Heterocyclic compound, organic light-emitting device including heterocyclic compound, and composition for organic material layer

Abstract

The present disclosure relates to a heterocyclic compound represented by Chemical Formula 1, an organic light-emitting device including the heterocyclic compound, and a composition for an organic material layer. The heterocyclic compound is represented by the following Chemical Formula 1: In Chemical Formula 1, the definition of each substituent is the same as that defined in the specification.

Description

[0001] Cross-referencing

[0002] This application claims priority to Korean Patent Application No. 10-2024-0125716, filed on September 13, 2024, the disclosure of which is incorporated herein by reference in its entirety. Technical Field

[0003] This disclosure relates to heterocyclic compounds, organic light-emitting devices including heterocyclic compounds, and compositions for use as organic material layers. Background Technology

[0004] Organic light-emitting devices are self-emitting display devices that offer advantages such as wide viewing angles, high response speeds, and excellent contrast.

[0005] Organic light-emitting devices have a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light-emitting device with this structure, electrons and holes injected from the two electrodes combine and pair in the organic thin film, and then emit light as these annihilate. The organic thin film can be formed in single or multiple layers as needed.

[0006] Depending on the requirements, organic thin film materials can possess light-emitting properties. For example, as materials for organic thin films, compounds that can independently form a light-emitting layer can be used, or compounds that can be used as a host or dopant in a host-dopant type light-emitting layer can be used. In addition, compounds capable of performing functions such as hole injection, hole transport, electron blocking, and electron transport and injection can also be used as materials for organic thin films.

[0007] To enhance the performance, lifespan, or efficiency of organic light-emitting devices, there has always been a need to develop organic thin film materials.

[0008] Existing technical documents

[0009] Patent documents

[0010] (Patent Document 1) U.S. Patent No. 4,356,429 Summary of the Invention

[0011] This disclosure relates to providing heterocyclic compounds, organic light-emitting devices including heterocyclic compounds, and compositions for use as organic material layers.

[0012] One embodiment of this disclosure provides a heterocyclic compound represented by the following chemical formula 1.

[0013] [Chemical Formula 1]

[0014]

[0015] In chemical formula 1,

[0016] X is either O or S.

[0017] R1 to R3 may be the same as or different from each other, and each is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted naphthyl; and naphthalene except for substituted or unsubstituted naphthalene. In addition to the alkyl group, substituted or unsubstituted C6 to C60 aryl groups; substituted or unsubstituted C2 to C60 heteroaryl groups; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 may be the same as or different from each other, and each independently is: a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0018] a is an integer from 0 to 2, and when a is 2, R1 is either the same or different from each other.

[0019] b is an integer from 0 to 4, and when b is 2 or greater, R² are either the same or different from each other.

[0020] c is an integer from 0 to 4, and when c is 2 or greater, R3 are either the same or different from each other.

[0021] Ar1 and Ar2 may be the same as or different from each other, and each independently consists of: a substituted or unsubstituted naphthyl group; a substituted or unsubstituted C6 to C60 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0022] L1 to L3 may be the same as or different from each other, and each is independently: a direct bond; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted C6 to C60 arylene group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0023] d is an integer from 0 to 5, and when d is 2 or greater, L1 is either the same or different from each other.

[0024] e is an integer from 0 to 5, and when e is 2 or greater, L2 values ​​are either the same or different.

[0025] f is an integer from 0 to 5, and when f is 2 or greater, L3 are either the same or different from each other.

[0026] L2 is a substituted or unsubstituted naphthyl group, or

[0027] At least one of Ar1, Ar2, and R3 is a substituted or unsubstituted naphthyl group.

[0028] Additionally, one embodiment of this disclosure provides an organic light-emitting device, comprising:

[0029] First electrode;

[0030] A second electrode is provided opposite to the first electrode; and

[0031] One or more organic material layers are provided between the first electrode and the second electrode.

[0032] One or more of the organic material layers include a heterocyclic compound represented by chemical formula 1.

[0033] In addition, one embodiment of this disclosure provides an organic light-emitting device, wherein the organic material layer further includes a heterocyclic compound represented by the following chemical formula 2.

[0034] [Chemical Formula 2]

[0035]

[0036] In chemical formula 2,

[0037] R11, R13, and R15 may be the same as or different from each other, and each is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C6 0 heteroaryl; -P(=O)R201R202; and -SiR201R202R203, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic ring, or a substituted or unsubstituted C2 to C60 heterocycle, and R201, R202, and R203 may be the same as or different from each other, and each independently is: a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl.

[0038] g is an integer from 0 to 4, and when g is 2 or greater, R11 are either the same or different from each other.

[0039] h is an integer from 0 to 3, and when h is 2 or greater, R15 are either the same or different from each other.

[0040] Either R12 or R14 is chemical formula 3 below, and the other is chemical formula 4 below.

[0041] [Chemical Formula 3]

[0042]

[0043] [Chemical Formula 4]

[0044]

[0045] In chemical formulas 3 and 4

[0046] Ar11 to Ar13 may be identical or different from each other, and each is independently: a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0047] L11 to L14 may be the same as or different from each other, and each independently consists of: a direct bond; a substituted or unsubstituted C6 to C60 arylene; or a substituted or unsubstituted C2 to C60 heteroarylene.

[0048] i is an integer from 0 to 5, and when i is 2 or greater, L11 are either the same or different from each other.

[0049] j is an integer from 0 to 5, and when j is 2 or greater, L12 are either the same or different from each other.

[0050] k is an integer from 0 to 5, and when k is 2 or greater, L13 are either the same or different from each other.

[0051] l is an integer from 0 to 5, and when l is 2 or greater, L14 are either the same or different from each other.

[0052] Additionally, one embodiment of this disclosure provides a composition for an organic material layer, the composition comprising: a heterocyclic compound represented by chemical formula 1; and a heterocyclic compound represented by chemical formula 2.

[0053] The compounds described in this specification can be used as organic material layers in organic light-emitting devices. These compounds can function as hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, and electron injection layer materials in organic light-emitting devices. Specifically, these compounds can be used as light-emitting layer materials in organic light-emitting devices. These compounds can be used alone as light-emitting materials, or as the host material or dopant material of the light-emitting layer.

[0054] Specifically, the compound can be used alone as a luminescent material, or as a host material or dopant material of the luminescent layer. When a heterocyclic compound represented by Formula 1 is used in the organic material layer, it is possible to reduce the driving voltage of the organic light-emitting device and improve the luminous efficiency and lifetime properties of the organic light-emitting device. Attached Figure Description

[0055] Figures 1 to 3 Each of the above diagrams schematically illustrates a laminated structure of an organic light-emitting device according to an embodiment of the present disclosure.

[0056] [Figure Labels]

[0057] 100: Base

[0058] 200: Positive electrode

[0059] 300: Organic material layer

[0060] 301: Hole Injection Layer

[0061] 302: Hole transport layer

[0062] 303: Emissive layer

[0063] 304: Cavity Blocking Layer

[0064] 305: Electron Transport Layer

[0065] 306: Electron Injection Layer

[0066] 400: Negative electrode Detailed Implementation

[0067] This disclosure will be described in more detail below.

[0068] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0069] In this specification, "substituted or unsubstituted" means: substituted by one or more substituents selected from the group consisting of: deuterium; halogen; cyano; C1 to C60 straight-chain or branched alkyl; C2 to C60 straight-chain or branched alkenyl; C2 to C60 straight-chain or branched alkynyl; C1 to C60 straight-chain, branched, or cyclic alkoxy; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocyclic alkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P( =O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine; or unsubstituted; or substituted or unsubstituted, wherein two or more substituents selected from the substituents exemplified above are linked together, and R, R' and R" are the same as or different from each other and are each independently: substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0070] In this specification, halogen can be: fluorine; chlorine; bromine; or iodine.

[0071] In this specification, alkyl groups comprise straight-chain or branched forms having 1 to 60 carbon atoms and may be further substituted with other substituents. The number of carbon atoms in an alkyl group can be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples of alkyl groups may include, but are not limited to: methyl; ethyl; n-propyl; isopropyl; n-butyl; isobutyl; tert-butyl; sec-butyl; 1-methyl-butyl; 1-ethyl-butyl; n-pentyl; isopentyl; neopentyl; tert-pentyl; n-hexyl; 1-methylpentyl; 2-methylpentyl; 4-methyl-2-pentyl; 3,3-dimethylbutyl; 2-ethylbutyl; n-heptyl; 1-methylhexyl; cyclopentylmethyl; cyclohexylmethyl; n-octyl; tert-octyl; 1-methylheptyl; 2-ethylhexyl; 2-propylpentyl; n-nonyl; 2,2-dimethylheptyl; 1-ethyl-propyl; 1,1-dimethyl-propyl; isohexyl; 4-methylhexyl; and 5-methylhexyl.

[0072] In this specification, alkenyl groups include straight-chain or branched forms having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in an alkenyl group can be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples of alkenyl groups may include: vinyl; 1-propenyl; isopropenyl; 1-butenyl; 2-butenyl; 3-butenyl; 1-pentenyl; 2-pentenyl; 3-pentenyl; 3-methyl-1-butenyl; 1,3-butadienyl; allyl; 1-phenylvinyl-1-yl; 2-phenylvinyl-1-yl; 2,2-diphenylvinyl-1-yl; 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl; 2,2-bis(diphenyl-1-yl)vinyl-1-yl; styryl; and styryl, etc., but are not limited thereto.

[0073] In this specification, the alkynyl group comprises a straight-chain or branched form having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkynyl group can be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0074] In this specification, alkoxy groups can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but is preferably from 1 to 20. Specific examples of alkoxy groups may include, but are not limited to: methoxy; ethoxy; n-propoxy; isopropoxy; n-butoxy; isobutoxy; tert-butoxy; sec-butoxy; n-pentoxy; neopentoxy; isopentoxy; n-hexyloxy; 3,3-dimethylbutoxy; 2-ethylbutoxy; n-octoxy; n-nonoxy; n-decoxy; benzyloxy; and p-methylbenzyloxy, etc.

[0075] In this specification, cycloalkyl groups include monocyclic or polycyclic groups having 3 to 60 carbon atoms and may be further substituted with other substituents. Polycyclic groups are defined herein as groups in which the cycloalkyl group is directly attached to or fused with another cyclic group. The other cyclic group may be cycloalkyl, but may also be different types of cyclic groups, such as heterocycloalkyl, aryl, and heteroaryl. The number of carbon atoms in a cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of cycloalkyl groups may include, but are not limited to, cyclopropyl; cyclobutyl; cyclopentyl; 3-methylcyclopentyl; 2,3-dimethylcyclopentyl; cyclohexyl; 3-methylcyclohexyl; 4-methylcyclohexyl; 2,3-dimethylcyclohexyl; 3,4,5-trimethylcyclohexyl; 4-tert-butylcyclohexyl; cycloheptyl; and cyclooctyl, etc.

[0076] In this specification, heterocyclic alkyl groups include O, S, Se, N, or Si as heteroatoms, comprising monocyclic or polycyclic groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. Hereinafter, a polycyclic group means a group in which a heterocyclic alkyl group is directly attached to or fused with another cyclic group. Hereinafter, the other cyclic group may be a heterocyclic alkyl group, but may also be a different type of cyclic group, such as cycloalkyl, aryl, and heteroaryl. The number of carbon atoms in a heterocyclic alkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0077] In this specification, aryl groups include monocyclic or polycyclic groups having 6 to 60 carbon atoms and may be further substituted with other substituents. Hereinafter, a polycyclic group means a group in which the aryl group is directly attached to or fused with another cyclic group. Hereinafter, the other cyclic group may be an aryl group, but may also be a different type of cyclic group, such as cycloalkyl, heterocycloalkyl, and heteroaryl. Aryl groups may include spirocyclic groups. The number of carbon atoms in an aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 20. Specific examples of aryl groups may include: phenyl; biphenyl; terphenyl; naphthyl; anthracene; ; phenanthrene; perylene; fluoranyl; benzophenanthrene; phenarenyl; pyrene; tetraphenyl; pentaphenyl; fluorenyl; indene; acenaphthene; benzofluorenyl; spirodifluorenyl; 2,3-dihydro-1H-indene; and their fused-ring groups, but not limited to these.

[0078] In this specification, the phosphine oxide group is represented by -P(=O)R101R102, and R101 and R102 may be the same as or different from each other, and may each be independently a substituent formed with at least one of the following groups: hydrogen; deuterium; halogen group; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heterocyclic group. Specifically, the phosphine oxide group may be substituted with an aryl group, and the above examples may be used as aryl groups. Examples of phosphine oxide groups may include, but are not limited to, diphenylphosphine oxide and dinaphthylphosphine oxide.

[0079] In this specification, silyl is a substituent comprising Si and having directly linked Si atoms as free radicals, and is represented by -SiR101R102R103. R101 to R103 may be the same as or different from each other, and may each be independently a substituent formed with at least one of the following groups: hydrogen; deuterium; halogen group; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heterocyclic group. Specific examples of silyl groups may include, but are not limited to, trimethylsilyl; triethylsilyl; tert-butyldimethylsilyl; vinyldimethylsilyl; propyldimethylsilyl; triphenylsilyl; diphenylsilyl; and phenylsilyl, etc.

[0080] In this specification, the fluorene group may be substituted, and adjacent substituents may bond to each other to form a ring.

[0081] When the fluorene group is substituted, it can include However, the structure is not limited to this.

[0082] In this specification, a spirocyclic group is a group that includes a spirocyclic structure and may have 15 to 60 carbon atoms. For example, a spirocyclic group may include a structure in which a 2,3-dihydro-1H-indenyl or cyclohexyl group is spirobonded to a fluorenyl group. Specifically, a spirocyclic group may include any of the groups in the following structural formulas.

[0083]

[0084] In this specification, heteroaryl groups include S, O, Se, N, or Si as heteroatoms, and include monocyclic or polycyclic groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. Hereinafter, a polycyclic group means a group in which a heteroaryl group is directly attached to or fused with another cyclic group. Hereinafter, the other cyclic group may be a heteroaryl group, but may also be a different type of cyclic group, such as cycloalkyl, heterocycloalkyl, and aryl. The number of carbon atoms in a heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of heteroaryl groups may include: pyridyl; pyrroloyl; pyrimidinyl; pyridazinyl; furanyl; thiopheneyl; imidazolyl; pyrazolyl; oxazolyl; isoxazolyl; thiazolyl; isothiazolyl; triazolyl; furazolyl; oxadiazolyl; thiazolyl; dithiazolyl; tetrazolyl; pyranyl; thiaranyl; diazinyl; oxazinyl; thiazolyl; dioxinyl; triazinyl; tetraazinyl; quinolinyl; isoquinolinyl; quinazolinyl; isoquinazolinyl; quinazolinyl; naphridinyl; acridineyl; phenanthridineyl; imidazopyridyl; Diazanaphthyl; Triazaindyl; 2-Indole; Indazinyl; Benzothiazolyl; Benzooxazolyl; Benzoimidazolyl; Benzothiopheneyl; Benzofuranyl; Dibenzothiopheneyl; Dibenzofuranyl; Carbazole; Benzocarbazole; Dibenzocarbazole; Phenazinyl; Dibenzothiophenolyl; Spirodi(Dibenzothiophenol)yl; Dihydrophenazinyl; Phenoxazinyl; Indolo[2,3-a]carbazole; Indolo[2,3-b]carbazole; Indololinyl; 10,11-Dihydro-Dibenzo[b,f]aza The group includes, but is not limited to, 9,10-dihydroacridinyl; phenanthreneyl; phenothiazinyl; phthalazinyl; phenanthrolinel; benzo[c][1,2,5]thiadiazolyl; 5,10-dihydrodibenzo[b,e][1,4]azasilyl; pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolel, pyrido[1,2-a]imidazo[1,2-e]indololinyl; and 5,11-dihydroindoxazo[1,2-b]carbazolel, etc.

[0085] In this specification, the amino group may be selected from the group consisting of monoalkylamino, monoarylamino, monoheteroarylamino, -NH2, dialkylamino, diarylamino, diheteroarylamino, alkylarylamino, alkylheteroarylamino, and arylheteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably from 1 to 30. Specific examples of amino groups may include: methylamino; dimethylamino; ethylamino; diethylamino; aniline; naphthylamino; biphenylamino; diphenylamino; anthraceneamino; 9-methyl-anthraylamino; diphenylamino; phenylnaphthylamino; xylylamino; phenyltolylamino; triphenylamino; biphenylnaphthylamino; phenylbiphenylamino; biphenylfluorenylamino; phenyltriphenylamine; biphenyltriphenylamine, etc., but are not limited thereto.

[0086] In this specification, arylene refers to an aryl group having two bonding sites, i.e., a divalent group. The above description of aryl groups can be applied to arylene groups, the difference being that each arylene group is a divalent group. Additionally, heteroarylene refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The above description of heteroaryl groups can be applied to heteroarylene groups, the difference being that each heteroarylene group is a divalent group.

[0087] In this specification, "adjacent" groups may mean: a substituent that replaces an atom directly bonded to the atom substituted by the corresponding substituent; a substituent that is spatially closest to the corresponding substituent; or another substituent that replaces the atom substituted by the corresponding substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon atom in an aliphatic ring can be interpreted as groups that are "adjacent" to each other.

[0088] In this disclosure, "in the case where no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, because deuterium ( 2 H and D are isotopes of hydrogen, so some hydrogen atoms can be deuterium.

[0089] In one embodiment of this disclosure, "where no substituent is indicated in the chemical formula or compound structure" can mean that all positions accessible to the substituent are either hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms can be deuterium as an isotope, and in this document, the deuterium content can be from 0% to 100%.

[0090] In one embodiment of this disclosure, hydrogen and deuterium can be used interchangeably in a compound when "no substituents are indicated in the chemical formula or compound structure" and deuterium is not explicitly excluded (such as "0% deuterium content", "100% hydrogen content" or "all substituents are hydrogen").

[0091] In one embodiment of this disclosure, deuterium is one of several isotopes of hydrogen, an element having a deuterium nucleus formed by one proton and one neutron as its atomic nucleus, and can be represented as hydrogen-2, and its element symbol can also be written as D or 2 H.

[0092] In one embodiment of this disclosure, an isotope means an atom having the same atomic number (Z) but different mass numbers (A), and can also be interpreted as an element having the same number of protons but different numbers of neutrons.

[0093] In one embodiment of this disclosure, when the total number of substituents that a basic compound may have is defined as T1 and the number of a specific substituent among these substituents is defined as T2, the content of the specific substituent T% can be defined as T2 / T1×100=T.

[0094] In other words, in one example, in the case of... The presence of 20% deuterium in a phenyl group can mean that the phenyl group can have a total of 5 substituents (T1 in the formula), and that there is 1 deuterium atom among these substituents (T2 in the formula). In other words, a phenyl group having 20% ​​deuterium content can be represented by the following structural formula.

[0095]

[0096] Additionally, in one embodiment of this disclosure, "phenyl with 0% deuterium content" may mean a phenyl that does not contain deuterium atoms, that is, a phenyl with 5 hydrogen atoms.

[0097] In this disclosure, C6 to C60 aromatic rings refer to compounds comprising aromatic rings formed from C6 to C60 carbons and hydrogens. Examples may include: phenyl; biphenyl; terphenyl; benzophenanthrene; naphthyl; anthraceneyl; phenatenyl; phenanthrene; fluorenyl; pyrene; The compounds include, but are not limited to, cycloalkanes; perylene groups; and chamomile cycloalkanes, and all aromatic hydrocarbon cyclic compounds known in the art that satisfy the above-mentioned number of carbon atoms.

[0098] One embodiment of this disclosure provides a heterocyclic compound represented by the following chemical formula 1.

[0099] [Chemical Formula 1]

[0100]

[0101] In chemical formula 1,

[0102] X is O or S.

[0103] R1 to R3 may be the same as or different from each other, and each is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted naphthyl; and naphthalene except for substituted or unsubstituted naphthalene. In addition to the alkyl group, substituted or unsubstituted C6 to C60 aryl groups; substituted or unsubstituted C2 to C60 heteroaryl groups; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 may be the same as or different from each other, and each independently is: a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0104] a is an integer from 0 to 2, and when a is 2, R1 is either the same or different from each other.

[0105] b is an integer from 0 to 4, and when b is 2 or greater, R² are either the same or different from each other.

[0106] c is an integer from 0 to 4, and when c is 2 or greater, R3 are either the same or different from each other.

[0107] Ar1 and Ar2 may be the same as or different from each other, and each independently consists of: a substituted or unsubstituted naphthyl group; a substituted or unsubstituted C6 to C60 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0108] L1 to L3 may be the same as or different from each other, and each is independently: a direct bond; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted C6 to C60 arylene group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0109] d is an integer from 0 to 5, and when d is 2 or greater, L1 is either the same or different from each other.

[0110] e is an integer from 0 to 5, and when e is 2 or greater, L2 values ​​are either the same or different.

[0111] f is an integer from 0 to 5, and when f is 2 or greater, L3 are either the same or different from each other.

[0112] L2 is a substituted or unsubstituted naphthyl group, or

[0113] At least one of Ar1, Ar2, and R3 is a substituted or unsubstituted naphthyl group.

[0114] In one embodiment of this disclosure, X can be 0.

[0115] In another embodiment of this disclosure, X can be S.

[0116] In one embodiment of this disclosure, R1 to R3 may be the same as or different from each other, and each independently represents: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C2 to C30 alkenyl; substituted or unsubstituted C2 to C30 alkoxy; substituted or unsubstituted C3 to C30 cycloalkyl; substituted or unsubstituted C2 to C30 heterocycloalkyl; substituted or unsubstituted naphthyl; other than substituted or unsubstituted... Other than naphthyl, substituted or unsubstituted C6 to C30 aryl; substituted or unsubstituted C2 to C30 heteroaryl; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, wherein R101, R102 and R103 may be the same as or different from each other, and may each independently be: substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

[0117] In another embodiment of this disclosure, R1 to R3 may be the same as or different from each other, and each independently represents: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted naphthyl; other than substituted or unsubstituted... Other than naphthyl, substituted or unsubstituted C6 to C20 aryl; substituted or unsubstituted C2 to C20 heteroaryl; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, wherein R101, R102 and R103 may be the same as or different from each other, and may each independently be: substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0118] In another embodiment of this disclosure, R1 to R3 may be the same as or different from each other, and may each be independently: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted naphthyl; substituted or unsubstituted C6 to C20 aryl in addition to substituted or unsubstituted naphthyl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0119] In another embodiment of this disclosure, R1 to R3 may be the same as or different from each other, and may each be independently: hydrogen; deuterium; substituted or unsubstituted naphthyl; substituted or unsubstituted C6 to C20 aryl in addition to substituted or unsubstituted naphthyl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0120] In another embodiment of this disclosure, R1 to R3 may be the same as or different from each other, and may each be independently: hydrogen; deuterium; substituted or unsubstituted naphthyl; or substituted or unsubstituted C6 to C20 aryl groups in addition to substituted or unsubstituted naphthyl groups.

[0121] In another embodiment of this disclosure, R1 and R2 may be the same or different from each other, and may each be hydrogen or deuterium independently.

[0122] In another embodiment of this disclosure, R3 may be the same as or different from each other, and may be independently: hydrogen; deuterium; substituted or unsubstituted naphthyl; or substituted or unsubstituted C6 to C20 aryl groups in addition to substituted or unsubstituted naphthyl groups.

[0123] In another embodiment of this disclosure, R3 may be the same as or different from each other, and may be independently: hydrogen; deuterium; substituted or unsubstituted phenyl; or substituted or unsubstituted naphthyl.

[0124] In one embodiment of this disclosure, Ar1 and Ar2 may be the same as or different from each other, and may each be independently: a substituted or unsubstituted naphthyl; a substituted or unsubstituted C6 to C30 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0125] In another embodiment of this disclosure, Ar1 and Ar2 may be the same as or different from each other, and may each be independently: a substituted or unsubstituted naphthyl; a substituted or unsubstituted C6 to C20 aryl in addition to the substituted or unsubstituted naphthyl; or a substituted or unsubstituted C2 to C20 heteroaryl.

[0126] In another embodiment of this disclosure, Ar1 and Ar2 may be the same as or different from each other, and may each be independently: substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothiophenyl; substituted or unsubstituted carbazoleyl; or substituted or unsubstituted benzocarbazoleyl.

[0127] In another embodiment of this disclosure, Ar1 can be: a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted carbazoleyl group; or a substituted or unsubstituted benzocarbazoleyl group.

[0128] In another embodiment of this disclosure, Ar2 may be: a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazoleyl group.

[0129] In one embodiment of this disclosure, L1 to L3 may be the same as or different from each other, and may each be independently: a direct bond; a substituted or unsubstituted naphthylene; a substituted or unsubstituted C6 to C30 arylene in addition to the substituted or unsubstituted naphthylene; or a substituted or unsubstituted C2 to C30 heteroarylene.

[0130] In another embodiment of this disclosure, L1 to L3 may be the same as or different from each other, and may each be independently: a direct bond; a substituted or unsubstituted naphthylene; a substituted or unsubstituted C6 to C20 arylene in addition to the substituted or unsubstituted naphthylene; or a substituted or unsubstituted C2 to C20 heteroarylene.

[0131] In another embodiment of this disclosure, L1 to L3 may be the same as or different from each other, and may each be independently: a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted naphthylene; or a substituted or unsubstituted carbazolyl group.

[0132] In another embodiment of this disclosure, L1 can be: a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted carbazolyl group.

[0133] In another embodiment of this disclosure, L2 can be: a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0134] In another embodiment of this disclosure, L3 can be: a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted carbazolyl group.

[0135] In one embodiment of this disclosure, when L2 is a substituted or unsubstituted naphthylene, Ar1, Ar2 and R3 may be unsubstituted or unsubstituted naphthylene.

[0136] In another embodiment of this disclosure, when L2 is a substituted or unsubstituted naphthylene, Ar1 and Ar2 may be the same as or different from each other, and each independently is: a substituted or unsubstituted C6 to C60 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and R3 may be the same as or different from each other, and each independently may be: hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0137] In another embodiment of this disclosure, when L2 is a substituted or unsubstituted naphthylene, Ar1 and Ar2 may be the same as or different from each other, and may each be independently: a substituted or unsubstituted C6 to C30 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C30 heteroaryl group, and R3 may be the same as or different from each other, and may each be independently: hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0138] In another embodiment of this disclosure, when L2 is a substituted or unsubstituted naphthylene, Ar1 and Ar2 may be the same as or different from each other, and may each be independently: a substituted or unsubstituted C6 to C20 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, and R3 may be the same as or different from each other, and may each be independently: hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0139] In another embodiment of this disclosure, when L2 is a substituted or unsubstituted naphthylene, Ar1 and Ar2 may be the same as or different from each other, and may each be independently: a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted phenanthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; a substituted or unsubstituted carbazoleyl; or a substituted or unsubstituted benzocarbazoleyl, and R3 may be the same as or different from each other, and may each be independently: hydrogen; deuterium; or a substituted or unsubstituted phenyl.

[0140] In another embodiment of this disclosure, when L2 is a substituted or unsubstituted naphthylene, Ar1 can be: a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted phenanthryl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; a substituted or unsubstituted carbazoleyl; or a substituted or unsubstituted benzocarbazoleyl, and Ar2 can be: a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted phenanthryl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; or a substituted or unsubstituted carbazoleyl, and R3 can be: hydrogen; deuterium; or a substituted or unsubstituted phenyl.

[0141] In one embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, at least one of Ar1, Ar2 and R3 may be a substituted or unsubstituted naphthyl group.

[0142] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar1 can be a substituted or unsubstituted naphthyl group, and Ar2 can be: a substituted or unsubstituted C6 to C60 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and R3 can be the same or different from each other, and can each be independently: hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0143] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar1 can be a substituted or unsubstituted naphthyl group, and Ar2 can be: a substituted or unsubstituted C6 to C30 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C30 heteroaryl group, and R3 can be the same or different from each other, and can each be independently: hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0144] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar1 can be a substituted or unsubstituted naphthyl group, and Ar2 can be: a substituted or unsubstituted C6 to C20 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, and R3 can be the same or different from each other, and can each be independently: hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0145] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar1 can be a substituted or unsubstituted naphthyl group, Ar2 can be: a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted phenanthyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazole group, and R3 can be: hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0146] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar2 can be a substituted or unsubstituted naphthyl group, and Ar1 can be: a substituted or unsubstituted C6 to C60 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and R3 can be the same or different from each other, and can each be independently: hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0147] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar2 can be a substituted or unsubstituted naphthyl group, and Ar1 can be: a substituted or unsubstituted C6 to C30 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C30 heteroaryl group, and R3 can be the same or different from each other, and can each be independently: hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0148] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar2 can be a substituted or unsubstituted naphthyl group, and Ar1 can be: a substituted or unsubstituted C6 to C20 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, and R3 can be the same or different from each other, and can each be independently: hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0149] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar2 can be a substituted or unsubstituted naphthyl group, Ar1 can be: a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted phenanthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted carbazoleyl group; or a substituted or unsubstituted benzocarbazoleyl group, and R3 can be: hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0150] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar1 and Ar2 can be substituted or unsubstituted naphthyl groups, and R3 can be the same as or different from each other, and can be independently: hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl groups other than substituted or unsubstituted naphthyl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups.

[0151] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar1 and Ar2 can be substituted or unsubstituted naphthyl groups, and R3 can be the same as or different from each other, and can be independently: hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl groups other than substituted or unsubstituted naphthyl groups; or substituted or unsubstituted C2 to C30 heteroaryl groups.

[0152] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar1 and Ar2 can be substituted or unsubstituted naphthyl groups, and R3 can be the same as or different from each other, and can be independently: hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl groups other than substituted or unsubstituted naphthyl groups; or substituted or unsubstituted C2 to C20 heteroaryl groups.

[0153] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar1 and Ar2 can be substituted or unsubstituted naphthyl groups, and R3 can be the same as or different from each other, and can be independently: hydrogen; deuterium; or substituted or unsubstituted phenyl.

[0154] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar1 and R3 can be substituted or unsubstituted naphthyl groups, and Ar2 can be: a substituted or unsubstituted C6 to C60 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0155] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar1 and R3 can be substituted or unsubstituted naphthyl groups, and Ar2 can be: a substituted or unsubstituted C6 to C30 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0156] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthyl group, Ar1 and R3 can be substituted or unsubstituted naphthyl groups, and Ar2 can be: a substituted or unsubstituted C6 to C20 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0157] In another embodiment of this disclosure, when L2 is not a substituted or unsubstituted naphthylene, Ar1 and R3 can be substituted or unsubstituted naphthylene, and Ar2 can be: a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted terphenylene; a substituted or unsubstituted phenanthrene; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiophenylene; or a substituted or unsubstituted carbazoleylene.

[0158] In one embodiment of this disclosure, the heterocyclic compound represented by chemical formula 1 may be represented by chemical formula 1-1 or chemical formula 1-2 below.

[0159] [Chemical Formula 1-1]

[0160]

[0161] [Chemical Formula 1-2]

[0162]

[0163] In chemical formulas 1-1 and 1-2,

[0164] X, R1 to R3, Ar1, Ar2, L1 to L3, and a to f have the same definitions as in Chemical Formula 1.

[0165] In one embodiment of this disclosure, R1 to R3, L1 to L3, Ar1 and Ar2 may all comprise undeuterated hydrogen (H).

[0166] In another embodiment of this disclosure, at least one of R1 to R3, L1 to L3, Ar1 and Ar2 includes deuterium (D), and at least one of R1 to R3, L1 to L3, Ar1 and Ar2 may include undeuterated hydrogen.

[0167] In another embodiment of this disclosure, R1 to R3, L1 to L3, Ar1 and Ar2 may all include deuterium.

[0168] In one embodiment of this disclosure, the heterocyclic compound represented by Formula 1 may not include deuterium as a substituent, or may have a deuterium content, for example, greater than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more and 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less, relative to the total number of hydrogen and deuterium atoms.

[0169] In another embodiment of this disclosure, the heterocyclic compound represented by Formula 1 may not include deuterium as a substituent, or may have a deuterium content of 1% to 100% relative to the total number of hydrogen and deuterium atoms.

[0170] In another embodiment of this disclosure, the heterocyclic compound represented by Formula 1 may not include deuterium as a substituent, or may have a deuterium content of 20% to 90% relative to the total number of hydrogen and deuterium atoms.

[0171] In another embodiment of this disclosure, the heterocyclic compound represented by Formula 1 may not include deuterium as a substituent, or may have a deuterium content of 30% to 80% relative to the total number of hydrogen and deuterium atoms.

[0172] In another embodiment of this disclosure, the heterocyclic compound represented by Formula 1 may not include deuterium as a substituent, or may have a deuterium content of 50% to 70% relative to the total number of hydrogen and deuterium atoms.

[0173] In one embodiment of this disclosure, the heterocyclic compound represented by Formula 1 may be represented by any of the following compounds.

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204] Furthermore, by introducing various substituents into the structure of Formula 1, compounds with unique properties of the introduced substituents can be synthesized. For example, by introducing substituents commonly used in the manufacture of hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, electron blocking layer materials, and charge generation layer materials for organic light-emitting devices into the core structure, materials that meet the requirements of each organic material layer can be synthesized.

[0205] Furthermore, by introducing various substituents into the structure of Formula 1, the band gap can be precisely controlled, and at the same time, the properties at the interface between organic materials can be improved, and the application of materials can be diversified.

[0206] Meanwhile, heterocyclic compounds possess high glass transition temperatures (Tg), and thus exhibit excellent thermal stability. This increased thermal stability is a crucial factor in providing driving stability to the device.

[0207] The heterocyclic compound according to one embodiment of this disclosure can be prepared using a multi-step chemical reaction. First, some intermediate compounds are prepared, and the compound of formula 1 can be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of this disclosure can be prepared based on preparation examples described later.

[0208] Another embodiment of this disclosure provides an organic light-emitting device comprising a heterocyclic compound represented by Formula 1. "Organic light-emitting device" can be expressed using terms such as "organic light-emitting diode," "OLED," "OLED device," and "organic electroluminescent device."

[0209] Additionally, one embodiment of this disclosure relates to an organic light-emitting device, comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the one or more organic material layers comprises a heterocyclic compound represented by chemical formula 1.

[0210] In one embodiment of this disclosure, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

[0211] In another embodiment, the first electrode may be a negative electrode, and the second electrode may be a positive electrode.

[0212] In one embodiment of this disclosure, the organic light-emitting device can be a red organic light-emitting device, and the heterocyclic compound represented by Formula 1 can be used as a material for the red organic light-emitting device.

[0213] In another embodiment of this disclosure, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as a material for the blue organic light-emitting device.

[0214] In another embodiment of this disclosure, the organic light-emitting device can be a green organic light-emitting device, and the heterocyclic compound represented by Formula 1 can be used as a material for the green organic light-emitting device.

[0215] In one embodiment of this disclosure, the organic light-emitting device can be a red organic light-emitting device, and the heterocyclic compound represented by Formula 1 can be used as the light-emitting layer material of the red organic light-emitting device.

[0216] In another embodiment of this disclosure, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Formula 1 may be used as the light-emitting layer material of the blue organic light-emitting device.

[0217] In another embodiment of this disclosure, the organic light-emitting device can be a green organic light-emitting device, and the heterocyclic compound represented by Formula 1 can be used as the light-emitting layer material of the green organic light-emitting device.

[0218] The specific description of the heterocyclic compound represented by chemical formula 1 is the same as that provided above.

[0219] The organic light-emitting device disclosed herein can be manufactured using common organic light-emitting device manufacturing methods and materials, the difference being that one or more layers of organic material are formed using the heterocyclic compound represented by chemical formula 1 described above.

[0220] When manufacturing organic light-emitting devices, heterocyclic compounds can be formed into organic material layers using solution coating and vacuum deposition methods. In this document, solution coating methods refer to spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating, but are not limited to these.

[0221] The organic material layers of the organic light-emitting device disclosed herein can be formed as a single layer, or as a multilayer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device of this disclosure can have a structure comprising a hole injection layer, an electron blocking layer, a hole transport layer, a light-emitting layer, an electron transport layer, a hole blocking layer, and an electron injection layer as organic material layers. However, the structure of the organic light-emitting device is not limited to this, and may include a smaller number of organic material layers.

[0222] In the organic light-emitting device of this disclosure, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by Formula 1. When a heterocyclic compound is used in the light-emitting layer, the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) are spatially separated, enabling strong charge transfer, and therefore, the driving efficiency and lifetime of the organic light-emitting device can become excellent.

[0223] One embodiment of this disclosure provides an organic light-emitting device, wherein the organic material layer comprising a heterocyclic compound represented by chemical formula 1 further comprises a heterocyclic compound represented by chemical formula 2 below.

[0224] [Chemical Formula 2]

[0225]

[0226] In chemical formula 2,

[0227] R11, R13, and R15 may be the same as or different from each other, and each is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C6 0 heteroaryl; -P(=O)R201R202; and -SiR201R202R203, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic ring, or a substituted or unsubstituted C2 to C60 heterocycle, and R201, R202, and R203 may be the same as or different from each other, and each independently is: a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl.

[0228] g is an integer from 0 to 4, and when g is 2 or greater, R11 are either the same or different from each other.

[0229] h is an integer from 0 to 3, and when h is 2 or greater, R15 are either the same or different from each other.

[0230] Either R12 or R14 is chemical formula 3 below, and the other is chemical formula 4 below.

[0231] [Chemical Formula 3]

[0232]

[0233] [Chemical Formula 4]

[0234]

[0235] In chemical formulas 3 and 4

[0236] Ar11 to Ar13 may be identical or different from each other, and each is independently: a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0237] L11 to L14 may be the same as or different from each other, and each independently consists of: a direct bond; a substituted or unsubstituted C6 to C60 arylene; or a substituted or unsubstituted C2 to C60 heteroarylene.

[0238] i is an integer from 0 to 5, and when i is 2 or greater, L11 are either the same or different from each other.

[0239] j is an integer from 0 to 5, and when j is 2 or greater, L12 are either the same or different from each other.

[0240] k is an integer from 0 to 5, and when k is 2 or greater, L13 are either the same or different from each other.

[0241] l is an integer from 0 to 5, and when l is 2 or greater, L14 are either the same or different from each other.

[0242] In one embodiment of this disclosure, R11, R13, and R15 may be the same as or different from each other, and each independently represents: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C2 to C30 alkenyl; substituted or unsubstituted C2 to C30 alkoxy; substituted or unsubstituted C3 to C30 cycloalkyl; substituted or unsubstituted C2 to C30 heterocycloalkyl; substituted or unsubstituted C6 to C30 aryl; substituted or unsubstituted C2 to C... 30 heteroaryl; -P(=O)R201R202; or -SiR201R202R203, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic ring, or a substituted or unsubstituted C2 to C30 heterocycle, and R201, R202 and R203 may be the same or different, and may each be independently: a substituted or unsubstituted C1 to C30 alkyl; a substituted or unsubstituted C6 to C30 aryl; or a substituted or unsubstituted C2 to C30 heteroaryl.

[0243] In another embodiment of this disclosure, R11, R13, and R15 may be the same as or different from each other, and each independently represents: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 to C20 aryl; substituted or unsubstituted C2 to C20 alkyl. 0 heteroaryl; -P(=O)R201R202; or -SiR201R202R203, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic ring, or a substituted or unsubstituted C2 to C20 heterocycle, and R201, R202 and R203 may be the same or different from each other, and may each be independently: a substituted or unsubstituted C1 to C20 alkyl; a substituted or unsubstituted C6 to C20 aryl; or a substituted or unsubstituted C2 to C20 heteroaryl.

[0244] In another embodiment of this disclosure, R11, R13, and R15 may be the same as or different from each other, and may each independently be: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0245] In another embodiment of this disclosure, R11, R13 and R15 may be the same as or different from each other, and may each be independently: hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0246] In another embodiment of this disclosure, R11, R13 and R15 may be the same as or different from each other, and may each be hydrogen or deuterium independently.

[0247] In one embodiment of this disclosure, R12 may be chemical formula 3 and R14 may be chemical formula 4.

[0248] In another embodiment of this disclosure, R12 may be chemical formula 4, and R14 may be chemical formula 3.

[0249] In one embodiment of this disclosure, L11 to L14 may be the same as or different from each other, and may each be independently: a direct bond; a substituted or unsubstituted C6 to C30 arylene; or a substituted or unsubstituted C2 to C30 heteroarylene.

[0250] In another embodiment of this disclosure, L11 to L14 may be the same as or different from each other, and may each be independently: a direct bond; a substituted or unsubstituted C6 to C20 arylene; or a substituted or unsubstituted C2 to C20 heteroarylene.

[0251] In another embodiment of this disclosure, L11 to L13 may be the same as or different from each other, and may each be independently: a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

[0252] In another embodiment of this disclosure, L11 to L13 may be the same as or different from each other, and may each be independently: a direct bond; or a substituted or unsubstituted C6 to C30 arylene group.

[0253] In another embodiment of this disclosure, L11 to L13 may be the same as or different from each other, and may each be independently: a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0254] In another embodiment of this disclosure, L11 to L13 may be the same as or different from each other, and may each be independently: a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0255] In another embodiment of this disclosure, L11 can be: a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0256] In another embodiment of this disclosure, L12 and L13 may be the same as or different from each other, and may each be independently: a direct bond; a substituted or unsubstituted phenylene; or a substituted or unsubstituted biphenylene.

[0257] In another embodiment of this disclosure, L14 can be: a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted carbazolyl group.

[0258] In one embodiment of this disclosure, Ar11 to Ar13 may be the same as or different from each other, and may each be independently: substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

[0259] In another embodiment of this disclosure, Ar11 to Ar13 may be the same as or different from each other, and may each be independently: substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0260] In another embodiment of this disclosure, Ar11 to Ar13 may be the same as or different from each other, and may each be independently: substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted spirodifluorenyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothiophenyl; or substituted or unsubstituted carbazoleyl.

[0261] In another embodiment of this disclosure, Ar11 and Ar12 may be the same as or different from each other, and may each be independently: substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted spirodifluorenyl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiopheneyl.

[0262] In another embodiment of this disclosure, Ar13 may be: a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiopheneyl; or a substituted or unsubstituted carbazoleyl.

[0263] In one embodiment of this disclosure, the heterocyclic compound represented by chemical formula 2 may be represented by chemical formula 2-1 or chemical formula 2-2 below.

[0264] [Chemical Formula 2-1]

[0265]

[0266] [Chemical Formula 2-2]

[0267]

[0268] In chemical formulas 2-1 and 2-2,

[0269] R11, R13, R15, g, and h have the same definitions as in chemical formula 2.

[0270] Ar11, Ar12, L11 to L13 and i to k have the same definitions as in chemical formula 3, and

[0271] Ar13, L14, and l have the same definitions as in chemical formula 4.

[0272] In one embodiment of this disclosure, R11, R13, R15, L11 to L14, and Ar11 to Ar13 may all comprise undeuterated hydrogen (H).

[0273] In another embodiment of this disclosure, at least one of R11, R13, R15, L11 to L14 and Ar11 to Ar13 includes deuterium (D), and at least one of R11, R13, R15, L11 to L14 and Ar11 to Ar13 may include undeuterated hydrogen.

[0274] In another embodiment of this disclosure, R11, R13, R15, L11 to L14 and Ar11 to Ar13 may all include deuterium.

[0275] In one embodiment of this disclosure, the heterocyclic compound represented by Formula 2 may not include deuterium as a substituent, or may have a deuterium content, for example, greater than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more and 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less, relative to the total number of hydrogen and deuterium atoms.

[0276] In another embodiment of this disclosure, the heterocyclic compound represented by Formula 2 may not include deuterium as a substituent, or may have a deuterium content of 1% to 100% relative to the total number of hydrogen and deuterium atoms.

[0277] In another embodiment of this disclosure, the heterocyclic compound represented by Formula 2 may not include deuterium as a substituent, or may have a deuterium content of 20% to 90% relative to the total number of hydrogen and deuterium atoms.

[0278] In another embodiment of this disclosure, the heterocyclic compound represented by Formula 2 may not include deuterium as a substituent, or may have a deuterium content of 30% to 80% relative to the total number of hydrogen and deuterium atoms.

[0279] In another embodiment of this disclosure, the heterocyclic compound represented by Formula 2 may not include deuterium as a substituent, or may have a deuterium content of 50% to 70% relative to the total number of hydrogen and deuterium atoms.

[0280] In one embodiment of this disclosure, the heterocyclic compound represented by Formula 2 may be represented by any of the following compounds.

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301] When both heterocyclic compounds represented by Formula 1 and Formula 2 are included, superior efficiency and lifetime are achieved. Therefore, it can be expected that an excitocomplexation phenomenon occurs when both compounds are included.

[0302] Exciton complexation is a phenomenon in which energy of varying magnitudes—the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host)—is released through electron exchange between two molecules. When exciton complexation occurs between the two molecules, reverse system crossing (RISC) takes place, and thus, the internal quantum efficiency of fluorescence can increase to 100%. When a donor (p-host) with good hole transport capability and an acceptor (n-host) with good electron transport capability are used as the host of the emitting layer, holes are injected into the p-host and electrons into the n-host, thus reducing the driving voltage and contributing to a longer lifetime. In other words, when the compound represented by Formula 2 is used as the donor and the compound represented by Formula 1 is used as the acceptor, excellent device properties are obtained.

[0303] In one embodiment of this disclosure, when both a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 are included, at least one of these compounds may not include deuterium as a substituent, or may have a deuterium content greater than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more and 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less, relative to the total number of hydrogen atoms and deuterium atoms.

[0304] In another embodiment of this disclosure, at least one of these compounds may not include deuterium as a substituent, or may have a deuterium content of 1% to 100% relative to the total number of hydrogen and deuterium atoms.

[0305] In another embodiment of this disclosure, at least one of these compounds may not include deuterium as a substituent, or may have a deuterium content of 20% to 90% relative to the total number of hydrogen and deuterium atoms.

[0306] In another embodiment of this disclosure, at least one of these compounds may not include deuterium as a substituent, or may have a deuterium content of 30% to 80% relative to the total number of hydrogen and deuterium atoms.

[0307] In another embodiment of this disclosure, at least one of these compounds may not include deuterium as a substituent, or may have a deuterium content of 50% to 70% relative to the total number of hydrogen and deuterium atoms.

[0308] Additionally, one embodiment of this disclosure provides a composition for an organic material layer, the composition comprising: a heterocyclic compound represented by chemical formula 1; and a heterocyclic compound represented by chemical formula 2.

[0309] The specific descriptions of the heterocyclic compounds represented by Formula 1 and Formula 2 are the same as those provided above.

[0310] In one embodiment of this disclosure, in the composition for use as an organic material layer, the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 may have a weight ratio of 1:9 to 9:1, 1:9 to 5:5 or 2:8 to 5:5, however, the ratio is not limited thereto.

[0311] When forming organic materials for an organic light-emitting device, a composition for an organic material layer can be used, and more preferably, when forming the body of the light-emitting layer, a composition for an organic material layer can be used.

[0312] In one embodiment of this disclosure, the organic material layer comprises a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2, and a phosphorescent dopant may be used therewith.

[0313] As phosphorescent dopant materials, phosphorescent dopant materials known in the art can be used. For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L2MX' and L3M can be used; however, the scope of this disclosure is not limited to these examples.

[0314] M can be iridium, platinum, or osmium, etc.

[0315] L is through sp 2 An anionic bidentate ligand coordinated to M with carbon and heteroatoms, and X can act as an electron or hole trapper. Non-limiting examples of L may include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothiophene pyridine, 3-methoxy-2-phenylpyridine, thiophene pyridine, and tolylpyridine, etc. Non-limiting examples of X' and X" may include acetylacetonate (acac), hexafluoroacetylacetonate, salicylyl, pyridine carboxylate, and 8-hydroxyquinoline ester, etc.

[0316] Specific examples of phosphorescent dopants are shown below; however, phosphorescent dopants are not limited to these examples.

[0317]

[0318] In one embodiment of this disclosure, the organic material layer comprises a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2, and an iridium-based dopant may be used therewith.

[0319] In one embodiment of this disclosure, (piq)2(Ir)(acac) can be used as a red phosphorescent dopant as an iridium-based dopant, or Ir(ppy)3 can be used as a green phosphorescent dopant.

[0320] In one embodiment of this disclosure, the dopant content can be 1% to 15%, preferably 2% to 10%, and more preferably 3% to 7%, based on the total weight of the light-emitting layer.

[0321] In an organic light-emitting device according to an embodiment of the present disclosure, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or electron transport layer may include a heterocyclic compound represented by chemical formula 1.

[0322] In another embodiment of the organic light-emitting device according to the present disclosure, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or hole blocking layer may include a heterocyclic compound represented by chemical formula 1.

[0323] In an organic light-emitting device according to another embodiment, the organic material layer includes an electron transport layer, a light-emitting layer, or a hole-blocking layer, and the electron transport layer, light-emitting layer, or hole-blocking layer may include a heterocyclic compound represented by chemical formula 1.

[0324] In an organic light-emitting device according to another embodiment, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by chemical formula 1.

[0325] In an organic light-emitting device according to another embodiment, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by chemical formula 1 and a heterocyclic compound represented by chemical formula 2.

[0326] In an organic light-emitting device according to another embodiment, the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include a heterocyclic compound represented by chemical formula 1.

[0327] In an organic light-emitting device according to another embodiment, the light-emitting layer may include two or more host materials. At least one of the host materials may include a heterocyclic compound represented by Formula 1, and another may include a heterocyclic compound represented by Formula 2.

[0328] In an organic light-emitting device according to another embodiment, two or more host materials may be premixed and used in the light-emitting layer. At least one of the two or more host materials may include a heterocyclic compound represented by Formula 1, and the other may include a heterocyclic compound represented by Formula 2.

[0329] Premixing means that before depositing two or more host materials onto an organic material layer, the materials are first placed in a supply source and mixed in a supply source.

[0330] An organic light-emitting device according to an embodiment of the present disclosure may further include one, two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

[0331] Figures 1 to 3 The lamination sequence of electrodes and organic material layers in an organic light-emitting device according to one embodiment of this disclosure is shown. However, the scope of this application is not intended to be limited to these figures, and structures of organic light-emitting devices known in the art can also be applied to this application.

[0332] Figure 1 An organic light-emitting device is shown in which a positive electrode 200, an organic material layer 300, and a negative electrode 400 are sequentially laminated on a substrate 100. However, the structure is not limited to this structure, and as shown... Figure 2 As shown, an organic light-emitting device in which a negative electrode, an organic material layer, and a positive electrode are sequentially laminated on a substrate can also be obtained.

[0333] Figure 3 This illustrates a case where the organic material layers are multiple. According to... Figure 3The organic light-emitting device includes a hole injection layer 301, a hole transport layer 302, a light-emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of this application is not limited to this laminated structure, and layers other than the light-emitting layer may be omitted as needed, and other necessary functional layers may be added further.

[0334] One embodiment of this disclosure provides a method for manufacturing an organic light-emitting device, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the one or more organic material layers, wherein forming the one or more organic material layers comprises forming the one or more organic material layers using a composition for organic material layers according to an embodiment of this disclosure.

[0335] In one embodiment of this disclosure, the organic material layer may be formed by using a thermal vacuum deposition method after premixing a heterocyclic compound represented by chemical formula 1 and a heterocyclic compound represented by chemical formula 2.

[0336] Premixing means that the materials are first placed in a supply source and mixed in a supply source before the heterocyclic compounds represented by Formula 1 and Formula 2 are deposited on the organic material layer.

[0337] The premixed material may be referred to as a composition for an organic material layer according to an embodiment of this application.

[0338] The organic material layer, which includes heterocyclic compounds represented by chemical formula 1, may also include other materials as needed.

[0339] The organic material layer, which includes heterocyclic compounds represented by chemical formula 1 and heterocyclic compounds represented by chemical formula 2, may also include other materials as needed.

[0340] In an organic light-emitting device according to one embodiment of the present disclosure, materials other than the heterocyclic compounds represented by chemical formula 1 and the heterocyclic compounds represented by chemical formula 2 are shown below. However, these are for illustrative purposes only and are not intended to limit the scope of the application, and these materials may be replaced by materials known in the art.

[0341] As positive electrode materials, materials with relatively large work functions can be used, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of positive electrode materials include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0342] As negative electrode materials, materials with relatively small work functions can be used, and metals, metal oxides, or conductive polymers can be used. Specific examples of negative electrode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer materials such as LiF / Al or LiO2 / Al.

[0343] As hole injection layer materials, known hole injection layer materials can be used, and for example, phthalocyanine compounds, such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or starburst-type amine derivatives, such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), or 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB) as described in the literature [Advanced Material, 6, p. 677 (1994)]; and conductive polymers with solubility, such as polyaniline / dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid or polyaniline / poly(4-styrenesulfonate), etc.

[0344] As hole transport layer materials, pyrazoline derivatives, arylamine derivatives, succinyl styrene derivatives, and triphenyl diamine derivatives can be used, and low-molecular-weight or high-molecular-weight materials can also be used.

[0345] Metal complexes of oxadiazole derivatives, anthraquinone dimethyl ether and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethyl ether and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, biphenylquinone derivatives and 8-hydroxyquinoline and its derivatives can be used as electron transport layer materials, as well as polymeric and low molecular weight materials.

[0346] LiF is commonly used in the art as an example of an electron injection layer material; however, this application is not limited thereto.

[0347] Red, green, or blue luminescent materials can be used as the luminescent layer material, and two or more luminescent materials can be mixed and used as needed. In this paper, two or more luminescent materials can be deposited as separate supply sources, or pre-mixed and deposited as a single supply source during use. Additionally, fluorescent materials can also be used as the luminescent layer material; however, phosphorescent materials can also be used. As the luminescent layer material, materials that emit light individually by combining holes and electrons injected separately from the positive and negative electrodes can be used; however, materials having a host material and a dopant material that participate in luminescence together can also be used.

[0348] When mixing and using the substrate of the luminescent layer material, substrates from the same series or different series can be mixed and used. For example, any two or more types of materials, such as n-type substrate materials and p-type substrate materials, can be selected and used as the substrate material of the luminescent layer.

[0349] Depending on the materials used, an organic light-emitting device according to an embodiment of this disclosure can be a top-emitting, bottom-emitting, or dual-emitting type.

[0350] Heterocyclic compounds according to an embodiment of this disclosure can also be used in organic electronic devices, including organic solar cells, organic photoconductors, and organic transistors, based on principles similar to those in organic light-emitting devices.

[0351] Preferred embodiments are provided below to aid in understanding this disclosure; however, the embodiments are provided only to facilitate a clearer understanding of this disclosure, and this disclosure is not limited thereto.

[0352] Preparation Example 1. Preparation of Compound 1-1

[0353]

[0354] Preparation Example 1-1. Preparation of Compound 1-1-1

[0355] 4-Bromo-1-chlorodibenzo[b,d]furan (10.0 g, 35.5 mmol), naphth-2-ylboronic acid (9.2 g, 53.3 mmol), Pd(PPh3)4 (2.1 g, 1.8 mmol) and K2CO3 (9.8 g, 71.0 mmol) were dissolved in 1,4-dioxane (100 mL) and water (20 mL), and the mixture was then refluxed for 3 hours.

[0356] After the reaction was complete, the reaction material was purified by column chromatography (dichloromethane:hexane = 1:1 (volume ratio)) and recrystallized with dichloromethane and methanol to obtain compound 1-1-1 (10.5 g, yield 90%).

[0357] Preparation Example 1-2. Preparation of Compound 1-1-2

[0358] Compound 1-1-1 (10.5 g, 32.0 mmol), bis(pinacol)diboron (12.2 g, 48.0 mmol), Pd2dba3 (1.5 g, 1.6 mmol), Xphos (1.5 g, 3.2 mmol) and KOAc (6.3 g, 64.0 mmol) were dissolved in 1,4-dioxane (100 mL), and the mixture was then refluxed for 3 hours.

[0359] After the reaction was complete, the reaction material was filtered under reduced pressure at room temperature, and the filtrate was then removed using a rotary evaporator. The result was dissolved in dichloromethane and purified by silica, and recrystallized from dichloromethane and methanol to obtain compound 1-1-2 (11.4 g, 85% yield).

[0360] Preparation Examples 1-3. Preparation of Compound 1-1

[0361] Compounds 1-1-2 (11.4 g, 27.2 mmol), 2-chloro-4-phenylquinazoline (6.5 g, 27.2 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol) and K2CO3 (7.5 g, 54.4 mmol) were dissolved in 1,4-dioxane (110 mL) and water (22 mL), and the mixture was then refluxed for 3 hours.

[0362] After the reaction was complete, the reaction material was purified by column chromatography (dichloromethane:hexane = 1:1 (volume ratio)) and recrystallized with dichloromethane and methanol to obtain compound 1-1 (10.8 g, yield 80%).

[0363] The target compounds were prepared in the same manner as in Preparation Example 1, as shown in Table 1 below, except that compound A from Table 1 below was used instead of 4-bromo-1-chlorodibenzo[b,d]furan, compound B from Table 1 below was used instead of naphth-2-ylboronic acid, and compound C from Table 1 below was used instead of 2-chloro-4-phenylquinazoline.

[0364] [Table 1]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393] Preparation Example 2. Preparation of Compound 1-132

[0394]

[0395] Preparation Example 2-1. Preparation of Compound 1-132-1

[0396] 3-Bromo-1-chlorodibenzo[b,d]furan (10.0 g, 35.5 mmol), 9H-carbazole (5.9 g, 35.5 mmol), Pd2(dba)3 (1.6 g, 1.8 mmol), Xphos (1.7 g, 3.6 mmol) and NaOtBu (6.8 g, 71.0 mmol) were dissolved in toluene (100 mL), and the mixture was then refluxed for 3 hours.

[0397] After the reaction was complete, the reaction material was purified by column chromatography (dichloromethane:hexane = 1:1 (volume ratio)) and recrystallized from dichloromethane and methanol to obtain compound 1-1-1 (11.7 g, yield 90%).

[0398] Preparation Example 2-2. Preparation of Compound 1-132-2

[0399] Compound 1-132-1 (11.7 g, 32.0 mmol), bis(pinacol)diboron (12.2 g, 48.0 mmol), Pd2dba3 (1.5 g, 1.6 mmol), Xphos (1.5 g, 3.2 mmol) and KOAc (6.3 g, 64.0 mmol) were dissolved in 1,4-dioxane (100 mL), and the mixture was then refluxed for 3 hours.

[0400] After the reaction was complete, the reaction material was filtered under reduced pressure at room temperature, and the filtrate was then removed using a rotary evaporator. The result was dissolved in dichloromethane and purified by silica, and recrystallized from dichloromethane and methanol to obtain compound 1-132-2 (12.5 g, 85% yield).

[0401] Preparation Examples 2-3. Preparation of Compound 1-132

[0402] Compound 1-132-2 (12.5 g, 27.2 mmol), 2-chloro-4-(naphth-2-yl)quinazoline (6.5 g, 27.2 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol) and K2CO3 (7.5 g, 54.4 mmol) were dissolved in 1,4-dioxane (110 mL) and water (22 mL), and the mixture was then refluxed for 3 hours.

[0403] After the reaction was complete, the reaction material was purified by column chromatography (dichloromethane:hexane = 1:1 (volume ratio)) and recrystallized from dichloromethane and methanol to obtain compound 1-132 (7.2 g, yield 74%).

[0404] The synthetic results of the compounds described in Preparation Example 1, Preparation Example 2, and Table 1 are shown in Tables 2 and 3 below. Table 2 below shows... 1 The measurements were obtained by H NMR (CDCl3, 400 MHz), and Table 3 below shows the measurements by field desorption mass spectrometry (FD-MS).

[0405] [Table 2]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419] [Table 3]

[0420]

[0421]

[0422]

[0423] Preparation Example 3. Preparation of Compound 3-147

[0424]

[0425] Preparation Example 3-1. Preparation of Compound 3-147-1

[0426] 8-Chloronaphtho[1,2-b]benzofuran (30.0 g, 118.7 mM) and N-bromosuccinimide (21.2 g, 118.7 mM) were dissolved in dimethylformamide (DMF) (300 mL), and the mixture was then refluxed.

[0427] After the reaction was complete, the reaction material was purified by recrystallization with methanol to obtain compound 3-147-1 (37.4 g, yield 95.0%).

[0428] Preparation Example 3-2. Preparation of Compound 3-147-2

[0429] Compound 3-147-1 (37.0 g, 111.6 mM), phenylboronic acid (13.6 g, 111.6 mM), Pd(PPh3)4 (6.4 g, 5.6 mM) and K2CO3 (30.8 g, 223.2 mM) were dissolved in 1,4-dioxane (400 mL) and distilled water (H2O) (80 mL), and the mixture was then stirred for 3 hours.

[0430] After the reaction was complete, the reaction material was purified by recrystallization with methanol to obtain compound 3-147-2 (32.5 g, yield 88.5%).

[0431] Preparation Example 3-3. Preparation of Compound 3-147

[0432] Compound 3-147-2 (15.0 g, 45.6 mM), N-([1,1'-biphenyl]-4-yl)-[1,1':4',1”-terphenyl]-4-amine (14.7 g, 45.6 mM), Pd2dba3 (2.1 g, 2.3 mM), Xphos (2.2 g, 4.6 mM), and NaOtBu (8.8 g, 91.2 mM) were dissolved in toluene (200 mL), and the mixture was then stirred for 3 hours.

[0433] The reaction material was purified by column chromatography (dichloromethane:hexane = 1:1 (volume ratio)) to obtain the target compound 3-147 (23.9 g, yield 85.3%).

[0434] The target compound was prepared in the same manner as in Preparation Example 3, except that compound D from Table 4 below was used instead of 8-chloronaphtho[1,2-b]benzofuran, compound E from Table 4 below was used instead of phenylboronic acid, and compound F from Table 4 below was used instead of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1”-terphenyl]-4-amine.

[0435] [Table 4]

[0436]

[0437] Preparation Example 4. Preparation of Compound 3-174

[0438]

[0439] Preparation Example 4-1. Preparation of Compound 3-174-1

[0440] 8-Chloronaphtho[1,2-b]benzofuran (30.0 g, 118.7 mM) and N-bromosuccinimide (21.2 g, 118.7 mM) were dissolved in dimethylformamide (DMF) (300 mL), and the mixture was then refluxed.

[0441] After the reaction was complete, the reaction material was purified by recrystallization with methanol to obtain compound 3-174-1 (37.4 g, yield 95.0%).

[0442] Preparation Example 4-2. Preparation of Compound 3-174-2

[0443] Compound 3-174-1 (37.0 g, 111.6 mM), phenylboronic acid (13.6 g, 111.6 mM), Pd(PPh3)4 (6.4 g, 5.6 mM) and K2CO3 (30.8 g, 223.2 mM) were dissolved in 1,4-dioxane (400 mL) and distilled water (H2O) (80 mL), and the mixture was then stirred for 3 hours.

[0444] After the reaction was complete, the reaction material was purified by recrystallization with methanol to obtain compound 3-174-2 (32.5 g, yield 88.5%).

[0445] Preparation Example 4-3. Preparation of Compound 3-174

[0446] Compound 3-174-2 (32.5 g, 98.8 mM), (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (36.1 g, 98.8 mM), Pd2dba3 (4.5 g, 4.9 mM), Xphos (4.7 g, 9.9 mM), and K2CO3 (27.3 g, 197.6 mM) were dissolved in 1,4-dioxane (300 mL) and water (60 mL), and the mixture was then stirred for 3 hours.

[0447] After the reaction was complete, the reaction material was purified by recrystallization with methanol to obtain the target compound 3-174 (47.3 g, yield 78.1%).

[0448] The target compound was prepared in the same manner as in Preparation Example 4, except that compound G from Table 5 below was used instead of 8-chloronaphtho[1,2-b]benzofuran, compound H from Table 5 below was used instead of phenylboronic acid, and compound 1 from Table 5 below was used instead of (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid.

[0449] Table 5

[0450]

[0451]

[0452] The synthetic results of the compounds described in Preparation Examples 3 and 4, and Tables 4 and 5, are shown in Tables 6 and 7 below. Table 6 below shows... 1 The measurements were obtained by H NMR (CDCl3, 400 MHz), and Table 7 below shows the measurements by field desorption mass spectrometry (FD-MS).

[0453] Table 6

[0454]

[0455] [Table 7]

[0456]

[0457] Experimental Example 1.

[0458] Experimental Example 1-1. Fabrication of an Organic Light-Emitting Device

[0459] The coating of ITO was ultrasonically cleaned with distilled water. A glass substrate with a film of a certain thickness. After cleaning with distilled water, the substrate is ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, then dried, and then treated with UVO (ultraviolet ozone) for 5 minutes in a UV cleaner. Afterward, the substrate is transferred to a plasma cleaner (PT) and then subjected to plasma treatment under vacuum to increase the work function of ITO and remove residual film, and then transferred to a thermal deposition apparatus for organic deposition.

[0460] On the transport ITO electrode (positive electrode), a hole injection layer 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA) and a hole transport layer N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) are deposited.

[0461]

[0462] The luminescent layer was then thermally vacuum-deposited on it as follows. A heterocyclic compound represented by chemical formula 1, as described in Table 8 below, was used as the red host, and Ir(piq)₂(acac) was used as the red phosphorescent dopant. The luminescent layer was deposited by doping the red phosphorescent dopant into the host at a rate of 3%. The thickness.

[0463] Subsequently, BCP was deposited to The thickness serves as a hole-blocking layer, and Alq3 is deposited on it to a depth of [missing information]. The thickness is used as the electron transport layer. Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of [missing information]. The thickness is such that an electron injection layer is formed, and then aluminum (Al) is deposited on the electron injection layer to a thickness of [missing information]. The thickness is increased to form the negative electrode, and thus, an organic electroluminescent device is manufactured.

[0464]

[0465] At the same time, for each material used in the manufacture of OLEDs (organic light-emitting devices), in 10 -8 Up to 10 -6 All the organic compounds needed to manufacture OLEDs are purified by vacuum sublimation.

[0466] Experimental Examples 1-2. Driving voltage, luminous efficiency, and lifetime of organic light-emitting devices.

[0467] For each of the multiple organic light-emitting devices manufactured as described above, the electroluminescence (EL) properties were measured using an M7000 manufactured by McScience Inc., and the measurement results were used to measure the luminance at a standard brightness of 6,000 cd / m² using a lifetime measurement system (M6000) manufactured by McScience Inc. 2 Time measurement T 90 The results of measurements of the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light-emitting device manufactured according to this disclosure are shown in Table 8 below.

[0468] T 90 This refers to lifespan (unit: hours), the time it takes for the brightness to decrease to 90% of its initial brightness.

[0469] Table 8

[0470]

[0471]

[0472]

[0473]

[0474] [Compare example compounds]

[0475]

[0476] As can be seen from the results in Table 8, the organic light-emitting device comprising the heterocyclic compound represented by Formula 1 of this disclosure in the organic material layer has excellent crystallinity due to L2 being a substituted or unsubstituted naphthyl group or at least one of Ar1, Ar2 and R3 having a substituted or unsubstituted naphthyl group, excellent luminous efficiency due to the extension of the conjugated structure, and excellent lifetime due to the stabilization of thermal stability.

[0477] On the other hand, the organic light-emitting device in the organic material layer, which includes the comparative example compound, has a higher driving voltage than the example, and lower luminous efficiency and lifetime compared to the example.

[0478] Comparative example compounds A, B, C, and G do not include substituted or unsubstituted naphthyl groups. Compound A has an unfavorable quinazoline substitution position, resulting in a broken conjugated structure, and therefore, the organic light-emitting device of Comparative Example 1 exhibits a high driving voltage and low luminous efficiency and lifetime properties. Compound C has a broken conjugated structure due to a bent linker, and therefore, the organic light-emitting device of Comparative Example 3 exhibits a high driving voltage and low luminous efficiency and lifetime properties. In compound B, both electron acceptor groups are substituted, and therefore, because the electron velocity is too fast, the electron and hole velocities differ, resulting in low luminous efficiency and lifetime properties for the organic light-emitting device of Comparative Example 2. Compound G does not include a naphthyl group, resulting in reduced crystallinity and slow charge mobility, making charge balance impossible, and resulting in a high driving voltage; compound G exhibits low luminous efficiency and lifetime properties. Compound D includes substituted or unsubstituted naphthyl groups, but has naphthobenzofuran in its core structure, and compound D exhibits low lifetime properties due to unstable thermal stability. Compounds E and F include substituted or unsubstituted naphthyl groups, but not Ar1, resulting in low charge mobility due to the weak extension of the conjugated structure. Consequently, the organic light-emitting devices of Comparative Example 5 and Comparative Example 6 exhibit high driving voltages and low luminous efficiency and lifetime properties.

[0479] Therefore, compared with the compounds of the comparative examples, the heterocyclic compounds represented by Formula 1 of this disclosure can have lower driving voltage, higher luminous efficiency and longer lifetime.

[0480] Experimental Example 2.

[0481] Experimental Example 2-1. Fabrication of an Organic Light-Emitting Device

[0482] The organic light-emitting device is manufactured in the same manner as in Experimental Example 1-1, except that, as the host of the light-emitting layer, a first host of one type (a heterocyclic compound represented by chemical formula 1, type N) and a second host of one type (a heterocyclic compound represented by chemical formula 2, type P) as described in Table 9 below are premixed and then deposited in a supply source.

[0483] Experimental Example 2-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0484] For each of the multiple organic light-emitting devices manufactured as described above, the electroluminescence (EL) properties were measured using an M7000 manufactured by McScience Inc., and the measurement results were used to measure the luminance at a standard brightness of 6,000 cd / m² using a lifetime measurement system (M6000) manufactured by McScience Inc. 2 Time measurement T 90 The results of measurements of the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light-emitting device manufactured according to this disclosure are shown in Table 9 below.

[0485] T 90 This refers to lifespan (unit: hours), the time it takes for the brightness to decrease to 90% of its initial brightness.

[0486] Table 9

[0487]

[0488] [Compare example compounds]

[0489]

[0490] Comparing the results in Table 9 with those in Table 8, it can be confirmed that when the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 of this disclosure are used simultaneously as the host of the light-emitting layer, the driving voltage, luminous efficiency and lifetime are all improved.

[0491] In other words, it can be confirmed that in this disclosure, when the heterocyclic compound represented by Chemical Formula 1 acts as the acceptor and the heterocyclic compound represented by Chemical Formula 2 acts as the donor, excellent device properties are obtained.

[0492] On the other hand, it can be seen that when both the comparative example compound and the heterocyclic compound represented by chemical formula 2 are used simultaneously, the performance in terms of driving voltage, luminous efficiency and lifetime decreases compared to the example.

[0493] Therefore, it can be confirmed that when the heterocyclic compound represented by chemical formula 1 and the heterocyclic compound represented by chemical formula 2 of this disclosure are used simultaneously as the host of the light-emitting layer, the driving voltage is low and the luminous efficiency and lifetime are significantly superior.

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] in, In chemical formula 1, X is either O or S; R1 to R3 may be the same as or different from each other, and each is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted naphthyl; and naphthalene except for substituted or unsubstituted naphthalene. In addition to the alkyl group, substituted or unsubstituted C6 to C60 aryl groups; substituted or unsubstituted C2 to C60 heteroaryl groups; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, wherein R101, R102, and R103 are the same as or different from each other, and each independently is: a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; a is an integer from 0 to 2, and when a is 2, R1 is either the same or different from each other. b is an integer from 0 to 4, and when b is 2 or greater, R² are either the same or different from each other. c is an integer from 0 to 4, and when c is 2 or greater, R3 are either the same or different from each other. Ar1 and Ar2 may be the same as or different from each other, and each independently consists of: a substituted or unsubstituted naphthyl group; a substituted or unsubstituted C6 to C60 aryl group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. L1 to L3 may be the same as or different from each other, and each is independently: a direct bond; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted C6 to C60 arylene group other than a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted C2 to C60 heteroarylene group. d is an integer from 0 to 5, and when d is 2 or greater, L1 is either the same or different from each other; e is an integer from 0 to 5, and when e is 2 or greater, L2 values ​​are either the same or different from each other; f is an integer from 0 to 5, and when f is 2 or greater, L3 are either the same or different from each other; and L2 is a substituted or unsubstituted naphthyl group, or At least one of Ar1, Ar2, and R3 is a substituted or unsubstituted naphthyl group.

2. The heterocyclic compound according to claim 1, wherein, The heterocyclic compound represented by chemical formula 1 is represented by chemical formula 1-1 or chemical formula 1-2 below: [Chemical Formula 1-1] [Chemical Formula 1-2] In chemical formulas 1-1 and 1-2, X, R1 to R3, Ar1, Ar2, L1 to L3, and a to f have the same definitions as in Chemical Formula 1.

3. The heterocyclic compound according to claim 1, wherein, When L2 is a substituted or unsubstituted naphthylene, Ar1, Ar2, and R3 are not substituted or unsubstituted naphthylene, and when L2 is not a substituted or unsubstituted naphthylene, at least one of Ar1, Ar2, and R3 is a substituted or unsubstituted naphthylene.

4. The heterocyclic compound according to claim 1, wherein, The heterocyclic compound represented by chemical formula 1 does not include deuterium as a substituent, or has a deuterium content of 1% to 100% relative to the total number of hydrogen and deuterium atoms.

5. The heterocyclic compound according to claim 1, wherein, The heterocyclic compound represented by chemical formula 1 is represented by any one of the following compounds:

6. An organic light-emitting device, comprising: First electrode; A second electrode is provided opposite to the first electrode; as well as One or more organic material layers are provided between the first electrode and the second electrode. Wherein, one or more of the one or more organic material layers comprise a heterocyclic compound according to any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6, wherein, The organic material layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.

8. The organic light-emitting device according to claim 6, wherein, The organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the heterocyclic compound.

9. The organic light-emitting device according to claim 6, wherein, The organic material layer also includes heterocyclic compounds represented by the following chemical formula 2: [Chemical Formula 2] In chemical formula 2, R11, R13, and R15 may be the same as or different from each other, and each is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C6 0 heteroaryl; -P(=O)R201R202; and -SiR201R202R203, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic ring, or a substituted or unsubstituted C2 to C60 heterocycle, and R201, R202 and R203 may be the same as or different from each other, and each independently is: a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl; g is an integer from 0 to 4, and when g is 2 or greater, R11 are either the same or different from each other; h is an integer from 0 to 3, and when h is 2 or greater, R15 are either the same or different from each other; and Either R12 or R14 is chemical formula 3 below, and the other is chemical formula 4 below. [Chemical Formula 3] [Chemical Formula 4] In chemical formulas 3 and 4 Ar11 to Ar13 may be the same as or different from each other, and each is independently: substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl; L11 to L14 may be the same as or different from each other, and each is independently: a direct bond; a substituted or unsubstituted C6 to C60 arylene; or a substituted or unsubstituted C2 to C60 heteroarylene; i is an integer from 0 to 5, and when i is 2 or greater, L11 are either the same or different from each other; j is an integer from 0 to 5, and when j is 2 or greater, L12 are either the same or different from each other; k is an integer from 0 to 5, and when k is 2 or greater, L13 are either the same or different from each other; and l is an integer from 0 to 5, and when l is 2 or greater, L14 are either the same or different from each other.

10. The organic light-emitting device according to claim 9, wherein, The heterocyclic compound represented by chemical formula 2 is represented by chemical formula 2-1 or chemical formula 2-2 as follows: [Chemical Formula 2-1] [Chemical Formula 2-2] In chemical formulas 2-1 and 2-2, R11, R13, R15, g, and h have the same definitions as in chemical formula 2; Ar11, Ar12, L11 to L13, and i to k have the same definitions as in chemical formula 3; and Ar13, L14, and l have the same definitions as in chemical formula 4.

11. The organic light-emitting device according to claim 9, wherein, Heterocyclic compounds represented by chemical formula 2 do not include deuterium as a substituent, or have a deuterium content of 1% to 100% relative to the total number of hydrogen and deuterium atoms.

12. The organic light-emitting device according to claim 9, wherein, Heterocyclic compounds represented by chemical formula 2 are represented by any of the following compounds:

13. The organic light-emitting device according to claim 9, wherein, The organic material layer includes a light-emitting layer, and the light-emitting layer includes a heterocyclic compound according to any one of claims 1 to 5 and a heterocyclic compound represented by chemical formula 2.

14. The organic light-emitting device according to claim 6 further comprises one, two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

15. A composition for an organic material layer, the composition comprising: The heterocyclic compound according to any one of claims 1 to 5; as well as Heterocyclic compounds represented by the following chemical formula 2: [Chemical Formula 2] In chemical formula 2, R11, R13, and R15 may be the same as or different from each other, and each is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C6 0 heteroaryl; -P(=O)R201R202; and -SiR201R202R203, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic ring, or a substituted or unsubstituted C2 to C60 heterocycle, and R201, R202 and R203 may be the same as or different from each other, and each independently is: a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl; g is an integer from 0 to 4, and when g is 2 or greater, R11 are either the same or different from each other. h is an integer from 0 to 3, and when h is 2 or greater, R15 are either the same or different from each other. Either R12 or R14 is chemical formula 3 below, and the other is chemical formula 4 below. [Chemical Formula 3] [Chemical Formula 4] In chemical formulas 3 and 4 Ar11 to Ar13 may be the same as or different from each other, and each is independently: substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl; L11 to L14 may be the same as or different from each other, and each is independently: a direct bond; a substituted or unsubstituted C6 to C60 arylene; or a substituted or unsubstituted C2 to C60 heteroarylene; i is an integer from 0 to 5, and when i is 2 or greater, L11 are either the same or different from each other. j is an integer from 0 to 5, and when j is 2 or greater, L12 are either the same or different from each other. k is an integer from 0 to 5, and when k is 2 or greater, L13 are either the same or different from each other. l is an integer from 0 to 5, and when l is 2 or greater, L14 are either the same or different from each other.

16. The composition according to claim 15, wherein, The heterocyclic compound represented by chemical formula 1 and the heterocyclic compound represented by chemical formula 2 have a weight ratio of 1:9 to 9:1.

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