Heterocyclic compound and organic light-emitting device comprising same

Abstract

In the present specification, the present invention provides a heterocyclic compound and an organic light-emitting device comprising the same.

Description

Technical Field

[0001] This application claims the priority and benefit of Korean Patent Application No. 10-2022-0134269, filed with the Korean Intellectual Property Office on October 18, 2022, the entire content of which is incorporated herein by reference.

[0002] This specification relates to a heterocyclic compound and an organic light-emitting device including the same. Background Art

[0003] An electroluminescent device is a self-luminous display device and has advantages such as a wide viewing angle, excellent contrast, and a fast response speed.

[0004] An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting device having this structure, electrons and holes injected from the two electrodes combine with each other in pairs in the organic thin film and then emit light while annihilating. If necessary, the organic thin film may be composed of a single layer or multiple layers.

[0005] If necessary, the material for the organic thin film may have a light-emitting function. For example, as the material for the organic thin film, a compound that can individually form a light-emitting layer by itself may also be used, or a compound that can be used as a host or a dopant for a host-dopant-based light-emitting layer may also be used. In addition, as the material for the organic thin film, a compound that can play the following roles may also be used: for example, hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection.

[0006] In order to improve the performance, service life, or efficiency of an organic light-emitting device, there is a continuous need to develop materials for organic thin films.

[0007] [Related Technical Documents]

[0008] U.S. Patent No. 4,356,429 Summary of the Invention

[0009] Technical Problem

[0010] The present invention is directed to providing a heterocyclic compound and an organic light-emitting device including the same.

[0011] Technical Solution

[0012] In an exemplary embodiment of the present application, a heterocyclic compound represented by the following Chemical Formula 1 is provided.

[0013] [Chemical Formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] X is O; or S,

[0017] R1 to R10 are the same as or different from each other, and each independently is represented by hydrogen, deuterium, the following Chemical Formula 2, or the following Chemical Formula 3,

[0018] One of R3 and R4 and R5 are represented by the following Chemical Formula 2 or the following Chemical Formula 3,

[0019] [Chemical Formula 2]

[0020]

[0021] [Chemical Formula 3]

[0022]

[0023] In Chemical Formula 2 and Chemical Formula 3,

[0024] L1 and L2 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6 to C60 arylene; or a substituted or unsubstituted C2 to C60 heteroarylene,

[0025] m and n are integers from 0 to 4,

[0026] Ar1 to Ar3 are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C3 to C60 cycloalkyl; a substituted or unsubstituted C2 to C60 heterocycloalkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl,

[0027] a, b and c are integers from 1 to 4, and

[0028] When m, n, a, b and c are 2 or greater, the substituents in the parentheses are the same as or different from each other.

[0029] In addition, in an exemplary embodiment of the present application, an organic light-emitting device is provided, which includes: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers in the organic material layer contain one or more of the heterocyclic compounds represented by Chemical Formula 1.

[0030] Beneficial effects

[0031] The compounds described in this specification can be used as materials for the organic material layer of an organic light-emitting device. The compound can be used as a hole injection material, a hole transport material, a light-emitting material, an electron transport material, an electron injection material, etc. in an organic light-emitting device. In particular, the compound can be used as a material for the hole transport layer or the hole auxiliary layer of an organic light-emitting device.

[0032] Specifically, the compound is characterized in that one of R3 and R4 and R5 is represented by Chemical Formula 2 or Chemical Formula 3. When a compound having the substituents and substitution positions as described above is used as a material for the hole transport layer in an organic light-emitting device, appropriate energy levels and an appropriate band gap are formed to increase excitons in the light-emitting region. Increasing excitons in the light-emitting region means having the effects of reducing the driving voltage of the device and improving the efficiency.

[0033] In addition, since the compound has the substituent positions in Chemical Formula 1 of the present application, the substituted structure delocalizes the highest occupied molecular orbital (HOMO) energy level, thereby increasing the hole transport ability and stabilizing the HOMO energy. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figures 1 to 3 Each is a diagram schematically showing the stacked structure of an organic light-emitting device according to an exemplary embodiment of the present application.

[0035] <DESCRIPTION OF THE REFERENCE NUMERALS>

[0036] 100: Substrate

[0037] 200: Anode

[0038] 300: Organic material layer

[0039] 301: Hole injection layer

[0040] 302: Hole transport layer

[0041] 303: Light-emitting layer

[0042] 304: Hole blocking layer

[0043] 305: Electron transport layer

[0044] 306: Electron injection layer

[0045] 400: Cathode DETAILED DESCRIPTION

[0046] Hereinafter, this specification will be described in more detail.

[0047] In this specification, when a part "comprises" a constituent element, unless otherwise specifically described, this does not mean excluding other constituent elements, but means that other constituent elements may also be comprised.

[0048] In this specification, for chemical formulas it means the position where constituent elements are bonded.

[0049] In this application, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound becomes another substituent, and there is no limitation on the position to be substituted as long as the position is where a hydrogen atom can be substituted (i.e., a position where a substituent can substitute), and when two or more substitutions occur, the two or more substituents may be the same or different from each other.

[0050] In this specification, "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the following: deuterium; halogen group; cyano group; C1 - C60 alkyl; C2 - C60 alkenyl; C2 - C60 alkynyl; C3 - C60 cycloalkyl; C2 - C60 heterocycloalkyl; C6 - C60 aryl; C2 - C60 heteroaryl; silyl; phosphinyl; and amino group, or substituted with a substituent bonded by two or more substituents selected from the exemplified substituents.

[0051] In this specification, "when a substituent is not shown in the chemical formula or the structure of a compound" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( 2 H) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0052] In an exemplary embodiment of this application, "when a substituent is not shown in the chemical formula or the structure of a compound" may mean that all positions where a substituent can reach are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some hydrogen atoms may be deuterium which is an isotope, and in this case, the content of deuterium may be 0% to 100%.

[0053] In an exemplary embodiment of this application, in the case of "when a substituent is not shown in the chemical formula or the structure of a compound", when the content of deuterium is 0%, the content of hydrogen is 100%, and since all substituents do not explicitly exclude deuterium such as hydrogen, hydrogen and deuterium can be mixed and used in the compound.

[0054] In an exemplary embodiment of this application, deuterium is one of the isotopes of hydrogen, is an element having a deuteron composed of one proton and one neutron as its nucleus, and can be represented by hydrogen - 2, and the element symbol can also be represented as D or 2 H.

[0055] In an exemplary embodiment of the present application, an isotope means an atom having the same atomic number (Z) but a different mass number (A), and can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0056] In an exemplary embodiment of the present application, when the total number of substituents of a base compound is defined as T1 and the number of a specific substituent among the substituents is defined as T2, the content T% of the specific substituent can be defined as T2 / T1×100 = T%.

[0057] That is, in one example, when the total number of substituents that a phenyl group can have is 5 (T1 in the formula) and the number of deuterium atoms among the substituents is 1 (T2 in the formula), The 20% deuterium content in the phenyl group represented by can be represented by 20%. That is, the 20% deuterium content in the phenyl group can be represented by the following structural formula.

[0058]

[0059] Furthermore, in an exemplary embodiment of the present application, a "phenyl group with a deuterium content of 0%" can mean a phenyl group that does not contain deuterium atoms, that is, a phenyl group having five hydrogen atoms.

[0060] In this specification, a halogen can be fluorine, chlorine, bromine, or iodine.

[0061] In this specification, an alkyl group includes a straight-chain or branched chain having 1 to 60 carbon atoms, and can be additionally substituted with additional substituents. The number of carbon atoms of the alkyl group can be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0062] In this specification, alkenyl includes straight-chain or branched-chain having 2 to 60 carbon atoms, and may be additionally substituted with additional substituents. The number of carbon atoms of alkenyl can be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples thereof 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-phenylethenyl-1-yl, 2-phenylethenyl-1-yl, 2,2-diphenylethenyl-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethenyl-1-yl, 2,2-bis(diphenyl-1-yl)ethenyl-1-yl, stilbenyl, styryl, etc., but are not limited thereto.

[0063] In this specification, alkynyl includes straight-chain or branched-chain having 2 to 60 carbon atoms, and may be additionally substituted with additional substituents. The number of carbon atoms of alkynyl can be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0064] In this specification, alkoxy may be straight-chain, branched-chain or cyclic. The number of carbon atoms of alkoxy is not particularly limited, but is preferably 1 to 20. Specific examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto.

[0065] In this specification, cycloalkyl includes monocyclic or polycyclic having 3 to 60 carbon atoms, and may be additionally substituted with additional substituents. Herein, polycyclic means a group in which cycloalkyl is directly connected or fused to another cyclic group. Herein, the other cyclic group may also be cycloalkyl, but may also be another cyclic group, such as heterocycloalkyl, aryl, heteroaryl, etc. The number of carbon atoms of cycloalkyl can be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0066] In the present specification, the heterocycloalkyl group contains O, S, Se, N or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be additionally substituted with additional substituents. Herein, the polycyclic group means a group in which the heterocycloalkyl group is directly connected or fused to another cyclic group. Herein, the another cyclic group may also be a heterocycloalkyl group, but may also be another cyclic group, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0067] In the present specification, the aryl group includes a monocyclic or polycyclic group having 6 to 60 carbon atoms, and may be additionally substituted with additional substituents. Herein, the polycyclic group means a group in which the aryl group is directly connected or fused to another cyclic group. Herein, the another cyclic group may also be an aryl group, but may also be another cyclic group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. The aryl group includes a spiro group. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, -yl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, indenyl, acenaphthylenyl, benzo[b]fluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, its fused cyclic groups, etc., but are not limited thereto.

[0068] In the present specification, the terphenyl may be selected from the following structures.

[0069]

[0070] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0071] When the fluorenyl group is substituted, the substituents may be the following structures, etc., but are not limited thereto.

[0072]

[0073] In the present specification, the heteroaryl group contains S, O, Se, N or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be additionally substituted with additional substituents. Herein, the polycyclic group means a group in which the heteroaryl group is directly connected or fused to another cyclic group. Herein, the another cyclic group may also be a heteroaryl group, but may also be another cyclic group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, azolyl, iso azolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, diazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, azinyl, thiazinyl, di dioxynyl group, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl group, isoquinazolinyl, quinozolilyl group, naphthyridinyl, acridinyl, phenanthridinyl, imidazopyridinyl, phthalazinyl, triazaindenyl, indolyl, indazolyl, benzothiazolyl, benzo azolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazinyl, dibenzosilolyl, spirobis(dibenzosilol), dihydrophenazinyl, phen azinyl, phenanthridinyl, imidazopyridinyl, thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, dihydroindolyl, 10,11-dihydro-dibenzo[b,f]azepinyl, 9,10-dihydroacridinyl, phenanthrazinyl group, phenothiazinyl, phthalazinyl, naphthyridinyl, phenanthroline, benzo[c][1,2,5]thiadiazolyl, 2,3-dihydrobenzothiophene, 2,3-dihydrobenzofuran, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]dihydroindolyl, 5,11-dihydroindeno[1,2-b]carbazolyl, etc., but not limited thereto.

[0074] In the present specification, silyl contains Si and is a substituent directly connected to the Si atom as a group, and is represented by -Si(R101)(R102)(R103), and R101 to R103 are the same or different from each other, and may each independently be a substituent composed of at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. Specific examples of silyl include (trimethylsilyl), (triethylsilyl), (tert-butyldimethylsilyl), (vinyldimethylsilyl), (propyldimethylsilyl), (triphenylsilyl), (diphenylsilyl), (Phenylsilyl) and the like, but not limited thereto.

[0075] In this specification, the phosphine oxide group is represented by -P(=O)(R104)(R105), and R104 and R105 are the same as or different from each other, and may each independently be a substituent composed of at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. Specifically, the phosphine oxide group may be substituted with an alkyl group or an aryl group, and the above examples may be applied to the alkyl group and the aryl group. Examples of the phosphine oxide group include dimethylphosphine oxide group, diphenylphosphine oxide group, dinaphthylphosphine, etc., but not limited thereto.

[0076] In this specification, the amino group is represented by -N(R106)(R107), and R106 and R107 are the same as or different from each other, and may each independently be a substituent composed of at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. The amino group may be selected from -NH 2 ; monoalkylamino; monoarylamino; monoheteroarylamino; dialkylamino; diarylamino; diheteroarylamino; alkylarylamino; alkylheteroarylamino; and arylheteroarylamino, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, dibiphenylamino, anthrylamino, 9-methyl-anthrylamino, diphenylamino, phenylnaphthylamino, xylarylamino, phenyltolylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenyltriphenylenylamino, biphenyltriphenylenylamino, etc., but not limited thereto.

[0077] In this specification, the above examples of the aryl group may be applied to the arylene group, except that the arylene group is divalent.

[0078] In this specification, the above examples of the heteroaryl group may be applied to the heteroarylene group, except that the heteroarylene group is divalent.

[0079] An exemplary embodiment of this specification provides a heterocyclic compound represented by Chemical Formula 1.

[0080] In an exemplary embodiment of the present application, a group not represented by a substituent or a group represented by hydrogen may mean that all may be substituted with deuterium. That is, in an exemplary embodiment of the present application, it may indicate that hydrogen and deuterium may replace each other.

[0081] In an exemplary embodiment of the present application, X is O; or S.

[0082] In an exemplary embodiment of the present application, X is O.

[0083] In an exemplary embodiment of the present application, X is S.

[0084] In an exemplary embodiment of the present application, R1 to R10 are the same as or different from each other, and each independently is represented by hydrogen, deuterium, Chemical Formula 2, or Chemical Formula 3, and one of R3 and R4 and R5 may be represented by Chemical Formula 2 or Chemical Formula 3.

[0085] In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formula 4 to Chemical Formula 7.

[0086] [Chemical Formula 4]

[0087]

[0088] [Chemical Formula 5]

[0089]

[0090] [Chemical Formula 6]

[0091]

[0092] [Chemical Formula 7]

[0093]

[0094] In Chemical Formula 4 to Chemical Formula 7,

[0095] the definitions of L1, L2, m, n, Ar1 to Ar3, X, a, b, and c are the same as those in Chemical Formula 1, and

[0096] R1 to R4 and R6 to R10 are the same as or different from each other, and each independently is hydrogen; or deuterium.

[0097] In an exemplary embodiment of the present application, L1 and L2 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6 - C60 arylene; or a substituted or unsubstituted C2 - C60 heteroarylene.

[0098] In another exemplary embodiment, L1 and L2 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6 - C40 arylene; or a substituted or unsubstituted C2 - C40 heteroarylene.

[0099] In yet another exemplary embodiment, L1 and L2 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C6-C20 arylene; or a substituted or unsubstituted C2-C20 heteroarylene.

[0100] In yet another exemplary embodiment, L1 and L2 are the same as or different from each other and are each independently a direct bond; a C6-C20 arylene; or a C2-C20 heteroarylene.

[0101] In yet another exemplary embodiment, L1 and L2 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0102] In yet another exemplary embodiment, L1 and L2 are the same as or different from each other and are each independently a direct bond; a phenylene; a biphenylene; or a naphthylene.

[0103] In an exemplary embodiment of the present application, L1 and L2 may be unsubstituted or deuterium-substituted.

[0104] In an exemplary embodiment of the present application, Ar1 to Ar3 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0105] In another exemplary embodiment, Ar1 to Ar3 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C40 alkyl group; a substituted or unsubstituted C3-C40 cycloalkyl group; a substituted or unsubstituted C2-C40 heterocycloalkyl group; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0106] In yet another exemplary embodiment, Ar1 to Ar3 are the same as or different from each other and are each independently a substituted or unsubstituted C1-C40 alkyl group; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0107] In yet another exemplary embodiment, Ar1 to Ar3 are the same as or different from each other and are each independently a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0108] In yet another exemplary embodiment, Ar1 to Ar3 are the same as or different from each other, and each independently is a C1-C20 alkyl group; a C6-C20 aryl group which is unsubstituted or substituted with a C6-C20 aryl group; or a C2-C20 heteroaryl group which is unsubstituted or substituted with a C6-C20 aryl group.

[0109] In a further exemplary embodiment, Ar1 to Ar3 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dimethylfluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted diphenylfluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0110] In yet another further exemplary embodiment, Ar1 to Ar3 are the same as or different from each other, and each independently is a phenyl group which is unsubstituted or substituted with a phenyl group or a phenanthryl group; a biphenyl group which is unsubstituted or substituted with a phenyl group; a naphthyl group; a terphenyl group; a phenanthryl group; a triphenylene group; a dimethylfluorenyl group; a spirobifluorenyl group; a diphenylfluorenyl group; a dibenzofuranyl group; or a dibenzothiophenyl group.

[0111] In an exemplary embodiment of the present application, Ar1 to Ar3 may be unsubstituted or substituted with deuterium.

[0112] In an exemplary embodiment of the present application, Chemical Formula 2 may be represented by any one of the following Chemical Formulas 2-1 to 2-3.

[0113] [Chemical Formula 2-1]

[0114]

[0115] [Chemical Formula 2-2]

[0116]

[0117] [Chemical Formula 2-3]

[0118]

[0119] In Chemical Formulas 2-1 to 2-3,

[0120] the definitions of L1 and m are the same as those in Chemical Formula 2,

[0121] L11 and L12 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6-C60 arylene; or a substituted or unsubstituted C2-C60 heteroarylene,

[0122] a1 and b1 are the same as or different from each other, and each independently is an integer from 0 to 3,

[0123] a2 and b2 are the same as or different from each other, and each independently is an integer from 1 to 3,

[0124] Ar11 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group,

[0125] Ar12 is a substituted or unsubstituted C6-C60 aryl group,

[0126] Xa is O; S; or NRc,

[0127] Ra, Rb, and Rc are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group,

[0128] a' and b' are integers from 0 to 4,

[0129] c' is an integer from 0 to 3, and

[0130] When a', b', c', a1, a2, b2, and b1 are 2 or greater, the substituents in the parentheses are the same as or different from each other.

[0131] In an exemplary embodiment of the present application, L11 and L12 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6-C60 arylene; or a substituted or unsubstituted C2-C60 heteroarylene.

[0132] In another exemplary embodiment, L11 and L12 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6-C40 arylene; or a substituted or unsubstituted C2-C40 heteroarylene.

[0133] In yet another exemplary embodiment, L11 and L12 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6-C20 arylene; or a substituted or unsubstituted C2-C20 heteroarylene.

[0134] In yet another exemplary embodiment, L11 and L12 are the same as or different from each other, and each independently is a direct bond; a C6-C20 arylene; or a C2-C20 heteroarylene.

[0135] In yet another exemplary embodiment, L11 and L12 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0136] In a further exemplary embodiment, L11 and L12 are the same as or different from each other, and each independently is a direct bond; a phenylene; a biphenylene; or a naphthylene.

[0137] In an exemplary embodiment of the present application, L11 and L12 may be unsubstituted or deuterium-substituted.

[0138] In an exemplary embodiment of the present application, Ar11 may be the same as the definition of Ar1 above.

[0139] In an exemplary embodiment of the present application, Ar12 is a substituted or unsubstituted C6-C60 aryl.

[0140] In an exemplary embodiment, Ar12 is a substituted or unsubstituted C6-C40 aryl.

[0141] In another exemplary embodiment, Ar12 is a substituted or unsubstituted C6-C20 aryl.

[0142] In yet another exemplary embodiment, Ar12 is a C6-C20 aryl.

[0143] In yet another exemplary embodiment, Ar12 is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted phenanthryl; a substituted or unsubstituted triphenylene; a substituted or unsubstituted dimethylfluorenyl; a substituted or unsubstituted spirobifluorenyl; or a substituted or unsubstituted diphenylfluorenyl.

[0144] In an exemplary embodiment of the present application, Ra, Rb, and Rc are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0145] In another exemplary embodiment, Ra, Rb, and Rc are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C40 alkyl group; a substituted or unsubstituted C3-C40 cycloalkyl group; a substituted or unsubstituted C2-C40 heterocycloalkyl group; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0146] In yet another exemplary embodiment, Ra, Rb, and Rc are the same as or different from each other, and each independently is hydrogen; deuterium; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0147] In yet another exemplary embodiment, Ra, Rb, and Rc are the same as or different from each other, and each is hydrogen; deuterium; a C6-C40 aryl group; or a C2-C40 heteroaryl group.

[0148] In yet another exemplary embodiment, Ra, Rb, and Rc are the same as or different from each other, and each may independently be hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0149] In a further exemplary embodiment, Ra, Rb, and Rc are the same as or different from each other, and each may independently be hydrogen; deuterium; or a phenyl group.

[0150] In an exemplary embodiment of the present application, the deuterium content of the heterocyclic compound of Formula 1 may be from 0% to 100%.

[0151] In another exemplary embodiment, the deuterium content of the heterocyclic compound of Formula 1 may be 0% or from 3% to 100%, 5% to 100%, 7% to 100%, 10% to 100%, 15% to 100%, or 20% to 100%.

[0152] Generally, hydrogen-bonded compounds and deuterium-substituted compounds exhibit differences in thermodynamic behavior. The reason is that the mass of a deuterium atom is twice as high as that of a hydrogen atom, but due to the difference in atomic mass, deuterium is characterized by having an even lower vibrational energy. In addition, the bond length between carbon and deuterium is shorter than that of the bond with hydrogen, and the dissociation energy required to break this bond is also stronger than that of the bond with hydrogen. This is because the van der Waals radius of deuterium is smaller than that of hydrogen, so the extent of the bond between carbon and deuterium becomes even narrower.

[0153] The deuterium-substituted compound in the heterocyclic compound of Chemical Formula 1 of the present invention is characterized in that the energy in the ground state is lower than that of the hydrogen-substituted compound, and the shorter the bond length between carbon and deuterium, the smaller the molecular hard-core volume. Therefore, the electric polarizability may decrease and the intermolecular interaction may weaken, making it possible for the volume of the device film to increase. These characteristics cause the effect of reducing crystallinity by generating an amorphous state of the film. Therefore, deuterium substitution in the heterocyclic compound of Chemical Formula 1 can be effective in improving the heat resistance of OLED devices, thereby improving the service life and driving characteristics.

[0154] In an exemplary embodiment of the present application, a heterocyclic compound is provided in which Chemical Formula 1 is represented by any one of the following compounds.

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] In addition, various substituents can be introduced into the structure of Formula 1 to synthesize compounds having the inherent properties of the introduced substituents. For example, materials that meet the requirements of each organic material layer can be synthesized by introducing substituents commonly used in materials for preparing hole injection layers, hole transport materials, light-emitting layer materials, electron transport layer materials, and charge generation layer materials for organic light-emitting devices into the nuclear structure.

[0192] In addition, the band gap can be finely adjusted by introducing various substituents into the structure of Formula 1. At the same time, the properties at the interface between organic materials can be improved and the uses of the materials can be diversified.

[0193] At the same time, the compound has a high glass transition temperature (Tg) and thus has excellent thermal stability. The increase in thermal stability becomes an important factor in providing driving stability for the device.

[0194] In addition, in an exemplary embodiment of the present application, an organic light-emitting device is provided, which includes: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contain one or more of the heterocyclic compounds represented by Formula 1.

[0195] In addition, in an exemplary embodiment of the present application, an organic light-emitting device is provided, which includes: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contain one or more of the heterocyclic compounds represented by Formula 1 and three or fewer.

[0196] In addition, in an exemplary embodiment of the present application, an organic light-emitting device is provided, which includes: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contain one or more of the heterocyclic compounds represented by Formula 1 and two or fewer.

[0197] In an exemplary embodiment of the present application, the first electrode can be a positive electrode, and the second electrode can be a negative electrode.

[0198] In another exemplary embodiment, the first electrode can be a negative electrode, and the second electrode can be a positive electrode.

[0199] In an exemplary embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocycle according to Chemical Formula 1 may be used as a material for the blue organic light-emitting device.

[0200] In an exemplary embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the compound represented by Chemical Formula 1 may be used as a material for the green organic light-emitting device.

[0201] In an exemplary embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the compound represented by Chemical Formula 1 may be used as a material for the red organic light-emitting device.

[0202] In an exemplary embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocycle according to Chemical Formula 1 may be used as a material for the light-emitting layer of the blue organic light-emitting device.

[0203] In an exemplary embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the compound represented by Chemical Formula 1 may be used as a material for the light-emitting layer of the green organic light-emitting device.

[0204] In an exemplary embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the compound represented by Chemical Formula 1 may be used as a material for the light-emitting layer of the red organic light-emitting device.

[0205] In an exemplary embodiment of the present application, the organic material layer contains one or both of the heterocyclic compounds represented by Chemical Formula 1 and may be used together with a phosphorescent dopant.

[0206] In an exemplary embodiment of the present application, the organic material layer contains one or both of the heterocyclic compounds represented by Chemical Formula 1 and may be used together with an iridium-based dopant.

[0207] As materials for the phosphorescent dopant, those known in the art may be used.

[0208] For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L2MX' and L3M may be used, but the scope of the present invention is not limited by these examples.

[0209] Here, L, L', L", X' and X" are different bidentate ligands from each other, and M is a metal forming an octahedral complex.

[0210] M may be iridium, platinum, osmium, etc.

[0211] L, L', and L'' are anionic bidentate ligands coordinated to M by sp2 carbon and heteroatoms with an iridium-based dopant, and X can act as an electron or hole trap. Non-limiting examples of L, L', and L'' include 2-(1-naphthyl)benzo oxazole, (2-phenylbenzo oxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8-benzoquinoline), (thienylpyrazine), phenylpyridine, benzothienylpyrazine, 3-methoxy-2-phenylpyridine, thienylpyrazine, tolylpyridine, etc. Non-limiting examples of X' and X'' include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, etc.

[0212] More specific examples thereof will be shown below, but the present application is not limited to these examples.

[0213]

[0214] In an exemplary embodiment of the present application, as the iridium-based dopant, Ir(ppy) 3 can be used as a green phosphorescent dopant.

[0215] In an exemplary embodiment of the present application, as the iridium-based dopant, Ir(piq) 2 (acac) can be used as a red phosphorescent dopant.

[0216] In an exemplary embodiment of the present application, based on the entire light-emitting layer, the content of the dopant can be 1% to 15%, preferably 3% to 10%, and more preferably 5% to 10%.

[0217] The specific content of the heterocyclic compound represented by Chemical Formula 1 is the same as that described above.

[0218] The organic light-emitting device of the present invention can be manufactured using typical manufacturing methods and materials for organic light-emitting devices, except that the above heterocyclic compound is used to form an organic material layer having one or more layers.

[0219] When manufacturing an organic light-emitting device, the heterocyclic compound can be formed into an organic material layer not only by vacuum deposition but also by solution coating. Herein, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating, etc., but is not limited thereto.

[0220] The organic material layer of the organic light-emitting device of the present invention may be composed of a single-layer structure, but may also be composed of a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic material layers.

[0221] In an exemplary embodiment of the present application, as an iridium-based dopant, Ir(ppy) 3 may be used as a green phosphorescent dopant.

[0222] In an exemplary embodiment of the present application, an organic light-emitting device is provided, in which the organic material layer of the organic light-emitting device includes a light-emitting layer, and the light-emitting layer contains the heterocyclic compound.

[0223] In an exemplary embodiment of the present application, an organic light-emitting device is provided, in which the organic material layer of the organic light-emitting device includes a light-emitting layer, and the light-emitting layer contains a host material, and the host material contains the heterocyclic compound.

[0224] In the organic light-emitting device of the present invention, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may contain the heterocyclic compound.

[0225] In another organic light-emitting device, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may contain the heterocyclic compound.

[0226] In yet another organic light-emitting device, the organic material layer includes an electron transport layer, a light-emitting layer or a hole blocking layer, and the electron transport layer, the light-emitting layer or the hole blocking layer may contain the heterocyclic compound.

[0227] The organic light-emitting device of the present invention may further include one or two or more layers selected from the following: 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.

[0228] Figures 1 to 3 The stacking order of the electrodes and the organic material layers of the organic light-emitting device according to an exemplary embodiment of the present application is illustrated. However, the scope of the present application is not intended to be limited by these drawings, and the structures of organic light-emitting devices known in the art may also be applied to the present application.

[0229] According to Figure 1, which shows an organic light-emitting device in which a positive electrode 200, an organic material layer 300, and a negative electrode 400 are sequentially stacked on a substrate 100. However, the organic light-emitting device is not limited to such a structure, and as Figure 2 shown, an organic light-emitting device in which a negative electrode, an organic material layer, and a positive electrode are sequentially stacked on a substrate can also be realized.

[0230] Figure 3 illustrates the case where the organic material layer is multilayer. According to Figure 3 The 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 the present application is not limited to the stacking structure described above, and if necessary, other layers except the light-emitting layer can be omitted, and additionally necessary functional layers can also be added.

[0231] The organic light-emitting device according to an exemplary embodiment of the present application can be manufactured by typical methods and materials for manufacturing an organic light-emitting device, except that an organic material layer having one or more layers is formed by using one or both or more of the heterocyclic compounds represented by Chemical Formula 1 described above.

[0232] In an exemplary embodiment of the present application, a composition for an organic material layer containing a heterocyclic compound represented by Chemical Formula 1 is provided.

[0233] Materials that can be included in the art in addition to the heterocyclic compound represented by Chemical Formula 1 can be included in the composition for the organic material layer.

[0234] In an exemplary embodiment of the present application, a method for manufacturing an organic light-emitting device is provided, the method including: preparing a substrate; forming a first electrode on the substrate; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer, wherein the formation of the organic material layer includes forming an organic material layer having one or more layers by using a composition for an organic material layer according to an exemplary embodiment of the present application.

[0235] In an exemplary embodiment of the present application, a method for manufacturing an organic light-emitting device is provided, wherein the formation of the organic material layer is by premixing two of the heterocyclic compounds represented by Chemical Formula 1 and using a thermal vacuum deposition method to form the organic material layer.

[0236] Premixing means that before depositing the compound of Chemical Formula 1 (N-type heterocyclic compound) and the compound of Chemical Formula 1 (P-type heterocyclic compound) on the organic material layer, the materials are first mixed and the mixture is accommodated in a common container and mixed.

[0237] The premixed material can be referred to as a composition for an organic material layer according to an exemplary embodiment of the present application.

[0238] In an organic light-emitting device according to an exemplary embodiment of the present application, materials other than the heterocyclic compound of Chemical Formula 1 will be illustrated below, but these materials are only illustrative and not intended to limit the scope of the present application, and can be replaced with materials well-known in the art.

[0239] As the positive electrode material, a material having a relatively high work function can be used, and a transparent conductive oxide, a metal, a conductive polymer, etc. can be used. Specific examples of the positive electrode material 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 SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; etc., but not limited thereto.

[0240] As the negative electrode material, a material having a relatively low work function can be used, and a metal, a metal oxide, a conductive polymer, etc. can be used. Specific examples of the negative electrode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO 2 / Al; etc., but not limited thereto.

[0241] As the hole injection material, well-known hole injection materials can also be used, and for example: phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or starburst amine derivatives described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB); polyaniline / dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) which are soluble conductive polymers; polyaniline / camphorsulfonic acid; or polyaniline / poly(4-styrene-sulfonate); etc.

[0242] As the hole transport material, pyrazoline derivatives, arylamine-based derivatives, stilbene derivatives, triphenyl diamine derivatives, etc. can be used, and low molecular weight materials or polymer materials can also be used.

[0243] As an electron transport material, it is possible to use diazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, biphenylenequinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc., and it is also possible to use low molecular weight materials and polymer materials.

[0244] As an electron injection material, for example, LiF is typically used in the art, but the present application is not limited thereto.

[0245] As a light-emitting material, it is possible to use materials that emit red, green, or blue light, and if necessary, two or more light-emitting materials can be mixed and used. In this case, two or more light-emitting materials are deposited and used as separate supply sources, or are premixed and deposited and used as one supply source. In addition, fluorescent materials can be used as light-emitting materials, but they can also be used as phosphorescent materials. As a light-emitting material, it is also possible to use alone a material that emits light by combining holes and electrons injected from the positive electrode and the negative electrode, respectively, but it is also possible to use a material in which the host material and the dopant material participate in light emission together.

[0246] When the hosts of the light-emitting materials are mixed and used, hosts of the same series can also be mixed and used, and hosts of different series can also be mixed and used. For example, it is possible to use two or more types of materials selected from n-type host materials or p-type host materials as the host material for the light-emitting layer.

[0247] Depending on the materials to be used, the organic light-emitting device according to an exemplary embodiment of the present application can be a top-emission type, a bottom-emission type, or a double-emission type.

[0248] Based on principles similar to those applied to organic light-emitting devices, the heterocyclic compounds according to an exemplary embodiment of the present application can function even in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, etc.

[0249] Embodiments of the Invention

[0250] Hereinafter, the present specification will be described in more detail by way of examples, but these examples are provided only for illustrating the present application and are not intended to limit the scope of the present application.

[0251] <Preparation Example>

[0252] [Preparation Example 1] Preparation of Compound 001

[0253]

[0254] 1) Preparation of Compound 001-P5

[0255] After dissolving 2-bromo-1-chloro-3-fluorobenzene (30 g, 0.1432 mol) and (2-methoxynaphthalen-1-yl)boronic acid (31.8 g, 0.1576 mol) in 500 ml of toluene, 100 mL of ethanol, and 150 mL of distilled water, Pd(PPh 3 ) 4 (8.3 g, 0.0072 mol) and K 2 CO 3 (49.5 g, 0.3581 mol) were added thereto, and the resulting mixture was stirred under reflux for 12 hours. After the reaction was completed, extraction was performed using dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO 4 , then the solvent was removed by a rotary evaporator, and then the residue was purified by column chromatography using dichloromethane and hexane as elution solvents to obtain Compound 001-P5 (30 g, 73%).

[0256] 2) Preparation of Compound 001-P4

[0257] After dissolving Compound 001-P5 (30 g, 0.1046 mol) in 500 mL of dichloromethane, BBr 3 (65.5 g, 0.2616 mol) was slowly added dropwise thereto, and then the resulting mixture was stirred under reflux at room temperature for 3 hours. After the reaction was completed, distilled water was slowly added thereto, extraction was performed using dichloromethane, the organic layer was dried over anhydrous MgSO 4 , then the solvent was removed by a rotary evaporator, and then Compound 001-P4 (25 g, 88%) was obtained.

[0258] 3) Preparation of Compound 001-P3

[0259] After dissolving Compound 001-P4 (25 g, 0.0917 mol) in 350 mL of dimethylformamide, N-bromosuccinimide (18 g, 0.1008 mol) was added thereto, and the resulting mixture was stirred at room temperature for 8 hours. After the reaction was completed, extraction was performed using dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO 4 , then the solvent was removed by a rotary evaporator, and then the residue was purified by column chromatography using dichloromethane and hexane as elution solvents to obtain Compound 001-P3 (28 g, 87%).

[0260] 4) Preparation of Compound 001-P2

[0261] Compound 001-P3 (28 g, 0.0796 mol) and cesium carbonate (51.9 g, 0.1593 mol) were added to 400 mL of DMA, and the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, MC was added to the reaction solution for dissolution, and then the resulting solution was extracted with distilled water. The organic layer was dried over anhydrous MgSO 4 and then the solvent was removed by a rotary evaporator. The residue was then purified by column chromatography using dichloromethane and hexane as elution solvents to obtain compound 001-P2 (23 g, 87%).

[0262] 5) Preparation of compound 001-P1

[0263] After dissolving compound 001-P2 (23 g, 0.0694 mol) and phenylboronic acid (10.2 g, 0.0832 mol) in 200 mL of toluene, 50 mL of ethanol, and 100 mL of distilled water, Pd(PPh 3 ) 4 (4 g, 0.0035 mol) and K 2 CO 3 (24 g, 0.1734 mol) were added thereto, and the resulting mixture was stirred under reflux for 12 hours. After the reaction was completed, MC was added to the reaction solution for dissolution, and then the resulting solution was extracted with distilled water. The organic layer was dried over anhydrous MgSO 4 and then the solvent was removed by a rotary evaporator. The residue was then purified by column chromatography using dichloromethane and hexane as elution solvents to obtain compound 001-P1 (16 g, 70%).

[0264] 6) Preparation of compound 001

[0265] After dissolving compound 001-P1 (16 g, 0.0487 mol) and diphenylamine (9.1 g, 0.0535 mmol) in 200 mL of toluene, Pd 2 (dba) 3 (2.2 g, 0.0024 mol), xphos (3.5 g, 0.0073 mol), and t-BuONa (9.4 g, 0.0973 mol) were added thereto, and the resulting mixture was stirred under reflux for 3 hours. After the reaction was completed, MC was added to the reaction solution for dissolution, and then the resulting solution was extracted with distilled water. The organic layer was dried over anhydrous MgSO 4 and then the solvent was removed by a rotary evaporator. The residue was then purified by column chromatography using dichloromethane and hexane as elution solvents to obtain compound 001 (15 g, 67%).

[0266] The target compound was synthesized in the same manner as in Preparation Example 1, except that in Preparation Example 1, Compound A in Table 1 below, Compound B in Table 1 below, and Compound C in Table 1 below were used instead of 2-bromo-1-chloro-3-fluorobenzene, phenylboronic acid, and diphenylamine, respectively.

[0267] [Table 1]

[0268]

[0269]

[0270]

[0271]

[0272] [Preparation Example 2] Preparation of Compound 020

[0273]

[0274] Preparation of Compound 020

[0275] After dissolving Compound 001-P1 (16 g, 0.0487 mol) and (4-(diphenylamino)phenyl)boronic acid (16.9 g, 0.0584 mol) in 250 mL of toluene and 50 mL of distilled water, Pd 2 (dba) 3 (2.23 g, 0.0024 mol), xphos (3.5 g, 0.0073 mol), and NaOH (3.9 g, 0.0973 mol) were added thereto, and the resulting mixture was stirred under reflux for 6 hours. After completion of the reaction, MC was added to the reaction solution for dissolution, and then the resulting solution was extracted with distilled water. The organic layer was dried over anhydrous MgSO 4 and then the solvent was removed by a rotary evaporator. Then, the residue was purified by column chromatography using dichloromethane and hexane as elution solvents to obtain Compound 020 (22 g, 84%).

[0276] The target compounds in Table 2 below were synthesized in the same manner as in Preparation Example 2, except that in Preparation Example 2, Compound D and Compound E were used instead of 001-P1 and (4-(diphenylamino)phenyl)boronic acid, respectively.

[0277] [Table 2]

[0278]

[0279]

[0280] [Preparation Example 3] Preparation of Compound 501

[0281]

[0282] 1) Preparation of Compound 501-P4

[0283] After dissolving (3-chloro-2-iodophenyl)(methyl)sulfane (30 g, 0.1054 mol) and (3-bromonaphthalen-1-yl)boronic acid (29.1 g, 0.1160 mol) in 500 ml of toluene, 100 mL of ethanol, and 100 mL of distilled water, Pd(PPh 3 ) 4 (6.1 g, 0.0053 mol) and K 2 CO 3 (29.1 g, 0.2109 mol) were added thereto, and the resulting mixture was stirred under reflux for 8 hours. After completion of the reaction, extraction was carried out using dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO 4 , then the solvent was removed by a rotary evaporator, and then the residue was purified by column chromatography using dichloromethane and hexane as elution solvents to obtain Compound 501-P4 (31 g, 81%).

[0284] 2) Preparation of Compound 501-P3

[0285] After dissolving Compound 501-P4 (31 g, 0.0852 mol) and hydrogen peroxide (10 mL) in acetic acid (350 mL), the resulting solution was stirred at room temperature for 3 hours. After completion of the reaction, acetic acid was removed, water was added thereto to obtain a solid, then the solid was dissolved in dichloromethane, and the resulting solution was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain Compound 501-P3 (28 g, 86%).

[0286] 3) Preparation of Compound 501-P2

[0287] After dissolving Compound 501-P3 (28 g, 0.1001 mol) in excess sulfuric acid (90 mL), the resulting solution was stirred at room temperature for 6 hours. After completion of the reaction, the reaction product was neutralized with an aqueous NaOH solution, then extraction was carried out using dichloromethane, the organic layer was dried over anhydrous MgSO 4 , then the solvent was removed by a rotary evaporator, and then the residue was purified by column chromatography using dichloromethane and hexane as elution solvents to obtain Compound 501-P2 (30 g, 86%).

[0288] 4) Preparation of Compound 501-P1

[0289] After dissolving compound 501-P2 (30 g, 0.0863 mol) and phenylboronic acid (12.63 g, 0.1036 mol) in 400 mL of toluene, 100 mL of ethanol, and 100 mL of distilled water, Pd(PPh 3 ) 4 (5 g, 0.0043 mol) and K 2 CO 3 (24 g, 0.1726 mol) were added thereto, and the resulting mixture was stirred under reflux for 8 hours. After completion of the reaction, MC was added to the reaction solution for dissolution, and then the resulting solution was extracted with distilled water. The organic layer was dried over anhydrous MgSO 4 , and then the solvent was removed by a rotary evaporator. Then, the residue was purified by column chromatography using dichloromethane and hexane as elution solvents to obtain compound 501-P1 (22 g, 74%).

[0290] 5) Preparation of compound 501

[0291] After dissolving compound 501-P1 (22 g, 0.0638 mol) and diphenylamine (11.9 g, 0.0702 mmol) in 300 ml of toluene, Pd 2 (dba) 3 (2.9 g, 0.0032 mol), xphos (4.6 g, 0.0096 mol), and t-BuONa (12.3 g, 0.1276 mol) were added thereto, and the resulting mixture was stirred under reflux for 3 hours. After completion of the reaction, MC was added to the reaction solution for dissolution, and then the resulting solution was extracted with distilled water. The organic layer was dried over anhydrous MgSO 4 , and then the solvent was removed by a rotary evaporator. Then, the residue was purified by column chromatography using dichloromethane and hexane as elution solvents to obtain compound 501 (22 g, 72%).

[0292] The target compounds in Table 3 below were synthesized in the same manner as in Preparation Example 3, except that in Preparation Example 3, compound F, compound G, and compound H were used instead of (3-chloro-2-iodophenyl)(methyl) sulfane, phenylboronic acid, and diphenylamine, respectively.

[0293] [Table 3]

[0294]

[0295]

[0296] [Preparation Example 4] Preparation of compound 241

[0297]

[0298] 1) Preparation of Compound 241-P1

[0299] After dissolving Compound 241-P2 (23 g, 0.0694 mol) and diphenylamine (12.9 g, 0.0763 mol) in 300 mL of toluene, Pd 2 (dba) 3 (3.2 g, 0.0035 mol), xphos (5 g, 0.0104 mol) and NaOt-Bu (13.3 g, 0.1387 mol) were added thereto, and the resulting mixture was stirred under reflux at 50 °C for 3 hours. After the reaction was completed, MC was added to the reaction solution for dissolution, and then the resulting solution was extracted with distilled water. The organic layer was dried over anhydrous MgSO 4 and then the solvent was removed by a rotary evaporator. Then, the residue was purified by column chromatography using dichloromethane and hexane as elution solvents to obtain Compound 241-P1 (18 g, 62%).

[0300] 2) Preparation of Compound 241

[0301] After dissolving Compound 241-P1 (18 g, 0.0429 mol) and phenylboronic acid (6.7 g, 0.0514 mol) in 200 mL of toluene and 50 mL of distilled water, Pd 2 (dba) 3 (2 g, 0.0021 mol), xphos (3.1 g, 0.0064 mol) and NaOH (3.4 g, 0.0857 mol) were added thereto, and the resulting mixture was stirred under reflux for 8 hours. After the reaction was completed, MC was added to the reaction solution for dissolution, and then the resulting solution was extracted with distilled water. The organic layer was dried over anhydrous MgSO 4 and then the solvent was removed by a rotary evaporator. Then, the residue was purified by column chromatography using dichloromethane and hexane as elution solvents to obtain Compound 241 (15 g, 76%).

[0302] The target compounds in Table 4 below were synthesized by preparing in the same manner as in Preparation Example 4, except that in Preparation Example 4, Compound I, Compound J and Compound K were used instead of 241-P2, diphenylamine and phenylboronic acid, respectively.

[0303] [Table 4]

[0304]

[0305]

[0306]

[0307]

[0308] [Preparation Example 5] Preparation of Compound 451

[0309]

[0310] Preparation of Compound 451

[0311] Compound 451-P1 (10 g, 0.0217 mol), benzene-D6 (100 mL, 10 T), and trifluoromethanesulfonic acid (9.6 mL, 0.1083 mol) were placed in a flask and stirred at 60 °C. After 4 hours, 300 mL of purified water and NaHCO 3 were added dropwise to terminate the reaction. After extraction with distilled water and drying the organic layer over anhydrous MgSO 4 , the solvent was removed by a rotary evaporator, and then the residue was purified by passing it through silica gel using dichloromethane and hexane as developing solvents to obtain Compound 451 (10 g, 95%).

[0312] The target compounds in Table 5 below were synthesized by preparing in the same manner as in Preparation Example 5, except that Compound L was used instead of 451-P1 in Preparation Example 5.

[0313] [Table 5]

[0314]

[0315]

[0316]

[0317] [Preparation Example 6] Preparation of Compound 482

[0318]

[0319] 1) Preparation of Compound 482-P1

[0320] Compound 482-P1 (10 g, 0.0247 mol), benzene-D6 (100 mL, 10 T), and trifluoromethanesulfonic acid (10.9 mL, 0.1235 mol) were placed in a flask and stirred at 60 °C. After 4 hours, 300 mL of purified water and NaHCO 3 were added dropwise to terminate the reaction. After extraction with distilled water and drying the organic layer over anhydrous MgSO 4After drying, the solvent was removed by a rotary evaporator, and the residue was then purified by passing it through silica gel using dichloromethane and hexane as developing solvents to obtain Compound 482-P1 (10 g, 96%).

[0321] 2) Preparation of Compound 482

[0322] After dissolving Compound 482-P1 (10 g, 0.0237 mol) and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (7.4 g, 0.0261 mmol) in 100 mL of toluene, Pd 2 (dba) 3 (1.1 g, 0.0012 mol), xphos (1.7 g, 0.0036 mol) and t-BuONa (4.6 g, 0.0474 mol) were added thereto, and the resulting mixture was stirred under reflux for 3 hours. After completion of the reaction, MC was added to the reaction solution for dissolution, and then the resulting solution was extracted with distilled water. The organic layer was dried over anhydrous MgSO 4 and the solvent was then removed by a rotary evaporator. The residue was then purified by column chromatography using dichloromethane and hexane as eluting solvents to obtain Compound 482 (8.5 g, 75%).

[0323] The target compounds in Table 6 below were synthesized in the same manner as in Preparation Example 6, except that Compound M and Compound N were used in Preparation Example 6 instead of 482-P2 and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, respectively.

[0324] [Table 6]

[0325]

[0326]

[0327] The compounds corresponding to Chemical Formula 1 were prepared in the same manner as in the Preparation Example, and the synthesis confirmation results are shown in Tables 7 and 8. Table 7 shows the measured values of 1H NMR (CDCl 3 , 300 MHz), and Table 8 shows the measured values of field desorption mass spectrometry (FD-MS).

[0328] [Table 7]

[0329]

[0330]

[0331]

[0332]

[0333] [Table 8]

[0334] Compound FD-MS Compound FD-MS 1 m / z = 461.18 (C34H23NO = 461.56) 377 m / z = 733.21 (C52H31NO2S = 733.88) 3 m / z = 613.24 (C46H31NO = 613.76) 401 m / z = 567.17 (C40H25NOS = 567.71) 5 m / z = 587.22 (C44H29NO = 587.72) 443 m / z = 729.30 (C55H39NO = 729.92) 11 m / z = 653.27 (C49H35NO = 653.82) 451 m / z = 484.32 (C34D23NO = 484.70) 19 m / z = 627.22 (C46H29NO2 = 627.74) 454 m / z = 688.49 (C49D35NO = 689.04) 20 m / z = 537.21 (C40H27NO = 537.66) 456 m / z = 672.38 (C46D29NOS = 672.98) 29 m / z = 689.27 (C52H35NO = 689.86) 459 m / z = 724.49 (C52D35NO = 725.07) 56 m / z = 637.24 (C48H31NO = 637.78) 482 m / z = 670.38 (C49H18D17NO = 670.93) 70 m / z = 613.24 (C46H31NO = 613.76) 485 m / z = 720.36 (C52H16D17NO2 = 720.94) 85 m / z = 729.30 (C55H39NO = 729.92) 489 m / z = 703.36 (C52H17D16NO = 703.94) 96 m / z = 765.30 (C58H39NO = 765.96) 490 m / z = 765.29 (C52H15D16NOS2 = 766.04) 101 m / z = 511.19 (C38H25NO = 511.61) 501 m / z = 477.16 (C34H23NS = 477.63) 107 m / z = 837.30 (C64H39NO = 838.02) 502 m / z = 669.25 (C49H35NS = 669.89) 113 m / z = 759.26 (C55H37NOS = 759.97) 512 m / z = 669.25 (C49H35NS = 669.89) 121 m / z = 461.18 (C34H23NO = 461.56) 522 m / z = 759.26 (C55H37NOS = 759.97) 127 m / z = 689.27 (C52H35NO = 689.86) 525 m / z = 477.16 (C34H23NS = 477.63) 128 m / z = 687.26 (C52H33NO = 687.84) 528 m / z = 659.17 (C46H29NS2 = 659.86) 129 m / z = 713.27 (C54H35NO = 713.88) 539 m / z = 781.28 (C58H39NS = 782.02) 130 m / z = 577.24 (C43H31NO = 577.73) 548 m / z = 683.23 (C49H33NOS = 683.87) 133 m / z = 693.30 (C52H39NO = 693.89) 549 m / z = 759.26 (C55H37NOS = 759.97) 136 m / z = 701.27 (C53H35NO = 701.87) 550 m / z = 477.16 (C34H23NS = 477.63)

[0335]

[0336] <Experimental Example 1> - Fabrication of Organic Light-Emitting Device

[0337] (1) Fabrication of Organic Light-Emitting Device

[0338] A glass substrate with ITO thinly coated thereon to a thickness of was ultrasonically washed with distilled water. When the washing with distilled water was completed, the glass substrate was ultrasonically washed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then subjected to UVO treatment using UV in a UV cleaner for 5 minutes. Thereafter, the substrate was transferred to a plasma washer (PT) and then subjected to plasma treatment under vacuum for ITO work function and for removing residual films, and transferred to a thermal deposition apparatus for organic deposition.

[0339]

[0340] Subsequently, the air in the chamber was evacuated until the vacuum degree in the chamber reached 10 -6 Torr, and then a hole injection layer with a thickness of was deposited on the ITO substrate by vapor-depositing 2-TNATA by applying current to the unit. A hole transport layer with a thickness of was deposited on the hole injection layer by placing N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) in another unit in the vacuum deposition apparatus and applying current to the unit to vapor-deposit NPB.

[0341]

[0342] The light-emitting layer was thermally vacuum deposited on the hole transport layer as follows. The compound 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-bi-9H-carbazole as the host was deposited to a thickness of , and the light-emitting layer was deposited by doping with 7% of the green phosphorescent dopant Ir(ppy) 3 . Thereafter, BCP as the hole blocking layer was deposited to a thickness of , and Alq 3 as the electron transport layer was deposited thereon to a thickness of Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of to form an electron injection layer, and then an aluminum (Al) negative electrode is deposited on the electron injection layer to a thickness of to form a negative electrode to fabricate an organic light emitting device (hereinafter, referred to as Comparative Example 1).

[0343] Meanwhile, all the organic compounds required for fabricating the organic light emitting device are subjected to vacuum sublimation purification under 10 -6 torr to 10 -8 torr and are used for fabricating the organic light emitting device.

[0344] In addition, an organic light emitting device is fabricated in the same manner as in Comparative Example 1, except that the compound described in Table 9 below is used instead of the compound NPB used when forming the hole transport layer in Comparative Example 1.

[0345] (2) Driving voltage and luminous efficiency of the organic light emitting device

[0346] For the organic light emitting device fabricated as above, the electroluminescence (EL) characteristics are measured using M7000 manufactured by McScience Inc., and using the measurement results, the service life T 95 (unit: h, hour) is measured using a service life measurement device (M6000) manufactured by McScience Inc., which is the time when the luminance becomes 95% compared to the initial luminance when the standard luminance is 6,000 cd / m 2 .

[0347] The characteristics of the organic light emitting device of the present invention shown together with the measurement results are shown in Table 9 below.

[0348] [Table 9]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354] <Experimental Example 2>

[0355] (1) Fabrication of the organic light emitting device

[0356] A thin film is coated with a thickness of The glass substrate of indium tin oxide (ITO) is ultrasonically washed with distilled water. When the washing with distilled water is completed, the glass substrate is ultrasonically washed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then subjected to UVO treatment with UV in a UV cleaner for 5 minutes. Thereafter, the substrate is transferred to a plasma washer (PT), and then subjected to plasma treatment under a vacuum state to increase the ITO work function and remove the residual film, and transferred to a thermal deposition device for organic deposition.

[0357] Subsequently, the air in the chamber is evacuated until the vacuum degree in the chamber reaches 10 -6 Torr, and then a hole injection layer with a thickness of is deposited on the ITO substrate by vapor-depositing 2-TNATA by applying a current to the unit. A hole transport layer with a thickness of is deposited on the hole injection layer by placing N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) in another unit in the vacuum deposition device and applying a current to the unit to vapor-deposit NPB. Thereafter, the compound shown in Table 10 below is deposited to a thickness of as a hole auxiliary layer.

[0358]

[0359] The light-emitting layer is thermally vacuum-deposited on the hole auxiliary layer as follows. The compound 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-bis-9H-carbazole as a host is deposited to a thickness of and doped with Ir(ppy) 3 as a green phosphorescent dopant at 7% of the deposition thickness of the light-emitting layer to deposit the light-emitting layer. Thereafter, bathocuproine (BCP) is deposited as a hole blocking layer to a thickness of and Alq 3 is deposited thereon as an electron transport layer to a thickness of Finally, lithium fluoride (LiF) is deposited on the electron transport layer to a thickness of to form an electron injection layer, and then aluminum (Al) negative electrode is deposited on the electron injection layer to a thickness of to form a negative electrode to fabricate an organic light-emitting device.

[0360]

[0361] Meanwhile, all the organic compounds required for manufacturing the organic light-emitting device are subjected to vacuum sublimation purification under 10 -6 Torr to 10 -8 Torr for each material and used for the manufacture of the organic light-emitting device.

[0362] (2) Driving voltage and luminous efficiency of the organic light-emitting device

[0363] For the organic light-emitting device fabricated as described above, the electroluminescence (EL) characteristics were measured using the M7000 manufactured by McScience Inc., and using the measurement results, the service life T was measured using the service life measurement device (M6000) manufactured by McScience Inc. 95 (Unit: h, hour), which is the time when the luminance becomes 95% compared to the initial luminance at a standard luminance of 6,000 cd / m 2 .

[0364] The characteristics of the organic light-emitting device of the present invention shown together with the measurement results are shown in Table 10 below.

[0365] [Table 10]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371] When the compound according to the present application is used in an organic light-emitting device, the driving voltage of the device can be reduced, the light efficiency of the device can be improved, and the service life characteristics of the device can be improved due to the thermal stability of the compound.

[0372] Specifically, when comparing NPB, which is the hole transport layer material of Comparative Example 1, with the compound represented by Chemical Formula 1 of the present invention, which is the hole transport layer material of Examples 1 to 73, it can be confirmed that the structures of some substituents are similar, but the substitution positions or types of the substituents are different.

[0373] Since Comparative Compounds A to C have high molecular weights and poor thermal stability, which makes the molecules unstable during deposition, resulting in a high driving voltage and a shortened service life.

[0374] In addition, since Comparative Compounds D to G have a structure in which the arylamine is disubstituted, the hole migration is much faster than in the structure in which the arylamine is monosubstituted, so that the charge balance between holes and electrons in the light-emitting layer is not achieved, preventing the formation of effective excitons. This increases the driving voltage of the device and reduces the efficiency of the device.

[0375] In the case of comparing Compounds H to N, the substituted positions in the present invention have relatively faster hole migration than the substituted positions in the comparative compounds, forming appropriate energy levels and an appropriate bandgap to increase the number of excitons in the light-emitting region. Increasing the number of excitons in the light-emitting region means having the effects of reducing the driving voltage of the device and improving the efficiency.

[0376] Therefore, considering the above, when using the heterocyclic compound of Chemical Formula 1 as a material for the hole transport layer in an organic light-emitting device, appropriate energy levels and an appropriate bandgap are formed to increase the number of excitons in the light-emitting region. Increasing the number of excitons in the light-emitting region means having the effects of reducing the driving voltage of the device and improving the efficiency.

Claims

1. A heterocyclic compound represented by the following Chemical Formula 1: [Chemical Formula 1] Wherein, In Chemical Formula 1, X is O; or S, R1 to R10 are the same as or different from each other, and each independently represents hydrogen, deuterium, the following Chemical Formula 2, or the following Chemical Formula 3, One of R3 and R4 and R5 are represented by the following Chemical Formula 2 or the following Chemical Formula 3, [Chemical Formula 2] [Chemical Formula 3] In Chemical Formula 2 and Chemical Formula 3, L1 and L2 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 - C60 arylene; or a substituted or unsubstituted C2 - C60 heteroarylene, m and n are integers from 0 to 4, Ar1 to Ar3 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 - C60 alkyl group; a substituted or unsubstituted C3 - C60 cycloalkyl group; a substituted or unsubstituted C2 - C60 heterocycloalkyl group; a substituted or unsubstituted C6 - C60 aryl group; or a substituted or unsubstituted C2 - C60 heteroaryl group, a, b and c are integers from 1 to 4, and When m, n, a, b and c are 2 or greater, the substituents in the brackets are the same as or different from each other.

2. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 4 to 7: [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] In Chemical Formulas 4 to 7, The definitions of L1, L2, m, n, Ar1 to Ar3, X, a, b and c are the same as those in Chemical Formula 1, and R1 to R4 and R6 to R10 are the same as or different from each other, and each independently represents hydrogen; or deuterium.

3. The heterocyclic compound according to claim 1, wherein Chemical Formula 2 is represented by any one of the following Chemical Formulas 2 - 1 to 2 - 3: [Chemical Formula 2 - 1] [Chemical Formula 2 - 2] [Chemical Formula 2 - 3] In Chemical Formulas 2 - 1 to 2 - 3, The definitions of L1 and m are the same as those in Chemical Formula 2, L11 and L12 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 - C60 arylene; or a substituted or unsubstituted C2 - C60 heteroarylene, a1 and b1 are the same as or different from each other, and each independently represents an integer from 0 to 3, a2 and b2 are the same as or different from each other, and each independently represents an integer from 1 to 3, Ar11 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 - C60 alkyl group; a substituted or unsubstituted C3 - C60 cycloalkyl group; a substituted or unsubstituted C2 - C60 heterocycloalkyl group; a substituted or unsubstituted C6 - C60 aryl group; or a substituted or unsubstituted C2 - C60 heteroaryl group, Ar12 is a substituted or unsubstituted C6 - C60 aryl group, Xa is O; S; or NRc, Ra, Rb, and Rc are the same as or different from one another and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, a' and b' are integers from 0 to 4, c' is an integer from 0 to 3, and when a', b', c', a1, a2, b2, and b1 are 2 or greater, the substituents in parentheses are the same as or different from one another.

4. The heterocyclic compound according to claim 1, wherein the deuterium content of the heterocyclic compound of Chemical Formula 1 is 0% or 3% to 100%.

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

6. An organic light-emitting device, comprising: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain one or more of the heterocyclic compounds 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 contains the heterocyclic compound.

8. The organic light-emitting device according to claim 6, wherein the organic material layer includes a hole-transporting layer or a hole-assist layer, and the hole-transporting layer or the hole-assist layer contains the heterocyclic compound.

9. The organic light-emitting device according to claim 6, further comprising one or two or more layers selected from the following: a light-emitting layer, a hole-injection layer, a hole-transporting layer, an electron-injection layer, an electron-transporting layer, an electron-blocking layer, and a hole-blocking layer.

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