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

Abstract

The present specification relates to: a heterocyclic compound of chemical formula 1; an organic light-emitting device comprising same; and a composition for an organic material layer of the organic light-emitting device. When the heterocyclic compound is used in an organic light-emitting device, it is possible not only to lower the driving voltage of the device and improve the light efficiency thereof, but also to improve the thermal stability of the heterocyclic compound, thus improving the lifespan characteristics of the device.

Description

Heterocyclic compounds, organic light-emitting diodes, and compositions for the organic layer of organic light-emitting diodes

[0001] This specification relates to heterocyclic compounds, organic light-emitting diodes, and compositions for organic layers of organic light-emitting diodes.

[0002] <Cross-reference of related applications>

[0003] This application claims the benefit of the filing date of Korean Patent Application No. 10-2024-0125364 filed with the Korean Intellectual Property Office on September 13, 2024, the entire contents of which are incorporated herein.

[0004] Light-emitting elements are a type of self-emissive display element that has the advantages of a wide viewing angle, excellent contrast, and fast response speed.

[0005] An organic light-emitting diode has a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting diode with such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs and then annihilate, emitting light. The organic thin film can be composed of a single layer or multiple layers as needed.

[0006] The materials of organic thin films may possess luminescence capabilities as needed. For example, compounds capable of independently constituting an emissive layer may be used as organic thin film materials, or compounds capable of acting as a host or dopant in a host-dopant emissive layer may be used. Furthermore, compounds capable of performing functions such as hole injection, hole transport, electron blocking, electron transport, and electron injection may also be used as organic thin film materials.

[0007] To improve the performance, lifespan, or efficiency of organic light-emitting diodes, the development of organic thin film materials is continuously required.

[0008] [Prior Art Literature]

[0009] (Patent Document 1) U.S. Patent No. 4,356,429

[0010] This specification aims to provide a heterocyclic compound, an organic light-emitting device, and a composition for an organic layer of an organic light-emitting device.

[0011] One embodiment of the present specification provides a heterocyclic compound represented by the following chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] R1 to R3 are identical or different from one another, and each is independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted C1 to C60 alkyl group, and

[0016] L1 and L2 are identical or different from each other and are each independently directly bonded; or are substituted or unsubstituted C6 to C60 arylene groups, and

[0017] Either one of the groups Ar1 and Ar2 is the following chemical formula N, and the other group is a substituted or unsubstituted C6 to C60 aryl group; or the following chemical formula K,

[0018] a is an integer from 0 to 4, and

[0019] b is 0 or 1, and

[0020] c is an integer from 0 to 3, and

[0021] Each m and n is an integer from 1 to 4, and

[0022] If each of a, c, m, and n is an integer greater than or equal to 2, the elements inside the parentheses are identical or different from each other, and

[0023] [Chemical Formula N]

[0024]

[0025] In the above chemical formula N,

[0026] is the position connected by the above chemical formula N, and

[0027] Among Y1 to Y5, two or more groups are N, one or more other groups are CRa, and the remaining group is CRb, and

[0028] Ra is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and

[0029] Rb is hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; or a substituted or unsubstituted C2 to C60 heterocycloalkyl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted ring, and

[0030] [Chemical Formula K]

[0031]

[0032] In the above chemical formula K,

[0033] is the position connected by the above chemical formula K, and

[0034] X is O; S; NRx; or CRyRz, and

[0035] Rk, Rx, Ry, and Rz are identical or different from one another, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, and

[0036] k is an integer from 0 to 7, and if k is an integer greater than or equal to 2, Rk are identical or different from each other, and

[0037] The term "substituted or unsubstituted" above means being substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C1 to C60 haloalkyl group; C1 to C60 alkoxy group; C6 to C60 aryloxy group; C1 to C60 alkylthioxy group; C6 to C60 arylthioxy group; C1 to C60 alkyl sulfoxy group; C6 to C60 aryl sulfoxy group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0038] R, R' and R" are each independently substituents consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group.

[0039] Another embodiment of the present specification provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise the heterocyclic compound described above.

[0040] The last embodiment of this specification provides a composition for an organic layer of an organic light-emitting device comprising a heterocyclic compound represented by the above formula 1 and a heterocyclic compound represented by the following formula 2.

[0041] [Chemical Formula 2]

[0042]

[0043] In the above chemical formula 2,

[0044] L3, L4, La and Lb are identical or different from each other and are each independently directly bonded; they are substituted or unsubstituted C6 to C60 arylene groups, and

[0045] Each of o, p, q, and r is an integer from 0 to 4, and

[0046] Ar4 to Ar6 are identical or different from one another and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and

[0047] R4 to R6 are identical or different from one another and each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 haloalkyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryloxy group; a substituted or unsubstituted C1 to C60 alkylthioxy group; a substituted or unsubstituted C6 to C60 arylthioxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; or -NRR' and,

[0048] R, R' and R" are each independently hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; or heteroaryl group, and

[0049] Each d and f is an integer from 0 to 4, and

[0050] e is an integer from 0 to 2, and

[0051] If each d, e, f, o, p, q, and r is 2 or an integer greater than 2, the substituents within the parentheses are identical or different from each other, and

[0052] The sum of d, e, and f is 8.

[0053] A heterocyclic compound according to one embodiment of the present application is a five-membered heterocyclic compound represented by Chemical Formula 1, characterized in that an intermediate benzene moiety and another terminal benzene moiety are substituted with different terminal groups (Ar1 and Ar2).

[0054] The heterocyclic compound represented by the above chemical formula 1 has an extended conjugation structure, and as the T1 level decreases, energy conversion as a dopant is smooth, so when used in an OLED, device performance can be improved (e.g., improved thermal stability, high glass transition temperature, low driving voltage, high efficiency, or long lifespan).

[0055] FIGS. 1 to 4 are drawings illustrating exemplary stacked structures of organic light-emitting diodes according to one embodiment of the present specification.

[0056] 100: Substrate

[0057] 200: Anode

[0058] 300: Organic layer

[0059] 301: Hole injection layer

[0060] 302: Precision Transport Layer

[0061] 303: Emissive layer

[0062] 304: Poison blockade layer

[0063] 305: Electron transport layer

[0064] 306: Electron injection layer

[0065] 400: Cathode

[0066] The present specification will be described in more detail below.

[0067] <Definition>

[0068] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0069] In this specification, any chemical formula or structural formula means the joint position.

[0070] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0071] In this specification, "substituted or unsubstituted" means being substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; C1 to C60 straight-chain or branched-chain alkyl group; C2 to C60 straight-chain or branched-chain alkenyl group; C2 to C60 straight-chain or branched-chain alkynyl group; C3 to C60 monocyclic or polycyclic cycloalkyl group; C2 to C60 monocyclic or polycyclic heterocycloalkyl group; C6 to C60 monocyclic or polycyclic aryl group; C2 to C60 monocyclic or polycyclic heteroaryl group; silyl group; phosphine oxide group; and amine group, or being substituted or unsubstituted with a substituent formed by connecting two or more substituents selected from the exemplified substituents.

[0072] In this specification, "where no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 Since H (Deuterium) or tritium corresponds to isotopes of hydrogen, it can be interpreted as a concept included in hydrogen unless explicitly excluded.

[0073] That is, in this application, deuterium is defined as having an equivalent effect or an improved effect in some evaluation criteria compared to hydrogen in terms of driving voltage, luminous efficiency, and lifespan, in accordance with Chem. Commun., 2014, 50, 14870. Since it falls within a range where a person skilled in the art can predict that it has an equivalent effect even without specific experiments, deuterium, which is an isotope of hydrogen, is interpreted as being included in hydrogen unless explicitly excluded.

[0074] According to one embodiment of the present specification, “where no substituents are indicated in the chemical formula or compound structure” may mean that all positions where substituents may be present are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium isotopes, and in this case, the content of deuterium may be 0% to 100%.

[0075] According to one embodiment of the present specification, in the case where "substituents are not indicated in the chemical formula or compound structure," the deuterium content is 0%, the hydrogen content is 100%, and all substituents do not explicitly exclude hydrogen or other deuterium, hydrogen and deuterium may be used in a mixture in the compound.

[0076] According to one embodiment of this specification, deuterium is one of the isotopes of hydrogen, an element having a deuteron as its nucleus, consisting of one proton and one neutron, and can be represented as hydrogen-2, and its element symbol is D or 2 It can also be written as H.

[0077] According to one embodiment of the present specification, an isotope, which means an atom having the same atomic number (Z) but different mass numbers (A), can also be interpreted as an element having the same number of protons but different numbers of neutrons.

[0078] According to one embodiment of the present specification, the meaning of the content T% of a specific substituent can be defined as T2 / T1 × 100 = T% when the total number of substituents that a basic compound may have is defined as T1 and the number of specific substituents among them is defined as T2.

[0079] in other words, Taking the phenyl group represented by as an example, the deuterium content of 20% here can be expressed as 20% when the total number of substituents the phenyl group can have is 5 (T1 in the formula) and the number of deuteriums among them is 1 (T2 in the formula). That is, a deuterium content of 20% in the phenyl group can be represented by the following structural formula.

[0080]

[0081] In addition, according to one embodiment of the present specification, “phenyl group with 0% deuterium content” may mean a phenyl group that does not contain deuterium atoms, i.e., has five hydrogen atoms.

[0082] In this specification, the cyano group may mean -CN.

[0083] In this specification, the halogen group may be fluorine, chlorine, bromine, or iodine.

[0084] In this specification, the alkyl group comprises a straight or branched chain having 1 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, more specifically 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, There are 2,2-dimethylheptyl groups, 1-ethyl-propyl groups, 1,1-dimethyl-propyl groups, isohexyl groups, 2-methylpentyl groups, 4-methylhexyl groups, 5-methylhexyl groups, etc., but are not limited to these.

[0085] In this specification, the alkenyl group comprises a straight chain or a branched chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically 2 to 20. Specific examples include vinyl groups, 1-propenyl groups, isopropenyl groups, 1-butenyl groups, 2-butenyl groups, 3-butenyl groups, 1-pentenyl groups, 2-pentenyl groups, 3-pentenyl groups, 3-methyl-1-butenyl groups, 1,3-butadienyl groups, allyl groups, 1-phenylvinyl-1-yl groups, 2-phenylvinyl-1-yl groups, 2,2-diphenylvinyl-1-yl groups, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl groups, 2,2-bis(diphenyl-1-yl)vinyl-1-yl groups, stilbenyl groups, styrenyl groups, etc., but are not limited to these.

[0086] In this specification, the alkynyl group comprises a straight or branched chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically 2 to 20.

[0087] In this specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferred to have 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.

[0088] In this specification, the cycloalkyl group comprises a monocyclic or polycyclic group having 3 to 60 carbon atoms and may be further substituted by other substituents. Here, polycyclic means a group in which the cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be other types of ring groups, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, there are cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, 3-methylcyclopentyl groups, 2,3-dimethylcyclopentyl groups, cyclohexyl groups, 3-methylcyclohexyl groups, 4-methylcyclohexyl groups, 2,3-dimethylcyclohexyl groups, 3,4,5-trimethylcyclohexyl groups, 4-tert-butylcyclohexyl groups, cycloheptyl groups, cyclooctyl groups, etc., but are not limited to these.

[0089] In this specification, the heterocycloalkyl group comprises O, S, Se, N, or Si as a heteroatom, comprises a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic means a group in which the heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be other types of ring groups, 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.

[0090] In this specification, the aryl group comprises a monocyclic or polycyclic group having 6 to 60 carbon atoms and may be further substituted by other substituents. Here, polycyclic means a group in which the aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be other types of ring groups, such as cycloalkyl groups, heterocycloalkyl groups, heteroaryl groups, etc. The aryl group comprises 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 above aryl groups include, but are not limited to, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, anthryl groups, chrysenyl groups, phenanthrenyl groups, perylenyl groups, fluoranthenyl groups, triphenylenyl groups, phenalenyl groups, pyrenyl groups, tetracenyl groups, pentacenyl groups, fluorenyl groups, indenyl groups, acenaphthylenyl groups, benzofluorenyl groups, spirobifluorenyl groups, 2,3-dihydro-1H-indenyl groups, and condensation rings thereof.

[0091] In this specification, the terphenyl group may be selected from the following structures.

[0092]

[0093] In this specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

[0094] When the above fluorenyl group is substituted, it may be selected from the following structures, but is not limited thereto.

[0095]

[0096] In this specification, the heteroaryl group comprises S, O, Se, N, or Si as a heteroatom and comprises a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic group means a group in which the heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be a different type of ring 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 above heteroaryl groups include pyridyl group, pyrrolyl group, pyrimidyl group, pyridazolyl group, furanyl group, thiophene group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazolyl group, oxazolyl group, thiazolyl group, deoxynyl group, triazolyl group, tetrazolyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozoliryl group, naphthalidyl group, acrridinyl group, phenanthridinyl group, imidazopyridinyl group, diazanaphthalenyl group, Triazindene group, indolyl group, indolinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophen group, benzofuran group, dibenzothiophen group, dibenzofuran group, carbazole group, benzocarbazole group, dibenzocarbazole group, phenazinyl group, dibenzosilol group, spirobi(dibenzosilol) group, dihydrophenazinyl group, phenoxazinyl group, phenantridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazole group, indolo[2,3-b]carbazole group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenantrazinyl group, phenothiathiazinyl group, Examples include phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, benzo[c][1,2,5]thiadiazolyl group, 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5,10-dihydrodibenzo[b,e][1,4]azacillinyl group, pyrazolo[1,5-c]quinazolinyl group, pyrido[1,2-b]indazolyl group, pyrido[1,2-a]imidazo[1,2-e]indolinyl group, 5,11-dihydroindeno[1,2-b]carbazole group, but are not limited to these.

[0097] In this specification, when a substituent is a carbazole group, it means bonding to the nitrogen or carbon of carbazole.

[0098] In this specification, when a carbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole.

[0099] In this specification, the benzocarbazole group may be any one of the following structures.

[0100]

[0101] In this specification, the dibenzocarbazole group may be any one of the following structures.

[0102]

[0103] In this specification, the naphthobenzofuran group may be any one of the following structures.

[0104]

[0105] In this specification, the naphthobenzothiophene group may be any one of the following structures.

[0106]

[0107] In the present specification, the silyl group is a substituent comprising Si and said Si atom directly connected as a radical, and is represented as -Si(R101)(R102)(R103), where R101 to R103 are identical or different from each other and may each be a substituent consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group.

[0108] Specific examples of silyl groups include (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), etc., are included, but are not limited to these.

[0109] In this specification, the phosphine oxide group is represented as -P(=O)(R104)(R105), and R104 and R105 are identical or different from each other and may each be a substituent consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group. Specifically, it may be substituted with an alkyl group or an aryl group, and the alkyl group and aryl group may be applied according to the examples described above. For example, the phosphine oxide group may include a dimethylphosphine oxide group, a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, etc., but is not limited thereto.

[0110] In this specification, the amine group is represented as -N(R106)(R107), and R106 and R107 are identical or different from each other and may each be a substituent consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group. The amine group may be selected from the group consisting of -NH2; monoalkylamine group; monoarylamine group; monoheteroarylamine group; dialkylamine group; diarylamine group; diheteroarylamine group; alkylarylamine group; alkylheteroarylamine group; and arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above amine groups include, but are not limited to, methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, dibiphenylamine, anthracenylamine, 9-methyl-anthracenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, triphenylamine, biphenylnaphthylamine, phenylbiphenylamine, biphenylfluorenylamine, phenyltriphenyllenylamine, biphenyltriphenyllenylamine, etc.

[0111] In this specification, the examples of aryl groups described above may be applied, except that the arylene group is a divalent group.

[0112] In this specification, the examples of the aforementioned heteroaryl groups may be applied, except that the heteroarylen group is a divalent group.

[0113] In this specification, "adjacent" groups may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the atom on which the substituent is substituted, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

[0114] The hydrocarbon rings and heterocycles that can be formed by adjacent groups include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles, and except that the rings are not monovalent groups, structures exemplified by the aforementioned cycloalkyl groups, aryl groups, heterocycloalkyl groups, and heteroaryl groups may be applied.

[0115] In one embodiment of the present specification, a group not represented as a substituent; or a group represented as hydrogen, may all mean that they are substitutable for deuterium. That is, hydrogen (H); or deuterium (D) may indicate that they are mutually substitutable.

[0116] In general, compounds bonded with hydrogen and compounds substituted with deuterium show differences in thermodynamic behavior. This is because the mass of a deuterium atom is twice that of hydrogen, and due to this difference in atomic mass, deuterium has the characteristic of having lower vibrational energy.

[0117] Furthermore, the single bond dissociation energy between carbon and deuterium is higher than that between carbon and hydrogen. Therefore, structures substituted with deuterium increase the thermal stability of the molecule, which has the effect of improving the lifespan of devices utilizing it.

[0118] When compounds are deposited on a silicon wafer, materials containing deuterium tend to be packed with tighter intermolecular distances. Furthermore, observation of the thin film surface using an Atomic Force Microscope (AFM) confirms that thin films fabricated with deuterium-containing compounds are deposited as a more uniform surface without any areas of aggregation.

[0119] Heterocyclic compounds

[0120] Hereinafter, heterocyclic compounds according to the present specification are described.

[0121] A heterocyclic compound according to one embodiment of the present specification may be represented by the following chemical formula 1.

[0122] [Chemical Formula 1]

[0123]

[0124] In the above chemical formula 1, the description of each substituent is as described above.

[0125] The heterocyclic compound represented by Chemical Formula 1 above has an expanded conjugation compared to unsubstituted or 1-substituted five-membered heterocyclic compounds. Accordingly, compounds having alternating single and double bonds expand conjugation using the p-orbital overlap of atoms, and as conjugation expands, the molecule becomes more stabilized and the T1 energy level is lowered due to electron delocalization.

[0126] According to one embodiment of the present specification, the formula 1 may be represented by any one of the following formulas 1-1 to 1-8.

[0127] [Chemical Formula 1-1]

[0128]

[0129] [Chemical Formula 1-2]

[0130]

[0131] [Chemical Formula 1-3]

[0132]

[0133] [Chemical Formula 1-4]

[0134]

[0135] [Chemical Formula 1-5]

[0136]

[0137] [Chemical Formula 1-6]

[0138]

[0139] [Chemical Formula 1-7]

[0140]

[0141] [Chemical Formula 1-8]

[0142]

[0143] In the above chemical formulas 1-1 to 1-8, the description of each substituent is as described above.

[0144] According to one embodiment of the present specification, the formula 1 may be represented by the following formula 1-11 or 1-12.

[0145] [Chemical Formula 1-11]

[0146]

[0147] [Chemical Formula 1-12]

[0148]

[0149] In the above chemical formulas 1-11 and 1-12, the description of each substituent is as described above, and

[0150] Ar11 is a substituted or unsubstituted C6 to C60 aryl group; or the above formula K.

[0151] When the heterocyclic compound according to the above embodiment is used in an organic light-emitting device, it may have low driving voltage, high luminous efficiency, and / or long lifespan characteristics.

[0152] According to one embodiment of the present specification, R1 to R3 may be identical or different from one another and may each independently be hydrogen; deuterium; a halogen group; or a substituted or unsubstituted C1 to C40 alkyl group.

[0153] According to one embodiment of the present specification, R1 to R3 may be identical or different from one another and may each independently be hydrogen; deuterium; a halogen group; or a substituted or unsubstituted C1 to C30 alkyl group.

[0154] According to one embodiment of the present specification, R1 to R3 may be identical or different from one another and may each independently be hydrogen; or deuterium.

[0155] According to one embodiment of the present specification, L1 and L2 may be identical or different from each other and each independently directly bonded; or may be substituted or unsubstituted arylene groups of C6 to C40.

[0156] According to one embodiment of the present specification, L1 and L2 may be identical or different from each other and each independently directly bonded; or may be substituted or unsubstituted arylene groups of C6 to C30.

[0157] According to one embodiment of the present specification, L1 and L2 may be identical or different from each other and each independently directly bonded; or may be C6 to C30 arylene groups substituted or unsubstituted with deuterium.

[0158] According to one embodiment of the present specification, L1 and L2 may be identical or different from each other and each independently directly bonded; or may be phenylene groups substituted or unsubstituted with deuterium.

[0159] According to one embodiment of the present specification, Ar1 is the formula N, and Ar2 may be a substituted or unsubstituted C6 to C60 aryl group; or the formula K.

[0160] According to one embodiment of the present specification, Ar2 is the formula N, and Ar1 may be a substituted or unsubstituted C6 to C60 aryl group; or the formula K.

[0161] According to one embodiment of the present specification, Ar1 may be the formula N, and Ar2 may be a substituted or unsubstituted C6 to C30 aryl group; or the formula K.

[0162] According to one embodiment of the present specification, Ar2 may be the formula N, and Ar1 may be a substituted or unsubstituted C6 to C30 aryl group; or the formula K.

[0163] According to one embodiment of the present specification, Ar1 may be the formula N, and Ar2 may be a C6 to C30 aryl group substituted or unsubstituted with deuterium; or the formula K.

[0164] According to one embodiment of the present specification, Ar2 may be the formula N, and Ar1 may be a C6 to C30 aryl group substituted or unsubstituted with deuterium; or the formula K.

[0165] According to one embodiment of the present specification, Ar1 is the formula N, and Ar2 may be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a triphenyl group substituted or unsubstituted with deuterium; or the formula K.

[0166] According to one embodiment of the present specification, Ar2 is the formula N, and Ar1 may be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a triphenyl group substituted or unsubstituted with deuterium; or the formula K.

[0167] According to one embodiment of the present specification, Ra may be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0168] According to one embodiment of the present specification, Ra may be a C6 to C30 aryl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen group, aryl group, and heteroaryl group; or a C2 to C30 heteroaryl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen group, aryl group, and heteroaryl group.

[0169] According to one embodiment of the present specification, Ra 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 phenanthrenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted naphthobenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted naphthobenzothiophenyl group; a substituted or unsubstituted carbazole group; or a substituted or unsubstituted benzocarbazole group.

[0170] According to one embodiment of the present specification, Ra comprises: a phenyl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, a halogen group, an aryl group, and a heteroaryl group; a biphenyl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, a halogen group, an aryl group, and a heteroaryl group; a terphenyl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, a halogen group, an aryl group, and a heteroaryl group; a naphthyl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, a halogen group, an aryl group, and a heteroaryl group; a phenanthrenyl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, a halogen group, an aryl group, and a heteroaryl group; and a triphenylene group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, a halogen group, an aryl group, and a heteroaryl group. A fluorenyl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen groups, alkyl groups, aryl groups, and heteroaryl groups; a dibenzofuranyl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen groups, aryl groups, and heteroaryl groups; a naphthobenzofuranyl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen groups, aryl groups, and heteroaryl groups; a dibenzothiophenyl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen groups, aryl groups, and heteroaryl groups; a naphthobenzothiophenyl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen groups, aryl groups, and heteroaryl groups; a carbazole group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen groups, aryl groups, and heteroaryl groups; Alternatively, it may be a benzocarbazole group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen groups, aryl groups, and heteroaryl groups.

[0171] According to one embodiment of the present specification, Ra may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted carbazole group; a phenyl group condensed into a substituted or unsubstituted aromatic hydrocarbon ring; a phenyl group condensed into a substituted or unsubstituted aromatic hetero ring; a carbazole group condensed into a substituted or unsubstituted aromatic hydrocarbon ring; or a carbazole group condensed into a substituted or unsubstituted aromatic hetero ring.

[0172] According to one embodiment of the present specification, Ra comprises: a phenyl group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen group, aryl group, and heteroaryl group; a carbazole group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen group, aryl group, and heteroaryl group; a phenyl group condensed into an aromatic hydrocarbon ring substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen group, aryl group, and heteroaryl group; a phenyl group condensed into an aromatic heterocyclic ring substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen group, aryl group, and heteroaryl group; and a carbazole group condensed into an aromatic hydrocarbon ring substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen group, aryl group, and heteroaryl group. Alternatively, it may be a carbazole group condensed into an aromatic heterocyclic group substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen groups, aryl groups, and heteroaryl groups.

[0173] According to one embodiment of the present specification, Ra is represented by any one of the following structural formulas and may be substituted or unsubstituted with a substituent selected from the group consisting of deuterium, halogen groups, aryl groups, and heteroaryl groups.

[0174]

[0175] is the location where the above structural formula connects.

[0176] According to one embodiment of the present specification, Rb may be hydrogen; or deuterium, or two or more adjacent groups may combine to form a substituted or unsubstituted ring.

[0177] According to one embodiment of the present specification, Rb may be hydrogen; or deuterium, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocycle.

[0178] According to one embodiment of the present specification, the chemical formula N is represented by any one of the following structural formulas and may be substituted or unsubstituted with a substituent selected from the group consisting of deuterium; a halogen group; and an aryl group having C6 to C60.

[0179]

[0180] In the above structural formula,

[0181] is the location where the above structural formula connects.

[0182] According to one embodiment of the present specification, Rk, Rx, Ry and Rz may be the same or different from each other and may each independently be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C30 alkyl group; or a substituted or unsubstituted C6 to C30 aryl group.

[0183] According to one embodiment of the present specification, Rk, Rx, Ry and Rz may be the same or different from each other and may each independently be hydrogen; deuterium; a halogen group; a C1 to C30 alkyl group substituted or unsubstituted with deuterium; or a C6 to C30 aryl group substituted or unsubstituted with deuterium.

[0184] According to one embodiment of the present specification, Rk, Rx, Ry, and Rz may be the same or different from each other and may each independently be hydrogen; deuterium; a halogen group; a methyl group; a phenyl group; or a naphthyl group.

[0185] According to one embodiment of the present specification, “substituted or unsubstituted” means deuterium; halogen group; C1 to C30 alkyl group; C2 to C30 alkenyl group; C2 to C30 alkynyl group; C1 to C30 haloalkyl group; C1 to C30 alkoxy group; C6 to C30 aryloxy group; C1 to C30 alkylthioxy group; C6 to C30 arylthioxy group; C1 to C30 alkyl sulfoxy group; C6 to C30 aryl sulfoxy group; C3 to C30 cycloalkyl group; C2 to C30 heterocycloalkyl group; C6 to C30 aryl group; C2 to C30 heteroaryl group; It means being substituted or unsubstituted with one or more substituents selected from the group consisting of -SiRR'R"; -P(=O)RR'; and -NRR', and R, R' and R" may each independently be a substituent consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group.

[0186] According to one embodiment of the present specification, “substituted or unsubstituted” may mean being substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; C1 to C30 alkyl group; and C6 to C30 aryl group.

[0187] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0% or 1% to 100%.

[0188] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0% or 10% to 100%.

[0189] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0% or 20% to 100%.

[0190] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0% or 30% to 100%.

[0191] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 1 may be 0% or 60% to 100%.

[0192] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0% or 80% to 100%.

[0193] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 1 may be 0% or 90% to 100%.

[0194] According to one embodiment of the present specification, the formula 1 may be represented by any one of the following.

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212] As long as the unique characteristics of the heterocyclic compound represented by Chemical Formula 1 above are maintained, it is possible to synthesize a heterocyclic compound with added characteristics of the introduced substituent by introducing various substituents other than the structure exemplified above. For example, by introducing substituents mainly used in hole injection layer materials, hole transport layer materials, hole transport assist layer materials, light-emitting layer materials, electron transport layer materials, electron transport assist layer materials, and electron blocking layer materials used in the manufacture of organic light-emitting devices into the core structure, it is possible to synthesize a material that satisfies the conditions required for each organic layer.

[0213] In addition, by introducing various substituents into the structure of the heterocyclic compound represented by Chemical Formula 1 above, the energy band gap can be finely tuned, while at the same time, the properties at the interface between organic materials can be improved and the uses of the material can be varied.

[0214] Organic light-emitting diodes

[0215] An organic light-emitting device according to one embodiment of the present specification comprises a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers may comprise the heterocyclic compound (represented by Chemical Formula 1) described above.

[0216] According to one embodiment of the present specification, the organic layer further comprises at least one of a hole transport layer and an electron blocking layer, and at least one of the hole transport layer and the electron blocking layer may comprise the heterocyclic compound (represented by Chemical Formula 1).

[0217] According to one embodiment of the present specification, the organic layer further comprises a hole transport layer, and the hole transport layer may comprise the heterocyclic compound (represented by Chemical Formula 1).

[0218] According to one embodiment of the present specification, the organic layer further comprises an electronic blocking layer, and the electronic blocking layer may comprise the heterocyclic compound (represented by Chemical Formula 1).

[0219] According to one embodiment of the present specification, the organic layer further comprises an emission layer, and the emission layer may comprise a heterocyclic compound represented by Chemical Formula 1.

[0220] In another embodiment of the present specification, the light-emitting layer may include a heterocyclic compound represented by Formula 1 as a host.

[0221] According to one embodiment of the present specification, the light-emitting layer may include a heterocyclic compound represented by Formula 1 as a red host.

[0222] According to one embodiment of the present specification, the light-emitting layer may include a heterocyclic compound represented by Formula 1 as a green host.

[0223] According to one embodiment of the present specification, the light-emitting layer may include a heterocyclic compound represented by Formula 1 as a blue host.

[0224] According to one embodiment of the present specification, the first electrode may be an anode and the second electrode may be a cathode.

[0225] According to one embodiment of the present specification, the first electrode may be a negative electrode, and the second electrode may be a positive electrode.

[0226] According to one embodiment of the present specification, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the blue organic light-emitting device.

[0227] According to one embodiment of the present specification, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the green organic light-emitting device.

[0228] According to one embodiment of the present specification, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the red organic light-emitting device.

[0229] According to one embodiment of the present specification, one or more of the organic layers may further include a heterocyclic compound represented by the following chemical formula 2.

[0230] [Chemical Formula 2]

[0231]

[0232] In the above chemical formula 2,

[0233] L3, L4, La and Lb are identical or different from each other and are each independently directly bonded; or are substituted or unsubstituted C6 to C60 arylene groups, and

[0234] Each of o, p, q, and r is an integer from 0 to 4, and

[0235] Ar4 to Ar6 are identical or different from one another and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and

[0236] R4 to R6 are identical or different from one another and each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 haloalkyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryloxy group; a substituted or unsubstituted C1 to C60 alkylthioxy group; a substituted or unsubstituted C6 to C60 arylthioxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; or -NRR' and,

[0237] R, R' and R" are each independently hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; or heteroaryl group, and

[0238] Each d and f is an integer from 0 to 4, and

[0239] e is an integer from 0 to 2, and

[0240] If each d, e, f, o, p, q, and r is 2 or an integer greater than 2, the substituents within the parentheses are identical or different from each other, and

[0241] The sum of d, e, and f is 8.

[0242] According to one embodiment of the present specification, the formula 2 may be represented by any one of the following formulas 2-1 to 2-3.

[0243] [Chemical Formula 2-1]

[0244]

[0245] [Chemical Formula 2-2]

[0246]

[0247] [Chemical Formula 2-3]

[0248]

[0249] In the above chemical formulas 2-1 to 2-3, each substituent is as defined in the above chemical formula 2.

[0250] According to one embodiment of the present specification, L3, L4, La and Lb may be identical or different from each other and each independently directly bonded; or may be substituted or unsubstituted C6 to C30 arylene groups.

[0251] According to one embodiment of the present specification, L3, L4, La and Lb may be identical or different from one another and each independently directly bonded; or may be C6 to C30 arylene groups substituted or unsubstituted with deuterium.

[0252] According to one embodiment of the present specification, L3, L4, La and Lb may be the same or different from each other and may each independently be a direct bond; a phenylene group; a biphenylene group; or a naphthylene group.

[0253] According to one embodiment of the present specification, Ar4 to Ar6 may be identical or different from one another and each independently substituted or unsubstituted C6 to C30 aryl groups; or substituted or unsubstituted C2 to C30 heteroaryl groups.

[0254] According to one embodiment of the present specification, Ar4 to Ar6 may be identical or different from one another and may be C6 to C30 aryl groups independently substituted or unsubstituted with deuterium; or C2 to C30 heteroaryl groups substituted or unsubstituted with a substituent selected from the group consisting of deuterium and aryl groups.

[0255] According to one embodiment of the present specification, Ar4 to Ar6 may be identical or different from one another and each independently a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a triphenylenyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a dibenzofuranyl group substituted or unsubstituted with deuterium; a dibenzothiophenyl group substituted or unsubstituted with deuterium; or a carbazole group substituted or unsubstituted with a substituent selected from the group consisting of deuterium and phenyl.

[0256] According to one embodiment of the present specification, R4 to R6 are identical or different from one another and each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 haloalkyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C6 to C30 aryloxy group; a substituted or unsubstituted C1 to C30 alkylthioxy group; a substituted or unsubstituted C6 to C30 arylthioxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; Substituted or unsubstituted C2 to C30 heteroaryl groups; -SiRR'R"; -P(=O)RR'; or -NRR', and

[0257] R, R' and R" may each independently be hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; or heteroaryl group.

[0258] According to one embodiment of the present specification, R4 to R6 may be identical or different from one another and may each independently be hydrogen; deuterium; a halogen group; a cyano group; or a substituted or unsubstituted C1 to C30 alkyl group.

[0259] According to one embodiment of the present specification, R4 to R6 may be the same or different from one another and may each independently be hydrogen; or deuterium.

[0260] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula 2 may be 0% or 1% to 100%.

[0261] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula 2 may be 0% or 10% to 100%.

[0262] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 2 may be 0% or 20% to 100%.

[0263] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 2 may be 0% or 30% to 100%.

[0264] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 2 may be 0% or 60% to 100%.

[0265] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 2 may be 0% or 80% to 100%.

[0266] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Chemical Formula 2 may be 0% or 90% to 100%.

[0267] According to one embodiment of the present specification, the formula 2 may be represented by any one of the following.

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284] As long as the unique characteristics of the heterocyclic compound represented by Chemical Formula 2 above are maintained, it is possible to synthesize a heterocyclic compound with added characteristics of the introduced substituent by introducing various substituents other than the structure exemplified above. For example, by introducing substituents mainly used in hole injection layer materials, hole transport layer materials, hole transport assist layer materials, light-emitting layer materials, electron transport layer materials, electron transport assist layer materials, and electron blocking layer materials used in the manufacture of organic light-emitting devices into the core structure, it is possible to synthesize a material that satisfies the conditions required for each organic layer.

[0285] In addition, by introducing various substituents into the structure of the heterocyclic compound represented by Chemical Formula 2 above, the energy band gap can be finely tuned, while at the same time, the properties at the interface between organic materials can be improved and the uses of the material can be varied.

[0286] According to one embodiment of the present specification, the organic layer may include an iridium-based dopant.

[0287] According to one embodiment of the present specification, the iridium-based dopant may be a blue phosphorescent dopant Ir(dpt)3, but is not limited thereto.

[0288] According to one embodiment of the present specification, the iridium-based dopant may be a green phosphorescent dopant Ir(ppy)3, but is not limited thereto.

[0289] According to one embodiment of the present specification, the iridium-based dopant may be a red phosphorescent dopant (piq)2(Ir)(acac), but is not limited thereto.

[0290] In the organic light-emitting device of the present specification, materials with a relatively large work function may be used as the anode material, and transparent conductive oxides, metals, or conductive polymers may be used. Specific examples of the anode 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 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.

[0291] In the organic light-emitting device of the present specification, materials with a relatively low work function may be used as the cathode material, and metals, metal oxides, or conductive polymers may be used. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0292] In the organic light-emitting device of this specification, known hole injection materials may be used as the hole injection material, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or starburst-type amine derivatives described in the document [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4''-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), or polyaniline / dodecylbenzenesulfonic acid, which is a soluble conductive polymer. Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), Polyaniline / Camphor sulfonic acid, or Polyaniline / Poly(4-styrene-sulfonate) can be used.

[0293] In the organic light-emitting device of the present specification, the hole transport material may include pyrazolin derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc., and may also include low molecular weight or high molecular weight materials.

[0294] In the organic light-emitting device of the present specification, the electron transport material may be an oxadiazole derivative, anthraquinodimethane and its derivative, benzoquinone and its derivative, naphthoquinone and its derivative, anthraquinone and its derivative, tetracyanoanthraquinodimethane and its derivative, fluorenone derivative, diphenyldicyanoethylene and its derivative, diphenoquinone derivative, metal complex of 8-hydroxyquinoline and its derivative, etc., and may be a high molecular weight material as well as a low molecular weight material.

[0295] In the organic light-emitting diode of this specification, for example, LiF is typically used as an electron injection material in the industry, but this specification is not limited thereto.

[0296] In the organic light-emitting device of the present specification, red, green, or blue light-emitting materials may be additionally used as light-emitting materials, and if necessary, two or more light-emitting materials may be mixed and used. In this case, two or more light-emitting materials may be deposited and used as individual sources, or they may be pre-mixed and deposited as a single source. Additionally, fluorescent materials may be used as light-emitting materials, but phosphorescent materials may also be used. As light-emitting materials, a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used alone, but materials in which a host material and a dopant material participate in light emission together may also be used.

[0297] When using a mixture of hosts for light-emitting materials, hosts of the same series may be mixed, or hosts of different series may be mixed. For example, two or more types of materials, such as N-Type host materials or P-Type host materials, may be selected and used as the host material for the light-emitting layer.

[0298] An organic light-emitting device according to one embodiment of the present specification may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0299] A heterocyclic compound according to one embodiment of the present specification can operate in organic electronic devices, including organic solar cells, organic photosensitive materials, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.

[0300] The organic light-emitting device of the present specification may further include one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport assist layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0301] FIGS. 1 to 4 illustrate the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present specification. However, the scope of the present application is not intended to be limited by these figures, and structures of organic light-emitting devices known in the art may be applied to the present application.

[0302] According to FIG. 1, an organic light-emitting device is illustrated in which an anode (200), an organic layer (300), and a cathode (400) are sequentially stacked on a substrate (100). However, the structure is not limited to this, and an organic light-emitting device may be implemented in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate as shown in FIG. 2. The composition for the organic light-emitting device may be included in the organic layer (300), and the organic layer (300) may be one or more layers.

[0303] FIGS. 3 and 4 illustrate a case where an organic layer provided between an anode (200) and a cathode (400) on a substrate (100) is multilayer. The organic light-emitting device according to FIG. 3 may include 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) as organic layers, and the organic light-emitting device according to FIG. 4 may further include an electron blocking layer (303) between the hole transport layer (302) and the light-emitting layer (304). The heterocyclic compound (represented by Chemical Formula 1) may be included in the light-emitting layer (304).

[0304] The scope of the present application is not limited by the stacked structure as described above, and, if necessary, the remaining layers excluding the hole transport layer and / or electron blocking layer may be omitted, and other necessary functional layers may be added.

[0305] The heterocyclic compound represented by the above chemical formula 1 can be used when forming an organic layer of an organic light-emitting device, and can be used more preferably as a host material.

[0306] If necessary, when a mixture is formed by mixing a compound of a different type other than the heterocyclic compound represented by Chemical Formula 1, the mixture may be in a pre-mixed form, and the material in powder form may be mixed before forming the organic layer of the organic light-emitting diode, or the compound in a liquid state at an appropriate temperature or higher may be mixed. The composition is in a solid state below the melting point of each material, and can be maintained in a liquid state by adjusting the temperature.

[0307] The heterocyclic compound represented by the above chemical formula 1 may additionally include materials known in the art, such as solvents and additives.

[0308] Method for manufacturing an organic light-emitting diode

[0309] In one embodiment of the present specification, a method for manufacturing an organic light-emitting device is provided, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layers, wherein the step of forming the organic layers includes forming one or more organic layers using a heterocyclic compound (represented by Chemical Formula 1) according to one embodiment of the present specification.

[0310] According to one embodiment of the present specification, the step of forming the organic layer may be to form a heterocyclic compound represented by Formula 1 using a thermal vacuum deposition method.

[0311] An organic light-emitting device according to one embodiment of the present specification can be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except that an organic layer is formed using the heterocyclic compound described above.

[0312] Specifically, the organic layer can be formed by a solution coating method as well as a vacuum deposition method when manufacturing the organic light-emitting device. Here, the term "solution coating method" refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0313] <Composition for the Organic Layer of an Organic Light-Emitting Device>

[0314] According to an embodiment of the present specification, a composition for an organic layer of an organic light-emitting device is provided, comprising a heterocyclic compound represented by the above chemical formula 1 and a heterocyclic compound represented by the following chemical formula 2.

[0315] [Chemical Formula 2]

[0316]

[0317] In the above chemical formula 2, the definition of each substituent is as described above.

[0318] According to an embodiment of the present specification, the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 may be 1:10 to 10:1.

[0319] According to an embodiment of the present specification, the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 may be 1:5 to 5:1.

[0320] According to an embodiment of the present specification, the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 may be 1:3 to 3:1.

[0321] According to an embodiment of the present specification, the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 may be 1:2 to 2:1.

[0322] The organic layer of the organic light-emitting device of the present specification may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present specification 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 layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller or larger number of organic layers.

[0323] The present specification is described in more detail below through examples, but these are for illustrative purposes only and are not intended to limit the scope of the present application.

[0324] Preparation Example.

[0325] [Preparation Example 1] Preparation of Compound A1

[0326]

[0327] 1) Preparation of intermediate A1-6

[0328] 3-iodo-2-methoxydibenzo[b,d]furan (50.0 g, 151 mmol, A1-7), phenylboronic acid (22.6 g, 181.4 mmol), Pd(PPh3)4 (6.99 g, 6.05 mmol), and K2CO3 (52.2 g, 378 mmol) were added to 1,4-Dioxane / H2O (500 mL / 150 mL) and stirred at 95 ℃ for 2 hours.

[0329] After cooling to room temperature, the resulting solid was filtered to obtain intermediate A1-6 (39.8 g, 96%).

[0330] 2) Preparation of intermediate A1-5

[0331] The above intermediates A1-6 (39.8 g, 145 mmol) and BBr3 (109 g, 435 mmol) were added to DCM (400 mL) and stirred at room temperature for 1 hour. The resulting solid was filtered to obtain intermediate A1-5 (37.8 g, 100%).

[0332] 3) Preparation of intermediate A1-4

[0333] The above intermediate A1-5 (37.7 g, 145 mmol) and NBS (28.4 g, 160 mmol) were added to CHCl3 (400 mL) and stirred at room temperature for 2 hours. The resulting solid was filtered to obtain intermediate A1-4 (33.6 g, 68%).

[0334] 4) Preparation of intermediate A1-3

[0335] The above intermediate A1-4 (33.0 g, 97.0 mmol), (5-chloro-2-fluorophenyl)boronic acid (25.4 g, 146 mmol), Pd(PPh3)4 (4.50 g, 3.89 mmol), and K2CO3 (33.6 g, 243 mmol) were added to 1,4-Dioxane / H2O (350 mL / 100 mL) and stirred at 95 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to obtain intermediate A1-3 (35.2 g, 93%).

[0336] 5) Preparation of intermediate A1-2

[0337] The above intermediate A1-3 (35.0 g, 90 mmol) and Cs2CO3 (58.7 g, 180 mmol) were placed in DMA (350 mL) and stirred at 180 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to obtain intermediate A1-2 (20.4 g, 61%).

[0338] 6) Preparation of intermediate A1-1

[0339] The above intermediates A1-2 (20.4 g, 55.3 mmol), B2pin2 (28.1 g, 110 mmol), Pd2(dba)3 (2.03 g, 2.21 mmol), Xphos (2.64 g, 5.53 mmol), and KOAc (13.6 g, 138 mmol) were added to 1,4-Dioxane (200 mL) and stirred at 120 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to obtain intermediate A1-1 (23.2 g, 91%).

[0340] 7) Preparation of Compound A1

[0341] The above intermediate A1-1 (9.0 g, 19.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.23 g, 19.6 mmol), Pd(PPh3)4 (0.9 g, 0.78 mmol), and K2CO3 (6.75 g, 48.9 mmol) were added to 1,4-Dioxane / H2O (100 mL / 30 mL) and stirred at 95 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to obtain compound A1 (10.2 g, 92%).

[0342] Except for changing (A), (B), (C), and (D) in Preparation Example 1 above to (A), (B), (C), and (D) of Table 1 below, the following compounds were synthesized in the same manner as the preparation of compound A1. For reference, (D) is identical to (D) used in the synthesis of A1, except for A276, A299, and A300 below.

[0343]

[0344]

[0345]

[0346]

[0347] [Preparation Example 2] Preparation of Compound A141

[0348]

[0349] 1) Preparation of intermediate A141-6

[0350] 3-iodo-2-methoxydibenzo[b,d]furan (20.0 g, 61.7 mmol, A141-7), B2pin2 (23.5 g, 92.6 mmol), Pd(dppf)Cl2 (1.81 g, 2.47 mmol), and KOAc (15.1 g, 154 mmol) were added to 1,4-Dioxane (200 mL) and stirred at 120 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to obtain the intermediate A141-6 (14.2 g, 72%).

[0351] Subsequently, compound A141 was prepared by proceeding in the same manner as the synthesis process of intermediates A1-6 to A1 in Preparation Example 1 above. Except for changing (A), (B), (C), and (D) in Preparation Example 2 above to (A), (B), (C), and (D) in Table 2 below, the following compounds were synthesized in the same manner as the preparation of compound A141 above. For reference, (D) is identical to (D) used in the synthesis of A141 above, except for A221, A223, and A280 below.

[0352]

[0353]

[0354] [Preparation Example 3] Preparation of Compound B3

[0355]

[0356] 1) Preparation of intermediate B3-1

[0357] 7-bromo-5-chloronaphtho[1,2-b]benzofuran (20.0 g, 60.1 mmol, B3-2), phenylboronic acid (8.22 g, 66.1 mmol), Pd(PPh3)4 (3.47 g, 3.00 mmol), and K2CO3 (20.8 g, 150 mmol) were added to 1,4-Dioxane / H2O (200 mL / 70 mL) and stirred at 95 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to obtain intermediate B3-1 (17.2 g, 87%).

[0358] 2) Preparation of Compound B3

[0359] The above intermediate B3-1 (17.2 g, 52.3 mmol), di([1,1'-biphenyl]-4-yl)amine (17.2 g, 52.3 mmol), Pd2(dba)3 (2.40 g, 2.62 mmol), Xphos (2.49 g, 5.23 mmol), and NaOtBu (10.1 g, 105 mmol) were added to Xylene (170 mL) and stirred at 150 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to obtain compound B3 (25.9 g, 81%).

[0360] Except for changing (A), (B), and (C) in Preparation Example 3 above to (A), (B), and (C) of Table 3 below, the following compounds were synthesized in the same manner as the preparation of compound B3.

[0361]

[0362]

[0363] [Preparation Example 4] Preparation of Compound B32

[0364]

[0365] 1) Manufacture of B32-1

[0366] Intermediate B32-1 was synthesized using the same method as the preparation method for intermediate B3-1.

[0367] 2) Preparation of Compound B32

[0368] The above intermediate B32-1 (17.2 g, 52.3 mmol), (4-([1,1'-biphenyl]-3-yl([1,1':4',1"-terphenyl]-4-yl)amino)phenyl)boronic acid (23.1 g, 52.3 mmol), Pd2(dba)3 (2.40 g, 2.62 mmol), Xphos (2.49 g, 5.23 mmol), and NaOH (4.19 g, 105 mmol) were added to 1,4-Dioxane / H2O (170 / 50 mL) and stirred at 120 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to obtain compound B32 (35.6 g, 89%).

[0369] Except for changing (A), (B), and (C) in Preparation Example 4 above to (A), (B), and (C) of Table 4 below, the following compounds were synthesized in the same manner as the preparation of compound B32 above.

[0370]

[0371] Compounds were prepared in the same manner as the above preparation examples, and the results of their synthesis confirmation are shown in Tables 5 and 6 below, respectively. Table 5 below is 1 The values ​​are from H NMR (CDCl3, 300 MHz), and Table 6 below shows the values ​​from FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0372] compound 1H NMR(CDCl3, 300MHz)A18.36 (ddd, 4H), 7.98 (dd, 1H), 7.83 (d, 1H), 7.76 (s, 1H), 7.69 (d, 1H), 7.63 (dd, 2H), 7.54-7.30 (m, 14H)A58.34 (ddd, 2H), 8.27-8.22 (m, 2H), 7.98 (dd, 1H), 7.84-7.74 (m, 4H), 7.70-7.61 (m, 4H), 7.57-7.29 (m, 14H)A218.37 (dd, 2H), 8.02-7.99 (m, 2H), 7.83 (d, 1H), 7.76 (s, 1H), 7.70-7.30 (m, 19H)A258.04-7.98 (m, 3H), 7.83 (d, 1H), 7.75 (s, 1H), 7.69-7.29 (m, 22H)A318.56 (ddd, 1H), 8.36 (ddd, 2H), 7.98 (dd, 1H), 7.83 (d, 1H), 7.76 (s, 1H), 7.64-7.29 (m, 22H), 7.18-7.10 (m, 2H)A328.54 (ddd, 1H), 8.38 (ddd, 2H), 8.19 (ddd, 1H), 7.99 (dd, 1H), 7.85 (d, 1H), 7.76 (s, 1H), 7.70-7.65 (m, 2H), 7.54-7.28 (m, 13H), 7.22-7.09 (m, 4H)A358.36 (ddd, 4H), 7.98 (dd, 1H), 7.94 (d, 1H), 7.83 (d, 1H), 7.76-7.30 (m, 19H)A418.36 (ddd, 4H), 7.98 (dd, 1H), 7.80-7.75 (m, 3H), 7.55-7.28 (m, 15H)A438.35 (ddd, 2H), 8.26 (dd, 2H), 7.96 (dd, 1H), 7.79-7.74 (m, 5H), 7.66-7.23 (m, 16H)A458.37 (ddd, 2H), 8.29-8.23 (m, 2H), 7.99 (dd, 1H), 7.80-7.74 (m, 5H), 7.65-7.28 (m, 16H)A618.37 (ddd, 2H), 7.99-7.93 (m, 2H), 7.79-7.74 (m, 3H), 7.60-7.27 (m, 18H)A688.45 (dd, 1H), 8.38 (dd, 2H), 7.99-7.95 (m, 2H), 7.86 (dd, 1H), 7.80-7.75 (m, 2H), 7.67 (dd, 1H), 7.58-7.30 (m, 15H)A778.35 (ddd, 4H), 8.01-7.97 (m, 2H), 7.79-7.75 (m, 4H), 7.58-7.48 (m, 9H), 7.41-7.29 (m, 4H)A818.37 (ddd, 4H), 8.08 (dd, 1H), 7.99 (dd, 1H), 7.75 (s, 1H), 7.64 (dd, 1H), 7.54-7.32 (m, 15H)A838.35 (ddd, 2H), 8.24 (dd, 2H), 8.08 (dd, 1H), 7.97 (dd, 1H), 7.78-7.75 (m, 3H), 7.63 (dd, 1H), 7.56-7.23 (m, 17H)A858.35 (ddd, 2H), 8.26-8.23 (m, 2H), 8.08 (dd, 1H), 7.98 (dd, 1H), 7.79-7.75 (m, 3H), 7.64-7.62 (m, 3H), 7.55-7.30 (m, 15H)A1018.38 (ddd, 2H), 8.09 (dd, 1H), 7.99-7.96 (m, 2H), 7.76 (s, 1H), 7.64-7.29 (m, 19H)A1158.35 (ddd, 4H), 8.09 (d, 1H), 7.99 (dd,1H), 7.94 (dd, 1H), 7.75-7.70 (m, 3H), 7.62-7.29 (m, 16H)A1218.36 (ddd, 4H), 7.98 (dd, 1H), 7.75 (s, 1H), 7.57-7.30 (m, 17H)A1418.37 (ddd, 4H), 7.98 (dd, 1H), 7.79-7.76 (m, 3H), 7.61-7.38 (m, 15H)A1448.36 (ddd, 4H), 7.99 (dd, 1H), 7.94 (dd, 1H), 7.80-7.70 (m, 5H), 7.61-7.26 (m, 15H)A1618.36 (ddd, 4H), 7.98 (dd, 1H), 7.83 (d, 1H), 7.76-7.62 (m, 5H), 7.55-7.30 (m, 12H)A1698.37 (ddd, 2H), 7.99-7.97 (m, 2H), 7.82 (s, 1H), 7.75-7.29 (m, 20H)A1818.36 (ddd, 4H), 7.98 (dd, 2H), 7.79-7.75 (m, 5H), 7.51-7.30 (m, 13H)A1937.99-7.95 (m, 3H), 7.78-7.74 (m, 5H), 7.58-7.32 (m, 19H)A1948.37 (ddd, 4H), 8.26 (dd, 2H), 7.99 (dd, 1H), 7.78-7.75 (m, 5H), 7.57-7.31 (m, 13H)A1977.98 (dd, 1H), 7.86-7.75 (m, 8H), 7.57-7.31 (m, 12H)A2018.36 (ddd, 4H), 8.09-7.97 (m, 3H), 7.76 (s, 1H), 7.55-7.30 (m, 15H)A2218.38 (ddd, 4H), 7.79 (dd, 1H), 7.80-7.77 (m, 2H), 7.60-7.38 (m, 16H)A2238.34 (ddd, 4H), 7.98 (dd, 1H), 7.79-7.75 (m, 4H), 7.58-7.30 (m, 14H)A2438.37 (ddd, 4H), 8.26 (dd, 2H), 7.98 (s, 1H), 7.79-7.76 (m, 3H), 7.57-7.30 (m, 17H)A2577.99 (dd, 1H), 7.87-7.75 (m, 7H), 7.58-7.31 (m, 13H)A2768.18 (s, 1H), 7.85 (s, 1H), 7.76 (s, 1H)A2807.70 (s, 1H), 7.67 (s, 2H), 7.58 (s, 1H), 7.51 (s, 1H)A2998.38 (ddd, 4H), 7.98 (dd, 1H), 7.79-7.74 (m, 2H), 7.58-7.29 (m, 16H)A3008.34 (ddd, 2H), 8.08 (dd, 1H), 7.98 (dd, 1H), 7.63 (dd, 1H), 7.55-7.29 (m, 16H)B38.97 (dd, 1H), 8.18 (dd, 1H), 7.79-7.74 (m, 5H), 7.64-7.41 (m, 16H), 7.27-7.16 (m, 6H), 6.91 (s, 1H)B58.95 (dd, 1H), 8.19 (dd, 1H), 7.79-7.75 (m, 4H), 7.65-7.40 (m, 16H), 7.28-7.15 (m, 10H), 6.93 (dd, 1H)B238.98 (dd, 1H), 8.55 (dd, 1H), 8.17 (dd, 1H), 7.83-7.75 (m, 6H), 7.62-7.41 (m, 20H), 7.38-7.10 (m, 6H), 6.91 (dd, 1H)B328.96 (dd, 1H), 8.17 (dd, 1H), 7.79-7.75 (m, 6H), 7.65-7.40 (m, 20H), 7.27-7.15 (m, 11H)B368.95 (dd, 1H), 8.19 (dd, 1H), 7.76-7.74 (m, 6H), 7.65-7.42 (m, 20H), 7.28-7.25 (m, 10H)B418.96 (dd, 1H), 8.55 (dd, 1H), 8.19 (dd, 1H), 7.89 (d, 1H), 7.75 (ddd, 4H), 7.64-7.41 (m, 20H), 7.27-7.11 (m, 8H), 6.91 (dd, 1H)B478.97 (dd, 1H), 8.15 (dd, 1H), 7.83-7.76 (m, 6H), 7.65-7.41 (m, 18H), 7.28-7.23 (m, 6H), 7.09-7.01 (m, 3H)B518.97 (dd, 1H), 8.22-8.19 (m, 2H), 7.80-7.74 (m, 6H), 7.65-7.41 (m, 17H), 7.28 (dd, 4H), 6.98 (dd, 1H)B1018.98 (dd, 1H), 8.17 (dd, 1H), 8.03 (d, 1H), 7.78-7.74 (m, 4H), 7.65-7.37 (m, 17H), 7.28-7.25 (m, 8H), 6.92 (dd, 1H)B1748.95 (dd, 1H), 8.19 (dd, 1H), 8.08 (dd, 1H), 8.02 (dd, 1H), 7.79-7.75 (m, 4H), 7.64 (ddd, 1H), 7.55-7.37 (m, 13H), 7.28-7.23 (m, 10H), 7.08-7.00 (m, 3H)B1958.98-8.95 (m, 2H), 8.03 (d, 1H), 7.79-7.74 (m, 6H), 7.56-7.41 (m, 11H), 7.31-7.27 (m, 5H), 6.90 (dd, 1H)B1978.99-8.95 (m, 2H), 8.04 (d, 1H), 7.80-7.75 (m, 6H), 7.56-7.40 (m, 16H), 7.27-7.24 (m, 8H), 6.93 (dd, 1H)B2278.99-8.95 (m, 2H), 8.21 (d, 1H), 7.80-7.75 (m, 6H), 7.56-7.40 (m, 16H), 7.31-7.26 (m, 5H), 6.98 (dd, 1H)B2618.22 (s, 1H), 8.18 (dd, 1H), 8.12 (dd, 1H), 7.79-7.75 (m, 6H), 7.65-7.41 (m, 18H), 7.28-7.26 (m, 8H)B3047.84 (s, 1H), 7.38 (s, 1H), 7.31-7.29 (m, 2H), 7.27 (s, 1H)B3088.03 (s, 1H), 7.84 (s, 1H), 7.31-7.29 (m, 5H).

[0373] 화합물FD-MS화합물FD-MSA1m / z= 565.18(C39H23N3O2, 565.63)A5m / z= 641.21(C45H27N3O2, 641.73)A21m / z= 655.19(C45H25N3O3, 655.71)A25m / z= 745.20(C51H27N3O4, 745.79)A31m / z= 730.24(C51H30N4O2, 730.83)A32m / z= 654.21(C45H26N4O2, 654.73)A35m / z= 641.21(C45H27N3O2, 641.73)A41m / z = 565.18(C39H23N3O2, 565.63)A43m / z = 641.21(C45H27N3O2, 641.73)A45m / z = 641.21(C45H27N3O2, 641.73)A61m / z = 655.19(C45H25N3O3, 655.71)A68m / z = 671.17(C45H25N3O2S, 671.77)A77m / z = 655.19(C45H25N3O3, 655.71)A81m / z = 565.18(C39H23N3O2, 565.63)A83m / z= 641.21(C45H27N3O2, 641.73)A85m / z= 641.21(C45H27N3O2, 641.73)A101m / z= 655.19(C45H25N3O3, 655.71)A115m / z= 641.21(C45H27N3O2, 641.73)A121m / z= 565.18(C39H23N3O2, 565.63)A141m / z= 565.18(C39H23N3O2, 565.63)A144m / z= 641.21(C45H27N3O2, 641.73)A161m / z= 565.18(C39H23N3O2, 565.63)A169m / z= 655.19(C45H25N3O3, 655.71)A181m / z= 565.18(C39H23N3O2, 565.63)A193m / z= 745.20(C51H27N3O4 745.79)A194m / z= 641.21(C45H27N3O2, 641.73)A197m / z= 594.14(C40H22N2O2S, 594.69)A201m / z= 565.18(C39H23N3O2, 565.63)A221m / z= 565.18(C39H23N3O2, 565.63)A223m / z= 565.18(C39H23N3O2, 565.63)A243m / z= 641.21(C45H27N3O2, 641.73)A257m / z= 594.14(C40H22N2O2S, 594.69)A276m / z= 637.33 (C43H3D22N3O2,637.83)A280m / z= 583.29(C39H5D18N3O2, 583.74)A299m / z= 565.18(C39H23N3O2, 565.63)A300m / z= 565.18(C39H23N3O2, 565.63)B3m / z= 613.24(C46H31NO, 613.76)B5m / z= 689.27(C52H35NO, 689.86)B23m / z= 778.30(C58H38N2O, 778.95)B32m / z= 765.30(C58H39NO, 765.96)B36m / z= 765.30(C58H39NO, 765.96)B41m / z= 778.30(C58H38N2O, 778.95)B47m / z= 689.27(C52H35NO, 689.86)B51m / z= 613.24(C46H31NO, 613.76)B101m / z= 689.27(C52H35NO, 689.86)B174m / z= 689.27(C52H35NO, 689.86)B195m / z= 613.24(C46H31NO, 613.76)B197m / z= 689.27(C52H35NO, 689.86)B227m / z= 613.24(C46H31NO, 613.76)B261m / z= 689.27(C52H35NO, 689.86)B304m / z= 799.52(C58H5D34NO, 800.16)B308m / z= 637.39(C46H7D24NO, 637.91).

[0374] <실험예 1> 유기 발광 소자의 제작

[0375] 1) 유기 발광 소자의 제조

[0376] A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was cleaned with distilled water ultrasonics. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) using UV light for 5 minutes in an Ultraviolet (UV) cleaner. Subsequently, the substrate was transferred to a plasma cleaner (PT), subjected to plasma treatment under vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0377] A common layer, a hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino] triphenylamine) and a hole transport layer NPB (N,N'-Di(1-naphthyl)-N,N'-biphenyl)-4,4'-diamine) were formed on the above ITO transparent electrode (anode).

[0378] A light-emitting layer was deposited on top of it as follows. Specifically, compounds described in Examples 1 to 36 of Table 7 below were used as the red host for the light-emitting layer, and a light-emitting layer with a thickness of 500 Å was deposited by doping the red host with 3 wt% of the red phosphorescent dopant (piq)2(Ir)(acac). Subsequently, 60 Å of Bathocuproine (hereinafter BCP) was deposited as a hole-blocking layer, and 200 Å of Alq3 was deposited as an electron-transporting layer on top of it.

[0379] Finally, an organic light-emitting diode was fabricated by forming an electron injection layer by depositing lithium fluoride (LiF) to a thickness of 10 Å on the electron transport layer, and then forming a cathode by depositing an aluminum (Al) cathode to a thickness of 1,200 Å on the electron injection layer.

[0380] Meanwhile, all organic compounds required for OLED device fabrication are 10 each for each material -8 ~10 -6It was purified by vacuum sublimation under torr and used for OLED fabrication.

[0381] 2) Driving voltage and luminous efficiency of organic light-emitting diodes

[0382] The electroluminescence (EL) characteristics of the organic light-emitting diodes of Examples 1 to 36 in Table 7, manufactured as described above, were measured using MaxScience’s M7000, and based on the measurement results, the reference brightness was 6,000 cd / m² using a lifetime measurement device (M6000) manufactured by MaxScience. 2 When, T 90 The above T was measured. 90 represents the lifetime (unit: h, hours) of the time it takes to reach 90% of the initial brightness.

[0383] The measured characteristics of the organic light-emitting diode were as shown in Table 7 below.

[0384] No. Compound threshold voltage (V on ) Driving voltage (V op )Efficiency(cd / A)Color coordinates(x, y)Lifetime(T 90Comparative Example 1A 3.366.157.5(0.682, 0.317)7 Comparative Example 2B 3.386.183.1(0.680, 0.318)3 Comparative Example 3C 3.676.580.5(0.677, 0.322)1 Comparative Example 4D 3.496.472.8(0.679, 0.321)4 Comparative Example 5E 3.406.434.7(0.685, 0.313)3 Comparative Example 6F 3.386.397.0(0.680, 0.318)8 Comparative Example 7G 3.416.447.6(0.682, 0.316)7 Comparative Example 8H 3.32 6.37 4.5 (0.679, 0.319) 6 Comparative Example 9I 3.41 6.46 6.6 (0.680, 0.317) 7 Comparative Example 10J 3.37 6.40 6.3 (0.681, 0.317) 6 Comparative Example 11K 3.45 6.47 5.2 (0.681, 0.316) 3 Comparative Example 12L 3.58 6.61 2.2 (0.683, 0.315) 3 Comparative Example 13M 3.36 6.29 6.3 (0.680, 0.317) 5 Comparative Example 14N 3.42 6.47 4.3 (0.678, 0.321) 1 Comparative Example 15O3.386.336.2(0.679, 0.320)4 Comparative Example 16P3.456.496.7(0.680, 0.318)3 Example 1A12.265.2737.2(0.681, 0.318)64 Example 2A52.295.2739.1(0.679, 0.320)62 Example 3A212.235.2636.9(0.680, 0.320)66 Example 4A252.225.2335.8(0.681, 0.317)68 Example 5A312.275.2535.2(0.683, 0.316)54 Example 6A322.285.2835.1(0.681, 0.318)55 Example 7A352.245.2637.8(0.681, 0.318)64 Example 8A412.175.1542.5(0.678, 0.320)75 Example 9A432.135.1142.0(0.682, 0.316)77 Example 10A452.185.2543.7(0.679, 0.319)73 Example 11A612.135.1442.9(0.680, 0.317)79 Example 12A682.135.1441.3(0.681, 0.317)75 Example 13A772.125.2342.6(0.680, 0.319)78 Example 14A812.355.3733.2(0.678, 0.321)56 Example 15A832.335.3533.0(0.682, 0.318)58 Example 16A852.375.3934.1(0.681, 0.316)51 Example 17A1012.365.3532.6(0.677, 0.323)55 Example 18A1152.365.3732.9(0.683, 0.317)53 Example 19A1212.725.7415.4(0.680, 0.321)23 Example 20A1412.565.5422.1(0.681, 0.318)36 Example 21A1442.595.5823.1(0.682, 0.316)32 Example 22A1612.465.4628.9(0.680, 0.319)41 Example 23A1692.435.4527.8(0.679, 0.320)44 Example 24A1812.435.4527.3(0.680, 0.319)44 Example 25A1932.475.4626.5(0.683, 0.316)46 Example 26A1942.435.4526.7(0.680, 0.317)47 Example 27A1972.715.7317.2(0.681, 0.318)20 Example 28A2012.555.5423.5(0.681, 0.317)31 Example 29A2212.585.5624.1(0.679, 0.320)33 Example 30A2232.525.5322.5(0.683, 0.315)38 Example 31A2432.165.1543.1(0.681, 0.318)73 Example 32A2572.755.7416.9(0.680, 0.319)21 Example 33A2762.065.0946.7(0.683, 0.317)84 Example 34A2802.355.3432.7(0.678, 0.319)53 Example 35A2992.545.5621.9(0.682, 0.316)35 Example 36A3002.545.5524.1(0.684, 0.314)32.

[0385] Comparative compounds A to P used in Table 7 above were as follows.

[0386]

[0387] As can be seen from the results in Table 7 above, when the organic layer of an organic light-emitting device is deposited with a heterocyclic compound of Formula 1 selected from heterocyclic compounds A1 to A332 according to the present application, it was confirmed that the organic light-emitting device can appropriately control the threshold voltage and driving voltage, and that efficiency or lifespan effects are improved.

[0388] On the other hand, comparative compounds A and M have a structure in which a cyano group is substituted at one end of a five-membered ring, comparative compound B has a structure in which one of the heteroatoms of a five-membered ring contains sulfur, comparative compounds C and D have a structure in which an azine-based substituent represented by the chemical formula N is missing, comparative compounds E and P have a structure different from the fused structure of the chemical formula 1, comparative compounds F and G have a structure in which an aryl group or a group represented by the chemical formula K is missing, comparative compounds H, I, J and K have a 1-substituted structure, comparative compound L has a structure outside the definition of Ar1 and Ar2, and comparative compounds N and O have a structure in which a benzene moiety is additionally fused in the middle of the core, so all of the comparative compounds A to P correspond to structures outside the definition of the chemical formula 1 of the present invention.

[0389] Compared to the example data using a compound conforming to Formula 1 of the present invention, the comparative example using a comparative compound showed an increase in threshold voltage of about 20%, an increase in driving voltage of about 7%, a decrease in efficiency of about 50%, and a decrease in lifespan of about 60%.

[0390] In summary, the heterocyclic compounds A1 to A332 according to the present application correspond to the heterocyclic compound structure represented by Chemical Formula 1 above and are characterized by a low threshold voltage, driving voltage, high efficiency, and / or long lifespan. It is determined that the compounds according to the present application have an expanded conjugation form due to the characteristic of being 2-substituted with specific substituents (Ar1 and Ar2) compared to comparative compounds A, F, G, H, I, J, K, and M, which results in a relatively low T1 level and smooth energy transfer to the dopant, thereby improving device performance. Furthermore, compared to unipolar p-Hosts such as comparative compounds B, D, and L, the electron flow is smooth, which is particularly advantageous for improving the driving voltage and for exciton emission.

[0391] In addition, when compared to comparative compounds C, E, K, N, and P, the steric hindrance of the comparative example is structurally very large or the molecular weight is very large, so the thermal stability is significantly reduced compared to the compound of the present application, and it can be determined that the degradation is increased and the device lifespan is reduced.

[0392] And in the case of comparative compound O, since the molecular planarity increases compared to the skeleton of the compound in this example and the rotation energy is low, T g It may be determined that the low value caused a degradation in device performance during device deposition.

[0393] <Experimental Example 2> Fabrication of an Organic Light-Emitting Device

[0394] 1) Fabrication of organic light-emitting diodes

[0395] A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was cleaned with distilled water ultrasonics. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) using UV light for 5 minutes in an Ultraviolet (UV) cleaner. Subsequently, the substrate was transferred to a plasma cleaner (PT), subjected to plasma treatment under vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0396] A common layer, a hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino] triphenylamine) and a hole transport layer NPB (N,N'-Di(1-naphthyl)-N,N'-biphenyl)-4,4'-diamine) were formed on the above ITO transparent electrode (anode).

[0397] A light-emitting layer was deposited on top of it using thermal vacuum deposition as follows. Specifically, as the red host of the light-emitting layer, a mixture of any one of A1 to A332 and any one of B3 to B308 from Examples 37 to 78 of Table 8 was used, and a light-emitting layer with a thickness of 500 Å was deposited by doping the red host with 3 wt% of the red phosphorescent dopant (piq)2(Ir)(acac). Subsequently, 60 Å of Bathocuproine (hereinafter BCP) was deposited as a hole-blocking layer, and 200 Å of Alq3 was deposited as an electron-transporting layer on top of it.

[0398] Finally, an organic light-emitting diode was fabricated by forming an electron injection layer by depositing lithium fluoride (LiF) to a thickness of 10 Å on the electron transport layer, and then forming a cathode by depositing an aluminum (Al) cathode to a thickness of 1,200 Å on the electron injection layer.

[0399] Meanwhile, all organic compounds required for OLED device fabrication are 10 each for each material -8 ~10 -6 It was purified by vacuum sublimation under torr and used for OLED fabrication.

[0400] 2) Driving voltage and luminous efficiency of organic light-emitting diodes

[0401] The electroluminescence (EL) characteristics of the organic light-emitting diodes of Examples 37 to 78 in Table 8, manufactured as described above, were measured using MaxScience’s M7000, and based on the measurement results, the reference brightness was 6,000 cd / m² using a lifetime measurement device (M6000) manufactured by MaxScience. 2 When, T 90 The above T was measured. 90 represents the lifetime (unit: h, hours) of the time it takes to reach 90% of the initial brightness.

[0402] The measured characteristics of the organic light-emitting diodes were as shown in Table 8 below. For reference, the following ratios are weight ratios, and Compound Group B (represented by Formula 2) was used as a P-Type host, and Compound Group A (represented by Formula 1) was used as an N-Type host.

[0403] No. Compound Ratio (p:n) Threshold Voltage (V on ) Driving voltage (V op )Efficiency(cd / A)Color coordinates(x, y)Lifetime(T 90)Comparative Example 17B3:A1:13.176.0212.6(0.680, 0.318)15 Comparative Example 18B101:B1:13.196.043.3(0.681, 0.317)7 Comparative Example 19B5:C1:13.476.341.1(0.680, 0.320)1 Comparative Example 20B51:D1:13.346.364.1(0.678, 0.321)12 Comparative Example 21B195:E1:13.316.316.7(0.683, 0.315)7 Comparative Example 22B227:F1:13.256.2310.1(0.679, 0.320)15 Comparative Example 23B36:G1:13.326.369.7(0.681, 0.318)13 Comparative Example 24B174:H1:13.256.285.6(0.680, 0.317)13 Comparative Example 25B41:I1:13.336.419.0(0.681, 0.318)15 Comparative Example 26B23:J1:13.286.308.2(0.679, 0.318)12 Comparative Example 27B197:K1:13.316.357.3(0.681, 0.317)5 Comparative Example 28B51:L1:13.456.544.3(0.682, 0.317)14 Comparative Example 29B195:M1:13.256.198.2(0.683, 0.317)12 Comparative Example 30B32:N1:13.386.366.6(0.678, 0.320)3 Comparative Example 31B261:O1:13.226.209.6(0.680, 0.318)11 Comparative Example 32B41:P1:13.326.347.9(0.677, 0.320)13 Example 37B51:A11:12.165.1742.3(0.679, 0.321)75 Example 38 B51:A11:22.145.1241.7(0.678, 0.320)77 Example 39 B51:A12:12.185.1943.6(0.682, 0.317)72 Example 40 B195:A51:12.195.1844.7(0.677, 0.319)71 Example 41 B101:A211:12.145.1541.3(0.680, 0.320)78 Example 42 B32:A251:12.125.1440.7(0.680, 0.318)76 Example 43B32:A311:12.165.1841.5(0.677, 0.321)70 Example 44B32:A311:22.145.1541.1(0.677, 0.319)75 Example 45 B32:A312:12.185.1940.7(0.679, 0.320)68 Example 46 B32:A321:12.175.1940.9(0.678, 0.320)68 Example 47 B5:A351:12.165.1542.4(0.682, 0.318)75 Example 48 B227:A411:12.065.0447.9(0.680, 0.317)88 Example 49 B197:A431:12.035.0248.2(0.679, 0.319)84 Example 50B261:A451:12.075.0647.6(0.678, 0.320)85 Example 51B23:A611:12.045.0347.5(0.681, 0.319)90 Example 52B47:A681:12.025.0146.8(0.683, 0.316)86 Example 53B41:A771:12.045.0547.2(0.680, 0.320)86 Example 54B174:A811:12.245.2638.6(0.679, 0.319)65 Example 55B36:A831:12.235.2439.5(0.681, 0.317)67 Example 56B3:A851:12.275.2836.4(0.680, 0.318)62 Example 57B195:A1011:12.255.2737.1(0.677, 0.322)65 Example 58B5:A1151:12.265.2638.2(0.680, 0.319)61 Example 59B51:A1211:12.705.7321.7(0.679, 0.320)35 Example 60B195:A1411:12.465.4527.6(0.681, 0.319)47 Example 61B195:A1411:22.435.4126.4(0.680, 0.319)49 Example 62B195:A1412:12.475.4828.5(0.683, 0.316)43 Example 63B261:A1441:12.485.4729.1(0.680, 0.318)43 Example 64B3:A1611:12.375.3834.0(0.679, 0.321)52 Example 65B36:A1691:12.345.3632.7(0.684, 0.315)56 Example 66B47:A1811:12.355.3631.9(0.682, 0.317)54 Example 67B32:A1931:12.335.3431.0(0.680, 0.318)55 Example 68B174:A1941:12.325.3332.0(0.681, 0.317)58 Example 69B41:A1971:12.595.6122.1(0.680, 0.319)32 Example 70B5:A2011:12.475.4828.6(0.679, 0.320)35 Example 71B3:A2211:12.455.4629.3(0.681, 0.316)31 Example 72B51:A2231:12.445.4327.6(0.679, 0.320)38 Example 73B101:A2431:12.045.0347.5(0.680, 0.318)84 Example 74B23:A2571:12.645.6623.6(0.682, 0.317)30 Example 75B197:A2761:11.984.9951.7(0.681, 0.316)93 Example 76B261:A2801:12.245.2638.9(0.680, 0.318)67 Example 77B195:A2991:12.425.4326.9(0.683, 0.316)36 Example 78B227:A3001:12.465.4427.3(0.680, 0.318)33.

[0404] The compounds A to P used in the above Table 8 were as follows.

[0405]

[0406] As can be seen from the results in Table 8 above, compared to the results in Table 7 (using only the heterocyclic compound according to the present application), when the organic layer of the organic light-emitting device is deposited by appropriately mixing the heterocyclic compounds according to the present application, it was confirmed that the organic light-emitting device can appropriately control the threshold voltage and driving voltage, and further improve efficiency or lifespan effects.

[0407] Comparative compounds A to P in Table 8 above all correspond to structures that deviate from the definition of Formula 1 of the present invention, as previously explained. When these are compared with example data using compounds conforming to Formula 1 of the present invention, the comparative examples using the comparative compounds showed an increase in threshold voltage of about 17%, an increase in driving voltage of about 8%, a decrease in efficiency of about 42%, and a decrease in lifespan of about 50%.

[0408] Accordingly, it was confirmed that the results of Examples 37 to 78 correspond to the case where an n-type host compound having strong electron transport characteristics is combined with a p-type host compound having strong hole transport characteristics, compared to Comparative Examples 17 to 32, which do not include a heterocyclic compound according to the present application in the organic layer of an organic light-emitting device, and thus the driving voltage, efficiency, and lifespan are significantly improved by playing a role in balancing the charge within the device.

Claims

1. Heterocyclic compounds represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R1 to R3 are identical or different from one another, and each is independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted C1 to C60 alkyl group, and L1 and L2 are identical or different from each other and are each independently directly bonded; or are substituted or unsubstituted C6 to C60 arylene groups, and Either one of the groups Ar1 and Ar2 is the following chemical formula N, and the other group is a substituted or unsubstituted C6 to C60 aryl group; or the following chemical formula K, a is an integer from 0 to 4, and b is 0 or 1, and c is an integer from 0 to 3, and Each m and n is an integer from 1 to 4, and If each of a, c, m, and n is an integer greater than or equal to 2, the elements inside the parentheses are identical or different from each other, and [Chemical Formula N] In the above chemical formula N, is the position connected by the above chemical formula N, and Among Y1 to Y5, two or more groups are N, one or more other groups are CRa, and the remaining group is CRb, and Ra is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and Rb is hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; or a substituted or unsubstituted C2 to C60 heterocycloalkyl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted ring, and [Chemical Formula K] In the above chemical formula K, is the position connected by the above chemical formula K, and X is O; S; NRx; or CRyRz, and Rk, Rx, Ry, and Rz are identical or different from one another, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, and k is an integer from 0 to 7, and if k is an integer greater than or equal to 2, Rk are identical or different from each other, and The term "substituted or unsubstituted" above means being substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C1 to C60 haloalkyl group; C1 to C60 alkoxy group; C6 to C60 aryloxy group; C1 to C60 alkylthioxy group; C6 to C60 arylthioxy group; C1 to C60 alkyl sulfoxy group; C6 to C60 aryl sulfoxy group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'. R, R' and R" are each independently substituents consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group.

2. In Claim 1, A heterocyclic compound in which the above chemical formula 1 is any one of the following chemical formulas 1-1 to 1-8: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] In the above chemical formulas 1-1 to 1-8, The definition of each substituent is as defined in Chemical Formula 1 above.

3. In Claim 1, R1 to R3 are identical or different from one another, and each independently is hydrogen; or deuterium, heterocyclic compounds.

4. In Claim 1, A heterocyclic compound in which Ra is a substituted or unsubstituted phenyl group; a substituted or unsubstituted carbazole group; a phenyl group condensed into a substituted or unsubstituted aromatic hydrocarbon ring; a phenyl group condensed into a substituted or unsubstituted aromatic heterocyclic ring; a carbazole group condensed into a substituted or unsubstituted aromatic hydrocarbon ring; or a carbazole group condensed into a substituted or unsubstituted aromatic heterocyclic ring.

5. In Claim 1, A heterocyclic compound in which the above chemical formula N is represented by any one of the following structural formulas and is substituted or unsubstituted with a substituent selected from the group consisting of deuterium; a halogen group; and an aryl group having C6 to C60: In the above structural formula, is the location where the above structural formula connects.

6. In Claim 1, A heterocyclic compound represented by the above chemical formula 1, wherein the deuterium content of the heterocyclic compound is 0% or 1% to 100%.

7. In Claim 1, A heterocyclic compound represented by any one of the following chemical formulas: .

8. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, An organic light-emitting device wherein one or more of the above organic layers comprise a heterocyclic compound according to any one of claims 1 to 7.

9. In Claim 8, An organic light-emitting device wherein one or more of the above organic layers further comprise a heterocyclic compound represented by the following chemical formula 2: [Chemical Formula 2] In the above chemical formula 2, L3, L4, La and Lb are identical or different from each other and are each independently directly bonded; or are substituted or unsubstituted C6 to C60 arylene groups, and Each of o, p, q, and r is an integer from 0 to 4, and Ar4 to Ar6 are identical or different from one another and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and R4 to R6 are identical or different from one another and each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 haloalkyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryloxy group; a substituted or unsubstituted C1 to C60 alkylthioxy group; a substituted or unsubstituted C6 to C60 arylthioxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; or -NRR' and, R, R' and R" are each independently hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; or heteroaryl group, and Each d and f is an integer from 0 to 4, and e is an integer from 0 to 2, and If each d, e, f, o, p, q, and r is 2 or an integer greater than 2, the substituents within the parentheses are identical or different from each other, and The sum of d, e, and f is 8.

10. In Claim 9, An organic light-emitting device in which the deuterium content of the heterocyclic compound represented by the above chemical formula 2 is 0% or 1% to 100%.

11. In Claim 9, An organic light-emitting device in which the above chemical formula 2 is represented by any one of the following: .

12. In claim 8, One or more of the above organic layers include a light-emitting layer, and the light-emitting layer includes the above heterocyclic compound, forming an organic light-emitting device.

13. In Claim 8, The above organic light-emitting device further comprises one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport assist layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

14. A composition for an organic layer of an organic light-emitting device comprising a heterocyclic compound according to any one of claims 1 to 7 and a heterocyclic compound represented by the following chemical formula 2: [Chemical Formula 2] In the above chemical formula 2, L3, L4, La and Lb are identical or different from each other and are each independently directly bonded; or are substituted or unsubstituted C6 to C60 arylene groups, and Each of o, p, q, and r is an integer from 0 to 4, and Ar4 to Ar6 are identical or different from one another and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and R4 to R6 are identical or different from one another and each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 haloalkyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryloxy group; a substituted or unsubstituted C1 to C60 alkylthioxy group; a substituted or unsubstituted C6 to C60 arylthioxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; or -NRR' and, R, R' and R" are each independently hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; or heteroaryl group, and Each d and f is an integer from 0 to 4, and e is an integer from 0 to 2, and If each d, e, f, o, p, q, and r is 2 or an integer greater than 2, the substituents within the parentheses are identical or different from each other, and The sum of d, e, and f is 8.

15. In Claim 14, A composition for an organic layer of an organic light-emitting device, wherein the weight ratio of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 is 1:10 to 10:1.

Images