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

Abstract

The present specification relates to a heterocyclic compound and an organic light-emitting device comprising same.

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] 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.

[0003] 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.

[0004] 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.

[0005] To improve the performance, efficiency, and lifespan of organic light-emitting diodes, the development of organic thin film materials is continuously required.

[0006] <Prior Art Literature>

[0007] (Patent Document 1) U.S. Patent No. 4,356,429

[0008] 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.

[0009] In one embodiment of the present application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] X is O; S; or CRaRb; and,

[0014] L is a directly bonded; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, and

[0015] l is an integer from 1 to 3, and if l is 2 or greater, L are equal to or different from each other, and

[0016] A is an aryl ring having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; or a heterocyclic ring having 2 to 60 carbon atoms substituted or unsubstituted with deuterium, and

[0017] Ra, Rb, Rd, Ar1 and Ar2 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and

[0018] a is an integer from 0 to 4, and if a is 2 or greater, Rd are equal or different, and

[0019] H is hydrogen, D is deuterium, and,

[0020] d is an integer from 1 to 6, and

[0021] The above chemical formula 1 is represented by the following structural formulas A to C, and

[0022] [Structural Formula A]

[0023]

[0024] [Structural Formula B]

[0025]

[0026] [Structural Formula C]

[0027]

[0028] In the above structural formulas A to C,

[0029] refers to the positions where they combine with each other,

[0030] The deuterium content of the above structural formula A is 20% or more and 100% or less.

[0031] 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.

[0032] 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.

[0033] [Chemical Formula 2]

[0034]

[0035] [Chemical Formula 3]

[0036]

[0037] In the above chemical formulas 2 and 3,

[0038] R1 to R9, Re and Rf are the same or different from each other and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to 60 alkyl group; substituted or unsubstituted C2 to 60 alkenyl group; substituted or unsubstituted C2 to 60 alkynyl group; substituted or unsubstituted C1 to 60 alkoxy group; substituted or unsubstituted C3 to 60 cycloalkyl group; substituted or unsubstituted C2 to 60 heterocycloalkyl group; substituted or unsubstituted C6 to 60 aryl group; substituted or unsubstituted C2 to 60 heteroaryl group; substituted or unsubstituted phosphine oxide group; Selected from the group consisting of substituted or unsubstituted amine groups, or two or more adjacent groups combine to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms, d is an integer from 0 to 2, where d is an integer from 2, R9 are the same or different, r and s are integers from 0 to 7, where r is an integer of 2 or more, Re are the same or different, and where s is an integer of 2 or more, Rf are the same or different.

[0039] L1, L2, L11 and L12 are the same or different from each other and each independently, directly bonded; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; and

[0040] Ar3 to Ar6 are the same or different from one another and each independently, deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or -SiR201R202R203; and

[0041] R201 to R203 are the same or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; and

[0042] m and n are integers from 0 to 4, and

[0043] p and q are integers from 1 to 6, and

[0044] If m, n, p, and q are 2 or more, the substituents within the parentheses are the same or different from each other.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] In addition, among the heterocyclic compounds represented by the above chemical formula 1, the deuterium substitution rate of structural formula A is 20% or more and 100% or less, so the vibration energy and rotation energy of the molecule are lowered, and the stability of the molecular structure is increased, so the lifespan of the device is excellent.

[0049] Furthermore, the expansion of the LUMO region allows the molecule to possess more electrons, resulting in excellent luminous efficiency. Substituting deuterium into the expanded LUMO region improves the efficiency of electron transfer not only within the molecule but also between molecules. Consequently, when combined with a p-host molecule that exhibits a fast hole mobility, capacitance is reduced, leading to superior performance in high refresh rate displays.

[0050] 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.

[0051] <Explanation of Symbols>

[0052] 100: Substrate

[0053] 200: Anode

[0054] 300: Organic layer

[0055] 301: Hole injection layer

[0056] 302: Precision Transport Layer

[0057] 303: Emissive layer

[0058] 304: Main barrier layer

[0059] 305: Electron transport layer

[0060] 306: Electron injection layer

[0061] 400: Cathode

[0062] The present specification will be described in more detail below.

[0063] 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.

[0064] In this specification, of the chemical formula means the position where it is combined.

[0065] 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.

[0066] 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.

[0067] 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', or two or more substituents selected from the substituents exemplified above are connected to a substituent, 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.

[0068] 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 or2 It can also be written as H.

[0069] 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.

[0070] 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.

[0071] 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.

[0072]

[0073] 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.

[0074] In this specification, the halogen may be fluorine, chlorine, bromine, or iodine.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] In this specification, the alkoxy group is represented as -O(R101), and R101 may be an example of the aforementioned alkyl group.

[0080] In this specification, the aryloxy group is represented as -O(R102), and R102 may be an example of the aryl group described above.

[0081] In this specification, the alkylthoxy group is represented as -S(R103), and R103 may be an example of the alkyl group described above.

[0082] In this specification, the arylthioxy group is represented as -S(R104), and R104 may be an example of the aryl group described above.

[0083] In this specification, the alkyl sulfoxy group is represented as -S(=0)2(R105), and R105 may be an example of the alkyl group described above.

[0084] 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.

[0085] 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.

[0086] 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.

[0087] 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.

[0088] In the present specification, the terphenyl group may be selected from the following structures.

[0089]

[0090] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

[0091] When the above fluorenyl group is substituted, it may be any one of the following structures, but is not limited thereto.

[0092]

[0093] 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.

[0094] In this specification, when a substituent is a carbazole group, it means bonding to the nitrogen or carbon of the carbazole.

[0095] In the present specification, when a carbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole.

[0096] In this specification, the benzocarbazole group may be any one of the following structures.

[0097]

[0098] In this specification, the dibenzocarbazole group may be any one of the following structures.

[0099]

[0100] In the present specification, the naphthobenzofuran group may be any one of the following structures.

[0101]

[0102] In the present specification, the naphthobenzothiophene group may be any one of the following structures.

[0103]

[0104] 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.

[0105] 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.

[0106] 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.

[0107] 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.

[0108] In this specification, the examples of aryl groups described above may be applied, except that the arylene group is a divalent group.

[0109] In this specification, the examples of the aforementioned heteroaryl groups may be applied, except that the heteroaryl group is a divalent group.

[0110] 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.

[0111] 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.

[0112] 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.

[0113] 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.

[0114] 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.

[0115] 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.

[0116] In one embodiment of the present application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[0117] [Chemical Formula 1]

[0118]

[0119] In the above chemical formula 1,

[0120] X is O; S; or CRaRb; and,

[0121] L is a directly bonded; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, and

[0122] l is an integer from 1 to 3, and if l is 2 or greater, L are equal to or different from each other, and

[0123] A is an aryl ring having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; or a heterocyclic ring having 2 to 60 carbon atoms substituted or unsubstituted with deuterium, and

[0124] Ra, Rb, Rd, Ar1 and Ar2 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and

[0125] a is an integer from 0 to 4, and if a is 2 or greater, Rd are equal or different, and

[0126] H is hydrogen, D is deuterium, and,

[0127] d is an integer from 1 to 6, and

[0128] The above chemical formula 1 is represented by the following structural formulas A to C, and

[0129] [Structural Formula A]

[0130]

[0131] [Structural Formula B]

[0132]

[0133] [Structural Formula C]

[0134]

[0135] In the above structural formulas A to C,

[0136] refers to the positions where they combine with each other,

[0137] The deuterium content of the above structural formula A is 20% or more and 100% or less.

[0138] 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.

[0139] 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.

[0140] In one embodiment of the present application, the deuterium content of the structural formula A may be 20% or more and 100% or less.

[0141] In another embodiment, the deuterium content of the above structural formula A may be 20% or more and 100% or less, specifically the deuterium content of the above structural formula A may be 25% or more and 100% or less, and more specifically the deuterium content of the above structural formula A may be 30% or more and 100% or less.

[0142] In addition, the present application satisfies the deuterium content of the above structural formula A, and at the same time, the deuterium content of structural formulas B and C may be as follows.

[0143] In one embodiment of the present application, the deuterium content of structural formula A is 20% or more and 100% or less, and the deuterium content of structural formulas B and C may be 10% or less.

[0144] In another embodiment, the deuterium content of the above structural formula A is 20% or more and 100% or less, and the deuterium content of structural formulas B and C may be 10% or less, 9% or less, 8% or less, and 5% or less, and may be 0% or more and 1% or more.

[0145] In this case, the deuterium content of structural formula A may be applied as described above.

[0146] Substituting hydrogen with deuterium in structural formula A, which corresponds to the LUMO region, increases the packing density of the LUMO region, thereby improving the efficiency of intermolecular electron transfer. When the compound of the present invention, which enhances the efficiency of intramolecular electron transfer through intermolecular electron transfer and through-space charge transfer (TSCT), is used in combination with a fast-moving p-host, the capacitance is reduced, resulting in excellent performance in high refresh rate displays.

[0147] In one embodiment of the present application, the deuterium content of structural formulas A and C is 20% or more and 100% or less, and the deuterium content of structural formula B may be 10% or less.

[0148] In another embodiment, the deuterium content of the structural formulas A and C is 20% or more and 100% or less, and the deuterium content of the structural formula B may be 10% or less, 9% or less, 8% or less, 5% or less, and 0% or more and 1% or more.

[0149] In addition to structural formula A, if the hydrogen in structural formula C, which acts as a linker connecting HOMO and LUMO, is replaced with deuterium, the rotation of HOMO and LUMO can be further restricted, thereby further maximizing the Through-space charge transfer (TSCT) effect.

[0150] In one embodiment of the present application, the deuterium content of the structural formulas A to C may be 20% or more and 100% or less.

[0151] In another embodiment, the deuterium content of the structural formulas A to C may be 20% or more and 100% or less, specifically the deuterium content of the structural formulas A to C may be 25% or more and 100% or less, and more specifically the deuterium content of the structural formulas A to C may be 30% or more and 100% or less.

[0152] The deuterium content of the above structural formulas A to C can consequently have the same meaning as the deuterium content of chemical formula 1.

[0153] When hydrogen in structural formulas A to C is substituted with deuterium, the thermal stability of the entire molecule increases, resulting in a very excellent lifetime. The packing density of the HOMO region as well as the LUMO region increases, further enhancing the mobility of electrons and holes, thereby providing characteristics of low driving voltage and high luminous efficiency.

[0154] In the present application, X is O; S; or CRaRb.

[0155] In the present application, X is O.

[0156] In the present application, X is S.

[0157] In the present application, X is CRaRb.

[0158] In the present application, Ra and Rb are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0159] In another embodiment, Ra and Rb may each independently be a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms.

[0160] In another embodiment, Ra and Rb may each independently be a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms.

[0161] In another embodiment, Ra and Rb may each independently be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0162] In another embodiment, Ra and Rb may each independently be a substituted or unsubstituted straight-chain alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted branched-chain alkyl group having 3 to 10 carbon atoms.

[0163] In another embodiment, Ra and Rb may each independently be a straight-chain alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; or a branched-chain alkyl group having 3 to 10 carbon atoms substituted or unsubstituted with deuterium.

[0164] In another embodiment, Ra and Rb may each independently be a methyl group substituted or unsubstituted with deuterium; and an ethyl group substituted or unsubstituted with deuterium.

[0165] In this case, for a methyl group substituted with deuterium, the deuterium includes all cases where one, two, or three deuterium atoms are substituted into the methyl group.

[0166] In the present application, Rd may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0167] In another embodiment, Rd may be hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0168] In another embodiment, Rd may be hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0169] In another embodiment, Rd may be hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0170] In another embodiment, Rd may be hydrogen; deuterium; an aryl group having 6 to 20 carbon atoms; or a heteroaryl group having 2 to 20 carbon atoms.

[0171] In another embodiment, Rd may be hydrogen; or deuterium.

[0172] In the present application, L may be a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0173] In another embodiment, L may be a directly bonded; or a substituted or unsubstituted arylene group having 6 to 40 carbon atoms.

[0174] In another embodiment, L may be a directly bonded; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0175] In another embodiment, L may be a direct bond; or an arylene group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0176] In another embodiment, L may be a direct bond; a phenylene group substituted or unsubstituted with deuterium; or a biphenylene group substituted or unsubstituted with deuterium.

[0177] In another embodiment, L may be a direct connection.

[0178] In one embodiment of the present application, Ar1 and Ar2 may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0179] In one embodiment of the present application, Ar1 and Ar2 may each independently be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0180] In another embodiment, Ar1 and Ar2 may each independently be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0181] In another embodiment, Ar1 and Ar2 may each independently be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0182] In another embodiment, Ar1 and Ar2 may each independently be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0183] In another embodiment, Ar1 and Ar2 may each independently be hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms containing O or S.

[0184] In another embodiment, Ar1 and Ar2 may each independently be hydrogen; deuterium; a monocyclic aryl group having 6 to 10 carbon atoms substituted or unsubstituted with deuterium; a polycyclic aryl group having 10 to 20 carbon atoms substituted or unsubstituted with deuterium; or a heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0185] In another embodiment, Ar1 and Ar2 may each independently be a monocyclic aryl group having 6 to 10 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of hydrogen; deuterium; and aryl groups having 6 to 10 carbon atoms substituted or unsubstituted with deuterium and deuterium; a polycyclic aryl group having 10 to 20 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of aryl groups having 6 to 10 carbon atoms substituted or unsubstituted with deuterium; or a heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0186] In another embodiment, Ar1 and Ar2 may each independently be hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophen group.

[0187] In another embodiment, Ar1 and Ar2 may each independently be hydrogen; 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; a triphenylenyl group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium.

[0188] In one embodiment of the present application, at least one of Ar1 and Ar2 may be a substituted or unsubstituted aryl group having 10 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0189] In another embodiment, at least one of Ar1 and Ar2 may be a substituted or unsubstituted aryl group having 10 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0190] In another embodiment, at least one of Ar1 and Ar2 may be a substituted or unsubstituted aryl group having 10 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0191] In another embodiment, at least one of Ar1 and Ar2 may be a substituted or unsubstituted polycyclic aryl group having 10 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0192] In another embodiment, at least one of Ar1 and Ar2 may be a polycyclic aryl group having 10 to 20 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and aryl groups having 6 to 10 carbon atoms substituted or unsubstituted with deuterium; or a heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0193] In another embodiment, at least one of Ar1 and Ar2 may be a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a triphenylenyl group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium.

[0194] As described above, when at least one substituent in the structure of the triazine has a long chain aryl group or a heteroaryl group, the number of electrons in the molecule increases and the LUMO region expands, so the electron mobility also increases and the driving voltage is lowered.

[0195] In the present application, A is an aryl ring having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; or a heterocyclic ring having 2 to 60 carbon atoms substituted or unsubstituted with deuterium.

[0196] In another embodiment, A may be an aryl ring having 6 to 60 carbon atoms that is substituted or unsubstituted with deuterium.

[0197] In another embodiment, A may be an aryl ring having 6 to 40 carbon atoms that is substituted or unsubstituted with deuterium.

[0198] In another embodiment, A may be an aryl ring having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0199] In another embodiment, A may be a single-ring aryl ring having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0200] In another embodiment, A may be a benzene ring substituted or unsubstituted with deuterium.

[0201] In this case, the deuterium content of A can be included in the deuterium content of structural formula B.

[0202] In the present application, the above A may be represented by the following structural formula A-1 or A-2.

[0203] [Structural Formula A-1]

[0204]

[0205] [Structural Formula A-1]

[0206]

[0207] In the above structural formulas A-1 and A-2,

[0208] represents the condensation location,

[0209] X3 is O; S; or NRe, and

[0210] R11 to R19 are the same or different from each other and are each independently hydrogen; or deuterium, and

[0211] Re is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and

[0212] The above a1 is an integer of 1 or 2, and

[0213] If a1 is 2, the substituents inside the parentheses are either the same or different.

[0214] In one embodiment of the present application, the formula 1 may be represented by any one of the following compounds.

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221] 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.

[0222] 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.

[0223] 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.

[0224] 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.

[0225] 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.

[0226] 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.

[0227] 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.

[0228] 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.

[0229] 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.

[0230] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0231] In another embodiment, the first electrode may be a negative electrode and the second electrode may be a positive electrode.

[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 material for 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 material for 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 material for the red organic light-emitting device.

[0235] 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.

[0236] 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.

[0237] 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.

[0238] 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.

[0239] 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.

[0240] 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.

[0241] 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.

[0242] In one embodiment of the present application, Ir(ppy)3, a green phosphorescent dopant, may be used as an iridium-based dopant.

[0243] In one embodiment of the present application, (piq)2(Ir)(acac), a red phosphorescent dopant, may be used as an iridium-based dopant.

[0244] 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.

[0245] 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.

[0246] 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.

[0247] In another organic light-emitting device, the organic layer includes a hole-blocking layer, and the hole-blocking layer may include the heterocyclic compound.

[0248] In another organic light-emitting device, the organic layer includes an electron blocking layer, and the electron blocking layer may include the heterocyclic compound.

[0249] 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.

[0250] 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.

[0251] 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.

[0252] 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.

[0253] As the hole injection material, known hole injection materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine or starburst-type amine derivatives described in the literature [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), soluble conductive polymers such as polyaniline / dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), Polyaniline / Camphor sulfonic acid or polyaniline / poly(4-styrene-sulfonate), etc., may be used.

[0254] 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.

[0255] 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.

[0256] For example, LiF is commonly used as an electron injection material in the industry, but the present application is not limited thereto.

[0257] 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.

[0258] 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.

[0259] 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.

[0260] 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.

[0261] 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.

[0262] 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.

[0263] 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.

[0264] 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.

[0265] Figure 3 illustrates a case where the organic layer is multilayered.

[0266] 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 (304), an electron transport layer (305), and an electron injection layer (306).

[0267] 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.

[0268] The organic layer containing the above chemical formula 1 may additionally include other materials as needed.

[0269] In one embodiment of the present application, an organic light-emitting device is provided in which the organic layer further comprises a heterocyclic compound represented by the following chemical formula 2 or chemical formula 3.

[0270] [Chemical Formula 2]

[0271]

[0272] [Chemical Formula 3]

[0273]

[0274] In the above chemical formulas 2 and 3,

[0275] R1 to R9, Re and Rf are the same or different from each other and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to 60 alkyl group; substituted or unsubstituted C2 to 60 alkenyl group; substituted or unsubstituted C2 to 60 alkynyl group; substituted or unsubstituted C1 to 60 alkoxy group; substituted or unsubstituted C3 to 60 cycloalkyl group; substituted or unsubstituted C2 to 60 heterocycloalkyl group; substituted or unsubstituted C6 to 60 aryl group; substituted or unsubstituted C2 to 60 heteroaryl group; substituted or unsubstituted phosphine oxide group; Selected from the group consisting of substituted or unsubstituted amine groups, or two or more adjacent groups combine to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms, d is an integer from 0 to 2, where d is an integer from 2, R9 are the same or different, r and s are integers from 0 to 7, where r is an integer of 2 or more, Re are the same or different, and where s is an integer of 2 or more, Rf are the same or different.

[0276] L1, L2, L11 and L12 are the same or different from each other and each independently, directly bonded; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; and

[0277] Ar3 to Ar6 are the same or different from one another and each independently, deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or -SiR201R202R203; and

[0278] R201 to R203 are the same or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; and

[0279] m and n are integers from 0 to 4, and

[0280] p and q are integers from 1 to 6, and

[0281] If m, n, p, and q are 2 or more, the substituents within the parentheses are the same or different from each other.

[0282] In the present application, the deuterium content of Formula 2 may be 30% or less or 40% or more.

[0283] In another embodiment, the deuterium content of the above formula 2 may be 30% or less, the deuterium content of the above formula 2 may be 20% or less, the deuterium content of the above formula 2 may be 10% or less, may be 5% or less, 0% or more, and 1% or more.

[0284] In another embodiment, the deuterium content of the above formula 2 may be 40% or more, the deuterium content of the above formula 2 may be 45% or more, the deuterium content of the above formula 2 may be 50% or more, and may be 100% or less.

[0285] In the present application, the deuterium content of the above chemical formula 3 may be 30% or less or 40% or more.

[0286] In another embodiment, the deuterium content of the above formula 3 may be 30% or less, the deuterium content of the above formula 3 may be 20% or less, the deuterium content of the above formula 3 may be 10% or less, 5% or less, 0% or more, or 1% or more.

[0287] In another embodiment, the deuterium content of the above formula 3 may be 40% or more, the deuterium content of the above formula 3 may be 45% or more, the deuterium content of the above formula 3 may be 50% or more, and may be 100% or less.

[0288] In the present application, the above chemical formula 3 may be represented by any one of the following chemical formulas 3-1 to 3-6.

[0289] [Chemical Formula 3-1]

[0290]

[0291] [Chemical Formula 3-2]

[0292]

[0293] [Chemical Formula 3-3]

[0294]

[0295] [Chemical Formula 3-4]

[0296]

[0297] [Chemical Formula 3-5]

[0298]

[0299] [Chemical Formula 3-6]

[0300]

[0301] In the above chemical formulas 3-1 to 3-6,

[0302] The definition of each substituent is the same as the definition in Chemical Formula 3 above.

[0303] In the present application, R1 to R9 are the same or different from one another and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; substituted or unsubstituted aryl group having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; substituted or unsubstituted phosphine oxide group; Two or more groups selected from the group consisting of substituted or unsubstituted amine groups, or adjacent to each other, combine to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms.

[0304] In another embodiment, R1 to R9 may be the same or different from each other and may each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0305] In another embodiment, R1 to R9 may be the same or different from each other and may each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0306] In another embodiment, R1 to R9 may be the same or different from each other and may each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0307] In another embodiment, R1 to R9 may be the same or different from each other and may each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0308] In another embodiment, R1 to R9 may be the same or different from each other and may each independently be hydrogen; or deuterium.

[0309] In the present application, L1 and L2 are the same or different from each other and each independently, directly bonded; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0310] In another embodiment, L1 and L2 are the same or different from each other and each independently, directly bonded; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0311] In another embodiment, L1 and L2 are the same or different from each other and each independently, directly bonded; an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; or a heteroarylene group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0312] In another embodiment, L1 and L2 may be the same or different from each other and each independently be a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; or a naphthalene group substituted or unsubstituted with deuterium.

[0313] In another embodiment, L1 and L2 may be the same or different from each other and each independently directly bonded; or a phenylene group substituted or unsubstituted with deuterium.

[0314] In the present application, Ar3 and Ar4 are the same or different from each other and are each independently deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0315] In another embodiment, Ar3 and Ar4 are the same or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0316] In another embodiment, Ar3 and Ar4 are the same or different from each other and each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0317] In another embodiment, Ar3 and Ar4 are the same or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0318] In another embodiment, Ar3 and Ar4 are each the same or different and independently an aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium; or a heteroaryl group having 2 to 20 carbon atoms that is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and an aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0319] In another embodiment, Ar3 and Ar4 may be the same or different from each other and each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophen group.

[0320] In another embodiment, Ar3 and Ar4 may be the same or different and each independently a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a triphenylenyl group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and a phenyl group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium and a phenyl group substituted or unsubstituted with deuterium.

[0321] In the present application, the above chemical formula 2 may be represented by the following chemical formula 2-1.

[0322] [Chemical Formula 2-1]

[0323]

[0324] In the above chemical formula 2-1,

[0325] The definition of each substituent is the same as the definition in Chemical Formula 2 described above.

[0326] In the present application, Re and Rf are the same or different from each other and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; substituted or unsubstituted aryl group having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; substituted or unsubstituted phosphine oxide group; Two or more groups selected from the group consisting of substituted or unsubstituted amine groups, or adjacent to each other, combine to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms.

[0327] In another embodiment, Re and Rf may be the same or different from each other and may each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0328] In another embodiment, Re and Rf may be the same or different from each other and may each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0329] In another embodiment, Re and Rf may be the same or different from each other and may each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0330] In another embodiment, Re and Rf may be the same or different from each other and may each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0331] In another embodiment, Re and Rf may be the same or different from each other and may each independently be hydrogen; or deuterium.

[0332] In the present application, L11 and L12 are the same or different from each other and each independently, directly bonded; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0333] In another embodiment, L11 and L12 are the same or different from each other and each independently, directly bonded; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0334] In another embodiment, L11 and L12 are the same or different from each other and each independently, directly bonded; an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; or a heteroarylene group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0335] In another embodiment, L11 and L12 may be the same or different from each other and each independently be a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; or a naphthalene group substituted or unsubstituted with deuterium.

[0336] In another embodiment, L11 and L12 may be the same or different from each other and each independently directly bonded; or a phenylene group substituted or unsubstituted with deuterium.

[0337] In the present application, Ar5 and Ar6 may be the same or different from each other and each independently be deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or -SiR201R202R203.

[0338] In another embodiment, Ar5 and Ar6 may be the same or different from each other and each independently be a cyano group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or -SiR201R202R203.

[0339] In another embodiment, Ar5 and Ar6 may be the same or different from each other and each independently be a cyano group; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; or -SiR201R202R203.

[0340] In another embodiment, Ar5 and Ar6 may be the same or different from each other and each independently be a cyano group; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; or -SiR201R202R203.

[0341] In another embodiment, Ar5 and Ar6 may be the same or different from each other and each independently be a cyano group; an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; a heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium; or -SiR201R202R203.

[0342] In another embodiment, Ar5 and Ar6 may be the same or different from each other and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; -SiRR'R"; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylenyl group; a cyano group; a substituted or unsubstituted dimethylfluorenyl group; a substituted or unsubstituted diphenylfluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted dibenzothiophen group; or a substituted or unsubstituted dibenzofuran group.

[0343] In another embodiment, Ar5 and Ar6 may be the same or different from each other and may each independently be a phenyl group substituted or unsubstituted with a deuterium or cyano group; a biphenyl group substituted or unsubstituted with a deuterium; a naphthyl group substituted or unsubstituted with a deuterium; -SiRR'R"; a terphenyl group substituted or unsubstituted with a deuterium; a triphenylenyl group substituted or unsubstituted with a deuterium; a cyano group; 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 dibenzothiophen group substituted or unsubstituted with a deuterium; or a dibenzofuran group substituted or unsubstituted with a deuterium.

[0344] In one embodiment of the present application, R201 to R203 are each independently substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, which are the same or different from each other; or heteroaryl groups having 2 to 60 carbon atoms, which are substituted or unsubstituted.

[0345] In another embodiment, R201 to R203 are aryl groups having 6 to 60 carbon atoms that are the same or different from each other and are each independently substituted or unsubstituted.

[0346] In another embodiment, R201 to R203 are aryl groups having 6 to 40 carbon atoms that are the same or different from each other and are each independently substituted or unsubstituted.

[0347] In another embodiment, R201 to R203 are aryl groups having 6 to 20 carbon atoms that are the same or different from each other and are each independently substituted or unsubstituted.

[0348] In another embodiment, R201 to R203 are aryl groups having 6 to 20 carbon atoms that are the same or different from each other and are each independently substituted or unsubstituted with deuterium.

[0349] In another embodiment, R201 to R203 are the same or different from each other and are each independently a phenyl group substituted or unsubstituted with deuterium.

[0350] 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.

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357] 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.

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364] 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.

[0365] 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.

[0366] 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.

[0367] 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 Formula 3 using a thermal vacuum deposition method.

[0368] 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 Chemical Formula 3.

[0369] 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.

[0370] 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.

[0371] The composition for the organic layer of the organic light-emitting device comprises a heterocyclic compound represented by Chemical Formula 1; and a heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3, wherein the weight ratio of the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 may be higher than the weight ratio of the heterocyclic compound represented by Chemical Formula 1.

[0372] In the present application, the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 or Formula 3 in the composition may be 20:80 to 45:55.

[0373] In another embodiment, the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 or Formula 3 in the composition may be 20:80 to 45:55, specifically 25:75 to 40:60, more specifically 30:70 to 40:60.

[0374] When the above weight ratio is satisfied, the mobility of holes and electrons is balanced, so the emission zone is located in the center of the EML layer. Specifically, the amount of holes injected into the light-emitting layer can increase. Basically, the more holes injected into a device with fast electron injection, the faster recombination occurs. Consequently, the number of electrons accumulated at the interface decreases, which lowers molecular instability caused by excess electrons and extends the device's lifespan. Additionally, as recombination occurs more rapidly, the number of annihilated excitons decreases, resulting in improved luminous efficiency.

[0375] 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.

[0376] 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.

[0377] 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 Formula 3 and using a thermal vacuum deposition method.

[0378] 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.

[0379] 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.

[0380] 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.

[0381] 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.

[0382] The above composition may additionally include materials known in the art, such as solvents and additives.

[0383] 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.

[0384] <Preparation Example>

[0385] [Preparation Example 1] Preparation of Compound 1-4

[0386]

[0387] 1) Preparation of intermediate 1-4-1

[0388] 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine [A] (10 g, 0.029 mol), Triflic acid (43.52 g, 0.29 mol), D6-Benzene (150 mL), and Chloroform (100 mL) were added to a one-neck round-bottom flask and refluxed at 80°C. After the reaction was complete, the mixture was cooled and water was added to neutralize it. The precipitated solid was filtered and mixed with methanol slurry and acetone slurry to obtain intermediate 1-4-1 (9.23 g, yield 89%).

[0389] The deuterium substitution rate can be controlled by manufacturing under reaction conditions as shown in Table 1 below.

[0390] Triflic acid D6-Benzene Chloroform Reaction Temperature Reaction Time Deuterium Substitution Rate Reaction Condition 1 14 eq 20 T 10 T 100℃ 5 h 100% Reaction Condition 2 10 eq 15 T 10 T 80℃ 3 h 51%~89% Reaction Condition 3 7 eq 10 T 15 T 50℃ 1 h 50% Reaction Condition 4 3 eq 3 T 10 T RT 3 h 10~49%

[0391] 2) Preparation of intermediate 1-4-2

[0392] Intermediate 1-4-1 (9.23 g, 0.026 mol), (2-fluorophenyl)boronic acid [B] (3.64 g, 0.026 mol), Pd(PPh3)4 (9.01 g, 0.00078 mol), K2CO3 (7.19 g, 0.052 mol), Dioxane (90 mL), and Water (27 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 110°C. After the reaction was complete, the precipitated solid was filtered, dissolved in 1,2-Dichlorobenzene, filtered via silica gel, and concentrated to obtain intermediate 1-4-2 (9.12 g, yield 84%).

[0393] 3) Preparation of Compounds 1-4

[0394] Intermediate 1-4 (9.12 g, 0.022 mol), 12H-benzo[4,5]thieno[2,3-a]carbazole [C] (6.01 g, 0.022 mol), Cs2CO3 (14.34 g, 0.044 mol), and DMA (90 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 Cs2CO3 was filtered, and the solution was concentrated. The concentrated compound was dissolved in 1,2-Dichlorobenzene, filtered via silica gel, and concentrated to obtain Compound 1-4 (13.58 g, yield 92%).

[0395] 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], [B], and [C] of the above preparation example were changed to reactants A, B, and C of Table 2 below.

[0396]

[0397] [Preparation Example 2] Preparation of Compound 1-38

[0398]

[0399] 1) Preparation of intermediate 1-38-1

[0400] 2-([1,1'-biphenyl]-4-yl)-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine [A] (12 g, 0.029 mol), Triflic acid (43.52 g, 0.290 mol), D6-Benzene (180 mL), and Chloroform (120 mL) were added to a one-neck round-bottom flask and refluxed at 80°C. After the reaction was complete, the mixture was cooled and water was added to neutralize it. The precipitated solid was filtered and mixed with methanol slurry and acetone slurry to obtain intermediate 1-38-1 (11.06 g, yield 92%).

[0401] The deuterium substitution rate can be controlled by manufacturing under reaction conditions as shown in Table 3 below.

[0402] Triflic acid D6-Benzene Chloroform Reaction Temperature Reaction Time Deuterium Substitution Rate Reaction Condition 1 14 eq 20 T 10 T 100℃ 5 h 100% Reaction Condition 2 10 eq 15 T 10 T 80℃ 3 h 51%~89% Reaction Condition 3 7 eq 10 T 15 T 50℃ 1 h 50% Reaction Condition 4 3 eq 3 T 10 T RT 3 h 10~49%

[0403] 2) Preparation of Compound 1-38: Intermediate 1-38-1 (11.06 g, 0.027 mol), 12H-benzo[4,5]thieno[2,3-a]carbazole [B] (7.38 g, 0.027 mol), Cs2CO3 (17.59 g, 0.054 mol), and DMA (110 mL) were added to a round-bottom flask, and the mixture was refluxed at 185°C. After the reaction was complete, the precipitated Cs2CO3 was filtered, and the solution was concentrated. The compound obtained by concentration was dissolved in 1,2-Dichlorobenzene, filtered via silica gel, and concentrated to obtain Compound 1-38 (16.61 g, yield 92%).

[0404] Target compound C of Table 4 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 4 below.

[0405]

[0406] [Preparation Example 3] Preparation of Compound 1-78

[0407]

[0408] 1) Preparation of intermediate 1-78-1

[0409] 2-([1,1'-biphenyl]-4-yl)-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine [A] (10 g, 0.022 mol), 12H-benzo[4,5]thieno[2,3-a]carbazole [B] (6.01 g, 0.022 mol), Cs2CO3 (14.34 g, 0.044 mol), and DMA (90 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 Cs2CO3 was filtered, and the solution was concentrated. The concentrated compound was dissolved in 1,2-Dichlorobenzene, filtered via silica gel, and concentrated to obtain intermediate 1-78-1 (13.58 g, yield 94%).

[0410] 2) Preparation of Compound 1-78

[0411] Intermediate 1-78-1 (13.58 g, 0.021 mol), Triflic acid (44.12 g, 0.294 mol), D6-Benzene (272 mL), and Chloroform (135 mL) were added to a one-neck round-bottom flask and refluxed at 100°C. After the reaction was complete, the mixture was cooled and water was added to neutralize it. The precipitated solid was filtered and mixed with methanol slurry and acetone slurry to obtain Compound 1-78 (12.95 g, yield 90%).

[0412] The deuterium substitution rate can be controlled by manufacturing under reaction conditions as shown in Table 5 below.

[0413] Triflic acid D6-Benzene Chloroform Reaction Temperature Reaction Time Deuterium Substitution Rate Reaction Condition 1 14 eq 20 T 10 T 100℃ 5 h 100% Reaction Condition 2 10 eq 15 T 10 T 80℃ 3 h 51%~89% Reaction Condition 3 7 eq 10 T 15 T 50℃ 1 h 50% Reaction Condition 4 3 eq 3 T 10 T RT 3 h 10~49%

[0414] The target compound C of Table 6 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 6 below.

[0415] [Preparation Example 4] Preparation of Compound 2-1

[0416]

[0417] 1) Preparation of intermediate 2-1-1

[0418] 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%).

[0419] 2) Preparation of Compound 2-1

[0420] 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%).

[0421] Target compound C 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.

[0422]

[0423] [Preparation Example 5] Preparation of Compound 2-82

[0424]

[0425] 1) Preparation of intermediate 2-82-1

[0426] 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%).

[0427] 2) Preparation of Compound 2-82

[0428] 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%).

[0429] Target compound C of Table 8 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 8 below, respectively.

[0430]

[0431] [Preparation Example 6] Preparation of Compound 3-4

[0432]

[0433] 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%).

[0434] Target compound C of Table 9 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 9 below, respectively.

[0435]

[0436] [Preparation Example 7] Preparation of Compound 3-80

[0437]

[0438] 1) Preparation of intermediate 3-80-1

[0439] 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%).

[0440] 2) Preparation of Compound 3-80

[0441] 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%).

[0442] Target compound C of Table 10 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 10 below, respectively.

[0443]

[0444] In addition to the compounds prepared in Preparation Examples 1 to 7 and Tables 1 to 10 above, compounds according to Chemical Formulas 1 to 3 described above were also synthesized in the same manner, and the compounds synthesized in the preparation examples above were confirmed through 1H-NMR and FD-mass spectrometry. Table 11 shows the measured values ​​from FD-mass spectrometry (FD-MS: Field desorption mass spectrometry), and Table 12 shows the measured values ​​from 1H NMR (DMSO, 300 MHz).

[0445] compoundFD-Mass화합물FD-Mass1-4m / z= 670.29 (C45H14D14N4S=670.89)1-7m / z= 666.27 (C45H18D10N4S=666.87)1-14m / z= 680.25 (C45H16D10N4OS=680.85)1-18m / z= 572.25 (C39H16D8N4O=572.70)1-24m / z= 725.31 (C51H23D9N4O=725.90)1-29m / z= 662.26 (C45H18D8N4O2=662.78)1-38m / z= 668.28 (C45H16D12N4S=668.88)1-46m / z= 747.33 (C51H17D15N4S=748.00)1-52m / z= 762.31 (C51H14D16N4OS=762.99)1-60m / z= 658.34 (C45H10D18N4O=658.86)1-67m / z= 734.37 (C51H14D18N4O=734.95)1-71m / z= 746.34 (C51H14D16N4O2=746.92)1-78m / z= 684.38 (C45D28N4S=684.98)1-84m / z= 753.37 (C51H11D21N4S=754.03)1-91m / z= 769.36 (C51H7D23N4OS=770.03)1-94m / z= 581.30 (C39H7D17N4O=581.75)1-100m / z= 666.39 (C45H2D26N4O=666.90)1-110m / z= 671.31 (C45H9D17N4O2=671.83)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).

[0446] compound 1H NMR(DMSO, 300Mz)1-4δ = 8.55 (1H, d), 8.45 (1H, d), 8.05 (1H, d), 7.94~7.90 (4H, m), 7.80 (1H, t), 7.60 (1H, d), 7.56 (1H, t), 7.49~7.46 (2H, m), 7.35 (1H, t), 7.16 (1H, t)1-7δ = 8.55 (1H, d), 8.45 (1H, d), 8.05~8.00 (2H, m), 7.95~7.90 (4H, m), 7.80 (1H, t), 7.71 (1H, t), 7.56~7.50 (3H, m), 7.49~7.45 (2H, m), 7.35~7.32 (2H, m), 7.16 (1H, t)1-14δ = 8.55 (1H, d), 8.45 (1H, d), 7.95~7.90 (4H, m),7.86~7.83 (3H, m), 7.55~7.50 (3H, m), 7.49~7.46 (2H, m), 7.35 (1H, t), 7.16 (1H, t)1-18δ = 8.55 (1H, d), 7.98~7.91 (4H, m), 7.80 (1H, t), 7.60 (1H, d), 7.55~7.52 (3H, m), 7.46 (1H, t), 7.39 (1H, t), 7.35 (1H, t), 7.31 (1H, t), 7.19~7.16 (2H, m)1-24δ = 8.55 (1H, d), 7.98~7.91 (6H, m), 7.85~7.78 (3H, m), 7.54~7.46 (7H, m), 7.39 (1H, t), 7.35~7.31 (2H, m), 7.25~7.21 (2H, m), 7.16 (1H, t)1-29δ = 8.55 (1H, d), 7.98~7.91 (5H, m), 7.80 (1H, t), 7.54~7.46 (4H, m), 7.42 (1H, s), 7.39~7.31 (5H, m), 7.16 (1H, t)1-38δ = 8.55 (1H, d), 8.45 (1H, d), 8.05 (1H, d), 7.94~7.92 (2H, m), 7.77~7.75 (2H, m), 7.60 (1H, d), 7.56~7.49 (6H, m), 7.35 (1H, t), 7.16 (1H, t)1-46δ = 8.55 (1H, d), 8.45 (1H, d), 8.01 (1H, s), 7.94~7.86 (4H, m), 7.78 (1H, s), 7.71 (1H, t), 7.64 (1H, d), 7.56~7.48 (5H, m), 7.35 (1H, t), 7.16 (1H, t)1-52δ = 8.55 (1H, d), 8.45 (1H, d), 8.08 (1H, d), 7.94~7.92 (3H, m), 7.80 (1H, d), 7.67 (1H, d), 7.57~7.49 (3H, m), 7.43 (1H, t),7.35 (1H, t), 7.16 (1H, t)1-60δ = 8.55 (1H, d), 7.98~7.94 (2H, m), 7.60~7.54 (2H, m), 7.39~7.31 (3H, m), 7.19~7.16 (2H, m)1-67δ = 8.55 (1H, d), 8.01~7.94 (3H, m), 7.64 (1H, d), 7.60~7.52 (5H, m), 7.39~7.31 (3H, m), 7.16 (1H, t)1-71δ = 8.55 (1H, d), 7.98~7.94 (2H, m), 7.81 (1H, d), 7.67~7.54 (5H, m), 7.39~7.31 (3H, m), 7.19~7.16 (2H, m)1-78δ = 중수소 함량 100%로. 1H NMR 피크 없음1-84δ = 7.96~7.94 (3H, m), 7.64 (1H, d), 7.52~7.41 (4H, m), 7.33 (1H, t), 7.25~7.23 (2H, m)1-91δ = 7.91 (1H, d), 7.81 (1H, d), 7.67 (2H, d), 7.57 (1H, t), 7.49 (1H, t), 7.51 (1H, t)1-94δ = 7.55~7.49 (5H, m), 7.42~7.40 (2H, m)1-100δ = 7.49 (1H, d), 7.41 (1H, d)1-110δ = 7.99 (1H, s), 7.77~7.72 (2H, m), 7.64 (1H, d), 7.52 (1H, t), 7.49~7.41 (3H, m), 7.36 (1H, t)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 at 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

[0447] <Experimental Example 1> 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 TCTA (tris(4-carbazoyl-9-ylphenyl)amine) and a hole transport layer mCP (1,3-bis(N-carbazolyl)benzene), was formed on the above ITO transparent electrode (anode).

[0450] An emissive layer was thermally vacuum deposited on top of it as follows. For the emissive layer, a compound represented by Chemical Formula 1 of the present application was deposited to a thickness of 400 Å as a host, and a green phosphorescent dopant, Ir(ppy)3, was deposited with 7% doping. Subsequently, BCP was deposited to a thickness of 60 Å as a hole blocking layer, and Alq3 was deposited to 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 to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing 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 1 above are as shown in Table 13 below. At this time, the light-emitting layer compound of the Comparative Example is as follows.

[0454]

[0455] Compound driving voltage efficiency color lifetime (V)(cd / A)(T 90Comparative Example 1A 7.8850.5Green50 Comparative Example 2B 7.3852.7Green70 Comparative Example 3C 7.1955.9Green77 Comparative Example 4D 7.4951.6Green65 Comparative Example 5E 7.2554.2Green74 Comparative Example 6F 7.1358.7Green80 Comparative Example 7G 7.1159.1Green82 Example 11-45.1287.2Green126 Example 21-75.1685.6Green129 Example 31-145.0586.4Green121 Example 41-185.5870.6Green103 Example 51-245.6572.3Green108 Example 61-295.6175.9 Green 110 Example 71-384.13105.3 Green 160 Example 81-464.25109.2 Green 164 Example 91-524.22108.7 Green 165 Example 101-604.7892.5 Green 142 Example 111-674.8295.3 Green 148 Example 121-714.8894.2 Green 144 Example 131-783.05128.7 Green 192 Example 141-845.5271.3 Green 105 Example 151-913.11126.8 Green 199 Example 161-943.82117.6 Green 172 Example 171-1003.88120.3Green175 Example 181-1103.86113.8Green178

[0456] The compound represented by Chemical Formula 1 of the present invention includes a phenyl linker between Fused Carbazole and Triazine, wherein the Fused Carbazole and Triazine have an ortho-position bond based on the phenyl linker. Through-Space Charge Transfer occurs as the Fused Carbazole and Triazine have an ortho-position bond. That is, not only electron transfer through intramolecular bonding but also electron transfer through intramolecular space is possible, so the electron transfer capability is excellent, and accordingly, it was confirmed that the driving voltage is excellent.

[0457] In addition, it was confirmed that the device has an excellent lifespan because the molecular structure's stability is increased by lowering the vibration energy and rotation energy of the molecule, which is a composition in which the deuterium substitution rate of structural formula A among the heterocyclic compounds represented by the above chemical formula 1 is 20% or more and 100% or less.

[0458] In Comparative Examples 1 to 6, a phenyl linker is included between Fused Carbazole and Triazine. In this case, the Fused Carbazole and Triazine do not have ortho bonds with respect to the phenyl linker, but rather meta or para bonds. When meta or para bonds are present, the rotation of Fused Carbazole, which acts as the HOMO, and Triazine, which acts as the LUMO, is freer than when they have ortho bonds. Consequently, because meta or para bonds form various conformations, the packing density is higher than when they have ortho bonds, resulting in relatively weaker intermolecular electron transfer. This leads to an increase in driving voltage and a decrease in luminescence efficiency. Furthermore, the increased rotational energy lowers molecular stability, resulting in an inferior lifetime.

[0459] Comparative Example 7 is a case where the ortho site bond is formed based on the phenyl linker, but only the linker portion is substituted with deuterium. In this case, if the triazine portion is not substituted with deuterium as in the present invention, the LUMO role is relatively weakened, so the capacitance increases, the driving voltage rises, and the lifespan decreases.

[0460] <Experimental Example 2> Fabrication of an Organic Light-Emitting Device

[0461] 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.

[0462] A common layer, a hole injection layer TCTA (tris(4-carbazoyl-9-ylphenyl)amine) and a hole transport layer mCP (1,3-bis(N-carbazolyl)benzene), was formed on the above ITO transparent electrode (anode).

[0463] 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 Chemical Formula 3 as a host, and a green phosphorescent dopant was deposited by doping Ir(ppy)3 with 7%. 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.

[0464] 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.

[0465] 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.

[0466] The driving voltage, luminous efficiency, and lifetime results of the organic electroluminescent device of Experimental Example 2 above are as shown in Table 14 below.

[0467] Compound Ratio Driving Voltage Efficiency Color Coordinates Lifetime (V) (cd / A) (T 90)Comparative Example 8A : 2-8240:605.6277.4Green90 Comparative Example 935:655.6876.2Green92 Comparative Example 1030:705.7274.8Green95 Comparative Example 11A : 3-8040:605.5679.2Green93 Comparative Example 1235:655.6478.5Green96 Comparative Example 1330:705.7277.6Green99 Comparative Example 14B : 2-8840:605.3284.8Green100 Comparative Example 1535:655.3683.2Green103 Comparative Example 1630:705.3982.7Green107 Comparative Example 17B : 3-11240:605.2985.5Green102 Comparative Example 1835:655.3384.8Green109 Comparative Example 1930:705.3883.2Green111 Comparative Example 20C : 2-440:605.1887.2Green108 Comparative Example 2135:655.2186.3Green110 Comparative Example 2230:705.2485.6Green118 Comparative Example 23C : 2-8940:605.1688.7Green111 Comparative Example 2435:655.2387.2Green116 Comparative Example 2530:705.2586.5Green120 Comparative Example 26D : 3-440:605.4281.9Green95 Comparative Example 2735:655.4981.5Green98 Comparative Example 2830:705.5380.7Green102 Comparative Example 29D : 3-8040:605.3882.7Green97 Comparative Example 3035:655.4181.2Green103 Comparative Example 3130:705.4980.3Green105 Comparative Example 32E : 3-11240:605.2386.4Green108 Comparative Example 3335:655.2585.6Green112 Comparative Example 3430:705.2884.8Green117 Comparative Example 35F : 3-8640:605.0290.2Green113 Comparative Example 3635:655.1389.7Green115 Comparative Example 3730:705.1888.6Green120 Comparative Example 38G : 3-8640:605.0092.1Green117 Comparative Example 3935:655.0591.5Green119 Comparative Example 4030:705.0890.4Green124 Example 191-4 : 3-9840:603.02128.7Green195 Example 2035:653.08127.5Green192 Example 2130:703.12126.4Green190 Example 221-7 : 3-11240:603.05125.6Green186 Example 2335:653.11124.8Green182 Example 2430:703.16123.7Green180 Example 251-14 : 3-9840:603.03126.6Green185 Example 2635:653.09125.8Green182 Example 2730:703.13124.7Green178 Example 281-18 : 3-8640:603.52115.6Green152 Example 2935:653.55114.2Green150 Example 3030:703.59113.8Green146 Example 311-24 : 3-8040:603.44118.7Green158 Example 3235:653.48117.2Green155 Example 3330:703.56116.5Green152 Example 341-29 : 2-2740:603.88109.4Green150 Example 3535:653.92108.2Green145 Example 3630:703.95105.2Green142 Example 371-29 : 2-8540:603.72113.6Green155 Example 3835:653.75112.8Green158 Example 3930:703.79111.5Green160 Example 401-38 : 3-3240:602.06155.6Green280 Example 4135:652.12154.2Green283 Example 4230:702.19152.7Green286 Example 431-38 : 3-11240:602.03158.7Green285 Example 4435:652.11157.4Green288 Example 4530:702.16156.2Green290 Example 461-46 : 3-8040:602.23157.3Green288 Example 4735:652.28156.5Green293 Example 4830:702.31155.2Green296 Example 491-52 : 2-8540:602.31156.3Green281 Example 5035:652.36155.1Green287 Example 5130:702.39154.7Green294 Example 521-60 : 2-8940:602.56146.2Green205 Example 5335:652.64143.6Green213 Example 5430:702.66142.7Green223 Example 551-67 : 2-8540:602.62148.6Green211 Example 5635:652.68147.2Green223 Example 5730:702.74145.5Green234 Example 581-71 : 2-8240:602.66140.2Green218 Example 5935:652.69138.5Green226 Example 6030:702.72135.2Green240 Example 611-78 : 3-9840:601.05187.6Green382 Example 6235:651.09186.2Green388 Example 6330:701.12185.5Green394 Example 641-84 : 3-8040:603.48119.3Green156 Example 6535:653.50118.1Green153 Example 6630:703.52117.4Green150 Example 671-91 : 2-8940:601.13180.3Green356 Example 6835:651.26178.2Green364 Example 6930:701.29177.6Green370 Example 701-94 : 2-8240:601.52170.6Green305 Example 7135:651.55168.2Green309 Example 7230:701.59166.5Green312 Example 731-100 : 2-8940:601.46172.3Green313 Example 7435:651.49171.2Green320 Example 7530:701.53168.5Green325 Example 761-110 : 2-8940:601.44174.4Green309 Example 7735:651.48173.5Green314 Example 7830:701.56172.1Green322.

[0468] Comparing the results of Table 14 above with the results of Table 13 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 superior effects in terms of efficiency and lifetime. This is due to the exciplex phenomenon, which is a phenomenon in which energy of the size of the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host) is released through electron exchange between two molecules. When the exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, and as a result, the internal quantum efficiency of fluorescence emission can increase up to 100%.

[0469] 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 Chemical Formula 1 acts as an acceptor and the heterocyclic compound of Chemical Formula 2 acts as a donor, and they are used together as hosts for the emissive layer, they exhibit excellent device characteristics.

[0470] 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.

Claims

1. Heterocyclic compounds represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is O; S; or CRaRb; and, L is a directly bonded; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, and l is an integer from 1 to 3, and if l is 2 or greater, L are equal to or different from each other, and A is an aryl ring having 6 to 60 carbon atoms substituted or unsubstituted with deuterium; or a heterocyclic ring having 2 to 60 carbon atoms substituted or unsubstituted with deuterium, and Ra, Rb, Rd, Ar1 and Ar2 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and a is an integer from 0 to 4, and if a is 2 or greater, Rd are equal or different, and H is hydrogen, D is deuterium, and, d is an integer from 1 to 6, and The above chemical formula 1 is represented by the following structural formulas A to C, and [Structural Formula A] [Structural Formula B] [Structural Formula C] In the above structural formulas A to C, refers to the positions where they combine with each other, The deuterium content of the above structural formula A is 20% or more and 100% or less.

2. In Claim 1, A heterocyclic compound in which the deuterium content of structural formula A is 20% or more and 100% or less, and the deuterium content of structural formulas B and C is 10% or less.

3. In Claim 1, A heterocyclic compound having a deuterium content of structural formulas A and C of 20% or more and 100% or less, and a deuterium content of structural formula B of 10% or less.

4. In Claim 1, A heterocyclic compound having a deuterium content of structural formulas A to C of the above, which is 20% or more and 100% or less.

5. In Claim 1, A heterocyclic compound wherein at least one of the above Ar1 and Ar2 is a substituted or unsubstituted aryl group having 10 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

6. The heterocyclic compound of Claim 1, wherein A is represented by the following structural formula A-1 or A-2: [Structural Formula A-1] [Structural Formula A-1] In the above structural formulas A-1 and A-2, represents the condensation location, X3 is O; S; or NRe, and R11 to R19 are the same or different from each other and are each independently hydrogen; or deuterium, and Re is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and The above a1 is an integer of 1 or 2, and If a1 is 2, the substituents inside the parentheses are either the same or different.

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] [Chemical Formula 3] In the above chemical formulas 2 and 3, R1 to R9, Re and Rf are the same or different from each other and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to 60 alkyl group; substituted or unsubstituted C2 to 60 alkenyl group; substituted or unsubstituted C2 to 60 alkynyl group; substituted or unsubstituted C1 to 60 alkoxy group; substituted or unsubstituted C3 to 60 cycloalkyl group; substituted or unsubstituted C2 to 60 heterocycloalkyl group; substituted or unsubstituted C6 to 60 aryl group; substituted or unsubstituted C2 to 60 heteroaryl group; substituted or unsubstituted phosphine oxide group; Selected from the group consisting of substituted or unsubstituted amine groups, or two or more adjacent groups combine to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms, d is an integer from 0 to 2, where d is an integer from 2, R9 are the same or different, r and s are integers from 0 to 7, where r is an integer of 2 or more, Re are the same or different, and where s is an integer of 2 or more, Rf are the same or different. L1, L2, L11 and L12 are the same or different from each other and each independently, directly bonded; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; and Ar3 to Ar6 are the same or different from one another and each independently, deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or -SiR201R202R203; and R201 to R203 are the same or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; and m and n are integers from 0 to 4, and p and q are integers from 1 to 6, and If m, n, p, and q are 2 or more, the substituents within the parentheses are 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. 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] [Chemical Formula 3] In the above chemical formulas 2 and 3, R1 to R9, Re and Rf are the same or different from each other and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to 60 alkyl group; substituted or unsubstituted C2 to 60 alkenyl group; substituted or unsubstituted C2 to 60 alkynyl group; substituted or unsubstituted C1 to 60 alkoxy group; substituted or unsubstituted C3 to 60 cycloalkyl group; substituted or unsubstituted C2 to 60 heterocycloalkyl group; substituted or unsubstituted C6 to 60 aryl group; substituted or unsubstituted C2 to 60 heteroaryl group; substituted or unsubstituted phosphine oxide group; Selected from the group consisting of substituted or unsubstituted amine groups, or two or more adjacent groups combine to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms, d is an integer from 0 to 2, where d is an integer from 2, R9 are the same or different, r and s are integers from 0 to 7, where r is an integer of 2 or more, Re are the same or different, and where s is an integer of 2 or more, Rf are the same or different. L1, L2, L11 and L12 are the same or different from each other and each independently, directly bonded; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; and Ar3 to Ar6 are the same or different from one another and each independently, deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or -SiR201R202R203; and R201 to R203 are the same or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; and m and n are integers from 0 to 4, and p and q are integers from 1 to 6, and If m, n, p, and q are 2 or more, the substituents within the parentheses are the same or different from each other.

15. In Claim 14, A composition for an organic layer of an organic light-emitting device, wherein the weight ratio of the heterocyclic compound represented by Formula 2 or Formula 3 in the composition is higher than the weight ratio of the heterocyclic compound represented by Formula 1.

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