-iodo-1,3-phthalate (compound (12)), 5.5 g (18 mmol) of cesium carbonate, 114 mg (1.8 mmol) of copper powder, 228 mg (1.2 mmol) of copper iodide, and 24 mL of dibutyl ether were added to a 100 mL Schlenk tube, and the mixture was heated under reflux for 5 days in a nitrogen atmosphere. After cooling to room temperature, water was added to the reaction solution. After separating the organic layer, the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with anhydrous magnesium sulfate. After removing the drying agent, the organic solvent was distilled off. The residue obtained was purified by silica gel column chromatography (eluent: dichloromethane-ethyl acetate) to obtain intermediate (13) (yield: 1.65 g, 43%).

[0424] Synthesis Example 3: Synthesis of Intermediate (14)

[0425]

[0426] 1.62 g (2.5 mmol) of intermediate (13) was added to a 100 mL flask, followed by 20 mL of dioxane, 20 mL of ethanol, and 20 mL of water. After adding 10 g (100 mmol) of a 10 mol (M) aqueous solution of sodium hydroxide, the mixture was heated and refluxed under a nitrogen atmosphere for 2 hours. After cooling to room temperature, the organic solvent was distilled off. After cooling the residue to 0 °C, the solution was acidified by adding hydrochloric acid until the pH reached 2–3. The precipitated solid was filtered off, washed repeatedly with water, and dried under vacuum to obtain intermediate (14) (yield 1.48 g, 100%).

[0427] Synthesis Example 4: Synthesis of Compound 1 and Compound 23

[0428]

[0429] 1.38 g (2.34 mmol) of intermediate (14) was added to a 300 mL three-necked flask, followed by 120 mL of dichloromethane. Then, N,N′-dimethylformamide (3 drops) and 0.90 mL (10.5 mmol) of oxaloyl chloride were added, followed by heating under reflux. After 2 hours, tin tetrachloride (IV) (10.5 mL of 1 M dichloromethane solution, 10.5 mmol) was added, and the mixture was heated under reflux for another 5 hours. After cooling to 0 °C, 100 mL of 1 M hydrochloric acid aqueous solution was added. After separating the organic layer, the aqueous layer was extracted using dichloromethane. The organic layer was washed with a saturated ammonium chloride aqueous solution and dried over anhydrous magnesium sulfate. After passing the resulting mixture through a silica gel pad to remove the drying agent, the organic solvent was distilled off. The resulting residue was suspended in dichloromethane, and the solid was separated by filtration to obtain compound 1. Furthermore, the obtained residue was purified by silica gel column chromatography (eluent: dichloromethane-ethyl acetate) to obtain compound 23.

[0430] Compound 1: Yield: 0.35 g, 30%; 1H-NMR: δ 7.54 (brs, 2H), 7.70–7.56 (m, 3H), 8.40–8.43 (m, 4H), 8.65–8.74 (m, 6H), 9.40–9.43 (brs, 1H) (see also...) Figure 5 ); LC-MS: 517([M+H] + )

[0431] Compound 23: Yield: 0.33 g, 26%; ¹H-NMR: δ 7.25–7.40 (m, 2H), 7.58–7.68 (m, 2H), 7.73 (t, 1H, J = 7.8 Hz), 7.82–7.89 (m, 1H), 8.30 (d, 1H, J = 9 Hz), 8.34–8.40 (m, 2H), 8.45–9.50 (m, 1H), 8.62–8.75 (m, 4H) (see also...) Figure 6 ); LC-MS: 517([M+H] + ).

[0432] Example 2

[0433] Synthesis Example 5: Synthesis of Intermediate (17)

[0434]

[0435] Intermediate (17) was obtained in the same manner as in Synthesis Example 1, except that 4-tert-butylaniline was used instead of aniline (yield 86%).

[0436] Synthesis Example 6: Synthesis of Intermediate (19)

[0437]

[0438] Intermediate (19) was obtained in the same manner as in Synthesis Example 2, except that intermediate (17) was used instead of intermediate (11), and compound (18) was used instead of compound (12) (yield 73%).

[0439] Synthesis Example 7: Synthesis of Intermediate (20)

[0440]

[0441] Intermediate (20) was obtained in the same manner as in Synthesis Example 3, except that intermediate (19) was used instead of intermediate (13) (yield 100%).

[0442] Synthesis Example 8: Synthesis of Compound 2 and Compound 26

[0443]

[0444] Compounds 2 and 26 were obtained in the same manner as in Synthesis Example 4, except that intermediate (20) was used instead of intermediate (14).

[0445] Compound 2: Yield 30%, LC-MS: 741 ([M+H]) + )

[0446] Compound 26: Yield 36%, LC-MS: 741 ([M+H]) + ).

[0447] Example 3

[0448] Synthesis Example 9: Synthesis of Intermediate (23)

[0449]

[0450] Intermediate (23) was obtained in the same manner as in Synthesis Example 2, except that compound (18) was used instead of compound (12) (yield 62%).

[0451] Synthesis Example 10: Synthesis of Intermediate (24)

[0452]

[0453] Intermediate (24) was obtained in the same manner as in Synthesis Example 3, except that intermediate (23) was used instead of intermediate (13) (yield 100%).

[0454] Synthesis Example 11: Synthesis of Compound 3 and Compound 25

[0455]

[0456] Compounds 3 and 25 were obtained in the same manner as in Synthesis Example 4, except that intermediate (24) was used instead of compound (14).

[0457] Compound 3: Yield 20%, LC-MS: 629 ([M+H]) + )

[0458] Compound 25: 33% yield, LC-MS: 629 g / ([M+H]) + ).

[0459] Comparative Example 1: Preparation of Comparative Compound 1

[0460] Quinolino[3,2,1-de]acridin-5,9-dione, represented by the following formula, was prepared as comparative compound 1.

[0461]

[0462] Evaluation Example 1: Measurement of HOMO and LUMO Levels

[0463] The compounds obtained above and the control compounds were prepared as sample solids. Next, the HOMO and LUMO energy levels were measured as follows.

[0464] 1. Preparation of measurement samples

[0465] (1) Prepare a sample solution such that the sample solid is 4 parts by weight based on 100 parts by weight of methyl benzoate as solvent.

[0466] (2) The sample solution prepared in part (1) was spin-coated onto each of the ITO substrate and the quartz substrate and dried to form a coating film with a dry film thickness of 50 nm. The resulting coating film was then subjected to 10... -1 Heated at 120°C for 1 hour under a vacuum pressure of Pa or lower. Then, at 10... -1 The coating film is cooled to room temperature under a vacuum pressure of Pa or lower to form a thin film layer (thin film sample).

[0467] 2. Measurement of HOMO levels

[0468] Using the thin film samples prepared in section 1.(2) on an ITO substrate, the HOMO levels of each compound were measured by photoelectron spectroscopy AC-3 (available from Rikoki Co., Ltd.).

[0469] 3. Measurement of LUMO level

[0470] Using the thin film sample prepared in section 1.(2) on a quartz substrate, the UV-Vis absorption spectrum was measured by a spectrophotometer U-3900 (available from Hitachi High-Technologies), thereby obtaining the band gap (Eg) value at its absorption end, and then the LUMO level was calculated by equation A. The calculation results are shown in Table 1.

[0471] Equation A

[0472] LUMO = HOMO + Eg

[0473] Evaluation Example 2: Measurement of Photoluminescence (PL) of Solution

[0474] The obtained compound and the comparative compound were each dissolved in toluene to prepare 1×10 -5 Solution M was filled into a 1 cm² four-sided transmission cell, and photoluminescence (PL) measurements were performed at room temperature using a fluorescence spectrometer F7000 (available from Hitachi High-Technologies Corporation). The peak wavelength, FWHM, and Stokes shift were calculated from the obtained emission spectra. The evaluation results are shown in Table 1.

[0475] Evaluation of Example 3: S1 value, T1 value, and ΔE ST Measurement of value

[0476] 1. Preparation of measurement samples

[0477] (1) The obtained compound or the comparative compound (sample solid) and polymethyl methacrylate (PMMA) were mixed and dissolved in toluene at a weight ratio of 99.5:0.5 to prepare a 5% toluene solution.

[0478] (2) The sample solution prepared in part (1) was spin-coated onto an ITO substrate and a quartz substrate using an MS-B100 spin coater (Mikasa Corporation) and dried to form a coating film with a dry film thickness of 500 nm. Subsequently, a thin film sample was prepared by heating at 120 °C for 1 hour.

[0479] 2. S1 value, T1 value, and ΔE ST Measurement of value

[0480] Using the thin film sample prepared in section 1.(2) on a quartz substrate, fluorescence and phosphorescence spectra were measured at 77 Kelvin (K) using a spectrophotometer (available from Hitachi High-Tech Co., Ltd.). The singlet energy S1 was calculated from the obtained fluorescence spectrum, and the triplet energy T1 was calculated from the phosphorescence spectrum. ΔE was obtained according to equation B. ST The evaluation results are shown in Table 1.

[0481] Equation B

[0482] ΔE st =S1-T1

[0483] Evaluation Example 4: Measurement of PLQY

[0484] In 10 -5 The compounds shown in Table 1 were vacuum co-deposited with the host compound 1,3-bis(carbazole-9-yl)benzene (mCP) at a weight ratio of 1% by weight under a vacuum pressure of Pa on a quartz substrate to prepare a thin film with a thickness of 50 nm. The PLQY was measured by measuring the emission spectra of the prepared thin films using a Quantaurus-QY Absolute PL quantum yield (PLQY) measurement system C11347-01 (Hamamatsu Photonics Co., Ltd.). In the measurement, the excitation wavelength was scanned from 300 nm to 400 nm at 10 nm intervals, and the excitation wavelength region in which the compound absorbance value showed a ratio of 10% or greater to the excitation light intensity was used. The highest value in the used excitation wavelength region was taken as the PLQY value. The evaluation results are shown in Table 1.

[0485] Table 1

[0486]

[0487] Example 4: Fabrication of Organic Light-Emitting Devices

[0488] Polymer P-1, represented by the following formula, was synthesized according to the preparation of compound T as described in WO 2011 / 159872. The number-average molecular weight (Mn) of P-1, measured by gel permeation chromatography (GPC), was 141,000 Daltons, and the weight-average molecular weight (Mw) was 511,000 Daltons.

[0489]

[0490] In addition, FA-14 was synthesized using the method described in US 2016 / 0315259 (incorporated herein by reference) (see below).

[0491]

[0492] As the first electrode (anode), a glass substrate is prepared on which indium tin oxide (ITO) in stripe form is deposited to a film thickness of 150 nm. On this glass substrate, a dry film thickness of poly(3,4-ethylenedioxythiophene) / poly(4-sulfonated styrene) (PEDOT / PSS) (available from Sigma-Aldrich) is applied to a thickness of 30 nm by spin coating, thereby forming a hole injection layer.

[0493] Next, a hole transport layer coating solution was prepared by dissolving P-1 and FA-14 in anisole as a solvent. The hole transport layer coating solution was prepared such that, based on the total weight of the hole transport layer, the amount of P-1 was 80% by weight, and the amount of FA-14 was 20% by weight. Subsequently, the obtained hole transport layer coating solution was spin-coated onto the hole injection layer to form a coating film with a dry film thickness of 125 nm. The obtained coating film was then subjected to 10... -1 Heated at 230°C for 1 hour under a vacuum pressure of Pa or lower. Then, at 10 -1 The coating film is cooled to room temperature under a vacuum pressure of Pa or lower to form a hole transport layer.

[0494] Next, mCP, the host material, and compound 1, the dopant material, are co-deposited on the hole transport layer in a weight ratio of 98.5:1.5 to form an emitter layer with a thickness of 55 nm.

[0495] Then, Liq and KLET-03 (Chemipro Kasei Kaisha Ltd.) were co-deposited on the emitter layer at a mass ratio of 2:8 to form an electron transport layer with a thickness of 20 nm.

[0496] Li was deposited on the electron transport layer using a vacuum deposition apparatus to form an electron injection layer with a thickness of 3.5 nm.

[0497] Subsequently, aluminum was deposited on the electron-injected layer using a vacuum deposition apparatus to form a second electrode (cathode) with a thickness of 100 nm.

[0498] Evaluation of organic light-emitting devices

[0499] The emission peak wavelength, FWHM, and maximum external quantum efficiency (EQE) were evaluated using the following method. The organic light-emitting device (OLED) was allowed to emit light by continuously varying the voltage applied to it using a DC constant voltage power supply (a 2400 source meter from KEITHLEY), and the brightness and emission spectra were measured using a luminance meter (a multi-channel spectrometer PMA12 available from Hamamatsu Photonics.Co.,Ltd.). Furthermore, the current value and EQE (%) were calculated from the measurement results. The wavelength showing the maximum EQE value in the EQE-wavelength plot was defined as the emission peak wavelength (nm), and the wavelength width corresponding to half of the emission peak wavelength (nm) was defined as the FWHM (nm). The maximum EQE shown here is 0.1 mA / m² calculated from the area of ​​the OLED during driving. 2 The EQE values ​​at the current density of ) are shown in Table 2. However, the EQE (relative values) in Table 2 are shown as relative values ​​to the value of 100 in Comparative Example 2.

[0500] Examples 5 and 6 and Comparative Example 2

[0501] The organic light-emitting device was manufactured in the same manner as in Example 4, except that compound 1 was changed to the compound shown in Table 2 during the formation of the emitting layer. The organic light-emitting device was evaluated. The evaluation results are shown in Table 2.

[0502] Table 2

[0503]

[0504] Referring to the results in Table 1, it was found that the heterocyclic compound according to the embodiments has a narrow emission spectrum with a peak wavelength in the blue wavelength region, and emits blue light with high color purity. Furthermore, it was found that the heterocyclic compound according to the embodiments exhibits high efficiency during emission, despite having a relatively large ΔE. ST .

[0505] Referring to the results in Table 2, it was found that the organic light-emitting device including the heterocyclic compound according to the embodiment has a narrow emission spectrum with a peak wavelength in the blue wavelength region and emits blue light with high color purity.

[0506] Furthermore, as shown in Table 2, compared with the organic light-emitting device using Comparative Compound 1, which is not within the scope of this disclosure, the EQE in the organic light-emitting devices of Examples 4-6 using compounds that are within the scope of this disclosure is improved by at least 1.5 times, and therefore the luminous efficiency is excellent.

[0507] As is clear from the previous description, organic light-emitting devices incorporating the aforementioned heterocyclic compounds can have improved efficiency and / or color purity.

[0508] It should be understood that the embodiments described herein should be considered in the descriptive sense only and are not intended to be limiting. The descriptions of features or aspects in each embodiment should typically be considered applicable to other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will further understand that various changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims.

Claims

1. Heterocyclic compounds, represented by formula 1-12: Formula 1-12 in, In Equation 1-12, X 11 -X 17 and X 21 -X 25 Each is an independent carbon atom. Y 11 For C(R) 101 ), Y 12 For C(R) 102 ), Y 13 For C(R) 103 ), Y 14 For C(R) 104 ), Y 15 For C(R) 105 ), Y 16 For C, Y 17 For C, Y 18 For C(R) 108 Z 11 For C(R) 111 Z 12 For C(R) 112 Z 13 For C(R) 113 ), Y 21 For C(R) 201 ), Y 22 For C(R) 202 ), Y 23 For C(R) 203 ), Y 24 For C(R) 204 Z 21 For C(R) 211 Z 22 For C(R) 212 ), and Z 23 For C(R) 213 ),and R 101 -R 105 R 108 R 111 -R 113 R 201 -R 204 and R 211 -R 213 Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a straight-chain or branched unsubstituted alkyl group having one or more and 20 or fewer carbon atoms, a substituted or unsubstituted cycloalkyl group having three or more and 10 or fewer carbon atoms, a straight-chain or branched unsubstituted haloalkyl group having one or more and 20 or fewer carbon atoms, a substituted or unsubstituted halocycloalkyl group having three or more and 10 or fewer carbon atoms, a straight-chain or branched unsubstituted alkoxy group having one or more and 20 or fewer carbon atoms, a substituted or unsubstituted alkylthio group having one or more and 20 or fewer carbon atoms, or a substituted or unsubstituted phenyl group. The substituted cycloalkyl group having 3 or more and 10 or fewer carbon atoms, the substituted halocycloalkyl group having 3 or more and 10 or fewer carbon atoms, the substituted alkithioyl group having 1 or more and 20 or fewer carbon atoms, and the substituted phenyl group are each independently an alkyl group, a deuterium atom, a halogen atom, a cyano group, an alkoxy group, an alkithioyl group, a silyl group, a germanyl group, a halogen-substituted alkyl group, or a deuterium-substituted alkyl group, wherein... The alkyl group is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, or n-decyl. The alkoxy group has one or more carbon atoms and 20 or fewer. The alkylthio group has one or more carbon atoms and 20 or fewer. The halogen-substituted alkyl group has one or more carbon atoms and 20 or fewer. The alkyl group substituted with a deuterium atom is a group represented by one of formulas 9-1 to 9-39, wherein at least one hydrogen atom is replaced by a deuterium atom, or R 101 -R 105 R 108 R 111 -R 113 R 201 -R 204 and R 211 -R 213 Each of the following groups is independently represented by one of formulas 9-1 to 9-39: -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, wherein at least one hydrogen atom is replaced by a deuterium atom; or a group represented by one of formulas 9-1 to 9-39, wherein at least one hydrogen atom is replaced by -F:

2. The heterocyclic compound of claim 1, wherein R 101 -R 105 R 108 R 111 -R 113 R 201 -R 204 and R 211 -R 213 Each of the following is independently represented by a hydrogen atom, a deuterium atom, -F, -CH3, a group represented by one of formulas 9-1 to 9-39, a group represented by one of formulas 10-12 to 10-58, 10-67 to 10-70, 10-72, 10-99 to 10-101, and 10-105 to 10-114, wherein at least one hydrogen atom is replaced by a deuterium atom; a group represented by one of formulas 10-12 to 10-58, 10-67 to 10-70, 10-72, 10-99 to 10-101, and 10-105 to 10-114, wherein at least one hydrogen atom is replaced by a deuterium atom; a group represented by one of formulas 10-12 to 10-58, 10-67 to 10-70, 10-72, 10-99 to 10-101, and 10-105 to 10-114, wherein at least one hydrogen atom is replaced by a deuterium atom; a group represented by one of formulas 10-12 to 10-58, 10-67 to 10-70, 10-72, 10-99 to 10-105 to 10-114, wherein at least one hydrogen atom is replaced by a deuterium atom. A group represented by one of -99 to 10⁻¹⁰¹ and 10⁻¹⁰⁵ to 10⁻¹¹⁴; a group represented by one of formulas 10⁻³⁶⁵, 10⁻³⁶⁶, 10⁻³⁷⁰ ... in, In equations 9-1 to 9-39, 10-12 to 10-58, 10-67 to 10-70, 10-72, 10-99 to 10-101, 10-105 to 10-114, 10-365, 10-366, 10-370, 10-372, 10-373, 10-377, and 10-378, * indicates a binding site with an adjacent atom. "TMS" represents trimethylsilyl and "TMG" represents trimethylgermanyl.

3. The heterocyclic compound of claim 1, wherein... R 112 and R 212 Each of the following is independently a straight-chain or branched unsubstituted alkyl group having one or more and 20 or fewer carbon atoms, a substituted or unsubstituted cycloalkyl group having three or more and 10 or fewer carbon atoms, a straight-chain or branched unsubstituted haloalkyl group having one or more and 20 or fewer carbon atoms, a substituted or unsubstituted halocycloalkyl group having three or more and 10 or fewer carbon atoms, a straight-chain or branched unsubstituted alkoxy group having one or more and 20 or fewer carbon atoms, a substituted or unsubstituted alkylthio group having one or more and 20 or fewer carbon atoms, or a substituted or unsubstituted phenyl group, or R 112 and R 212 Each of the following groups is independently represented by one of formulas 9-1 to 9-39: -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, wherein at least one hydrogen atom is replaced by a deuterium atom, or a group represented by one of formulas 9-1 to 9-39, wherein at least one hydrogen atom is replaced by -F.

4. The heterocyclic compound of claim 1, wherein... R 112 R 212 R 103 and R 203 Each of the following is independently a straight-chain or branched unsubstituted alkyl group having one or more and 20 or fewer carbon atoms, a substituted or unsubstituted cycloalkyl group having three or more and 10 or fewer carbon atoms, a straight-chain or branched unsubstituted haloalkyl group having one or more and 20 or fewer carbon atoms, a substituted or unsubstituted halocycloalkyl group having three or more and 10 or fewer carbon atoms, a straight-chain or branched unsubstituted alkoxy group having one or more and 20 or fewer carbon atoms, a substituted or unsubstituted alkylthio group having one or more and 20 or fewer carbon atoms, or a substituted or unsubstituted phenyl group, or R 112 R 212 R 103 and R 203 Each of the following groups is independently represented by one of formulas 9-1 to 9-39: -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, wherein at least one hydrogen atom is replaced by a deuterium atom, or a group represented by one of formulas 9-1 to 9-39, wherein at least one hydrogen atom is replaced by -F.

5. The heterocyclic compound of claim 1, wherein the heterocyclic compound represented by formulas 1-12 is selected from compounds 1 to 3, 5 to 7, 9, 10, and 12 to 22: in, In compounds 16 and 17, "Ph" indicates an unsubstituted phenyl group.

6. The heterocyclic compound of claim 1, wherein the heterocyclic compound satisfies conditions 1-4; Condition 1 ΔE ST >ΔE ST2 +ΔE’ TT Condition 2 0eV<ΔE ST2 +ΔE’ TT ≤1.0eV Condition 3 0eV<ΔE’ TT ≤0.15eV Condition 4 ΔE ST2 >0eV in, In conditions 1-4, ΔE ST This represents the difference between the lowest excited singlet energy level calculated based on the S1 equilibrium structure of the heterocyclic compound and the lowest excited triplet energy level calculated based on the T1 equilibrium structure of the heterocyclic compound. ΔE ST2 This represents the difference between the lowest excited singlet state energy level calculated based on the S1 equilibrium structure of the heterocyclic compound and the second low-excited triplet state energy level calculated based on the T2 equilibrium structure of the heterocyclic compound, and... ΔE′ TT This represents the difference between the second low-excited triplet energy level calculated using the T2 equilibrium structure of the heterocyclic compound and the lowest excited triplet energy level calculated using the T2 equilibrium structure of the heterocyclic compound.

7. The heterocyclic compound of claim 6, wherein the heterocyclic compound further satisfies condition 5: Condition 5 ΔE ST2 ≤0.1eV in, In condition 5, ΔE ST2 This represents the difference between the lowest excited singlet state energy level calculated based on the S1 equilibrium structure of the heterocyclic compound and the second low-excited triplet state energy level calculated based on the T2 equilibrium structure of the heterocyclic compound.

8. Organic light-emitting devices, including: First electrode; Second electrode; And an organic layer between the first electrode and the second electrode, including an emission layer, The organic light-emitting device described herein comprises a heterocyclic compound as described in any one of claims 1-7.

9. The organic light-emitting device of claim 8, wherein the emitting layer comprises the heterocyclic compound.

10. The organic light-emitting device of claim 9, wherein the emitting layer further comprises a body, the body and the heterocyclic compound being distinct from each other, and the emitting layer is composed of the body and the heterocyclic compound.

11. The organic light-emitting device of claim 10, wherein the host does not emit light, and the heterocyclic compound emits light.

12. The organic light-emitting device of claim 9, wherein... The emitter layer further includes a host and a dopant. The host, the dopant, and the heterocyclic compound are different from each other. The emitter layer is composed of the host, the dopant, and the heterocyclic compound.

13. The organic light-emitting device of claim 12, wherein the host and the heterocyclic compound each do not emit light, and the dopant emits light.

14. An electronic device comprising an organic light-emitting device as claimed in any one of claims 8-13.

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