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

Abstract

The present invention relates to a heterocyclic compound represented by chemical formula 1, an organic light-emitting device comprising same, and a composition for an organic material layer of an organic light-emitting device.

Description

Heterocyclic compounds, organic light-emitting devices containing the same, and compositions for the organic layer of organic light-emitting devices

[0001] The present invention relates to a heterocyclic compound, an organic light-emitting device containing the same, and a composition for an organic layer of an organic light-emitting device.

[0002] The present application claims the benefit of the filing dates of Korean Patent Application No. 10-2024-0148376 filed with the Korean Intellectual Property Office on October 28, 2024, Korean Patent Application No. 10-2024-0190780 filed with the Korean Intellectual Property Office on December 19, 2024, and Korean Patent Application No. 10-2025-0156807 filed with the Korean Intellectual Property Office on October 27, 2025, the entire contents of which are incorporated herein by reference.

[0003] Electroluminescent devices are a type of self-emissive display device that has the advantages of a wide viewing angle, excellent contrast, and fast response speed.

[0004] 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.

[0005] 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. In addition, compounds capable of performing functions such as hole injection, hole transport, electron blocking, and electron injection may also be used as organic thin film materials.

[0006] To improve the performance, efficiency, and lifespan of organic light-emitting diodes, the development of organic thin film materials is continuously required.

[0007] The present invention aims to provide a heterocyclic compound, an organic light-emitting device comprising the same, and a composition for the organic layer of an organic light-emitting device.

[0008] In one embodiment of the present application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[0009] [Chemical Formula 1]

[0010]

[0011] X and Y are equal to or different from each other and are each independently O, S, NR, or CR'R'', and

[0012] R, R' and R'' are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, and

[0013] R1 to R4 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and

[0014] Ar1 is a substituted or unsubstituted C6 to C60 aryl group, and

[0015] r1 is an integer from 1 to 10, and if r1 is 2 or more, R1 are the same or different from each other, and

[0016] r2 is an integer from 1 to 6, and if r2 is 2 or more, R2 are the same or different from each other, and

[0017] r3 is an integer from 0 to 4, and if r3 is 2 or greater, R3 are the same or different from each other, and

[0018] r4 is an integer from 0 to 5, and if r4 is 2 or greater, R4 are the same or different from each other, and

[0019] The deuterium substitution rate of the compound of Chemical Formula 1 above is greater than 0% and less than or equal to 100%.

[0020] In addition, in one embodiment of the present application, an organic light-emitting device is provided 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 a heterocyclic compound represented by the aforementioned chemical formula 1.

[0021] In addition, in one embodiment of the present application, a composition for an organic layer of an organic light-emitting device is provided, comprising a heterocyclic compound represented by the above formula 1; and a heterocyclic compound represented by the following formula 2 or formula 3.

[0022] When the compounds described in this specification are used in the light-emitting layer of an organic light-emitting device, they can lower the driving voltage of the device, improve the luminous efficiency, and improve the lifespan characteristics of the device.

[0023] Specifically, it has the characteristic of excellent electron transfer capability within the device due to the through-space charge transfer action between the triazine and the substituent bonded to the ortho site.

[0024] In addition, the expansion of the LUMO region allows for more electrons within the molecule, resulting in excellent luminescence efficiency.

[0025] FIGS. 1 to 3 are schematic diagrams illustrating the stacked structure of an organic light-emitting device according to one embodiment of the present application.

[0026] The present specification will be described in more detail below.

[0027] 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.

[0028] In this specification, of the chemical formula means the position where it is combined.

[0029] In this specification, n of Cn means the number of carbon atoms. That is, for example, C6 to C60 means 6 to 60 carbon atoms.

[0030] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution location is not limited to the location where the hydrogen atom is substituted, that is, any location 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.

[0031] In this specification, "substituted or unsubstituted" means deuterium; halogen group; -CN; 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; It means that one or more substituents selected from the group consisting of -SiRR'R"; -P(=O)RR'; and -NRR' are substituted or unsubstituted with a substituent connected to two or more substituents selected from the above substituents, and 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.

[0032] 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) is an isotope of hydrogen, some hydrogen atoms can be deuterium.

[0033] In one embodiment of the present application, "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%.

[0034] In one embodiment of the present application, where "substituents are not indicated in the chemical formula or compound structure," if 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.

[0035] In one embodiment of the present application, 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.

[0036] In one embodiment of the present application, an isotope, which means an atom having the same atomic number (Z) but different mass number (A), can also be interpreted as an element having the same number of protons but different number of neutrons.

[0037] In one embodiment of the present application, the meaning of the content T% of a specific substituent can be defined as T2 / T1Y100 = 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.

[0038] That is, in one example, A deuterium content of 20% in a phenyl group represented by can be expressed as 20% when the total number of substituents that 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 a phenyl group can be represented by the following structural formula.

[0039]

[0040] In addition, in one embodiment of the present application, "phenyl group having 0% deuterium content" may mean a phenyl group that does not contain deuterium atoms, i.e., has five hydrogen atoms.

[0041] In this specification, the halogen may be fluorine, chlorine, bromine, or iodine.

[0042] In the present 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, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, There are 1,1-dimethyl-propyl groups, isohexyl groups, 2-methylpentyl groups, 4-methylhexyl groups, 5-methylhexyl groups, etc., but are not limited to these.

[0043] In the present specification, the alkenyl 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 alkenyl group may be 2 to 60, specifically 2 to 40, more specifically 2 to 20. Specific examples include, but are not limited to, 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.

[0044] In the present 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.

[0045] In this specification, a haloalkyl group refers to an alkyl group substituted with a halogen group, and specific examples include -CF3, -CF2CF3, etc., but are not limited thereto.

[0046] In this specification, the alkoxy group is represented as -O(R101), and R101 may be an example of the aforementioned alkyl group.

[0047] In this specification, the aryloxy group is represented as -O(R102), and R102 may be an example of the aryl group described above.

[0048] In this specification, the alkylthoxy group is represented as -S(R103), and R103 may be an example of the alkyl group described above.

[0049] In this specification, the arylthioxy group is represented as -S(R104), and R104 may be an example of the aryl group described above.

[0050] In this specification, the alkyl sulfoxy group is represented as -S(=0)2(R105), and R105 may be an example of the aforementioned alkyl group.

[0051] In this specification, the aryl sulfoxy group is represented as -S(=0)2(R106), and R106 may be an example of the aryl group described above.

[0052] 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, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc. are included, but are not limited thereto.

[0053] 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.

[0054] 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 includes a spiro group. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the 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.

[0055] In the present specification, the terphenyl group may be selected from the following structures.

[0056]

[0057] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

[0058] When the above fluorenyl group is substituted, it may be any one of the following structures, but is not limited thereto.

[0059]

[0060] 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 pyridine group, pyrrole group, pyrimidine group, pyridazine group, furan group, thiophene group, imidazole group, pyrazol group, oxazole group, isoxazole group, thiazole group, isothiaazole group, triazole group, furazane group, oxadiazole group, thiadiazole group, dithiazole group, tetrazolyl group, pyran group, thiopyran group, diazine group, oxazine group, thiazine group, dioxin group, triazine group, tetrazine group, quinoline group, isoquinoline group, quinazolin group, isoquinazolin group, quinozolin group, naphthiridine group, acridine group, phenanthridine group, imidazopyridine group, diazanaphthalene group, triazinidene group, indole group, indolizine group, benzothiazole group, benzoxazole group, Benzimidazole group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazole group, benzocarbazole group, dibenzocarbazole group, phenazine group, dibenzosilol group, Spirobi(dibenzosilol), dihydrophenazine group, phenoxazine group, phenanthridine group, thienyl group, indolo[2,3-a]carbazole group, indolo[2,3-b]carbazole group, indolin group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridine group, phenanthrazine group, phenothiathiazine group, phthalazine group, phenanthroline group, naphthobenzofuran group, naphthobenzothiophene group, benzo[c][1,2,5]thiadiazole group, Examples include 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5,10-dihydrodibenzo[b,e][1,4]azacillin group, pyrazolo[1,5-c]quinazolin group, pyrido[1,2-b]indazole group, pyrido[1,2-a]imidazo[1,2-e]indolin group, 5,11-dihydroindeno[1,2-b]carbazole group, but are not limited to these.

[0061] In this specification, when a substituent is a carbazole group, it means bonding to the nitrogen or carbon of the carbazole.

[0062] In the present specification, when a carbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole.

[0063] In this specification, the benzocarbazole group may be any one of the following structures.

[0064]

[0065] In this specification, the dibenzocarbazole group may be any one of the following structures.

[0066]

[0067] In the present specification, the naphthobenzofuran group may be any one of the following structures.

[0068]

[0069] In the present specification, the naphthobenzothiophene group may be any one of the following structures.

[0070]

[0071] In the present specification, the silyl group is a substituent comprising Si and in which the Si atom is directly connected as a radical, and is represented as -Si(R107)(R108)(R109), and R107 to R109 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.

[0072] 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 thereto.

[0073] In this specification, the phosphine oxide group is represented as -P(=O)(R110)(R111), and R110 and R111 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 examples described above may apply to the alkyl group and the aryl group. For example, the phosphine oxide group may include dimethylphosphine oxide, diphenylphosphine oxide, dinaphthylphosphine oxide, etc., but is not limited thereto.

[0074] In the present specification, the amine group is represented as -N(R112)(R113), and R112 and R113 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.

[0075] In this specification, the examples of aryl groups described above may be applied, except that the arylene group is a divalent group.

[0076] In this specification, the examples of the aforementioned heteroaryl groups may be applied, except that the heteroaryl group is a divalent group.

[0077] 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.

[0078] 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.

[0079] In one embodiment of the present application, a group not represented by a substituent; or a group represented by hydrogen, may all mean that they are substitutable for deuterium. That is, hydrogen; or deuterium may indicate a state in which they are mutually substitutable.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] In one embodiment of the present application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[0084] [Chemical Formula 1]

[0085]

[0086] X and Y are equal to or different from each other and are each independently O, S, NR, or CR'R'', and

[0087] R, R' and R'' are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, and

[0088] R1 to R4 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and

[0089] Ar1 is a substituted or unsubstituted C6 to C60 aryl group, and

[0090] r1 is an integer from 1 to 10, and if r1 is 2 or more, R1 are the same or different from each other, and

[0091] r2 is an integer from 1 to 6, and if r2 is 2 or more, R2 are the same or different from each other, and

[0092] r3 is an integer from 0 to 4, and if r3 is 2 or greater, R3 are the same or different from each other, and

[0093] r4 is an integer from 0 to 5, and if r4 is 2 or greater, R4 are the same or different from each other, and

[0094] The deuterium substitution rate of the compound of Chemical Formula 1 above is greater than 0% and less than or equal to 100%.

[0095] The heterocyclic compound represented by the above chemical formula 1 contains a phenyl linker between Fused Carbazole and Triazine, wherein the Fused Carbazole and Triazine have an ortho bond based on the phenyl linker.

[0096] Through-Space Charge Transfer occurs because the above-mentioned Fused Carbazole and triazine have ortho-site bonds. That is, not only electron transfer through intramolecular bonds but also electron transfer through intramolecular space is possible, so it has excellent electron transfer capability and, accordingly, has the characteristic of excellent driving voltage.

[0097] In addition, the heterocyclic compound represented by the above chemical formula 1 has a composition in which the deuterium substitution rate is greater than 0% and less than or equal to 100%, which lowers the vibration energy and rotation energy of the molecule and increases the stability of the molecular structure, thereby providing excellent device lifespan.

[0098] In one embodiment of the present application, the formula 1 It may be represented by any one of the following chemical formulas 1-1 to 1-6.

[0099] [Chemical Formula 1-1]

[0100]

[0101] [Chemical Formula 1-2]

[0102]

[0103] [Chemical Formula 1-3]

[0104]

[0105] [Chemical Formula 1-4]

[0106]

[0107] [Chemical Formula 1-5]

[0108]

[0109] [Chemical Formula 1-6]

[0110]

[0111] In chemical formulas 1-1 to 1-6, X, R1 and r1 are the same as defined in chemical formula 1.

[0112] In one embodiment of the present application, the formula 1 may be represented by any one of the following formulas 1-7 to 1-12.

[0113] [Chemical Formula 1-7]

[0114]

[0115] [Chemical Formula 1-8]

[0116]

[0117] [Chemical Formula 1-9]

[0118]

[0119] [Chemical Formula 1-10]

[0120]

[0121] [Chemical Formula 1-11]

[0122]

[0123] [Chemical Formula 1-12]

[0124]

[0125] In the above chemical formulas 1-7 to 1-12,

[0126] X and Y are identical to the definitions in Claim 1 described above, and

[0127] Ar2 is a C6 to C60 aryl group, and

[0128] [D] represents deuterium substitution, n1 is 1 to 10, and n2 is 3 to 11.

[0129] In one example, In the phenyl group represented by [D]1, [D]1 means that any one of the five total substituents the phenyl group can have is a deuterium. For example, it means any one of the following structural formulas.

[0130]

[0131] In one embodiment of the present application, the formula 1 may be represented by any one of the following formulas 1-13 to 1-16.

[0132] [Chemical Formula 1-13]

[0133]

[0134] [Chemical Formula 1-14]

[0135]

[0136] [Chemical Formula 1-15]

[0137]

[0138] [Chemical Formula 1-16]

[0139]

[0140] In the above chemical formulas 1-13 to 1-16, X, Y, R1 to R4, Ar1 and r1 to r4 are the same as the definitions in chemical formula 1.

[0141] In one embodiment of the present application, the above chemical formula 1 may be formed by combining the following structural formulas A, B, and C.

[0142] [Structural Formula A]

[0143]

[0144] [Structural Formula B]

[0145]

[0146] [Structural Formula C]

[0147]

[0148] In structural formulas A, B, and C,

[0149] X, Y, R1 to R4, Ar1, and r1 to r4 are identical to the definitions in Chemical Formula 1 above, and

[0150] represents the region where structural formula A and structural formula B are combined, and represents the region where structural formula B and structural formula C are combined.

[0151] In one embodiment of the present application, the deuterium substitution rate of the structural formula A may be 10% to 90%.

[0152] In another embodiment, the deuterium substitution rate of the above structural formula A may be 20% to 85%.

[0153] In another embodiment, the deuterium substitution rate of the above structural formula A may be 30% to 80%.

[0154] In another embodiment, the deuterium substitution rate of the above structural formula A may be 30% to 75%.

[0155] In another embodiment, the deuterium substitution rate of the above structural formula A may be 30% to 70%.

[0156] In one embodiment of the present application, the deuterium substitution rate of the structural formula B may be 0%.

[0157] In one embodiment of the present application, the deuterium substitution rate of the structural formula C may be 10% to 90%.

[0158] In another embodiment, the deuterium substitution rate of the above structural formula C may be 20% to 90%.

[0159] In another embodiment, the deuterium substitution rate of the structural formula C may be 25% to 85%.

[0160] In another embodiment, the deuterium substitution rate of the structural formula C may be 30% to 85%.

[0161] In another embodiment, the deuterium substitution rate of the structural formula C may be 35% to 85%.

[0162] In one embodiment of the present application, Ar1 may be a substituted or unsubstituted C6 to C40 aryl group.

[0163] In another embodiment, the Ar1 may be a substituted or unsubstituted C6 to C20 aryl group.

[0164] In another embodiment, the Ar1 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; or a substituted or unsubstituted fluorenyl group.

[0165] In another embodiment, the Ar1 may be a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group.

[0166] In another embodiment, the Ar1 may be a phenyl group; or a biphenyl group.

[0167] In the present application, the substituent range of Ar2 may be the same as the substituent range of Ar1.

[0168] In one embodiment of the present application, R1 to R4 may be the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0169] In another embodiment, R1 to R4 may be the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0170] In another embodiment, R1 to R4 may be the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0171] In another embodiment, R1 to R4 may be the same or different from each other and each independently be hydrogen; deuterium; methyl group; ethyl group; propyl group; butyl group; phenyl group; biphenyl group; terphenyl group; dibenzofuran group; or dibenzothiophene group.

[0172] In another embodiment, R1 to R4 may be the same or different from each other and each independently be hydrogen; or deuterium.

[0173] In one embodiment of the present application, R, R' and R'' may be the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group.

[0174] In another embodiment, R, R' and R'' may be the same or different from each other and each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 aryl group.

[0175] In another embodiment, R, R' and R'' may be the same or different from each other and each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; or a substituted or unsubstituted C6 to C20 aryl group.

[0176] In another embodiment, R, R' and R'' may be the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group.

[0177] In another embodiment, R, R' and R'' may be the same or different from each other and each independently hydrogen; deuterium; a methyl group substituted or unsubstituted with deuterium; an ethyl group substituted or unsubstituted with deuterium; a propyl group substituted or unsubstituted with deuterium; a butyl group substituted or unsubstituted with deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium.

[0178] In another embodiment, R, R' and R'' may be the same or different from each other and each independently be hydrogen; deuterium; a methyl group substituted or unsubstituted with deuterium; or a phenyl group substituted or unsubstituted with deuterium.

[0179] In another embodiment, the R may be a phenyl group substituted or unsubstituted with deuterium.

[0180] In another embodiment, the R' and R'' may be the same or different from each other and each independently a methyl group substituted or unsubstituted with deuterium.

[0181] In one embodiment of the present application, r1 is an integer from 1 to 5, and if r1 is 2 or more, R1 may be the same or different from each other.

[0182] In another embodiment, r1 is an integer from 1 to 3, and if r1 is 2 or more, R1 may be the same or different from each other.

[0183] In another embodiment, the above r1 may be 1.

[0184] In one embodiment of the present application, r2 is an integer from 1 to 3, and if r2 is 2 or more, R2 may be the same or different from each other.

[0185] In another embodiment, r2 is an integer from 1 to 2, and if r2 is 2 or more, R2 may be the same or different from each other.

[0186] In another embodiment, the above r2 may be 1.

[0187] In one embodiment of the present application, r3 is an integer from 0 to 2, and if r3 is 2 or more, R3 may be the same or different from each other.

[0188] In another embodiment, the r3 may be 0 or 1.

[0189] In one embodiment of the present application, r4 is an integer from 0 to 3, and if r4 is 2 or more, R4 may be the same or different from each other.

[0190] In another embodiment, the r4 may be 0 or 1.

[0191] In one embodiment of the present application, the deuterium substitution rate of the compound of Formula 1 may be 10% to 90%.

[0192] In another embodiment, the deuterium substitution rate of the compound of Formula 1 may be 10% to 80%.

[0193] In another embodiment, the deuterium substitution rate of the compound of Formula 1 may be 10% to 70%.

[0194] In another embodiment, the deuterium substitution rate of the compound of Formula 1 may be 10% to 60%.

[0195] In another embodiment, the deuterium substitution rate of the compound of Formula 1 may be 15% to 60%.

[0196] In one embodiment of the present application, the formula 1 may be represented by any one of the following compounds.

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218] In one embodiment of the present application, the compound is an example and is not limited thereto, and may include other compounds of Formula 1 that include additional substituents. In addition, regarding the substitution positions of deuterium in the compound, specific positions may be excluded during the deuterium substitution and synthesis process, and hydrogen and deuterium may exist in a mixed state.

[0219] In addition, by introducing various substituents into the structure of Chemical Formula 1, compounds having the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials used in the manufacture of organic light-emitting devices into the core structure, materials that satisfy the conditions required for each organic layer can be synthesized.

[0220] In addition, the band gap can be finely controlled by introducing various substituents into the structure of Chemical Formula 1 or by changing the bonding position, and at the same time, the properties at the interface between organic layers can be improved.

[0221] In addition, the compound of Chemical Formula 1 has excellent thermal stability, and this thermal stability provides driving stability to the organic light-emitting device and improves lifespan characteristics.

[0222] In one embodiment of the present application, an organic light-emitting device is provided 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 a heterocyclic compound represented by Chemical Formula 1.

[0223] In another embodiment, an organic light-emitting device is provided 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 one type of heterocyclic compound represented by Chemical Formula 1.

[0224] In another embodiment, an organic light-emitting device is provided 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 two or more heterocyclic compounds represented by Chemical Formula 1.

[0225] In another embodiment, the heterocyclic compound represented by the above chemical formula 1 can be used as a light-emitting material for the light-emitting layer of an organic light-emitting device.

[0226] In another embodiment, the heterocyclic compound represented by the above chemical formula 1 can be used as a host material for the light-emitting layer of an organic light-emitting device.

[0227] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0228] In another embodiment, the first electrode may be a negative electrode and the second electrode may be a positive electrode.

[0229] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a material for the blue organic light-emitting device.

[0230] In one embodiment of the present application, 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.

[0231] In one embodiment of the present application, 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.

[0232] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

[0233] In one embodiment of the present application, 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 light-emitting layer material of the green organic light-emitting device.

[0234] In one embodiment of the present application, 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 light-emitting layer material of the red organic light-emitting device.

[0235] In one embodiment of the present application, the specific details regarding the heterocyclic compound represented by Chemical Formula 1 are the same as those described above.

[0236] The organic light-emitting device of the present invention can be manufactured by conventional methods and materials for manufacturing organic light-emitting devices, except that one or more organic layers are formed using the aforementioned heterocyclic compound.

[0237] The above heterocyclic compound can be formed as an organic layer by vacuum deposition as well as solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0238] The organic layer of the organic light-emitting device of the present invention 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 invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0239] In one embodiment of the present application, Ir(ppy)3, a green phosphorescent dopant, may be used as an iridium-based dopant.

[0240] In one embodiment of the present application, (piq)2(Ir)(acac), a red phosphorescent dopant, may be used as an iridium-based dopant.

[0241] In one embodiment of the present application, the organic light-emitting element comprises an organic layer comprising a light-emitting layer, and the light-emitting layer comprises the heterocyclic compound.

[0242] In one embodiment of the present application, the organic light-emitting element comprises an organic layer comprising a light-emitting layer, wherein the light-emitting layer comprises a host material, and the host material comprises the heterocyclic compound.

[0243] In the organic light-emitting device of the present invention, the organic layer comprises an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may comprise the heterocyclic compound.

[0244] In another organic light-emitting device, the organic layer includes a hole-blocking layer, and the hole-blocking layer may include the heterocyclic compound.

[0245] In another organic light-emitting device, the organic layer includes an electron blocking layer, and the electron blocking layer may include the heterocyclic compound.

[0246] In another organic light-emitting device, the organic layer comprises a hole transport layer, a light-emitting layer, or an electron blocking layer, and the hole transport layer, the light-emitting layer, or the electron blocking layer may comprise the heterocyclic compound.

[0247] In another organic light-emitting device, the organic layer comprises a hole transport layer or a hole transport auxiliary layer, and the hole transport layer or the hole transport auxiliary layer may comprise the heterocyclic compound.

[0248] In the organic light-emitting device of the present application, 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.

[0249] Materials with a relatively low work function can be used as cathode materials, and metals, metal oxides, or conductive polymers can be used. Specific examples of the above cathode materials 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 to these.

[0250] As the hole injection material, known hole injection materials may be used, 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, or Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), Polyaniline / Camphor sulfonic acid, or Polyaniline / Poly(4-styrene-sulfonate) can be used.

[0251] Pyrazolin derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc., may be used as hole transport materials, and low molecular weight or high molecular weight materials may also be used.

[0252] As electron transport materials, metal complexes of oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives, etc., may be used, and not only low molecular weight materials but also high molecular weight materials may be used.

[0253] For example, LiF is commonly used as an electron injection material in the industry, but the present application is not limited thereto.

[0254] As the light-emitting material, red, green, or blue light-emitting materials may be used, 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, or phosphorescent materials may be used. As the light-emitting material, 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.

[0255] 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.

[0256] An organic light-emitting device according to one embodiment of the present application may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0257] A heterocyclic compound according to one embodiment of the present application can operate in organic electronic devices, including organic solar cells, organic photosensitive materials, and organic transistors, on a principle similar to that applied to organic light-emitting devices.

[0258] The organic light-emitting device of the present invention 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 blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0259] The organic light-emitting device of the present invention 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, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0260] FIGS. 1 to 3 illustrate the stacking sequence of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present application. 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.

[0261] According to FIG. 1, an organic light-emitting device is shown 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 in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate may be implemented as shown in FIG. 2.

[0262] Figure 3 illustrates a case where the organic layer is multilayered.

[0263] The organic light-emitting device according to FIG. 3 includes a hole injection layer (301), a hole transport layer (302), a light-emitting layer (303), a hole blocking layer (307), an electron transport layer (304), and an electron injection layer (305).

[0264] However, the scope of the present application is not limited by such a stacked structure, and, if necessary, layers other than the light-emitting layer may be omitted, or other necessary functional layers may be added.

[0265] The organic layer containing the above chemical formula 1 may additionally include other materials as needed.

[0266] In one embodiment of the present application, an organic light-emitting device is provided in which the host material further comprises a heterocyclic compound represented by the following chemical formula 2 or chemical formula 3.

[0267] [Chemical Formula 2]

[0268]

[0269] In Chemical Formula 2,

[0270] R21 and R22 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and

[0271] R7 and R8 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and

[0272] r7 and r8 are each integers from 0 to 7, and if r7 is 2 or more, R7 are the same or different from each other, and if r8 is 2 or more, R8 are the same or different from each other, and

[0273] [Chemical Formula 3]

[0274]

[0275] In Chemical Formula 3,

[0276] A is a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring, and

[0277] R23 and R24 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and

[0278] R9 and R10 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and

[0279] r9 and r10 are each integers from 0 to 4, and if r9 is 2 or more, R9 is the same or different from each other, and if r10 is 2 or more, R10 is the same or different from each other.

[0280] In one embodiment of the present application, R21 and R22 may be the same or different from each other and each independently substituted or unsubstituted C6 to C40 aryl groups; or substituted or unsubstituted C2 to C40 heteroaryl groups.

[0281] In another embodiment, R21 and R22 may be the same or different from each other and each independently substituted or unsubstituted C6 to C20 aryl groups; or substituted or unsubstituted C2 to C20 heteroaryl groups.

[0282] In another embodiment, R21 and R22 may be the same or different from each other and each independently 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 fluorenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0283] In another embodiment, R21 and R22 may be the same or different from each other and each independently a phenyl group substituted or unsubstituted with a deuterium, a cyano group, or a substituted or unsubstituted silyl group; a biphenyl group substituted or unsubstituted with a deuterium; a terphenyl group substituted or unsubstituted with a deuterium; a naphthyl group substituted or unsubstituted with a deuterium; a dimethylfluorenyl group substituted or unsubstituted with a deuterium; a diphenylfluorenyl group substituted or unsubstituted with a deuterium; a spirobifluorenyl group substituted or unsubstituted with a deuterium; a phenanthrene group substituted or unsubstituted with a deuterium; a triphenylene group substituted or unsubstituted with a deuterium; a dibenzofuran group substituted or unsubstituted with a deuterium; or a dibenzothiophene group substituted or unsubstituted with a deuterium.

[0284] In one embodiment of the present application, R7 and R8 may be the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0285] In another embodiment, R7 and R8 may be the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophen group.

[0286] In another embodiment, R7 and R8 may be the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

[0287] In another embodiment, R7 and R8 may be the same or different from each other and each independently hydrogen; or deuterium.

[0288] In one embodiment of the present application, A may be a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring.

[0289] In another embodiment, A may be a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.

[0290] In another embodiment, A may be a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring.

[0291] In another embodiment, the above A may be a substituted or unsubstituted benzene ring.

[0292] In another embodiment, the above A may be a benzene ring substituted or unsubstituted with deuterium.

[0293] In one embodiment of the present application, R23 and R24 may be the same or different from each other and each independently substituted or unsubstituted C6 to C40 aryl groups; or substituted or unsubstituted C2 to C40 heteroaryl groups.

[0294] In another embodiment, R23 and R24 may be the same or different from each other and each independently substituted or unsubstituted C6 to C20 aryl groups; or substituted or unsubstituted C2 to C20 heteroaryl groups.

[0295] In another embodiment, R23 and R24 may be the same or different from each other and each independently 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 fluorenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0296] In one embodiment of the present application, R9 and R10 may be the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0297] In another embodiment, R9 and R10 may be the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophen group.

[0298] In another embodiment, R9 and R10 may be the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

[0299] In another embodiment, R9 and R10 may be the same or different from each other and each independently hydrogen; or deuterium.

[0300] In one embodiment of the present application, the deuterium content of Formula 2 may be 0% to 100%.

[0301] In another embodiment, the deuterium content of the above chemical formula 2 may be 0% or 20% to 100%.

[0302] In another embodiment, the deuterium content of the above chemical formula 2 may be 0% or 40% to 100%.

[0303] In another embodiment, the deuterium content of the above chemical formula 2 may be 0% or 60% to 100%.

[0304] In another embodiment, the deuterium content of the above chemical formula 2 may be 0% or 80% to 100%.

[0305] In another embodiment, the deuterium content of the above chemical formula 2 may be 0% or 100%.

[0306] In one embodiment of the present application, the deuterium content of Formula 3 may be 0% to 100%.

[0307] In another embodiment, the deuterium content of the above chemical formula 3 may be 0% or 20% to 100%.

[0308] In another embodiment, the deuterium content of the above chemical formula 3 may be 0% or 40% to 100%.

[0309] In another embodiment, the deuterium content of the above chemical formula 3 may be 0% or 60% to 100%.

[0310] In another embodiment, the deuterium content of the above chemical formula 3 may be 0% or 80% to 100%.

[0311] In another embodiment, the deuterium content of the above chemical formula 3 may be 0% or 100%.

[0312] In one embodiment of the present application, an organic light-emitting device is provided in which the chemical formula 2 is represented by any one of the following compounds.

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319] In one embodiment of the present application, an organic light-emitting device is provided in which the chemical formula 3 is represented by any one of the following compounds.

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326] An organic light-emitting device further comprising a heterocyclic compound represented by the above chemical formula 2 or 3 may be subject to the provisions regarding an organic light-emitting device comprising a heterocyclic compound represented by the above chemical formula 1.

[0327] In another embodiment, the heterocyclic compound represented by the above chemical formula 2 or 3 can be used as a light-emitting material for the light-emitting layer of an organic light-emitting device.

[0328] In another embodiment, the heterocyclic compound represented by the chemical formula 2 or 3 can be used as a light-emitting material in the light-emitting layer of an organic light-emitting device and can be used as a p-type host material.

[0329] In the organic light-emitting device of the present invention, the organic layer may include a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 or Formula 3. The organic layer may be formed by pre-mixing the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 or 3 using a thermal vacuum deposition method.

[0330] In another organic light-emitting device, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host material, and the host material may comprise a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2 or 3.

[0331] In another organic light-emitting device, the organic layer comprises a light-emitting layer, and the n-type host material of the light-emitting layer may include a heterocyclic compound represented by Chemical Formula 1, and the p-type host material may include a heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3.

[0332] In one embodiment of the present application, 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 composition for organic layers according to one embodiment of the present application.

[0333] In one embodiment of the present application, the step of forming the organic layer is to supply the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 or Formula 3 to their respective individual sources, and then form the layer using a thermal vacuum deposition method, thereby providing a method for manufacturing an organic light-emitting device.

[0334] In one embodiment of the present application, a method for manufacturing an organic light-emitting device is provided, wherein the step of forming the organic layer is formed by pre-mixing a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 or 3 and using a thermal vacuum deposition method.

[0335] An organic light-emitting device according to one embodiment of the present application can be manufactured by a conventional method and material for manufacturing organic light-emitting devices, except that an organic layer is formed using the aforementioned heterocyclic compound.

[0336] The organic light-emitting device of the present invention 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, an electron blocking layer, an electron injection layer, an electron transport layer, a hole assist layer, and a hole blocking layer.

[0337] In one embodiment of the present application, a composition for an organic layer of an organic light-emitting device is provided, comprising a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 or Formula 3.

[0338] The heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 have similar thermal stability, so they can be deposited in a constant ratio. In addition, the composition for the organic layer of the organic light-emitting device of the present application has a high glass transition temperature (Tg), so the material can be deposited more stably on the substrate.

[0339] The weight ratio of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 may be 1:1 to 1:10, or the weight ratio of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 3 may be 1:1 to 1:10.

[0340] The weight ratio of the heterocyclic compound represented by Formula 1 to the heterocyclic compound represented by Formula 2 in the above composition may be 1:1 to 1:8, 1:1 to 1:5, 1:1 to 1:4, and preferably 1:1 to 1:3.

[0341] The weight ratio of the heterocyclic compound represented by Formula 1 to the heterocyclic compound represented by Formula 3 in the above composition may be 1:1 to 1:8, 1:1 to 1:5, 1:1 to 1:4, and preferably 1:1 to 1:3.

[0342] As the weight ratio increases, the amount of holes injected into the light-emitting layer increases, and basically, the more holes injected into the device, the faster recombination occurs. Consequently, the number of electrons accumulated at the interface decreases, which lowers molecular instability caused by excess electrons and can increase the lifespan of the device.

[0343] When the weight ratio between the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, or the weight ratio between the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 3, satisfies the aforementioned range, the mobility speeds of holes and electrons are balanced, and the emission zone is located in the center of the EML layer.

[0344] When a heterocyclic compound represented by the above chemical formula 1 is included in larger quantities, the ratio of electrons to holes in the light-emitting layer is not balanced, resulting in a shortage of holes and the accumulation of electrons, which in turn leads to inferior efficiency and lifespan of the device.

[0345] The above composition can be used when forming an organic layer of an organic light-emitting device, and can be used more preferably as a host material for a light-emitting layer.

[0346] The above composition is in the form of a simple mixture of two or more compounds. Before forming the organic layer of the organic light-emitting diode, materials in a powder state may be mixed, or compounds that are in a liquid state at an appropriate temperature or higher may be mixed. The above 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.

[0347] The above composition may additionally include materials known in the art, such as solvents and additives.

[0348] 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.

[0349] <Synthetic Example>

[0350] [Preparation Example 1] Preparation of Compound 1-1

[0351]

[0352] 1) Preparation of intermediate 1-1-1

[0353] 12H-benzo[4,5]thieno[2,3-a]carbazole [A] (10 g, 0.037 mol), Triflic acid (78.04 g, 0.52 mol), and D6-Benzene (200 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 100°C for 5 hours. After the reaction was complete, H2O (100 mL) was added to neutralize the mixture. The precipitated solid was filtered to obtain intermediate 1-1-1 (8.48 g, yield 82%).

[0354] 2) Preparation of Intermediate 1-1-2

[0355] 2-chloro-4-phenyl-6-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,5-triazine [B] (5 g, 0.012 mol), (2-fluorophenyl)boronic acid (1.85 g, 0.013 mol), Pd(PPh3)4 (0.42 g, 0.00036 mol), K2CO3 (3.32 g, 0.024 mol), and 1,4-Dioxane (50 mL) / H2O (10 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 120°C. After cooling, extraction was performed, and the organic layer was filtered using a silica gel filter to obtain intermediate 1-1-2 (5.15 g, yield 87%).

[0356] 3) Preparation of Compound 1-1

[0357] Intermediate 1-1-2 (5.15 g, 0.010 mol), intermediate 1-1-1 (3.07 g, 0.011 mol), Cs2CO3 (6.52 g, 0.020 mol), and DMA (50 mL) were placed in a one-neck round-bottom flask, and the mixture was refluxed at 185°C. After the reaction was complete, the precipitated solid was filtered, dissolved in 1,2-Dichlorobenzene, filtered via silica gel, and concentrated to obtain compound 1-1 (5.72 g, yield 76%).

[0358] The target compound C of Table 1 below was obtained by synthesizing in the same manner as the above preparation example, except that the reactants [A] and [B] of the above preparation example were changed to reactants A and B of Table 1 below.

[0359] [Table 1]

[0360]

[0361]

[0362]

[0363]

[0364] [Preparation Example 2] Preparation of Compound 1-41

[0365]

[0366] 1) Preparation of intermediate 1-41-1

[0367] (9-phenyldibenzo[b,d]furan-3-yl)boronic acid [A] (10 g, 0.035 mol), Triflic acid (73.54 g, 0.49 mol), and D6-Benzene (200 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 100°C for 5 hours. After the reaction was complete, H2O (100 mL) was added to neutralize the mixture. The precipitated solid was filtered to obtain intermediate 1-41-1 (8.96 g, yield 87%).

[0368] 2) Preparation of intermediate 1-41-2

[0369] 2-chloro-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine (5 g, 0.018 mol), intermediate 1-41-1 (5.88 g, 0.020 mol), Pd(PPh3)4 (0.62 g, 0.00054 mol), K2CO3 (4.98 g, 0.036 mol), and 1,4-Dioxane (50 mL) / H2O (10 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 120°C. After cooling, extraction was performed, and the organic layer was filtered using silica gel to obtain intermediate 1-41-2 (6.83 g, yield 76%).

[0370] 3) Preparation of Compound 1-41

[0371] Intermediate 1-41-2 (6.83 g, 0.014 mol), 12H-benzo[4,5]thieno[2,3-a]carbazole [B] (4.21 g, 0.015 mol), Cs2CO3 (9.12 g, 0.028 mol), and DMA (50 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 185°C. After the reaction was complete, the precipitated solid was filtered, dissolved in 1,2-Dichlorobenzene, filtered via silica gel, and concentrated to obtain compound 1-41 (7.17 g, yield 68%).

[0372] The target compound D of Table 2 below was obtained by synthesizing in the same manner as the above preparation example, except that the reactants [A] and [B] of the above preparation example were changed to reactants A and B of Table 2 below.

[0373] [Table 2]

[0374]

[0375]

[0376]

[0377] [Preparation Example 3] Preparation of Compound 1-82

[0378]

[0379] 1) Preparation of intermediate 1-82-1

[0380] (9-phenyldibenzo[b,d]furan-4-yl)boronic acid [A] (10 g, 0.035 mol), Triflic acid (73.54 g, 0.49 mol), and D6-Benzene (200 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 100°C for 5 hours. After the reaction was complete, H2O (100 mL) was added to neutralize the mixture. The precipitated solid was filtered to obtain intermediate 1-82-1 (9.43 g, yield 91%).

[0381] 2) Preparation of intermediate 1-82-2

[0382] 12H-benzo[4,5]thieno[2,3-a]carbazole [B] (10 g, 0.037 mol), Triflic acid (78.04 g, 0.52 mol), and D6-Benzene (200 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 100°C for 5 hours. After the reaction was complete, H2O (100 mL) was added to neutralize the mixture. The precipitated solid was filtered to obtain intermediate 1-82-2 (8.59 g, yield 84%).

[0383] 3) Preparation of intermediate 1-82-3

[0384] 2-chloro-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine (5 g, 0.018 mol), intermediate 1-82-1 (5.92 g, 0.020 mol), Pd(PPh3)4 (0.62 g, 0.00054 mol), K2CO3 (4.98 g, 0.036 mol), and 1,4-Dioxane (50 mL) / H2O (10 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 120°C. After cooling, extraction was performed, and the organic layer was filtered using silica gel to obtain intermediate 1-82-3 (7.31 g, yield 81%).

[0385] 4) Preparation of Compound 1-82

[0386] Intermediate 1-82-3 (7.31 g, 0.015 mol), intermediate 1-82-2 (4.19 g, 0.015 mol), Cs2CO3 (9.77 g, 0.030 mol), and DMA (70 mL) were placed in a one-neck round-bottom flask, and the mixture was refluxed at 185°C. After the reaction was complete, the precipitated solid was filtered, dissolved in 1,2-Dichlorobenzene, filtered via silica gel, and concentrated to obtain compound 1-82 (8.68 g, yield 76%).

[0387] The target compound E of Table 3 below was obtained by synthesizing in the same manner as the above preparation example, except that the reactants [A] and [B] of the above preparation example were changed to reactants A and B of Table 3 below.

[0388] [Table 3]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394] [Preparation Example 4] Preparation of Compound 2-1

[0395]

[0396] 1) Preparation of intermediate 2-1-1

[0397] 3-bromo-9H-carbazole (10 g, 0.041 mol), bromobenzene [A] (6.41 g, 0.041 mol), Pd2(dba)3 (3.75 g, 0.0041 mol), P(t-Bu)3 (1.66 g, 0.0082 mmol), NaOtBu (7.88 g, 0.082 mol), and toluene (100 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 100°C. After the reaction was complete and the mixture was cooled, it was extracted, and the organic layer was filtered using silica gel to obtain intermediate 2-1-1 (9.51 g, yield 72%).

[0398] 2) Preparation of Compound 2-1

[0399] Intermediate 2-1-1 (9.51 g, 0.030 mol), (9-phenyl-9H-carbazol-3-yl)boronic acid [B] (8.61 g, 0.030 mol), Pd(PPh3)4 (1.73 g, 0.0015 mol), K2CO3 (8.29 g, 0.06 mol), and 1,4-Dioxane (90 mL) / H2O (30 mL) were added to a single-neck round-bottom flask, and the mixture was refluxed at 125°C. After cooling and extraction, the organic layer was column-purified to obtain compound 2-1 (9.89 g, yield 68%).

[0400] Target compound F of Table 4 below was prepared in the same manner, except that [A] and [B] of the above preparation example were replaced with reactants A and B of Table 4 below, respectively.

[0401] [Table 4]

[0402]

[0403]

[0404] [Preparation Example 5] Preparation of Compound 2-82

[0405]

[0406] 1) Preparation of intermediate 2-82-1

[0407] 9-([1,1'-biphenyl]-4-yl)-9H,9'H-3,3'-bicarbazole [A] (10 g, 0.021 mol), 4-bromo-1,1'-biphenyl [B] (5.38 g, 0.023 mol), CuI (0.40 g, 0.0021 mol), trans-1,4-diaminocyclohexane (0.024 g, 0.0021 mol), K3PO4 (8.92 g, 0.042 mol), and 1,4-dioxane (100 mL) were added to a round-bottom flask, and the mixture was refluxed at 125°C for 8 hours. After the reaction was complete, distilled water and dichloromethane (DCM) were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactants were purified by column chromatography (DCM:Hexane=1:3) and recrystallized with methanol to obtain intermediate 2-82-1 (12.17 g, 91%).

[0408] 2) Preparation of Compound 2-82

[0409] A mixture of intermediate 2-82-1 (9.89 g, 0.016 mol), CF3SO3H (33.02 g, 0.22 mol), and D6-Benzene (200 mL) was refluxed in a one-neck round-bottom flask at 90°C for 24 hours. After the reaction was complete, H2O (1 L) was slowly added for quenching, and the precipitated solid was filtered to obtain compound 2-82 (8.88 g, yield 83%).

[0410] Target compound G of Table 5 below was prepared in the same manner, except that [A] and [B] of the above preparation example were replaced with reactants A and B of Table 5 below, respectively.

[0411] [Table 5]

[0412]

[0413] [Preparation Example 6] Preparation of Compound 3-4

[0414]

[0415] 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindolo[2,3-c]carbazole [A] (10 g, 0.024 mol), 4-bromo-1,1'-biphenyl [B] (5.71 g, 0.024 mol), Pd2(dba)3 (1.10 g, 0.0012 mol), SPhos (1.97 g, 0.0048 mmol), NaOH (1.92 g, 0.048 mol), and Xylene (100 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 153 °C. After the reaction was complete, the mixture was cooled and extracted, and the organic layer was filtered using silica gel to obtain Compound 3-4 (8.48 g, yield 63%).

[0416] Target compound H of Table 6 below was prepared in the same manner, except that [A] and [B] of the above preparation example were replaced with reactants A and B of Table 6 below, respectively.

[0417] [Table 6]

[0418]

[0419]

[0420] [Preparation Example 7] Preparation of Compound 3-80

[0421]

[0422] 1) Preparation of intermediate 3-80-1

[0423] 5-([1,1'-biphenyl]-3-yl)-5,8-dihydroindolo[2,3-c]carbazole [A] (10 g, 0.024 mol), 4-bromo-1,1':4',1''-terphenyl [B] (7.42 g, 0.024 mol), Pd2(dba)3 (1.10 g, 0.0012 mol), SPhos (1.97 g, 0.0048 mmol), NaOH (1.92 g, 0.048 mol), and Xylene (100 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 153 °C. After cooling, extraction was performed, and the organic layer was filtered using silica gel to obtain intermediate 3-80-1 (9.93 g, yield 65%).

[0424] 2) Preparation of Compound 3-80

[0425] Intermediate 3-80-1 (9.93 g, 0.016 mol), Triflic acid (40.8 g, 0.27 mol), and D6-Benzene (120 mL) were added to a single-neck round-bottom flask, and the mixture was refluxed at 70°C. The mixture was quenched and extracted with DCM and H2O, concentrated, and filtered using a silica gel filter. After concentration, the solution was treated with methanol to obtain Compound 3-80 (6.74 g, 63%).

[0426] Target compound I of Table 7 below was prepared in the same manner, except that [A] and [B] of the above preparation example were replaced with reactants A and B of Table 7 below, respectively.

[0427] [Table 7]

[0428]

[0429] The compounds synthesized in the above preparation examples were confirmed through 1H-NMR and FD-mass spectrometry. Table 8 shows the measurements from FD-mass spectrometry (FD-MS: Field desorption mass spectrometry), and Table 9 shows the measurements from 1H NMR (DMSO, 300 MHz).

[0430] 화합물FD-Mass화합물FD-Mass1-1m / z= 752.25 (C51H24D6N4OS=752.25)1-3m / z= 753.26 (C51H23D7N4OS=753.93)1-7m / z= 827.30 (C57H29D6N5S=728.04)1-11m / z= 812.33 (C57H27D7N5O=812.98)1-12m / z= 812.33 (C57H28D7N5O=812.98)1-17m / z= 813.33 (C57H27D8N5O=813.99)1-21m / z= 752.25 (C51H24D6N4OS=752.92)1-24m / z= 769.24 (C51H23D7N4S2=769.99)1-27m / z= 827.30 (C57H29D6N5S=828.04)1-33m / z= 815.35 (C57H25D10N5O=815.35)1-35m / z= 812.33 (C57H28D7N5O=812.98)1-40m / z= 828.31 (C57H28D7N5S=829.04)1-41m / z= 752.25 (C51H24D6N4OS=752.92)1-47m / z= 827.30 (C57H29D6N5S=827.30)1-50m / z= 751.25 (C51H25D5N4OS=751.92)1-58m / z= 751.25 (C51H24D5N4OS=751.92)1-59m / z= 777.30 (C54H31D5N4S=778.00)1-61m / z= 752.25 (C51H24D6N4OS=752.92)1-64m / z= 769.24 (C51H23D7N4S2=769.99)1-69m / z= 736.27 (C51H24D6N4O2=736.86)1-72m / z= 764.34 (C54H28D8N4O=764.96)1-76m / z= 814.34 (C57H26D9N5O=815.00)1-78m / z= 736.27 (C51H24D6N4O2=736.86)1-82m / z= 760.30 (C51H16D14N4OS=760.97)1-86m / z= 776.28 (C51H16D14N4S2=777.03)1-87m / z= 832.33 (C57H24D11N5S=833.07)1-89m / z= 739.29 (C51H21D9N4O2=739.88)1-92m / z= 815.35 (C57H25D10N5O=816.00)1-97m / z= 759.30 (C51H17D13N4OS=759.97)1-100m / z= 819.37 (C57H21D14N5O=820.03)1-101m / z= 756.28 (C51H20D10N4OS=756.95)1-104m / z= 775.27 (C51H17D13N4S2=776.03)1-107m / z= 833.34 (C57H23D12N5S=834.08)1-109m / z= 741.31 (C51H19D11N4O2=741.89)1-111m / z= 821.38 (C57H19D16N5O=822.04)1-116m / z= 820.38 (C57H20D15N5O=821.03)1-118m / z= 758.29 (C51H18D12N4OS=758.96)1-120m / z= 819.37 (C57H21D14N5O=820.03)1-125m / z= 769.24 (C51H23D7N4S2=769.24)1-132m / z= 751.25 (C51H25D5N4OS=751.92)1-145m / z= 769.24 (C51H23D7N4S2=769.99)1-150m / z= 755.27 (C51H21D9N4OS=755.94)1-166m / z= 756.95 (C51H20D10N4OS=756.95)1-172m / z= 770.24 (C51H22D8N4S2=771.00)1-180m / z= 754.26 (C51H22D8N4OS=754.94)1-192m / z= 770.24 (C51H22D8N4S2=771.00)1-200m / z= 752.25 (C51H24D6N4OS=752.92)1-211m / z= 768.23 (C51H24D6N4S2=768.99)1-230m / z= 835.27 (C51H25D5N4O2=735.86)1-237m / z= 752.25 (C51H24D6N4OS=752.92)1-251m / z= 736.27 (C51H24D6N4O2=736.86)1-258m / z= 753.26 (C51H23D7N4OS=753.93)1-264m / z= 752.25 (C51H24D6N4OS=752.92)1-275m / z= 753.26 (C51H23D7N4OS=753.93)1-284m / z= 752.25 (C51H24D6N4OS=752.92)1-300m / z= 773.26 (C51H19D11N4S2=774.02)1-306m / z= 758.29 (C51H18D12N4OS=758.96)1-336m / z= 757.96 (C51H19D11N4OS=757.96)1-348m / z= 767.36 (C54H25D11N4O=767.98)1-350m / z= 756.28 (C51H20D10N4OS=756.95)1-362m / z= 759.30 (C51H17D13N4OS=759.97)1-372m / z= 742.31 (C51H18D12N4O2=742.90)1-385m / z= 835.35 (C57H21D14N5S=836.09)1-394m / z= 756.28 (C51H20D10N4OS=756.95)2-1m / z= 484.59(C36H24N2=484.19)2-3m / z= 560.23 (C42H28N2=560.70)2-4m / z= 560.23 (C42H28N2=560.70)2-16m / z= 634.24 (C48H30N2=634.78)2-27m / z= 636.26 (C48H32N2=636.80)2-28m / z= 636.26 (C48H32N2=636.80)2-32m / z= 636.26 (C48H32N2=636.80)2-82m / z= 668.46 (C48D32N2=668.99)2-85m / z= 668.46 (C48D32N2=668.99)2-88m / z= 668.46 (C48D32N2=668.99)2-89m / z= 668.46 (C48D32N2=668.99)3-4m / z= 560.23 (C42H28N2=560.70)3-11m / z= 574.20 (C42H26N2O=574.68)3-12m / z= 560.23 (C42H28N2=560.70)3-32m / z= 560.23 (C42H28N2=560.70)3-41m / z= 560.23 (C42H28N2=560.70)3-80m / z= 668.46 (C48D32N2=668.99)3-86m / z= 588.40 (C42D28N2=588.87)3-98m / z= 588.40 (C42D28N2=588.87)3-112m / z= 587.39 (C42HD27N2=587.86).

[0431] compound 1H NMR(DMSO, 300Mz)1-1δ = 8.36 (2H, d), 8.03 (1H, d), 7.91~7.94 (3H, m), 7.69~7.82 (7H, m), 7.33~7.57 (11H, m)1-3δ = 8.36 (2H, d), 8.03 (1H, d), 7.33~7.92 (11H, m), 7.33~7.50 (9H, m)1-7δ = 8.22 (1H, d), 8.36 (2H, d), 8.22 (1H, d), 7.91~7.94 (4H, m), 7.33~7.80 (21H, m)1-11δ = 8.36 (2H, m), 8.03 (1H, d), 7.91~7.92 (2H, d), 7.76~7.82 (7H, m), 7.41~7.69 (15H, m)1-12δ = 8.36 (2H, m), 8.03 (2H, d), 7.91~7.92 (2H, d), 7.75~7.82 (8H, m), 7.41~7.92 (14H, m)1-17δ = 8.36 (2H, m), 8.12 (1H, d), 8.03 (1H, d), 7.91~7.92 (2H, d), 7.69~7.82 (10H, m), 7.41~7.57 (11H, m)1-21δ = 8.36 (2H, m), 7.79~7.98 (9H, m), 7.31~7.54 (13H, m)1-24δ = 8.45 (1H, d), 8.30~8.36 (3H, m), 8.01 (1H, s), 7.91~7.94 (4H, m), 7.79~7.80 (3H, m), 7.33~7.56 (11H, m)1-27δ = 8.36 (2H, m), 8.19 (1H, d), 7.91~7.94 (3H, m), 7.79~7.84 (4H, m), 7.41~7.62 (18H, m), 7.20 (1H, t)1-33δ = 8.36 (2H, m), 7.79~7.98 (9H, m), 7.31~7.54 (13H, m)1-35δ = 8.36 (2H, m), 8.19 (1H, d), 7.91~7.92 (2H, d), 7.79~7.84 (5H, m), 7.36~7.62 (17H, m), 7.20 (1H, t)1-40δ = 8.49 (1H, d), 8.36~8.41 (3H, m), 8.19 (1H, d), 7.91~7.92 (2H, m), 7.80~7.81 (2H, m), 7.41~7.62 (13H, m), 7.19~7.20 (5H, m)1-41δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 8.03~8.05 (2H, m), 7.91~7.94 (4H, m), 7.80~7.82 (2H, m), 7.67~7.70 (2H, m), 7.46~7.60 (8H, m), 7.35 (1H, t), 7.16 (1H, t)1-47δ = 8.55~8.62 (1H, m), 8.45 (1H, d), 8.36 (2H, m), 8.22 (1H, d), 8.05 (1H, d), 7.91~7.94 (5H, m), 7.74~7.80 (2H, m), 7.49~7.67 (13H, m), 7.16 (1H, t), 7.16 (1H, t)1-50δ = 8.55 (1H, d), 8.36 (2H, m), 8.20~8.24 (2H, m), 7.77~7.98 (8H, m), 7.67 (1H, s), 7.31~7.54 (10H, m), 7.16 (1H, t)1-58δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, d), 8.03~8.05 (2H, m), 7.91~7.94 (4H, m), 7.76~7.82 (3H, m), 7.67 (2H, s), 7.46~7.56 (6H, m), 7.33~7.35 (2H, m), 7.16 (1H, t)1-59δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, d), 8.09 (1H, d), 7.77~7.94 (9H, m), 7.67 (1H, s), 7.46~7.56 (7H, m), 7.35 (1H, t), 7.16 (1H, t)1-61δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, d), 8.04~8.05 (2H, d), 7.84~7.94 (6H, m), 7.67 (1H, s), 7.46~7.60 (8H, m), 7.35~7.36 (2H, m), 7.16 (1H, t)1-64δ = 8.55 (1H, d), 8.45 (1H, d), 8.30~8.36 (3H, m), 7.91~8.05 (6H, m), 7.80 (1H, t), 7.67 (1H, s), 7.46~7.60 (8H, m), 7.35 (1H, t), 7.16 (1H, t)1-69δ = 8.55 (1H, d), 8.36 (2H, d), 7.80~8.04 (8H, m), 7.67 (1H, s), 7.31~7.54 (10H, m), 7.16 (1H, t)1-72δ = 8.55 (1H, d), 8.36 (2H, d), 8.21~8.24 (2H, m), 8.09 (1H, s), 7.90~7.94 (4H, m), 7.74~7.80 (2H, m), 7.35~7.57 (9H, m), 7.16 (1H, t)1-76δ = 8.55 (1H, d), 8.36 (2H, m), 8.25 (1H, s), 7.67~7.98 (11H, m), 7.31~7.54 (10H, m), 7.16 (1H, t)1-78δ = 8.55 (1H, d), 8.36 (2H, m), 7.91~8.04 (5H, m), 7.80 (1H, t), 7.31~7.72 (14H, m), 7.16 (1H, t)1-82δ = 8.36 (2H, d), 7.91~7.94 (3H, m), 7.76~7.80 (2H, m), 7.67 (2H, s), 7.33~7.50 (7H, m)1-86δ = 8.55 (1H, d), 8.36 (2H, d), 7.91~7.99 (4H, m), 7.80 (2H, m), 7.67 (1H, s), 7.46~7.50 (4H, m), 7.35 (1H, t), 7.16 (1H, t)1-87δ = 8.62 (1H, d), 8.36 (2H, d), 8.22 (1H, d), 7.91~7.94 (4H, m), 7.74~7.80 (2H, m), 7.41~7.67 (13H, m)1-89δ = 8.36 (2H, m), 8.03 (1H, d), 7.33~7.92 (3H, m), 7.76~7.82 (3H, m), 7.65~7.70 (3H, m), 7.33~7.52 (11H, m)1-92δ = 8.55 (1H, d), 8.36 (2H, m), 7.91~7.99 (5H, m), 7.80~7.81 (2H, m), 7.46~7.70 (12H, m), 7.35 (1H, t), 7.16 (1H, t)1-97δ = 8.36 (2H, m), 7.91~8.03 (6H, m), 7.75~7.82 (4H, m), 7.46~7.52 (5H, m)1-100δ = 8.36 (2H, m), 8.22 (1H, d), 7.72~7.94 (4H, m), 7.65~7.80 (5H, m), 7.45~7.52 (8H, m)1-101δ = 8.55 (1H, d), 8.36 (2H, m), 8.04 (1H, s), 7.80~7.94 (5H, m), 7.67 (1H, s), 7.44~7.52 (7H, m), 7.35~7.36 (2H, m), 7.16 (1H, t)1-104δ = 8.30~8.36 (3H, m), 7.91~8.01 (4H, m), 7.80 (1H, t), 7.67 (1H, s), 7.33~7.50 (8H, m)1-107δ = 8.55 (1H, d), 8.36 (2H, m), 8.08 (1H, s), 7.91~7.94 (5H, m), 7.80~7.82 (2H, m), 7.46~7.67 (10H, m), 7.35 (1H, t), 7.16 (1H, t)1-109δ = 8.55 (1H, d), 8.36 (2H, d), 8.04 (1H, s), 7.80~7.94 (5H, m), 7.67 (1H, s), 7.46~7.52 (5H, m), 7.35~7.36 (2H, m), 7.16 (1H, t)1-111δ = 8.36 (2H, m), 7.91~7.96 (4H, m), 7.72~7.81 (4H, m), 7.42~7.52 (9H, m)1-116δ = 8.36 (2H, m), 8.25 (1H, s), 7.91~7.97 (3H, m), 7.67~7.82 (7H, m), 7.41~7.50 (7H, m)1-118δ = 8.36 (2H, m), 8.04 (1H, s), 7.91~7.96 (4H, m), 7.80 (1H, t), 7.65~7.72 (4H, m), 7.46~7.50 (4H, m), 7.31 (1H, d)1-120δ = 8.36 (2H, m), 8.19 (1H, d), 8.02 (1H, s), 7.80~7.92 (4H, m), 7.45~7.60 (10H, m), 7.36 (1H, d), 7.19~7.20 (2H, m)1-125δ = 8.55 (1H, d), 8.36 (2H, m), 8.17~8.24 (3H, m), 7.91~7.92 (4H, m), 7.70~7.80 (4H, m), 7.41~7.50 (9H, m)1-132δ = 8.36 (2H, m), 8.05~8.08 (2H, m), 7.79~7.94 (8H, m), 7.69 (1H, d), 7.33~7.57 (12H, m)1-145δ = 8.36 (2H, d), 8.20~8.24 (2H, m), 8.03 (1H, d), 7.91~7.94 (5H, m), 7.79~7.80 (2H, m), 7.68 (1H, t), 7.33~7.50 (9H, m)1-150δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 8.08 (1H, d), 7.91~7.94 (4H, m), 7.76~7.80 (3H, m), 7.70 (1H, s), 7.46~7.56 (6H, m), 7.35 (1H, t), 7.16 (1H, t)1-166δ = 8.55 (1H, d), 8.36 (2H, m), 7.91~7.98 (4H, m), 7.80 (2H, m), 7.31~7.54 (10H, m), 7.16 (1H, t)1-172δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 7.80~7.93 (9H, m), 7.67 (1H, s), 7.46~7.56 (6H, m), 7.35 (1H, t), 7.16 (1H, t)1-180δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 8.06 (1H, s), 7.91~7.96 (5H, m), 7.80 (1H, t), 7.67 (1H, s), 7.46~7.61 (7H, m), 7.31~7.35 (2H, m), 7.16 (1H, t)1-192δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, d), 8.05~8.10 (2H, m), 7.91~7.93 (3H, m), 7.80 (2H, m), 7.46~7.56 (6H, m), 7.33~7.35 (2H, m), 7.16 (1H, t)1-200δ = 8.36 (2H, m), 7.75~7.99 (11H, m), 7.31~7.54 (11H, m)1-211δ = 8.45 (1H, d), 8.30~8.36 (3H, m), 7.91~8.01 (4H, m), 7.79~7.81 (4H, m), 7.41~7.56 (10H, m)1-230δ = 8.36 (2H, m), 7.72~7.98 (10H, m), 7.39~7.60 (12H, m), 7.19 (1H, d)1-237δ = 8.36 (2H, m), 7.79~8.05 (11H, m), 7.31~7.54 (12H, m)1-251δ = 8.55 (1H, d), 8.36 (2H, m), 7.91~8.04 (5H, m), 7.80 (1H, t), 7.31~7.67 (14H, m), 7.16 (1H, t)1-258δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 8.25 (1H, s), 7.78~7.93 (7H, m), 7.67 (2H, s), 7.35~7.56 (7H, m), 7.16 (1H, t)1-264δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 8.04 (1H, s), 7.78~7.94 (7H, m), 7.67 (2H, s), 7.35~7.56 (9H, m), 7.16 (1H, t)1-275δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 7.91~7.96 (5H, m), 7.80 (1H, t), 7.67 (2H, s), 7.31~7.50 (8H, m), 7.16 (1H, t)1-284δ = 8.55 (1H, d), 8.45 (1H, d), 8.36 (2H, m), 8.16 (1H, s), 8.05 (1H, d), 7.91~7.94 (3H, m), 7.80 (1H, t), 7.67 (2H, s), 7.33~7.56 (10H, m), 7.16 (1H, t)1-300δ = 8.36 (2H, m), 8.05 (1H, d), 7.91~7.94 (3H, m), 7.77~7.80 (3H, m), 7.65~7.67 (2H, d), 7.33~7.52 (8H, m)1-306δ = 8.36 (2H, m), 7.91~7.99 (7H, m), 7.80 (1H, t), 7.67 (1H, s), 7.33~7.50 (7H, m)1-336δ = 8.55 (1H, d), 8.36 (2H, m), 8.25 (1H, s), 8.06 (1H, d), 7.91~7.94 (3H, m), 7.77~7.80 (2H, m), 7.63 (1H, d), 7.35~7.52 (6H, m), 7.16 (1H, t)1-348δ = 8.36 (2H, m), 7.91~8.03 (5H, m), 7.77~7.83 (4H, m), 7.67 (1H, s), 7.41~7.52 (6H, m), 7.33 (1H, t)1-350δ = 8.36 (2H, m), 8.04 (1H, s), 7.91~7.96 (5H, m), 7.80 (1H, t), 7.67 (2H, s), 7.33~7.50 (9H, m)1-362δ = 8.36 (2H, m), 8.25 (1H, s), 7.91~7.99 (4H, m), 7.80 (1H, t), 7.67 (2H, s), 7.33~7.50 (7H, m)1-372δ = 8.36 (2H, m), 8.10 (1H, s), 7.91~7.94 (3H, m), 7.80 (1H, t), 7.67~7.72 (3H, s), 7.41~7.50 (8H, m)1-385δ = 8.36 (2H, d), 8.14 (1H, s), 7.91~7.96 (4H, m), 7.80~7.81 (2H, m), 7.67 (2H, s), 7.29~7.50 (10H, m)1-394δ = 8.36 (2H, m), 8.14 (1H, s), 7.80~7.94 (5H, m), 7.67 (2H, s), 7.33~7.50 (8H, m), 7.13 (1H, s)2-1δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.19 (2H, m), 7.89~7.99 (4H, m), 7.77 (1H, d), 7.50~7.62 (12H, m), 7.35 (1H, t), 7.16~7.20 (2H, t)2-3δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.21 (3H, m), 7.89~7.99 (4H, m), 7.35~7.77 (17H, m), 7.16~7.20 (2H, m)2-4δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.19 (2H, m), 7.89~7.99 (8H, m), 7.75~7.77 (3H, m), 7.35~7.62 (11H, m), 7.16~7.20 (2H, m)2-16δ = 9.05 (1H, s), 8.55 (1H, d), 8.13~8.33 (7H, m), 7.89~7.99 (5H, m), 7.50~7.77 (13H, m), 7.35 (1H, t), 7.16~7.20 (2H, t)2-27δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.21 (3H, m), 7.89~7.99 (8H, m), 7.35~7.77 (17H, m), 7.16~7.20 (2H, m)2-28δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.21 (3H, m), 7.89~7.99 (8H, m),2-32δ = 8.55 (1H, d), 8.30 (1H, d), 8.13~8.19 (2H, m), 7.89~7.99 (12H, m), 7.75~7.77 (5H, m), 7.58 (1H, d), 7.35~7.50 (8H, m), 7.16~7.20 (2H, m)2-82δ = deuterium content to 100%. 1 No 1H NMR peak 2-85δ = deuterium content 100% 1 No 1H NMR peak 2-88δ = deuterium content 100% 1 No 1H NMR peak 2-89δ = deuterium content 100% 1 No H NMR peak3-4δ = 8.55 (2H, d), 7.91~7.94 (10H, m), 7.75 (4H, d), 7.35~7.49 (10H, m), 7.16 (2H, t)3-11δ = 8.55 (2H, d), 7.91~7.94 (7H, m), 7.73~7.75 (3H, m), 7.35~7.62 (18H, m), 7.26 (1H, d), 7.16 (2H, t)3-12δ = 8.55 (2H, d), 7.91~7.94 (10H, m), 7.75 (4H, d), 7.58 (1H, d), 7.35~7.49 (8H, m), 7.25 (4H, d), 7.16 (1H, t)3-32δ = 8.55 (1H, d), 8.19 (1H, d), 7.91–7.94 (9H, m), 7.75 (4H, d), 7.35–7.58 (11H, m), 7.16–7.20 (2H, m)3-41δ = 8.55 (2H, d), 7.91–7.94 (10H, m), 7.75 (4H, d), 7.35–7.49 (8H, m), 7.16 (2H, t)3-80δ = Deuterium content 100% 1 No 1H NMR peak 3-86δ = deuterium content 100% 1 No 1 H NMR peak 3-98δ = deuterium content 100% 1 No 1 H NMR peak 3-112δ = deuterium content 100% 1 No H NMR peaks

[0432] <Experimental Example 1> Fabrication of an Organic Light-Emitting Device

[0433] A glass substrate coated with a thin film of 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 UVO treatment was performed using UV light in a UV cleaner for 5 minutes. Subsequently, the substrate was transferred to a plasma cleaner (PT), and plasma treatment was performed under vacuum to remove the ITO work function and residual film, after which it was transferred to a thermal evaporation equipment for organic deposition.

[0434] 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'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed on the above ITO transparent electrode (anode).

[0435] An emissive layer was thermally vacuum deposited on top of it as follows. A compound represented by Chemical Formula 1 of the present application was deposited to a thickness of 400 Å, and a green phosphorescent dopant was deposited by doping 7% with Ir(ppy)3. Subsequently, BCP was deposited as a hole blocking layer to a thickness of 60 Å, and Alq3 was deposited as an electron transport layer to a thickness of 200 Å on top of it. Finally, an electron injection layer was formed by depositing lithium fluoride (LiF) to a thickness of 10 Å on the electron transport layer, and then an aluminum (Al) cathode was formed by depositing an aluminum cathode to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing an organic electroluminescent device.

[0436] 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.

[0437] The electroluminescence (EL) characteristics of the organic electroluminescent device fabricated as described above were measured using Maxi's M7000, and based on the measurement results, the reference brightness was 6,000 cd / m² using a lifetime measurement device (M6000) manufactured by Maxi's 2 When, T 90 Measured.

[0438] The driving voltage, luminous efficiency, and lifetime results of the organic electroluminescent device of Experimental Example 1 above are as shown in Table 10 below. At this time, the comparative light-emitting layer compound is as follows.

[0439]

[0440] Compound driving voltage (V), efficiency (cd / A), color lifetime (T 90Comparative Example 1A 6.326 0.2Green85 Comparative Example 2B 6.355 9.4Green82 Comparative Example 3C 6.385 5.3Green72 Comparative Example 4D 6.415 6.2Green75 Comparative Example 5E 6.505 0.2Green70 Comparative Example 6F 6.485 1.3Green72 Comparative Example 7G 6.405 4.2Green79 Comparative Example 8H 6.425 5.9Green77 Comparative Example 9I 6.455 2.3Green71 Comparative Example 10J 6.485 3.2Green75 Comparative Example 11K 6.525 6.3Green76 Comparative Example 12L 6.445 7.1Green80 Example 11-13.021 10.2Green163 Example 21-33.15 109.4 Green 170 Example 31-73.19 105.6 Green 162 Example 41-113.05 100.2 Green 158 Example 51-123.21 113.8 Green 166 Example 61-173.22 115.2 Green 162 Example 71-213.48 102.3 Green 152 Example 81-243.44 109.6 Green 155 Example 91-273.51 108.7 Green 143 Example 101-333.35 110.6 Green 148 Example 111-353.49 112.9 Green 150 Example 121-403.52 111.2 Green 140 Example 131-414.61134.6Green131 Example 141-474.60133.8Green132 Example 151-504.53130.1Green133 Example 161-584.62132.8Green135 Example 171-594.55135.2Green130 Example 181-615.02120.3Green100 Example 191-644.93121.8Green102 Example 201-694.75124.3Green111 Example 211-724.88122.6Green115 Example 221-764.79125.9Green109 Example 231-784.87124.7Green107 Example 241-822.52146.2Green177 Example 251-862.55148.7Green185 Example 261-872.51149.6Green183 Example 271-892.64151.9Green177 Example 281-922.61150.3Green182 Example 291 - 972.66155.6 Green175 Example 301 - 1002.74152.8 Green200 Example 311 - 1013.02140.3 Green198 Example 321 - 1042.98142.6 Green190 Example 331 - 1072.87141.8 Green192 Example 341 - 1092.96145.6 Green187 Example 351 - 1112.79149.2 Green185 Example 361 - 1162.89144.8 Green180 Example 371 - 1182.83145.7 Green183 Example 381-1202.85142.3Green199 Example 391-1253.18105.2Green152 Example 401-1323.26113.8Green155 Example 411-1453.23110.6Green164 Example 421-1504.59124.7Green130 Example 431-1664.83125.3Green125 Example 441-1724.66121.6Green122 Example 451-1804.74120.4Green121 Example 461-1924.67123.9Green134 Example 471-2003.30115.2Green142 Example 481-2113.34110.4 Green 144 Example 491-2303.22112.6 Green 158 Example 501-2373.26113.8 Green 154 Example 511-2514.56124.5 Green 130 Example 521-2584.63130.7 Green 124 Example 531-2644.52126.8 Green 121 Example 541-2754.64125.6 Green 128 Example 551-2844.55124.9 Green 131 Example 561-3002.53143.8 Green 175 Example 571-3062.52145.2 Green 183 Example 581-3362.55141.7Green177 Example 591-3482.50142.5Green180 Example 601-3502.64147.2Green189 Example 611-3622.66146.5Green184 Example 621-3722.75148.7Green188 Example 631-3852.71140.6Green180 Example 641-3942.69142.8Green186.

[0441] The compound represented by Chemical Formula 1 of the present invention is composed of the combination of the aforementioned structural formulas A, B, and C, and has the characteristic that some substituents are substituted with deuterium.

[0442] Comparative Examples 1, 2, 7, and 8 differ from the present invention in that they use comparative compounds A, B, G, and H, in which structural formula C is not bonded to the triazine. By bonding structural formula C, they have more electrons in the LUMO region than the comparative examples, and by further expanding the LUMO region, electron transfer is made easier. Accordingly, it was confirmed that when the compounds of the present invention are used in organic light-emitting diodes where electron transfer is important, the driving voltage is about 20% lower, the efficiency is about 66% higher, and the lifespan is about 18% higher compared to when comparative compounds A, B, G, and H are used.

[0443] In addition, in the case of Examples 1 to 38, which used compounds in which the hydrogen of a substituent was substituted with deuterium having a larger molecular weight as in Chemical Formula 1, the molecular vibrational and rotational energies were lower than those of Comparative Examples 3 to 6, which used Comparative Examples C to F, in which deuterium was not substituted, thereby increasing the stability of the molecule. Furthermore, the deuterium-substituted portions were stacked closer together in the molecules to further maximize the role of the corresponding substituent, and it was confirmed that compared to Comparative Examples 3 to 6, which used Comparative Examples C to F, the driving voltage was lowered by about 22% or more, the efficiency increased by about 78% or more, and the lifespan increased by about 33% or more.

[0444] In cases where there is no phenyl linker between the triazine and structural formula A, as in Comparative Example Compound I, intramolecular electron transfer through direct bonding between the HOMO and LUMO is possible, resulting in an imbalance in the mobility rates of electrons and holes.

[0445] In addition, as in Comparative Examples J, K, and L, when structural formulas A and B are bonded to the phenyl linker at the meta and para positions, the electron mobility can be tuned by controlling the appropriate overlap between the HOMO and LUMO, but the Through-Space Charge Transfer characteristics of the HOMO and LUMO are not maximized.

[0446] The compound of the present invention balances the mobility of holes and electrons through appropriate overlap between HOMO and LUMO by using a phenyl linker between structural formula A and structural formula B, and improves driving voltage, efficiency, and lifespan by maximizing the Through-Space Charge Transfer characteristics of HOMO and LUMO by attaching a substituent to the ortho site. Since Comparative Examples I, J, K, and L only possess Through-Bond Charge Transfer characteristics, it was confirmed that when the compound of the present invention is used in an organic light-emitting diode, the driving voltage is about 23% lower, the efficiency is about 75% higher, and the lifespan is about 25% higher compared to when Comparative Examples A, B, G, and H are used.

[0447] <Experimental Example 2> Fabrication of an Organic Light-Emitting Device

[0448] A glass substrate coated with a thin film of 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 UVO treatment was performed using UV light in a UV cleaner for 5 minutes. Subsequently, the substrate was transferred to a plasma cleaner (PT), and plasma treatment was performed under vacuum to remove the ITO work function and residual film, after which it was transferred to a thermal evaporation equipment for organic deposition.

[0449] 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'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed on the above ITO transparent electrode (anode).

[0450] An emissive layer was thermally vacuum deposited on top of it as follows. The emissive layer was deposited at a thickness of 400 Å from a single source after pre-mixing one compound described in Chemical Formula 1 and one compound described in Chemical Formula 2 or 3 as a host, and a green phosphorescent dopant was deposited by doping 7% with Ir(ppy)3. Subsequently, BCP was deposited at a thickness of 60 Å as a hole blocking layer, and Alq3 was deposited at a thickness of 200 Å on top of it as an electron transport layer. Finally, an electron injection layer was formed by depositing lithium fluoride (LiF) to a thickness of 10 Å on the electron transport layer, and then an aluminum (Al) cathode was formed by depositing an aluminum cathode to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby fabricating an organic electroluminescent device.

[0451] 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.

[0452] The electroluminescence (EL) characteristics of the organic electroluminescent device fabricated as described above were measured using Maxi's M7000, and based on the measurement results, the reference brightness was 6,000 cd / m² using a lifetime measurement device (M6000) manufactured by Maxi's 2 When, T 90 Measured.

[0453] The driving voltage, luminous efficiency, and lifetime results of the organic electroluminescent device of Experimental Example 2 above are as shown in Table 11 below.

[0454] Compound Ratio Driving Voltage (V) Efficiency (cd / A) Color Coordinates Lifetime (T 90Comparative Example 13[A] : 2-891 : 15.8090.2Green106 Comparative Example 141 : 25.8189.7Green109 Comparative Example 151 : 35.8388.5Green110 Comparative Example 16[B] : 2-851 : 15.8289.4Green105 Comparative Example 171 : 25.8588.2Green108 Comparative Example 181 : 35.8787.6Green112 Comparative Example 19[C] : 3-861 : 15.9085.2Green98 Comparative Example 201 : 25.9284.1Green102 Comparative Example 211 : 35.9583.9Green105 Comparative Example 22[D] : 2-821 : 15.8884.8Green103 Comparative Example 231 : 25.9384.1Green105 Comparative Example 241 : 35.9983.2Green109 Comparative Example 25[E] : 3-861 : 16.0883.2Green95 Comparative Example 261 : 26.1282.6Green97 Comparative Example 271 : 36.1581.4Green99 Comparative Example 28[F] : 3-1121 : 16.1082.7Green98 Comparative Example 291 : 26.1381.5Green100 Comparative Example 301 : 36.1980.3Green104 Comparative Example 31[G] : 2-891 : 15.8784.2Green105 Comparative Example 321 : 25.9483.5Green109 Comparative Example 331 : 35.9883.1Green111 Comparative Example 34[H] : 2-891 : 15.7886.4Green100 Comparative Example 351 : 25.8385.2Green102 Comparative Example 361 : 35.8884.6Green106 Comparative Example 37[I] : 3-1121 : 16.1287.5Green96 Comparative Example 381 : 26.2386.1Green99 Comparative Example 391 : 36.2585.2Green100 Comparative Example 40[J] : 3-801 : 15.9485.9Green102 Comparative Example 411 : 25.9884.2Green103 Comparative Example 421 : 36.0283.7 Green105 Comparative Example 43[K] : 3-861 : 15.9286.5 Green98 Comparative Example 441 : 25.9785.2 Green101 Comparative Example 451 : 35.9984.9Green103 Comparative Example 46[L] : 3-801 : 15.8185.2Green99 Comparative Example 471 : 25.8384.6Green102 Comparative Example 481 : 35.8483.7Green104 Example 651-1 : 2-881 : 12.50135.2Green187 Example 661 : 22.53134.3Green189 Example 671 : 32.55132.9Green193 Example 681-3 : 2-891 : 12.63130.7Green188 Example 691 : 22.65129.4Green192 Example 701 : 32.68128.4Green195 Example 711-7 : 2-821 : 12.51 131.6 Green 179 Example 721 : 22.58 130.5 Green 182 Example 731 : 32.60 129.4 Green 185 Example 741-11 : 2-891 : 12.56 131.6 Green 186 Example 751 : 22.63 130.5 Green 189 Example 761 : 32.66 129.7 Green 192 Example 771-12 : 2-891 : 12.61 134.6 Green 193 Example 781 : 22.64 133.2 Green 195 Example 791 : 32.65 132.9 Green 199 Example 801-17 : 2-881 : 12.59 130.8 Green182 Example 811 : 22.63 129.6 Green184 Example 821 : 32.68 128.4 Green187 Example 831-21 : 2-881 : 12.87 125.3 Green175 Example 841 : 22.89 124.7 Green177 Example 851 : 32.90 123.4 Green180 Example 861-24 : 2-891 : 12.91 122.9 Green183 Example 871 : 22.93 121.7 Green185 Example 881 : 32.96 120.3 Green188 Example 891-27 : 2-851 : 12.76 124.8 Green177 Example 901 : 22.79 123.6 Green179 Example 911 : 32.8 3122.4 Green182 Example 921-33 : 2-821 : 12.75 121.6Green180 Example 931 : 22.77120.4 Green182 Example 941 : 32.80120.1 Green187 Example 951-35 : 2-821 : 12.86123.9 Green176 Example 961 : 22.90122.7 Green179 Example 971 : 32.94121.3 Green183 Example 981-40 : 2-891 : 12.87122.7 Green177 Example 991 : 22.89121.3 Green179 Example 1001 : 32.93120.5 Green181 Example 1011-41 : 3-801 : 14.02155.2Green148 Example 1021 : 24.11154.1Green150 Example 1031 : 34.15153.8Green152 Example 1041-47 : 3-981 : 14.09150.3Green145 Example 1051 : 24.13149.7Green149 Example 1061 : 34.18148.5Green150 Example 1071-50 : 3-1121 : 14.13153.2Green138 Example 1081 : 24.18152.6Green140 Example 1091 : 34.20151.8Green143 Example 1101-58 : 3-861 : 14.05 154.9 Green144 Example 1111 : 24.09 153.2 Green146 Example 1121 : 34.13 153.8 Green152 Example 1131-59 : 3-801 : 14.10 150.2 Green142 Example 1141 : 24.16 149.6 Green148 Example 1151 : 34.20 148.7 Green150 Example 1161-61 : 3-981 : 14.25 145.2 Green135 Example 1171 : 24.28 144.9 Green139 Example 1181 : 34.30 143.2 Green140 Example 1191-64 : 3-981 : 14.22143.8Green137 Example 1201 : 24.26142.6Green142 Example 1211 : 34.29141.3Green144 Example 1221-69 : 3-861 : 14.20144.9Green136 Example 1231 : 24.23143.2Green138 Example 1241 : 34.25140.6Green141 Example 1251-72 : 3-861 : 14.21142.9Green142 Example 1261 : 24.24141.2Green144 Example 1271 : 34.29140.8Green145 Example 1281-76 : 3-1121 : 14.28143.5Green137 Example 1291 : 24.30143.2Green140 Example 1301 : 34.32142.6Green142 Example 1311-78 : 3-981 : 14.25141.9Green135 Example 1321 : 24.28 141.0 Green 139 Example 1331 : 34.30 140.2 Green 142 Example 1341-82 : 2-851 : 11.05 175.3 Green 225 Example 1351 : 21.09 174.2 Green 229 Example 1361 : 31.12 173.8 Green 230 Example 1371-86 : 2-891 : 11.07 170.5 Green 221 Example 1381 : 21.10 168.7 Green 223 Example 1391 : 31.13 167.5 Green 228 Example 1401-87 : 3-981 : 11.11 174.2 Green 226 Example 1411 : 21.15 173.5 Green230 Example 1421 : 31.19 172.6 Green231 Example 1431-89 : 3-981 : 11.09 173.8 Green227 Example 1441 : 21.15 173.4 Green230 Example 1451 : 31.18 172.7 Green231 Example 1461-92 : 3-1121 : 11.15 169.5 Green226 Example 1471 : 21.19 168.2 Green230 Example 1481 : 31.23 167.7 Green231 Example 1491-97 : 3-981 : 11.16 170.8 Green233 Example 1501 : 21.20169.5Green235 Example 1511 : 31.22168.2Green237 Example 1521-100 : 3-801 : 11.09174.3Green220 Example 1531 : 21.13173.5 Green222 Example 1541 : 31.15 170.2 Green226 Example 1551-101 : 2-891 : 12.25 165.3 Green200 Example 1561 : 22.29 164.2 Green208 Example 1571 : 32.30 163.8 Green210 Example 1581-104 : 2-851 : 12.27 163.2 Green206 Example 1591 : 22.31 162.9 Green211 Example 1601 : 32.33 161.4 Green215 Example 1611-107 : 2-881 : 12.17 164.9 Green213 Example 1621 : 22.19 163.2 Green223 Example 1631 : 32.20 162.5 Green229 Example 1641-109 : 2-891 : 12.24 163.5 Green213 Example 1651 : 22.27 162.8 Green219 Example 1661 : 32.30 161.7 Green220 Example 1671-111 : 2-851 : 12.15 164.8 Green215 Example 1681 : 22.19 163.2 Green217 Example 1691 : 32.20 162.9 Green220 Example 1701-116 : 3-981 : 12.17 162.8 Green208 Example 1711 : 22.23 162.7 Green216 Example 1721 : 32.26 161.5 Green219 Example 1731-118 : 3-801 : 12.11 163.9 Green209 Example 1741 : 22.14 163.2 Green213 Example 1751 : 32.19 162.7 Green218 Example 1761-120 : 2-851 : 12.23 162.5 Green205 Example 1771 : 22.25 161.8 Green216 Example 1781 : 32.31 160.2 Green220 Example 1791-125 : 2-881 : 12.64 134.8 Green175 Example 1801 : 22.66 133.2 Green179 Example 1811 : 32.69 130.6 Green183 Example 1821-132 : 2-881 : 12.56 128.7 Green177 Example 1831 : 22.58 126.5Green180 Example 1841 : 32.60 126.1 Green185 Example 1851-145 : 3-981 : 12.52 127.9 Green180 Example 1861 : 22.55 126.3 Green183 Example 1871 : 32.61 125.8 Green188 Example 1881-150 : 3-1121 : 14.26 150.6 Green136 Example 1891 : 24.31 148.7 Green142 Example 1901 : 34.33 147.5 Green144 Example 1911-166 : 3-981 : 14.12 154.6 Green140 Example 1921 : 24.15 153.2 Green142 Example 1931 : 34.19 152.7 Green149 Example 1941-172 : 3-981 : 14.22 153.5 Green143 Example 1951 : 24.26 152.6 Green144 Example 1961 : 34.28 151.7 Green150 Example 1971-180 : 2-891 : 14.09 150.3 Green142 Example 1981 : 24.13 149.7 Green145 Example 1991 : 34.22 148.3 Green147 Example 2001-192 : 3-801 : 14.05 152.6 Green148 Example 2011 : 24.11151.7Green151 Example 2021 : 34.16150.3Green153 Example 2031-200 : 2-891 : 12.64135.2Green178 Example 2041 : 22.66133.8Green180 Example 2051 : 32.69132.6Green184 Example 2061-211 : 2-881 : 12.55128.7Green185 Example 2071 : 22.60127.1Green189 Example 2081 : 32.61126.5Green191 Example 2091-230 : 3-1121 : 12.55125.4Green182 Example 2101 : 22.61123.8Green188 Example 2111 : 32.67122.6Green194 Example 2121-237 : 3-981 : 12.56130.8Green187 Example 2131 : 22.64129.7Green193 Example 2141 : 32.66128.5Green197 Example 2151-251 : 3-981 : 14.12150.3Green142 Example 2161 : 24.23148.7Green144 Example 2171 : 34.33145.2Green149 Example 2181-258 : 3-801 : 14.15152.3Green138 Example 2191 : 24.17151.8Green141 Example 2201 : 34.19150.9Green149 Example 2211-264 : 3-861 : 14.23148.7Green145 Example 2221 : 24.32146.5Green148 Example 2231 : 34.33145.2Green150 Example 2241-275 : 2-851 : 14.21150.6Green139 Example 2251 : 24.25149.7Green142 Example 2261 : 34.29148.3Green144 Example 2271-284 : 2-821 : 14.05147.2Green145 Example 2281 : 24.11146.5Green147 Example 2291 : 34.13145.3Green150 Example 2301-300 : 3-801 : 11.05165.2Green200 Example 2311 : 21.13 163.5 Green 209 Example 2321 : 31.15 162.8 Green 213 Example 2331-306 : 2-891 : 11.23 166.2 Green 212 Example 2341 : 21.26 165.4 Green 216 Example 2351 : 31.31 163.8 Green 217 Example 2361-336 : 3-981 : 11.18 170.6 Green 208 Example 2371 : 21.25 169.1 Green 215 Example 2381 : 31.28 168.2 Green 219 Example 2391-348 : 2-881 : 11.15174.3Green223 Example 2401 : 21.19172.8Green230 Example 2411 : 31.26170.2Green231 Example 2421-350 : 3-801 : 11.87167.3Green218 Example 2431 : 21.93165.2Green222 Example 2441 : 31.99164.2 Green229 Example 2451-362 : 2-881 : 11.83165.9 Green215 Example 2461 : 21.88164.7 Green220 Example 2471 : 31.94163.5 Green226 Example 2481-372 : 2-821 : 11.74166.8 Green207 Example 2491 : 21.79165.2 Green216 Example 2501 : 31.85164.7 Green219 Example 2511-385 : 3-981 : 11.85174.2 Green205 Example 2521 : 21.93173.5Green209 Example 2531 : 31.99170.6Green211 Example 2541-394 : 3-801 : 11.72173.2Green208 Example 2551 : 21.84172.6Green216 Example 2561 : 31.89171.3Green222.

[0455] When comparing the results of Table 11 above with the results of Table 10 above, it was confirmed that when the compound of the present invention is used together with a heterocyclic compound of Formula 2 or 3, it provides a superior effect in terms of efficiency and lifespan.

[0456] This is due to the exciplex phenomenon, which is a phenomenon in which electron exchange between two molecules releases energy equivalent to the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host). When the exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) takes place, which can increase the internal quantum efficiency of fluorescence emission to 100%.

[0457] When a donor (p-host) with good hole transport capability and an acceptor (n-host) with good electron transport capability are used as hosts for the emissive layer, holes are injected into the p-host and electrons are injected into the n-host. At this time, due to intermolecular electron exchange, excitons are not quenched, and the lifetime of excitons capable of holding energy is increased. Consequently, overall current efficiency is improved, and it can help extend the lifespan of the device. In the present invention, it was confirmed that when the compound of Formula 1 acts as an acceptor and the heterocyclic compound of Formula 2 or 3 acts as a donor, and they are used together as hosts for the emissive layer, they exhibit excellent device characteristics.

[0458] When a compound of Chemical Formula 1 and a heterocyclic compound of Chemical Formula 2 or 3 are mixed and used as a material for the light-emitting layer, not only can the current efficiency of the light-emitting layer be partially improved, but a device with long lifespan characteristics can also be constructed. In some cases, the driving voltage may increase when the exciplex phenomenon occurs, which is due to an imbalance of holes and electrons in the light-emitting layer of the device. This is a problem caused by the deviation in hole and electron mobility between the mixed host materials. Therefore, a device capable of optimal performance can be constructed only by properly maintaining the balance of electron flow within the device, and this problem could be solved by adjusting the ratio between the acceptor and the donor.

[0459] As a result, it was confirmed that by mixing the compound of Formula 1 and the heterocyclic compound of Formula 2 or 3 and using them as a light-emitting layer material, the driving voltage decreased by about 26% or more, the efficiency increased by about 33% or more, and the lifespan increased by about 20% or more compared to when the compound shown in Comparative Examples 13 to 48 and the heterocyclic compound of Formula 2 or 3 were mixed and used as a light-emitting layer material instead of the compound of Formula 1.

Claims

1. Heterocyclic compounds represented by the following chemical formula 1: [Chemical Formula 1] X and Y are equal to or different from each other and are each independently O, S, NR, or CR'R'', and R, R' and R'' are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, and R1 to R4 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and Ar1 is a substituted or unsubstituted C6 to C60 aryl group, and r1 is an integer from 1 to 10, and if r1 is 2 or more, R1 are the same or different from each other, and r2 is an integer from 1 to 6, and if r2 is 2 or more, R2 are the same or different from each other, and r3 is an integer from 0 to 4, and if r3 is 2 or greater, R3 are the same or different from each other, and r4 is an integer from 0 to 5, and if r4 is 2 or greater, R4 are the same or different from each other, and The deuterium substitution rate of the compound of Chemical Formula 1 above is greater than 0% and less than or equal to 100%.

2. In Claim 1, the above formula 1 A heterocyclic compound represented by any one of the following chemical formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-1 to 1-6, X, R1 and r1 are identical to the definitions in Chemical Formula 1 above.

3. A heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-7 to 1-12: [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] In the above chemical formulas 1-7 to 1-12, X and Y are identical to the definitions in Chemical Formula 1 above, and Ar2 is a C6 to C60 aryl group, and [D] represents deuterium substitution, n1 is 1 to 10, and n2 is 3 to 11.

4. A heterocyclic compound according to claim 1, wherein Ar1 is a substituted or unsubstituted C6 to C20 aryl group.

5. A heterocyclic compound according to claim 1, wherein R1 to R4 are the same or different from each other and each independently hydrogen; or deuterium.

6. A heterocyclic compound according to Claim 1, wherein the deuterium substitution rate of the compound of Formula 1 is 10 to 80%.

7. In Claim 1, The above chemical formula 1 is a heterocyclic compound represented by any one of the following compounds: .

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, wherein one or more of the organic layers comprise a heterocyclic compound according to any one of claims 1 to 7.

9. An organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the heterocyclic compound.

10. An organic light-emitting device according to claim 9, wherein the light-emitting layer comprises a host material, and the host material comprises the heterocyclic compound.

11. An organic light-emitting device according to claim 10, wherein the host material further comprises a heterocyclic compound represented by the following chemical formula 2 or chemical formula 3: [Chemical Formula 2] In Chemical Formula 2, R21 and R22 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and R7 and R8 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and r7 and r8 are each integers from 0 to 7, and if r7 is 2 or more, R7 are the same or different from each other, and if r8 is 2 or more, R8 are the same or different from each other, and [Chemical Formula 3] In Chemical Formula 3, A is a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring, and R23 and R24 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and R9 and R10 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and r9 and r10 are each integers from 0 to 4, and if r9 is 2 or more, R9 is the same or different from each other, and if r10 is 2 or more, R10 is the same or different from each other.

12. An organic light-emitting device according to claim 11, wherein the chemical formula 2 is represented by any one of the following compounds: .

13. An organic light-emitting device according to claim 11, wherein the chemical formula 3 is represented by any one of the following compounds: .

14. An organic light-emitting device according to claim 11, wherein the weight ratio of the compound represented by Chemical Formula 1 to the compound represented by Chemical Formula 2 is 1:1 to 1:10, or the weight ratio of the compound represented by Chemical Formula 1 to the compound represented by Chemical Formula 3 is 1:1 to 1:

10.

15. A heterocyclic compound represented by Formula 1 according to any one of claims 1 to 7; and a composition for an organic layer of an organic light-emitting device comprising a heterocyclic compound represented by Formula 2 or Formula 3 below: [Chemical Formula 2] In Chemical Formula 2, R21 and R22 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and R7 and R8 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and r7 and r8 are each integers from 0 to 7, and if r7 is 2 or more, R7 are the same or different from each other, and if r8 is 2 or more, R8 are the same or different from each other, and [Chemical Formula 3] In Chemical Formula 3, A is a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring, and R23 and R24 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and R9 and R10 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and r9 and r10 are each integers from 0 to 4, and if r9 is 2 or more, R9 is the same or different from each other, and if r10 is 2 or more, R10 is the same or different from each other.

16. A composition for an organic layer of an organic light-emitting device according to claim 15, wherein the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 in the composition for the organic layer of the organic light-emitting device is 1:1 to 1:10, or the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 3 is 1:1 to 1:10.

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