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

Abstract

The present specification relates to a heterocyclic compound and an organic light-emitting element 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 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, 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] H is hydrogen, D is deuterium, and,

[0019] d is an integer from 1 to 6, and

[0020] The above chemical formula 1 is represented by the following structural formulas A to C, and

[0021] [Structural Formula A]

[0022]

[0023] [Structural Formula B]

[0024]

[0025] [Structural Formula C]

[0026]

[0027] In the above structural formulas A to C,

[0028] refers to the positions where they combine with each other,

[0029] The combined deuterium content of the above structural formulas A and B; or the combined deuterium content of the above structural formulas C and B; is 50% or more and 100% or less.

[0030] 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.

[0031] 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.

[0032] [Chemical Formula 2]

[0033]

[0034] In the above chemical formula 2,

[0035] 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; Selected from the group consisting of substituted or unsubstituted amine groups, or two or more adjacent groups are combined 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, and when d is an integer of 2, R9 are the same or different from each other, and

[0036] 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; and

[0037] Ar3 and Ar4 are the same or different from each other and each independently are 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

[0038] m and n are integers from 0 to 4, and

[0039] p and q are integers from 1 to 6, and

[0040] If m, n, p, and q are 2 or more, the substituents within the parentheses are the same or different from each other.

[0041] 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.

[0042] The heterocyclic compound represented by Formula 1 according to the present invention has a structure in which a triazine (Structural Formula A) is bonded to a linker (Structural Formula C) centered around a skeleton of Fused Carbazole (Structural Formula B), and the carbon-hydrogen bonds at the sites where the Fused Carbazole portion is bonded to the triazine or linker are substituted with deuterium in a specific amount.

[0043] That is, the present invention is characterized by necessarily substituting the structural formula B portion with deuterium. The structural formula B portion is a HOMO portion responsible for hole transport, and substituting this portion with deuterium increases the packing density, thereby enabling excellent driving voltage and luminous efficiency.

[0044] In addition to the deuterium substitution effect of structural formula B, if structural formula C is also substituted with deuterium, the rotation of HOMO and LUMO is relatively restricted. Consequently, since the rotation energy is reduced, the stability of the molecule is increased, which can lead to an improved device lifespan.

[0045] Substituting part B of the structural formula with deuterium improves hole stability and mobility. By the same principle, substituting part A of the structural formula with deuterium can increase electron stability and mobility. Substituting both parts A and B with deuterium balances charge and hole mobilities, causing the recombination zone to be located in the center of the emissive layer and thereby increasing luminous efficiency. Furthermore, it enhances the overall thermal stability of the molecule, contributing to an extended device lifespan.

[0046] 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.

[0047] <Explanation of Symbols>

[0048] 100: Substrate

[0049] 200: Anode

[0050] 300: Organic layer

[0051] 301: Hole injection layer

[0052] 302: Precision Transport Layer

[0053] 303: Emissive layer

[0054] 304: Main barrier layer

[0055] 305: Electron transport layer

[0056] 306: Electron injection layer

[0057] 400: Cathode

[0058] The present specification will be described in more detail below.

[0059] 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.

[0060] In this specification, of the chemical formula means the position where it is combined.

[0061] 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.

[0062] 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.

[0063] 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 examples 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.

[0064] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, an element having a deuteron as its nucleus, consisting of one proton and one neutron, and can be represented as hydrogen-2, and its element symbol is D or 2 It can also be written as H.

[0065] 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.

[0066] 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.

[0067] 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.

[0068]

[0069] 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.

[0070] In this specification, the halogen may be fluorine, chlorine, bromine, or iodine.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] In this specification, the alkoxy group is represented as -O(R101), and R101 may be an example of the aforementioned alkyl group.

[0076] In this specification, the aryloxy group is represented as -O(R102), and R102 may be an example of the aryl group described above.

[0077] In this specification, the alkylthoxy group is represented as -S(R103), and R103 may be an example of the alkyl group described above.

[0078] In this specification, the arylthioxy group is represented as -S(R104), and R104 may be an example of the aryl group described above.

[0079] In this specification, the alkyl sulfoxy group is represented as -S(=0)2(R105), and R105 may be an example of the aforementioned alkyl group.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] In the present specification, the terphenyl group may be selected from the following structures.

[0085]

[0086] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

[0087] When the above fluorenyl group is substituted, it may be any one of the following structures, but is not limited thereto.

[0088]

[0089] 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.

[0090] In this specification, when a substituent is a carbazole group, it means bonding to the nitrogen or carbon of the carbazole.

[0091] In the present specification, when a carbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole.

[0092] In this specification, the benzocarbazole group may be any one of the following structures.

[0093]

[0094] In this specification, the dibenzocarbazole group may be any one of the following structures.

[0095]

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

[0097]

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

[0099]

[0100] 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.

[0101] 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.

[0102] 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.

[0103] 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.

[0104] In this specification, the examples of aryl groups described above may be applied, except that the arylene group is a divalent group.

[0105] In this specification, the examples of the aforementioned heteroaryl groups may be applied, except that the heteroaryl group is a divalent group.

[0106] 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.

[0107] 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.

[0108] 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.

[0109] 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.

[0110] 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.

[0111] 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.

[0112] In one embodiment of the present application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[0113] [Chemical Formula 1]

[0114]

[0115] In the above chemical formula 1,

[0116] X is O; S; or CRaRb; and,

[0117] L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, and

[0118] 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

[0119] 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

[0120] Ra, Rb, 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

[0121] H is hydrogen, D is deuterium, and,

[0122] d is an integer from 1 to 6, and

[0123] The above chemical formula 1 is represented by the following structural formulas A to C, and

[0124] [Structural Formula A]

[0125]

[0126] [Structural Formula B]

[0127]

[0128] [Structural Formula C]

[0129]

[0130] In the above structural formulas A to C,

[0131] refers to the positions where they combine with each other,

[0132] The combined deuterium content of the above structural formulas A and B; or the combined deuterium content of the above structural formulas C and B; is 50% or more and 100% or less.

[0133] The heterocyclic compound represented by Formula 1 according to the present invention has a structure in which a triazine (Structural Formula A) is bonded to a linker (Structural Formula C) centered around a skeleton of Fused Carbazole (Structural Formula B), and the carbon-hydrogen bonds at the sites where the Fused Carbazole portion is bonded to the triazine or linker are substituted with deuterium in a specific amount.

[0134] First, the binding site between Fused Carbazole and the triazine or linker serves as a key pathway for molecular energy transfer and charge transport. By substituting the CH bonds at this site with a specific amount of CD bonds, the bond dissociation energy increases and the vibrational energy level is lowered. Consequently, non-radiative decay and the thermal decay of CH bonds are suppressed, resulting in a significantly improved device lifespan.

[0135] In addition, deuteration of the triazine or linker portion based on Fused Carbazole increases the stability of the electron transport pathway and balances the hole transport characteristics of the Fused Carbazole portion, resulting in improved charge recombination efficiency. Consequently, the current efficiency and external quantum efficiency increase, and the driving voltage decreases, thereby improving the performance of the device.

[0136] In the present application, the combined deuterium content of structural formula A and structural formula B is 50% or more and 100% or less, and the deuterium content of structural formula C may be 10% or less.

[0137] Specifically, the combined deuterium content of the above structural formulas A and B is 50% or more and 100% or less, and the deuterium content of the above structural formula C may be 10% or less, 8% or less, 5% or less, 0% or more, and 1% or more.

[0138] Structural formula B is the HOMO region responsible for hole transport; additionally substituting this region with deuterium increases packing density, thereby improving hole mobility and stability. Consequently, it can exhibit characteristics that allow for a lower driving voltage. By the same principle, substituting structural formula A with deuterium can increase electron stability and mobility. Substituting both structural formulas A and B with deuterium balances charge and hole mobilities, causing the recombination zone to be located in the center of the emissive layer and increasing luminous efficiency. Furthermore, it enhances the overall thermal stability of the molecule, contributing to an extended device lifespan.

[0139] In the present application, the combined deuterium content of structural formulas B and C is 50% or more and 100% or less, and the deuterium content of structural formula A may be 10% or less.

[0140] Specifically, the combined deuterium content of the above structural formulas B and C is 50% or more and 100% or less, and the deuterium content of the above structural formula A may be 10% or less, 8% or less, 5% or less, 0% or more, and 1% or more.

[0141] In addition to the deuterium substitution effect of structural formula B, if structural formula C is also substituted with deuterium, the rotation of HOMO and LUMO is relatively restricted. Consequently, since the rotation energy is reduced, the stability of the molecule is increased, which can lead to an improved device lifespan.

[0142] In the present application, the above formula 1 may be represented by any one of the following formulas 1-1-1 to 1-1-6.

[0143] [Chemical Formula 1-1-1]

[0144]

[0145] [Chemical Formula 1-1-2]

[0146]

[0147] [Chemical Formula 1-1-3]

[0148]

[0149] [Chemical Formula 1-1-4]

[0150]

[0151] [Chemical Formula 1-1-5]

[0152]

[0153] [Chemical Formula 1-1-6]

[0154]

[0155] In the above chemical formulas 1-1-1 to 1-1-6,

[0156] H1 to H12 are each independently hydrogen; or deuterium, and among H1 to H12, 5 to 12 are deuterium, and the definition of the remaining substituents is the same as the definition in Chemical Formula 1.

[0157] In the present application, X is O; S; or CRaRb.

[0158] In the present application, X is O.

[0159] In the present application, X is S.

[0160] In the present application, X is CRaRb.

[0161] 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.

[0162] In another embodiment, Ra and Rb may each independently be a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms.

[0163] In another embodiment, Ra and Rb may each independently be a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms.

[0164] In another embodiment, Ra and Rb may each independently be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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.

[0169] In the present application, L may be a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0170] In another embodiment, L may be a substituted or unsubstituted arylene group having 6 to 40 carbon atoms.

[0171] In another embodiment, L may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0172] In another embodiment, L may be an arylene group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0173] In another embodiment, L may 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.

[0174] In the present application, the above L may be represented as one of the following connectors.

[0175]

[0176] In the above connector, means the position where they combine with each other.

[0177] At this time, the above connector denoted by L has a deuterium content of structural formula C.

[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 substituted or unsubstituted monocyclic aryl group having 6 to 10 carbon atoms; 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.

[0185] 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.

[0186] 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.

[0187] 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.

[0188] 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.

[0189] In another embodiment, at least one of Ar1 and Ar2 may be a substituted or unsubstituted aryl group having 10 or more and 20 or fewer carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

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

[0192] 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.

[0193] 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.

[0194] In another embodiment, A may be an aryl ring having 6 to 60 carbon atoms that is substituted or unsubstituted with deuterium.

[0195] In another embodiment, A may be an aryl ring having 6 to 40 carbon atoms that is substituted or unsubstituted with deuterium.

[0196] In another embodiment, A may be an aryl ring having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0197] In another embodiment, A may be a single-ring aryl ring having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0198] In another embodiment, A may be a benzene ring substituted or unsubstituted with deuterium.

[0199] In this case, the deuterium content of A can be included in the deuterium content of structural formula B.

[0200] In the present application, the above A may be represented by the following structural formula A-1 or A-2.

[0201] [Structural Formula A-1]

[0202]

[0203] [Structural Formula A-2]

[0204]

[0205] In the above structural formulas A-1 and A-2,

[0206] represents the condensation location,

[0207] X3 is O; S; or NRe, and

[0208] R11 to R19 are the same or different from each other and are each independently hydrogen; or deuterium, and

[0209] 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

[0210] The above a1 is an integer of 1 or 2, and

[0211] If a1 is 2, the substituents inside the parentheses are either the same or different.

[0212] In one embodiment of the present application, the deuterium substitution rate of the compound of Formula 1 may be 20% or more and 95% or less.

[0213] In another embodiment, the deuterium substitution rate of the compound of Formula 1 may be 25% or more and 95% or less.

[0214] In another embodiment, the deuterium substitution rate of the compound of Formula 1 may be 30% or more and 90% or less.

[0215] In one embodiment of the present application, the formula 1 may be represented by any one of the following compounds.

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246] 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.

[0247] 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.

[0248] 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.

[0249] 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.

[0250] 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.

[0251] 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.

[0252] 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.

[0253] 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.

[0254] 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.

[0255] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0256] In another embodiment, the first electrode may be a negative electrode and the second electrode may be a positive electrode.

[0257] 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.

[0258] 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.

[0259] 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.

[0260] 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.

[0261] 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.

[0262] 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.

[0263] 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.

[0264] 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.

[0265] 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.

[0266] 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.

[0267] In one embodiment of the present application, Ir(ppy)3, a green phosphorescent dopant, may be used as an iridium-based dopant.

[0268] In one embodiment of the present application, (piq)2(Ir)(acac), a red phosphorescent dopant, may be used as an iridium-based dopant.

[0269] 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.

[0270] 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.

[0271] 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.

[0272] In another organic light-emitting device, the organic layer includes a hole-blocking layer, and the hole-blocking layer may include the heterocyclic compound.

[0273] In another organic light-emitting device, the organic layer includes an electron blocking layer, and the electron blocking layer may include the heterocyclic compound.

[0274] 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.

[0275] 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.

[0276] 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.

[0277] 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.

[0278] 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.

[0279] 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.

[0280] 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.

[0281] For example, LiF is commonly used as an electron injection material in the industry, but the present application is not limited thereto.

[0282] 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.

[0283] 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.

[0284] 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.

[0285] 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.

[0286] 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.

[0287] 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.

[0288] 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.

[0289] 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.

[0290] Figure 3 illustrates a case where the organic layer is multilayered.

[0291] 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).

[0292] However, the scope of the present application is not limited by such a stacked structure, and, if necessary, the remaining layers excluding the light-emitting layer may be omitted, and other necessary functional layers may be added.

[0293] The organic layer containing the above chemical formula 1 may additionally include other materials as needed.

[0294] 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.

[0295] [Chemical Formula 2]

[0296]

[0297] In the above chemical formula 2,

[0298] 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; Selected from the group consisting of substituted or unsubstituted amine groups, or two or more adjacent groups are combined 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, and when d is an integer of 2, R9 are the same or different from each other, and

[0299] 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; and

[0300] Ar3 and Ar4 are the same or different from each other and each independently are 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

[0301] m and n are integers from 0 to 4, and

[0302] p and q are integers from 1 to 6, and

[0303] If m, n, p, and q are 2 or more, the substituents within the parentheses are the same or different from each other.

[0304] In the present application, the deuterium content of Formula 2 may be 30% or less or 40% or more.

[0305] 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.

[0306] 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.

[0307] In the present application, the above chemical formula 2 may be represented by any one of the following chemical formulas 2-1 to 2-6.

[0308] [Chemical Formula 2-1]

[0309]

[0310] [Chemical Formula 2-2]

[0311]

[0312] [Chemical Formula 2-3]

[0313]

[0314] [Chemical Formula 2-4]

[0315]

[0316] [Chemical Formula 2-5]

[0317]

[0318] [Chemical Formula 2-6]

[0319]

[0320] In the above chemical formulas 2-1 to 2-6,

[0321] The definition of each substituent is the same as the definition in Chemical Formula 2 above.

[0322] 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.

[0323] 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.

[0324] 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.

[0325] 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.

[0326] 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.

[0327] In another embodiment, R1 to R9 may be the same or different from each other and may each independently be hydrogen; or deuterium.

[0328] 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.

[0329] 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.

[0330] 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.

[0331] 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.

[0332] 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.

[0333] 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.

[0334] 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.

[0335] 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.

[0336] 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.

[0337] 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.

[0338] 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.

[0339] 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.

[0340] 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.

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347] An organic light-emitting device further comprising a heterocyclic compound represented by the above chemical formula 2 may be subject to the provisions regarding an organic light-emitting device comprising a heterocyclic compound represented by the above chemical formula 1.

[0348] In another embodiment, the heterocyclic compound represented by the above chemical formula 2 can be used as a light-emitting material for the light-emitting layer of an organic light-emitting device.

[0349] In another embodiment, the heterocyclic compound represented by the above chemical formula 2 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.

[0350] 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. The organic layer may be formed by pre-mixing the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 and using a thermal vacuum deposition method.

[0351] 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.

[0352] 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.

[0353] 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.

[0354] 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, wherein the weight ratio of the heterocyclic compound represented by Chemical Formula 2 may be higher than the weight ratio of the heterocyclic compound represented by Chemical Formula 1.

[0355] In the present application, the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 in the composition may be 20:80 to 45:55.

[0356] In another embodiment, the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 in the composition may be 20:80 to 45:55, specifically 25:75 to 40:60, and more specifically 30:70 to 40:60.

[0357] 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. As recombination occurs more rapidly, the number of annihilated excitons decreases, resulting in improved luminous efficiency.

[0358] 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.

[0359] 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 supplying the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 as separate sources, and then forming the layer using a thermal vacuum deposition method.

[0360] 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 and using a thermal vacuum deposition method.

[0361] 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.

[0362] 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.

[0363] 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.

[0364] 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.

[0365] The above composition may additionally include materials known in the art, such as solvents and additives.

[0366] In the following, the present specification is explained in more detail through examples, but these are for illustrative purposes only and are not intended to limit the scope of the present application.

[0367] <Preparation Example>

[0368] [Preparation Example 1] Preparation of Compound 2

[0369]

[0370] 1) Preparation of Intermediate 2-1

[0371] 12H-benzo[4,5]thieno[2,3-a]carbazole [A] (10 g, 0.037 mol), Triflic acid (77.74 g, 0.52 mol), D6-Benzene (200 mL), and Chloroform (100 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 intermediate 2-1 (9.92 g, yield 95%).

[0372] The deuterium substitution rate can be controlled by manufacturing under reaction conditions as shown in Table 1 below.

[0373] 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%

[0374] 2) Preparation of Intermediate 2-2

[0375] Intermediate 2-1 (9.92 g, 0.035 mol), 1-bromo-4-iodobenzene (9.90 g, 0.035 mol), Pd2(dba)3 (2.74 g, 0.003 mol), Sphos (2.46 g, 0.006 mol), NaOtBu (6.72 g, 0.07 mol), and Toluene (100 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 130°C. After the reaction was complete, the precipitated solid was filtered, dissolved in 1,2-Dichlorobenzene, filtered via silica gel, and concentrated to obtain Compound 2-2 (13.81 g, yield 90%).

[0376] 3) Preparation of Intermediate 2-3

[0377] Intermediate 2-3 (13.81 g, 0.032 mol), Bis(pinacolato)diboron (9.65 g, 0.038 mol), Pd2(dba)3 (2.74 g, 0.003 mol), Sphos (2.46 g, 0.006 mol), NaOtBu (7.11 g, 0.074 mol), and Dioxane (140 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 120°C. After the reaction was complete, the mixture was concentrated, dissolved in DCM, filtered via silica gel, and concentrated to obtain Compound 2-3 (14.45 g, yield 93%).

[0378] 4) Preparation of Intermediate 2-4

[0379] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine [B] (10 g, 0.029 mol), Triflic acid (60.93 g, 0.406 mol), D6-Benzene (200 mL), and Chloroform (100 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 intermediate 2-4 (9.23 g, yield 89%).

[0380] 5) Preparation of Compound 2

[0381] Intermediate 2-3 (12.04 g, 0.025 mol), Intermediate 2-4 (10.73 g, 0.025 mol), Pd(PPh3)4 (1.04 g, 0.001 mol), K2CO3 (8.29 g, 0.06 mol), Dioxane (100 mL), and Water (30 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 Compound 2 (15.83 g, yield 95%).

[0382] The target compound D of Table 2 below was obtained by synthesizing in the same manner as the above preparation example, except that the reactants [A] and [B] of the above preparation example were changed to reactants A, B, and C of Table 2 below.

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401] [Preparation Example 2] Preparation of Compound 436

[0402]

[0403] 1) Preparation of intermediate 436-1

[0404] Intermediate 2-4 (9.92 g, 0.035 mol), (4'-fluoro-[1,1'-biphenyl]-3-yl)boronic acid [B] (7.56 g, 0.035 mol), Pd(PPh3)4 (1.04 g, 0.001 mol), K2CO3 (8.29 g, 0.06 mol), Dioxane (100 mL), and Water (30 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 100°C. After the reaction was complete, the precipitated solid was filtered, dissolved in 1,2-Dichlorobenzene, filtered via silica gel, and concentrated to obtain Compound 436-1 (15.37 g, yield 89%).

[0405] 2) Preparation of Compound 436

[0406] Intermediate 436-1 (15.37 g, 0.031 mol), 2-1 [B] (8.78 g, 0.035 mol), Cs2CO3 (22.81 g, 0.07 mol), and DMA (100 mL) were placed in a one-neck round-bottom flask, and the mixture was refluxed at 185°C. After the reaction was complete, the precipitated solid was filtered, dissolved in 1,2-Dichlorobenzene, filtered via silica gel, and concentrated to obtain compound 436 (18.30 g, yield 78%).

[0407] Target compound D of Table 3 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 3 below.

[0408]

[0409] [Preparation Example 3] Preparation of Compound 449

[0410]

[0411] 1) Preparation of intermediate 449-1

[0412] 12-(4-chlorophenyl)-12H-benzo[4,5]thieno[2,3-a]carbazole [A] (13.43 g, 0.035 mol), Triflic acid (77.74 g, 0.52 mol), D6-Benzene (200 mL), and Chloroform (100 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 intermediate 449-1 (12.67 g, yield 91%).

[0413] The deuterium substitution rate can be controlled by manufacturing it in the same way as the aforementioned intermediate 2-1.

[0414] 2) Preparation of Intermediate 449-2

[0415] Intermediate 449-1 (12.67 g, 0.031 mol), Bis(pinacolato)diboron (9.65 g, 0.038 mol), Pd2(dba)3 (2.74 g, 0.003 mol), Sphos (2.46 g, 0.006 mol), KOAc (7.26 g, 0.074 mol), and Dioxane (120 mL) were added to a one-neck round-bottom flask, and the mixture was refluxed at 120°C. After the reaction was complete, the mixture was concentrated, dissolved in DCM, filtered via silica gel, and concentrated to obtain compound 449-2 (13.51 g, yield 89%).

[0416] 3) Preparation of Compound 449

[0417] Intermediate 449-2 (13.51 g, 0.028 mol), Intermediate 2-4 (12.01 g, 0.028 mol), Pd(PPh3)4 (1.04 g, 0.001 mol), K2CO3 (8.29 g, 0.06 mol), Dioxane (150 mL), and Water (50 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 Compound 449 (15.78 g, yield 84%).

[0418] The 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.

[0419]

[0420]

[0421] [Preparation Example 4] Preparation of Compound 2-4

[0422]

[0423] 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 2-4 (8.48 g, yield 63%).

[0424] Target compound C of Table 5 below was prepared in the same manner, except that [A] and [B] of the above preparation example were replaced with reactants A and B of Table 5 below, respectively.

[0425]

[0426]

[0427] [Preparation Example 5] Preparation of Compound 3-20

[0428]

[0429] 1) Preparation of intermediate 3-20-1

[0430] 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 3-20-1 (9.93 g, yield 65%).

[0431] 2) Preparation of Compound 3-20

[0432] Intermediate 3-20-1 (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 3-20 (6.74 g, 63%).

[0433] Target compound C of Table 6 below was prepared in the same manner, except that [A] and [B] of the above preparation example were replaced with reactants A and B of Table 6 below, respectively.

[0434]

[0435] In addition to the compounds prepared in Preparation Examples 1 to 5 and Tables 2 to 6 above, compounds according to Chemical Formula 1 and Chemical Formula 2 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 7 shows the measured values ​​from FD-mass spectrometry (FD-MS: Field desorption mass spectrometry), and Table 8 shows the measured values ​​from 1H NMR (DMSO, 300 MHz).

[0436] 화합물FD-Mass화합물FD-Mass2m / z= 680.35 (C45H4D24N4S=680.95)11m / z= 760.41 (C51H4D28N4S=761.08)14m / z= 692.32 (C45H4D22N4OS=692.92)17m / z= 590.23 (C39H14D10N4S=590.77)24m / z= 668.28 (C45H16D12N4S=668.88)29m / z= 746.32 (C51H18D14N4S=746.99)35m / z=672.30 (C45H12D16N4S=672.90)42m / z= 751.35 (C51H13D19N4S=752.02)47m / z= 685.28 (C45H11D15N4OS=685.88)49m / z= 600.30 (C39H4D20N4S=600.83)55m / z= 680.35 (C45H4D24N4S=680.95)62m / z= 692.32 (C45H4D22N4OS=692.92)68m / z= 746.3 (C51H18D14N4S=747.0)74m / z= 746.3 (C51H18D14N4S=747.0)79m / z= 681.3 (C45H15D11N4OS=681.9)82m / z= 671.3 (C45H13D15N4S=671.9)88m / z= 673.3 (C45H11D17N4S=673.9)93m / z= 754.4 (C51H10D22N4S=755.0)98m / z= 680.4 (C45H4D24N4S=681.0)99m / z= 680.4 (C45H4D24N4S=681.0)103m / z= 680.4 (C45H4D24N4S=681.0)107m / z= 760.4 (C51H4D28N4S=761.1)110m / z= 692.3 (C45H4D22N4OS=692.9)115m / z= 668.3 (C45H16D12N4S=668.9)122m / z= 746.3 (C51H18D14N4S=747.0)126m / z= 681.3 (C45H15D11N4OS=681.9)129m / z= 596.3 (C39H8D16N4S=596.8)131m / z=673.3 (C45H11D17N4S=673.9)139m / z=751.4 (C51H13D19N4S=752.0)142m / z= 686.3 (C45H10D16N4OS=686.9)145m / z= 584.3 (C39H4D20N4O=584.8)150m / z= 664.4 (C45H4D24N4O=664.9)159m / z= 676.3 (C45H4D22N4O2=676.9)161m / z= 574.3 (C39H14D10N4O=574.7)166m / z= 652.3 (C45H16D12N4O=652.8)175m / z= 665.3 (C45H15D11N4O2=665.8)179m / z= 656.3 (C45H12D16N4O=656.8)181m / z= 734.4 (C51H14D18N4O=735.0)188m / z= 734.4 (C51H14D18N4O=735.0)190m / z= 669.3 (C45H11D15N4O2=669.8)195m / z= 664.4 (C45H4D24N4O=664.9)198m / z= 664.4 (C45H4D24N4O=664.9)203m / z= 744.4 (C51H4D28N4O=745.0)206m / z= 676.3 (C45H4D22N4O2=676.9)210m / z= 652.3 (C45H16D12N4O=652.8)218m / z= 730.3 (C51H18D14N4O=730.9)224m / z= 756.3 (C51H16D12N4O3=756.9)226m / z= 655.3 (C45H13D15N4O=655.8)231m / z= 656.3 (C45H12D16N4O=656.8)234m / z= 738.4 (C51H10D22N4O=739.0)239m / z= 670.3 (C45H10D16N4O2=670.8)242m / z= 664.4 (C45H4D24N4O=664.9)250m / z= 744.4 (C51H4D28N4O=745.0)256m / z= 768.4 (C51H4D24N4O3=769.0)258m / z= 652.3 (C45H16D12N4O=652.8)267m / z= 730.3 (C51H18D14N4O=730.9)270m / z= 665.3 (C45H15D11N4O2=665.8)274m / z= 655.3 (C45H13D15N4O=655.8)282m / z= 738.4 (C51H10D22N4O=739.0)287m / z= 670.3 (C45H10D16N4O2=670.8)290m / z= 696.5 (C48H4D30N4=697.0)293m / z= 776.5 (C54H4D34N4=777.1)300m / z= 776.5 (C54H4D34N4=777.1)302m / z= 708.4 (C48H4D28N4O=709.0)305m / z= 603.3 (C42H17D13N4=603.8)306m / z= 681.4 (C48H19D15N4=681.9)318m / z= 694.3 (C48H18D14N4O=694.9)320m / z= 785.4 (C54H19D15N4O2=786.0)323m / z= 687.4 (C48H13D21N4=688.0)331m / z= 766.5 (C54H14D24N4=747.1)334m / z= 699.4 (C48H13D19N4O=699.9)340m / z= 776.5 (C54H4D34N4=777.1)348m / z= 776.5 (C54H4D34N4=777.1)351m / z= 708.4 (C48H4D28N4O=709.0)353m / z= 603.3 (C42H17D13N4=603.8)360m / z= 681.4 (C48H19D15N4=681.9)361m / z= 759.4 (C54H21D17N4=760.0)365m / z= 759.4 (C54H21D17N4=760.0)370m / z= 686.4 (C48H14D20N4=687.0)375m / z= 684.4 (C48H16D18N4=684.9)379m / z= 766.5 (C54H14D24N4=767.1)382m / z= 699.4 (C48H13D19N4O=699.9)391m / z= 696.5 (C48H4D30N4=697.0)394m / z= 776.5 (C54H4D34N=777.1)400m / z= 800.5 (C54H4D30N4O2=801.1)402m / z= 681.4 (C48H19D15N4=681.9)409m / z= 759.4 (C54H21D17N4=760.0)416m / z= 785.4 (C54H19D15N4O2=786.0)418m / z= 687.4 (C48H13D21N4=688.0)427m / z= 768.5 (C54H12D26N4=769.1)431m / z= 700.4 (C48H12D20N4O=700.9)436m / z= 836.4 (C57H8D28N4S=837.2)438m / z= 756.4 (C51H8D24N4S=757.1)448m / z= 670.3 (C45H14D14N4S=670.9)449m / z= 670.3 (C45H14D14N4S=670.9)450m / z= 746.3 (C51H18D14N4S=747.0)455m / z= 668.3 (C45H12D14N4O2=668.8)459m / z= 760.3 (C51H16D14N4OS=761.0)464m / z= 756.4 (C54H24D14N4=757.0)465m / z= 693.3 (C48H19D13N4O=693.9)467m / z= 651.3 (C45H17D11N4O=651.8)2-4m / z= 560.23 (C. 42 H 28 N2=560.70)2-5m / z= 560.23 (C 42 H 28 N2=560.70)2-6m / z= 636.26 (C 48 H 32 N2=636.80)2-11m / z= 560.23 (C 42 H 28 N2=560.70)2-27m / z= 650.24 (C 48 H 30 N2O=650.78)2-43m / z= 560.23 (C 42 H 28 N2=560.70)2-54m / z= 560.23 (C 42 H 28 N2=560.70)3-20m / z= 660.41 (C48H8D24N2=660.94)3-29m / z= 584.38 (C42H4D24N2=584.85)3-38m / z= 588.40 (C42D28N2=588.87)3-43m / z= 584.38 (C42H4D24N2=584.85)3-54m / z= 507.34 (C36HD23N2=507.74)

[0437] compound 1H NMR(DMSO, 300Mz)2δ = 7.91~7.92 (4H, m)11δ = 7.91~7.92 (4H, m)14δ = 7.91~7.92 (4H, m)17δ = 7.96~7.99 (2H, d), 7.91~7.92 (5H, m), 7.67 (2H, s), 7.52 (2H, s), 7.43~49 (3H, m)24δ = 7.99~8.01 (2H, d), 7.91~7.92 (5H, m), 7.81 (1H, s), 7.71 (1H, s), 7.67 (2H, d), 7.52 (2H, s), 7.41~7.44 (3H, m)29δ = 8.11 (1H, d), 7.91~7.96 (6H, m), 7.77~7.81 (2H, m), 7.67 (2H, d), 7.52 (4H, m), 7.41~7.44 (3H, m)35δ = 7.99 (1H, s), 7.91~7.92 (5H, m), 7.77 (1H,s) 7.67 (2H, s), 7.52 (2H, s), 7.41 (1H, s)42δ = 8.01 (1H, s), 7.91~7.94 (6H, m), 7.67 (1H, s), 7.49~7.52 (4H, m), 7.44 (1H, s)47δ = 7.91~7.92 (5H, m), 7.76 (1H, s)m 7.67 (1H, d), 7.49 (1H, s), 7.43~7.44 (2H, m), 7.36 (1H, s)49δ = 8.21~8.24 (2H, m), 7.68 (1H, t), 7.60 (1H, m)55δ = 8.21~8.24 (2H, m), 7.68 (1H, t), 7.60 (1H, m)62δ = 8.21~8.24 (2H, m), 7.68 (1H, t), 7.60 (1H, m)68δ = 8.21~8.24 (2H, m), 7.99 (1H, s), 7.96 (1H, s), 7.91 (1H, s), 7.86 (4H, s), 7.81 (1H, s), 7.60~7.68 (4H, m), 7.43~7.52 (4H, m)74δ = 8.21~8.24 (2H, m), 8.01 (1H, t), 7.99 (1H, t), 7.96 (1H, s), 7.91 (1H, s), 7.86 (2H, s), 7.81 (1H, s), 7.77 (2H, d), 7.60~7.68 (2H, m), 7.52 (4H, s), 7.46 (1H, d)79δ = 8.21~8.24 (2H, m), 7.99 (2H, s), 7.91 (1H, s), 7.76 (1H, s), 7.60~7.68 (5H, m), 7.50 (1H, d), 7.42~7.43 (2H, m), 7.36 (1H, d)82δ = 8.21~8.24 (2H, m), 7.96 (1H, s), 7.86 (2H, s), 7.81 (1H, s), 7.77 (2H, m), 7.68 (1H, t), 7.60 (1H, m), 7.52 (2H, d), 7.46 (1H, s)88δ = 8.21~8.24 (2H, m), 7.91 (1H, s), 7.71 (1H, s), 7.67~7.68 (4H, m), 7.60 (1H, m), 7.52 (1H, s), 7.49 (1H, s)93δ = 8.21~8.24 (2H, m), 7.91 (1H, s), 7.68 (1H, t), 7.60 (1H, m), 7.52 (3H, s), 7.49 (1H, s), 7.44 (1H, s)98δ = 7.92 (1H, m), 7.91 (1H, m), 7.80 (1H, m), 7.46 (1H, m)99δ = 7.92 (1H, m), 7.91 (1H, m), 7.80 (1H, m), 7.46 (1H, m)103δ = 7.92 (1H, m), 7.91 (1H, m), 7.80 (1H, m), 7.46 (1H, m)107δ = 7.92 (1H, m), 7.91 (1H, m), 7.80 (1H, m), 7.46 (1H, m)110δ = 7.92 (1H, m), 7.91 (1H, m), 7.80 (1H, m), 7.46 (1H, m)115δ = 8.01 (1H, s), 7.91~7.99 (5H, m), 7.80 (1H, t), 7.71 (1H, s), 7.67 (2H, d), 7.52 (2H, s), 7.43~7.49 (4H, m)122δ = 7.99~8.01 (2H, m), 7.96 (1H, s), 7.91~7.92 (3H, m), 7.86 (2H, s), 7.80~7.81 (2H, m), 7.77 (2H, m), 7.52 (4H, s), 7.46 (2H, m)126δ = 7.91~7.96 (5H, m), 7.7~7.81 (3H, m), 7.70 (1H, s), 7.65~7.67 (2H,m), 7.44~7.52 (3H, m), 7.36 (1H, d)129δ = 7.96 (1H, s), 7.91~7.92 (2H, m), 7.80 (1H, m), 7.67 (1H, s), 7.52 (2H, s), 7.46 (1H, m)131δ = 7.99 (1H, s), 7.91~7.92 (3H, m), 7.77~7.80 (2H, m), 7.67 (2H, s), 7.52 (1H, s), 7.46 (1H, m), 7.41 (1H, s)139δ = 7.99 (1H, d), 7.91~7.92 (2H, m), 7.80 (1H, m), 7.77 (1H, s), 7.71 (1H, s), 7.67 (1H, d), 7.52 (2H, s), 7.43~7.49 (4H, m)142δ = 7.91~7.92 (4H, m), 7.80 (1H, m), 7.67 (1H, s), 7.52 (1H, s), 7.46~7.49 (3H, m)145δ = 7.91~7.92 (4H, m)150δ = 7.91~7.92 (4H, m)159δ = 7.91~7.92 (4H, m)161δ = 7.96 (1H, d), 7.91~7.92 (4H, m), 7.72 (1H, s), 7.67 (2H, d), 7.65 (1H, d), 7.52 (2H, s), 7.49 (1H, d), 7.43 (1H, t), 7.36 (1H, d)166δ = 7.98 (1H, s), 7.91~7.92 (4H, m), 7.87 (1H, d), 7.65~7.72 (5H, m), 7.52 (2H, s), 7.50 (1H, s), 7.42~7.43 (2H, t)175δ = 7.91~7.92 (4H, m), 7.76 (1H, s), 7.72 (1H, s), 7.65~7.67 (5H, m), 7.50 (1H, d), 7.42~7.43 (2H, m), 7.36 (1H, d)179δ = 7.91~7.92 (4H, m), 7.77 (1H, s), 7.72 (1H, s), 7.65~7.67 (3H, d), 7.52 (2H, s), 7.41 (1H, s)181δ = 7.91~7.92 (4H, m), 7.77 (1H, s), 7.71~7.72 (2H, m), 7.65~7.67 (3H, d), 7.52 (2H, s), 7.42 (2H, s)188δ = 7.96 (1H, d), 7.91~7.92(4H, m), 7.86 (1H, s), 7.71 (1H, s), 7.65~7.67 (2H, m), 7.52 (2H, s), 7.49 (1H, d), 7.43 (1H, d), 7.36 (1H, s)190δ = 7.91~7.92 (5H, m), 7.72 (1H, s), 7.65~7.67 (2H, d), 7.49~7.52 (2H, d), 7.36 (1H, s)195δ = 8.21~8.24 (2H, m), 7.68 (1H, t), 7.60 (1H, m)198δ = 8.21~8.24 (2H, m), 7.68 (1H, t), 7.60 (1H, m)203δ = 8.21~8.24 (2H, m), 7.68 (1H, t), 7.60 (1H, m)206δ = 8.21~8.24 (2H, m), 7.68 (1H, t), 7.60 (1H, m)210δ = 8.21~8.24 (2H, m), 7.86 (2H, s), 7.81 (1H, s), 7.60~7.72 (5H, m), 7.52 (2H, s), 7.41~7.43 (3H, m), 7.36 (1H, s)218δ = 8.21~8.24 (2H, m), 8.01 (1H, t), 7.96 (1H, s), 7.86 (2H, s), 7.81 (1H, s), 7.77 (2H, s), 7.72 (1H, s), 7.60~7.68 (3H, m), 7.52 (4H, s), 7.36 (1H, d)224δ = 8.21~8.24 (2H, m), 7.99 (1H, s), 7.91 (1H, s), 7.70~7.72 (2H, m), 7.68 (1H, m), 7.60~7.65 (4H, m), 7.49 (1H, s), 7.42 (1H, s), 7.36 (2H, s), 7.19 (1H, d)226δ = 8.21~8.24 (2H, m), 7.96 (1H, s), 7.86 (2H, s), 7.81 (1H, s), 7.68~7.77 (3H, m), 7.60 (1H, m), 7.52 (2H, d), 7.36 (1H, s)231δ = 8.21~8.24 (2H, m), 7.96 (1H, d), 7.86 (1H, s), 7.67~7.72 (3H, m), 7.60 (1H, m), 7.52 (2H, s), 7.49 (1H, d), 7.42 (1H, s)234δ = 8.21~8.24 (2H, m), 7.94 (1H. d), 7.72 (1H, s), 7.68 (1H, t), 7.60 (1H, m), 7.52 (2H, s), 7.49 (1H, d), 7.42 (1H, s)239δ = 8.21~8.24 (2H, m), 7.76 (1H, s), 7.72 (1H, s), 7.68 (1H, t), 7.60 (1H, m), 7.49 (1H, s), 7.42~7.43 (2H, d), 7.36 (1H, s)242δ = 7.92 (1H, m), 7.91 (1H, m), 7.80 (1H, m), 7.46 (1H, m)250δ = 7.92 (1H, m), 7.91 (1H, m), 7.80 (1H, m), 7.46 (1H, m)256δ = 7.92 (1H, m), 7.91 (1H, m), 7.80 (1H, m), 7.46 (1H, m)258δ = 7.91~7.92 (2H, m), 7.86 (2H, s), 7.80~7.81 (2H, m), 7.72 (1H, s), 7.76 (2H, s), 7.52 (2H, s), 7.41~7.46 (4H, m), 7.36 (1H, s)267δ = 8.01 (1H, d), 7.91~7.92 (2H, m), 7.80 (1H, m), 7.77 (3H, s), 7.72 (2H, s), 7.67 (3H, s), 7.60 (1H, d), 7.52 (1H, s), 7.41~7.46 (4H, m)270δ = 7.96 (1H, s), 7.91~7.92 (2H, m), 7.77~7.81 (3H, m), 7.72 (1H, d), 7.70 (1H, d), 7.65~7.67 (2H, m), 7.60 (1H, d), 7.52 (1H, d), 7.46 (1H, m), 7.42 (1H, d), 7.36 (1H, d)274δ = 7.96 (1H, s), 7.91~7.92 (2H, m), 7.86 (2H, s), 7.77~7.81 (4H, m), 7.46~7.52 (3H, m), 7.36 (1H, s)282δ = 7.91~7.94 (3H, m), 7.80 (1H, m), 7.72 (1H, s), 7.46~7.52 (4H, m), 7.42 (1H, s)287δ = 7.91~7.92 (2H, m), 7.80 (1H, m), 7.76 (1H, s), 7.72 (1H, d), 7.42~7.49 (4H, m), 7.36 (1H, s)290δ = 7.91~7.92 (4H, m)293δ = 7.91~7.92 (4H, m)300δ = 7.91~7.92 (4H, m)302δ = 7.91~7.92 (4H, m)305δ = 7.96 (1H, s), 7.91~7.92 (4H, m), 7.75 (1H, s), 7.67 (2H, s), 7.52 (3H, s), 7.49 (1H, d), 7.43 (1H, t), 7.35 (1H, d), 2.2 (1H, s), 1.80~2.0 (2H, m)306δ = 8.06 (1H, s) ,7.96 (1H, s), 7.91~7.92 (4H, m), 7.86 (2H, s), 7.81 (1H, s), 7.67 (2H, d), 7.52 (2H, s), 7.41~7.43 (2H, m),7.16 (1H, s), 2.2 (1H, s), 1.80~2.0 (2H, m)318δ = 7.96 (1H, s), 7.91~7.92 (4H, m), 7.81 (1H, s), 7.75~7.77 (2H, m), 7.70 (1H, s), 7.65~7.76 (2H, m), 7.52 (2H, d), 7.36 (1H, d), 7.16 (1H, d), 2.2 (1H, s), 1.80~2.0 (2H, m)320δ = 7.99 (1H, s), 7.91~7.92 (5H, m), 7.70~7.72 (2H, m), 7.64~7.67 (3H, m), 7.52 (1H, d), 7.49 (1H, s), 7.42 (1H, d), 7.35~7.36 (2H, t), 2.2 (1H, s), 1.80~2.0 (2H, m)323δ = 7.96 (1H, s), 7.91~7.92 (4H, m),7.77 (1H, s), 7.67 (2H, s), 7.52 (3H, s), 7.41 (1H, s), 2.2 (1H, s)331δ = 7.91~7.92 (4H, m), 7.77 (1H, s), 7.71 (1H, s), 7.67 (1H, d), 7.52 (3H, s), 7.49 (1H, s), 7.43 (1H, s), 7.35 (1H, d), 2.2 (1H, s)334δ = 7.91~7.92 (5H, m), 7.75 (1H, s), 7.65~7.67 (2H, d), 7.49~7.52 (2H, d), 7.35 (1H, s), 2.2 (2H, s)340δ = 8.21~8.24 (2H, m), 7.68 (1H, t), 7.60 (1H, m)348δ = 8.21~8.24 (2H, m), 7.68 (1H, t), 7.60 (1H, m)351δ = 8.21~8.24 (2H, m), 7.68 (1H, t), 7.60 (1H, m)353δ = 8.21~8.24 (2H, m), 7.96 (1H, d), 7.75 (1H, s), 7.67~7.68 (3H, m), 7.60 (1H, m), 7.52 (3H, s), 7.49 (1H, d), 7.43 (1H, t), 7.35 (1H, d), 2.2 (1H, s), 1.80~2.0 (2H, m)360δ = 8.21~8.24 (3H, m), 8.01 (1H, s), 7.96 (1H, d), 7.81 (1H, d), 7.71 (1H, s), 7.67~7.68 (3H, m), 7.60 (1H, m), 7.52 (2H, s), 7.41~7.43 (2H, m), 7.16 (1H, d), 2.2 (1H, s), 1.80~2.0 (2H, m)361δ = 8.21~8.24 (2H, m), 8.06 (1H, s), 7.96 (1H, d), 7.86 (4H, s), 7.81 (1H, s), 7.67~7.68 (3H, m), 7.60 (1H, m), 7.52 (2H, s), 7.41~7.43 (2H, m), 7.16 (1H, d), 2.2 (1H, s), 1.80~2.0 (2H, m)365δ = 8.21~8.24 (2H, m), 8.11 (1H, s), 7.75~7.81 (3H, m), 7.67~7.68 (3H, m), 7.60 (1H, m), 7.52 (5H, t), 7.41~7.43 (2H, m), 7.16 (1H, d), 2.2 (1H, s), 1.80~2.0 (2H, m)370δ = 8.21~8.24 (2H, m), 7.96 (1H, s), 7.86 (2H, s), 7.81 (1H, s), 7.67~7.68 (2H, m), 7.60 (1H, m), 7.52 (2H, s), 7.35 (1H, s) 2.2 (2H, s)375δ = 8.21~8.24 (2H, m), 7.96 (2H, d), 7.86 (2H, s), 7.67~7.68 (2H, m), 7.60 (1H, m), 7.52 (3H, s), 7.49 (1H, d), 7.16 (1H, d), 2.2 (2H, s)379δ = 8.21~8.24 (2H, m), 7.77 (1H, s), 7.71 (1H, s), 7.67~7.68 (2H, m), 7.60(1H, m), 7.52 (3H, s), 7.49 (1H, s), 7.43 (1H, d), 7.35 (1H, d), 2.2 (1H, s)382δ = 8.21~8.24 (2H, m), 7.91 (1H, s), 7.75 (1H, s), 7.65~7.68 (3H, m), 7.60 (1H, m), 7.52 (1H, s), 7.49 (1H, s), 7.35 (1H, s), 2.2 (2H, s)391δ = 7.92 (1H, m), 7.91 (1H, m), 7.80 (1H, m), 7.46 (1H, m)394δ = 7.92 (1H, m), 7.91 (1H, m), 7.80 (1H, m), 7.46 (1H, m)400δ = 7.92 (1H, m), 7.91 (1H, m), 7.80 (1H, m), 7.46 (1H, m)402δ = 8.06 (1H, s), 7.96 (1H, s), 7.91~7.92 (2H, m), 7.86 (2H, s), 7.80~7.81 (2H, m), 7.67 (2H, d), 7.52 (2H, s), 7.41~7.46 (3H, m), 7.16 (1H, s), 2.2 (1H, s), 1.80~2.0 (2H, m)409δ = 8.06 (1H, s), 7.96 (1H, d), 7.91~7.92 (2H, m), 7.86 (4H, s), 7.80~7.81 (2H, m), 7.67 (2H, d), 7.52 (2H, s), 7.41~7.46 (3H, m), 7.16 (1H, s), 2.2 (1H, s), 1.80~2.0 (2H, m)416δ = 7.99 (1H, s), 7.91~7.92 (3H, m), 7.80 (1H, m), 7.70~7.72 (2H, m), 7.64~7.67 (3H, m), 7.52 (1H, d), 7.49 (1H, s), 7.42~7.46 (2H, m), 7.35~7.36 (2H, t), 2.2 (1H, s), 1.80~2.0 (2H, m)418δ = 7.96 (1H, s), 7.91~79.2 (2H, m), 7.86 (2H, s), 7.80 (1H, m), 7.67 (1H, s), 7.52 (2H, s), 7.46 (1H, t), 7.35 (1H, s), 2.2 (2H, s)427δ = 7.91~7.92 (2H, m), 7.8 (1H, m), 7.77 (1H, s), 7.71 (1H, s), 7.52 (3H, s), 7.49 (1H, s), 7.46 (1H, m), 7.35 (1H, d), 2.2 (1H, s)431δ = 7.96 (1H, d), 7.91~7.92 (2H, m), 7.80 (1H, m), 7.76 (1H, s), 7.67 (1H, d), 7.49 (1H, s), 7.43~7.46 (2H, m), 7.36 (1H, s), 7.16 (1H, s), 2.2 (1H, s)436δ = 8.38 (1H, m), 7.91~7.94 (5H, m), 7.73 (1H, t), 7.61 (1H, m)438δ = 8.38 (1H, m), 7.91~7.94 (3H, m), 7.80(1H, m), 7.73 (1H, t), 7.61 (1H, m), 7.46 (1H, m)448δ = 8.36 (2H, m), 7.96 (2H, d), 7.75 (2H, d), 7.50 (3H, m), 7.49 (2H, m), 7.41 (1H, t), 7.25 (2H, m)449δ = 8.36~8.38 (3H, m), 7.94 (1H, s), 7.75 (2H, m), 7.73 (1H, s), 7.61 (1H, m), 7.49~7.50 (5H, m), 7.41 (1H, m)450δ = 8.36 (2H, m), 7.96 (2H, d), 7.75 (2H, d), 7.49~7.50 (5H, m), 7.41 (1H, m), 7.25 (6H, m)455δ = 8.36 (2H, m), 8.03 (1H, d), 7.98 (1H, m), 7.82 (1H, m), 7.76 (1H, d), 7.50~7.54 (4H, m), 7.39 (1H, t), 7.31 (1H, t)459δ = 8.36 (2H, m), 8.03 (1H, d), 7.98~7.99 (2H, m), 7.91 (1H, s), 7.82 (1H, d), 7.76 (1H, s), 7.62 (1H, s), 7.57 (1H, s), 7.50~7.54 (4H, m), 7.39 (1H, t), 7.31 (1H, t)464δ = 8.36 (2H, m), 8.04 (3H, s), 7.96 (1H, s), 7.75 (5H, t), 7.49~7.50 (8H, m), 7.41 (2H, m), 7.35 (1H, s), 2.2 (2H, s)465δ = 8.36 (2H, m), 8.06 (1H, d), 8.03 (1H, s), 7.98 (1H, d), 7.81~7.82 (2H, m), 7.76 (1H, d), 7.48~7.57 (6H, m), 7.31~7.41 (3H, m), 7.16 (1H, s), 2.2 (1H, s)467δ = 8.36 (2H, m), 7.96 (2H, d), 7.75 (2H, d), 7.60~7.64 (2H, m), 7.41~7.50 (6H, m), 7.19~7.25 (3H, m)2-4δ = 8.55 (2H, d), 7.91~7.94 (10H, m), 7.75 (4H, d), 7.35~7.49 (10H, m), 7.16 (2H, t)2-5δ = 8.55 (2H, d), 8.21 (1H, s), 7.91~7.94 (6H, m), 7.35~7.75 (16H, m), 7.58 (1H, d), 7.16 (2H, t)2-6δ = 855 (2H, d), 7.91~7.94 (11H, m), 7.73~7.75 (5H, m), 7.61 (2H, m), 7.35~7.49 (8H, m), 7.26 (1H, d), 7.16 (2H, t)2-11δ = 8.55 (2H, d), 7.91~7.94 (7H, m), 7.73~7.75 (3H, m), 7.35~7.62 (23H, m), 7.26 (1H, d), 7.16 (1H, t)2-27δ = 8.55 (1H, d), 8.19~8.21 (2H, m), 7.94~7.98 (2H, m), 7.35~7.82 (22H, m), 7.16~7.25 (3H, m)2-43δ = 8.55 (2H, d), 8.21 (2H, s), 7.94 (2H, d), 7.84 (2H, s), 7.60~7.75 (8H, m), 7.35~7.49 (10H, m), 7.16 (2H, t)2-54δ = 8.55 (2H, d), 8.21 (1H, s), 8.12 (1H, d), 7.91~7.94 (6H, m), 7.60~7.75 (6H, m), 7.35~7.49 (9H, m), 7.16~7.18 (3H, m)3-20δ = 7.96 (1H, s), 7.81~7.86 (3H, d), 7.64~7.67 (3H, d), 7.50 (1H, s)3-29δ = 7.96 (1H, s), 7.77 (1H, s), 7.47~7.50 (2H, d)3-38δ = Deuterium content at 100%. 1 H NMR no peaks 3-43δ = 7.82 (1H, s), 7.64–7.67 (2H, d), 7.52 (1H, s) 3-54δ = 7.49 (1H, s)

[0438] <Experimental Example 1> Fabrication of an Organic Light-Emitting Device

[0439] 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.

[0440] A common layer, a hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), was formed on the above ITO transparent electrode (anode).

[0441] 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.

[0442] 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.

[0443] 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.

[0444] The driving voltage, luminous efficiency, and lifetime results of the organic electroluminescent device of Experimental Example 1 above are as shown in Table 9 below. At this time, the light-emitting layer compound of the Comparative Example is as follows.

[0445]

[0446] Compound driving voltage efficiency color lifetime (V)(cd / A)(T 90Comparative Example 1A 7.3248.3Green84 Comparative Example 2B 7.4046.9Green80 Comparative Example 3C 7.2549.8Green92 Comparative Example 4D 7.4446.5Green75 Comparative Example 5E 7.4646.3Green73 Comparative Example 6F 7.5045.2Green70 Example 1 24.70138.2Green246 Example 2 114.73135.4Green250 Example 3 144.72139.5Green241 Example 4 176.5565.8Green122 Example 5 244.91119.3Green230 Example 6 294.90120.7Green228 Example 7 354.83132.6Green242 Example 8424.88130.4 Green239 Example 9474.82132.6 Green240 Example 10496.4366.2 Green123 Example 11553.52199.4 Green310 Example 12623.54195.3 Green305 Example 13683.87173.2 Green284 Example 14743.89175.6 Green287 Example 15793.90177.8 Green281 Example 16823.72182.6 Green294 Example 17883.77184.8 Green290 Example 18933.75186.9 Green297 Example 19982.05258.7 Green370 Example 20992.12260.0 Green365 Example 211032.15252.7 Green366 Example 221072.02255.3 Green362 Example 231102.09257.4 Green369 Example 241152.87234.7 Green345 Example 251222.74235.6 Green352 Example 261262.80237.4 Green350 Example 271296.4565.5 Green130 Example 281312.55243.7 Green366 Example 291392.46248.5 Green364 Example 301422.50245.3Green362 Example 311456.4267.4Green132 Example 321505.1194.6Green215 Example 331595.1593.7Green218 Example 341616.6268.3Green135 Example 351665.33106.5Green200 Example 36 1755.39 107.7 Green197 Example 37 1795.26 98.4 Green212 Example 38 1815.30 99.5 Green210 Example 39 1885.29 99.0 Green214 Example 40 1905.25 97.3 Green211 Example 41 1954.05 168.7 Green277 Example 42 1984.09 169.3 Green278 Example 43 2034.13 167.2 Green280 Example 44 2064.15 145.6 Green275 Example 45 2104.5 2144.8 Green251 Example 462184.50148.7 Green255 Example 472244.46153.2 Green259 Example 482264.32155.6 Green263 Example 492314.36152.8 Green266 Example 502344.39151.7 Green265 Example 512394.41154.3 Green263 Example 522423.05228.7 Green340 Example 532503.09226.5 Green335 Example 542563.08227.4 Green338 Example 552583.32203.7 Green311 Example 562673.35210.4 Green318 Example 572703.39208.6Green315 Example 582743.21218.6Green327 Example 592823.22220.3Green330 Example 602873.25219.7Green329 Example 612906.5263.7Green130 Example 622936.5563.0Green127 Example 633006.5463.2Green121 Example 643026.5063.9Green125 Example 653056.7760.2Green120 Example 663066.7760.8Green126 Example 673186.7560.5Green124 Example 683206.7261.2Green121 Example 693236.6262.4Green126 Example 703316.6062.8Green129 Example 713346.6563.5Green130 Example 723406.2469.8Green158 Example 733486.2967.8Green160 Example 743516.2168.3Green155 Example 753536.3565.2 Green131 Example 763606.3965.0 Green138 Example 773616.3765.5 Green135 Example 783656.3865.9 Green136 Example 793706.3068.5 Green148 Example 803756.3168.2 Green145 Example 813796.3368.0 Green142 Example 823826.3568.8 Green146 Example 833915.5289.3 Green187 Example 843945.5589.9 Green190 Example 854005.5388.7 Green188 Example 864026.0571.5Green162 Example 874096.0871.3Green168 Example 884166.0372.6Green170 Example 894185.8275.3Green176 Example 904275.8876.5Green180 Example 914315.7978.3Green177 Example 924366.5560.2Green122 Example 934386.6261.3Green125 Example 944486.2169.2Green160 Example 954496.2269.0Green158 Example 964506.3465.6Green134 Example 974556.2566.2Green142 Example 984597.0255.8Green116 Example 994646.5563.2Green128 Example 1004656.5262.5Green121 Example 1014676.3266.8Green142.

[0447] The heterocyclic compound represented by Chemical Formula 1 according to the present invention has a structure in which a triazine (Structural Formula A) is bonded to a linker (Structural Formula C) centered around a skeleton of Fused Carbazole (Structural Formula B), and the carbon-hydrogen bonds at the sites where the Fused Carbazole portion is bonded to the triazine or linker are substituted with deuterium in a specific amount.

[0448] First, the binding site between Fused Carbazole and the triazine or linker serves as a key pathway for molecular energy transfer and charge transport. By substituting the CH bonds at this site with CD bonds of a specific content, the bond dissociation energy increases and the vibrational energy level is lowered. Consequently, it was confirmed that non-radiative decay and the thermal decay of CH bonds are suppressed, resulting in a significantly improved device lifespan.

[0449] In addition, deuteration of the triazine or linker portion based on Fused Carbazole increases the stability of the electron transport pathway and balances the hole transport characteristics of the Fused Carbazole portion, resulting in improved charge recombination efficiency. Consequently, it was found that the device performance is enhanced by increasing current efficiency and external quantum efficiency, and lowering the driving voltage.

[0450] Comparative Examples 1 to 4 describe compounds substituted with deuterium, but they correspond to cases where they do not have deuterium substitution positions of structural formulas A and B or structural formulas B and C, as in the present invention. Specifically, Comparative Examples 1 and 2 have a deuterium content of structural formula B of 0%, Comparative Example 3 has only structural formula B substituted with deuterium, and Comparative Example 4 has structural formulas A to C all substituted with deuterium.

[0451] Structural formula B is a HOMO portion responsible for hole transport, and if this portion is substituted with deuterium, the packing density increases, resulting in excellent driving voltage and luminous efficiency. Accordingly, as in Comparative Examples 1 and 2, if the deuterium content of structural formula B is 0%, the hole mobility is relatively reduced, which not only increases the driving voltage but also causes holes to enter slowly compared to the rapid electron transport, leading to damage to the organic material due to excess electrons and a decrease in lifespan.

[0452] As in Comparative Example 3, if the C portion of the structural formula acting as a linker is not substituted with deuterium, the rotation of Fused Carbazole acting as the HOMO and Triazine acting as the LUMO becomes relatively freer. Accordingly, Comparative Example 3 has a more diverse molecular stereochemical arrangement and higher rotational energy than the compound in which the C portion of the structural formula is substituted with deuterium. Consequently, the stability of the molecule itself decreases, and it is difficult to obtain a uniform stacking pattern during organic deposition, resulting in inferior device lifespan.

[0453] In the case of Comparative Examples 5 and 6, the substitution positions of deuterium (structural formulas A and B or structural formulas B and C) are all satisfied, but the deuterium substitution rate is not satisfied. When the deuterium substitution rate is low, as in Comparative Examples 5 and 6, the effect obtained by substituting deuterium is negligible, so the driving voltage, luminous efficiency, and lifetime are similar to those of a compound without deuterium substitution.

[0454] <Experimental Example 2> Fabrication of an Organic Light-Emitting Device

[0455] 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.

[0456] A common layer, a hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), was formed on the above ITO transparent electrode (anode).

[0457] 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 as hosts, and a green phosphorescent dopant was deposited by doping 7% with Ir(ppy)3. Subsequently, BCP was deposited at a thickness of 60 Å as a hole blocking layer, and Alq3 was deposited at a thickness of 200 Å on top of it as an electron transport layer. Finally, an electron injection layer was formed by depositing lithium fluoride (LiF) to a thickness of 10 Å on the electron transport layer, and then an aluminum (Al) cathode was formed by depositing an aluminum cathode to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby fabricating an organic electroluminescent device.

[0458] 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.

[0459] 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.

[0460] The driving voltage, luminous efficiency, and lifetime results of the organic electroluminescent device of Experimental Example 2 above are as shown in Table 10 below.

[0461]

[0462] Compound Ratio Driving Voltage Efficiency Color Coordinates Lifetime (V) (cd / A) (T 90)Comparative Example 7A : 2-440 : 606.5365.8Green123 Comparative Example 835 : 656.5565.2Green126 Comparative Example 930 : 706.5864.7Green129 Comparative Example 10A : 3-2040 : 606.5166.3Green125 Comparative Example 1135 : 656.5265.7Green129 Comparative Example 1230 : 706.5465.2Green131 Comparative Example 13B : 3-3840 : 606.5664.5Green120 Comparative Example 1435 : 656.5863.2Green123 Comparative Example 1530 : 706.5962.1Green125 Comparative Example 16C : 3-5440 : 606.5068.9Green126 Comparative Example 1735 : 656.5267.6Green129 Comparative Example 1830 : 706.5567.1Green130 Comparative Example 19D : 3-4340 : 606.6263.3Green117 Comparative Example 2035 : 656.6462.8Green120 Comparative Example 2130 : 706.6762.5Green121 Comparative Example 22E : 2-640 : 606.6562.7Green114 Comparative Example 2335 : 656.6762.5Green116 Comparative Example 2430 : 706.7062.0Green120 Comparative Example 25F : 2-5440 : 606.6862.3Green110 Comparative Example 2635 : 656.7162.0Green112 Comparative Example 2730 : 706.7861.8Green115 Example 1022 : 3-2040 : 603.70190.0Green283 Example 10335 : 653.72187.3Green286 Example 10430 : 703.75186.2Green288 Example 10511 : 3-5440 : 603.73185.3Green280 Example 10635 : 653.74183.2Green281 Example 10730 : 703.76181.6Green287 Example 10814 : 3-2940 : 603.71187.7Green284 Example 10935 : 653.74186.5Green286 Example 11030 : 703.78185.3Green290 Example 11117 : 3-3840 : 605.5687.4Green142 Example 11235 : 655.5985.2 Green144 Example 11330 : 705.6384.3 Green149 Example 11424 : 3-2940 : 603.88173.2 Green265 Example 11535 : 653.91172.8 Green270 Example 11630 : 703.94171.3 Green272 Example 11729 : 3-2040 : 603.85170.6 Green263 Example 11835 : 653.87169.3 Green268 Example 11930 : 703.91167.5 Green274 Example 12035 : 2-440 : 603.81178.9Green279 Example 12135 : 653.83177.6Green282 Example 12230 : 703.85176.3Green285 Example 12342 : 2-2740 : 603.80177.6Green280 Example 12435 : 653.82176.3Green283 Example 12530 : 703.88175.9Green285 Example 12647 : 2-4340 : 603.83179.3Green277 Example 12735 : 653.84178.6Green280 Example 12830 : 703.87177.7Green282 Example 12949 : 3-4340 : 605.33100.2Green172 Example 13035 : 655.3898.4Green177 Example 13130 ​​: 705.4297.1Green180 Example 13255 : 3-5440 : 602.50240.0Green340 Example 13335 : 652.51239.5Green343 Example 13430 : 702.53238.7Green345 Example 13562 : 3-4340 : 602.53239.5Green341 Example 13635 : 652.55238.2Green346 Example 13730 : 702.57237.4Green349 Example 13868 : 2-1140 : 602.85219.8Green321 Example 13935 : 652.88218.2Green324 Example 14030 : 702.91217.4Green328 Example 14174 : 2-4340 : 602.87215.6Green322 Example 14235 : 652.89214.8Green327 Example 14330 : 702.94213.6Green330 Example 14479 : 2-640 : 602.85217.7Green327 Example 14535 : 652.86216.4Green331 Example 14630 : 702.89215.8Green336 Example 14782 : 2-540 : 602.72226.7Green335 Example 14835 : 652.75225.3Green331 Example 14930 : 702.78224.5Green330 Example 15088 : 2-2740 : 602.71229.4Green337 Example 15135 : 652.74228.7Green335 Example 15230 : 702.76226.4Green332 Example 15393 : 2-2740 : 602.73225.9Green339 Example 15435 : 652.75224.7Green337 Example 15530 : 702.77223.3Green335 Example 15698 : 3-3840 : 601.02299.7Green402 Example 15735 : 651.05298.6Green409 Example 15830 : 701.07297.4Green410 Example 15999 : 3-5440 : 601.01295.4Green405 Example 16035 : 651.03294.3Green408 Example 16130 : 701.05292.1Green411 Example 162103 : 3-2940 : 601.04297.7Green400 Example 16335 : 651.06296.4Green402 Example 16430 : 701.08295.3Green405 Example 165107 : 3-2940 : 601.02296.8Green406 Example 16635 : 651.05295.7Green408 Example 16730 : 701.06294.8Green410 Example 168110 : 3-2040 : 601.07299.1Green401 Example 16935 : 651.09298.3Green404 Example 17030 : 701.10297.7 Green407 Example 171115 : 3-2940 : 601.82278.3 Green381 Example 17235 : 651.84277.6 Green384 Example 17330 : 701.86276.4 Green388 Example 174122 : 3-5440 : 601.85279.4 Green385 Example 17535 : 651.87278.8 Green387 Example 17630 : 701.89277.6 Green390 Example 177126 : 3-3840 : 601.83279.2 Green374 Example 17835 : 651.85278.3Green376 Example 17930 : 701.89277.1Green377 Example 180129 : 3-2940 : 605.3695.4Green161 Example 18135 : 655.3894.2Green168 Example 18230 : 705.4293.7Green172 Example 183131 : 3-4340 : 601.43285.6Green391 Example 18435 : 651.46284.6Green394 Example 18530 : 701.47283.8Green396 Example 186139 : 3-2940 : 601.53284.2Green387 Example 18735 : 651.57283.8Green390 Example 18830 : 701.62282.6Green392 Example 189142 : 3-2040 : 601.49285.9Green393 Example 19035 : 651.53284.7Green395 Example 19130 : 701.58283.5Green400 Example 192145 : 3-2040 : 605.2295.3Green165 Example 19335 : 655.2594.1Green169 Example 19430 : 705.2793.0Green173 Example 195150 : 3-5440 : 604.13158.3Green254 Example 19635 : 654.16157.2Green256 Example 19730 : 704.17156.3Green259 Example 198159 : 3-5440 : 604.12159.7Green252 Example 19935 : 654.15158.3 Green255 Example 20030 : 704.18157.6 Green258 Example 201161 : 3-2040 : 605.3299.2 Green163 Example 20235 : 655.3598.1 Green168 Example 20330 : 705.3997.4 Green172 Example 204166 : 3-2940 : 604.36136.4 Green233 Example 20535 : 654.38135.6 Green235 Example 20630 : 704.41134.2 Green238 Example 207175 : 3-5440 : 604.32134.2Green231 Example 20835 : 654.35133.6Green234 Example 20930 : 704.38132.8Green238 Example 210179 : 2-640 : 604.21146.2Green250 Example 21135 : 654.24145.7Green252 Example 21230 : 704.27144.2Green255 Example 213181 : 2-2740 : 604.25145.3Green249 Example 21435 : 654.28143.2Green253 Example 21530 : 704.30142.7Green256 Example 216188 : 2-4340 : 604.22149.3Green258 Example 21735 : 654.26148.2Green260 Example 21830 : 704.29147.7Green262 Example 219190 : 2-1140 : 604.21147.6Green255 Example 22035 : 654.24146.4Green263 Example 22130 : 704.27145.3Green266 Example 222195 : 3-3840 : 603.05208.7Green315 Example 22335 : 653.07207.6Green318 Example 22430 : 703.09206.4Green320 Example 225198 : 3-2940 : 603.08207.7Green311 Example 22635 : 653.10206.5Green316 Example 22730 : 703.12205.5Green319 Example 228203 : 3-3840 : 603.02209.4 Green310 Example 22935 : 653.06208.7 Green312 Example 23030 : 703.09207.7 Green318 Example 231206 : 3-2940 : 603.04210.0 Green313 Example 23235 : 653.07209.7 Green315 Example 23330 : 703.09208.4 Green318 Example 234210 : 3-2940 : 603.55200.2 Green193 Example 23535 : 653.58199.4 Green195 Example 23630 : 703.60198.2Green199 Example 237218 : 3-5440 : 603.54198.7Green190 Example 23835 : 653.57197.4Green192 Example 23930 : 703.59196.5Green194 Example 240224 : 3-2940 : 603.52196.8Green191 Example 24135 : 653.55195.2Green193 Example 24230 : 703.58194.7Green194 Example 243226 : 2-1140 : 603.12200.3Green300 Example 24435 : 653.15199.1 Green305 Example 24530 : 703.18198.7 Green308 Example 246231 : 2-2740 : 603.16202.5 Green302 Example 24735 : 653.18200.6 Green305 Example 24830 : 703.21199.4 Green309 Example 249234 : 2-4340 : 603.21201.8 Green305 Example 25035 : 653.23200.3 Green308 Example 25130 : 703.28199.0 Green310 Example 252239 : 2-5440 : 603.12205.3Green304 Example 25335 : 653.15204.1Green306 Example 25430 : 703.19202.6Green310 Example 255242 : 3-2040 : 602.05268.3Green374 Example 25635 : 652.08267.7Green377 Example 25730 : 702.10266.4 Green380 Example 258250 : 3-3840 : 602.02267.9 Green370 Example 25935 : 652.06266.4 Green372 Example 26030 : 702.09265.8 Green374 Example 261256 : 3-4340 : 602.00265.7 Green371 Example 26235 : 652.05264.9 Green375 Example 26330 : 702.09263.5 Green377 Example 264258 : 2-440 : 602.35244.6 Green354 Example 26535 : 652.38243.8Green356 Example 26630 : 702.40242.1Green359 Example 267267 : 2-2740 : 602.32245.5Green351 Example 26835 : 652.35244.8Green355 Example 26930 : 702.38243.1Green358 Example 270270 : 2-4340 : 602.36246.9Green353 Example 27135 : 652.39245.2Green357 Example 27230 : 702.40244.6Green360 Example 273274 : 2-640 : 602.26260.5Green361 Example 27435 : 652.28259.7Green363 Example 27530 : 702.31258.4Green365 Example 276282 : 2-2740 : 602.18258.3Green360 Example 27735 : 652.23257.1Green362 Example 27830 : 702.25256.5Green366 Example 279287 : 2-4340 : 602.15260.1Green359 Example 28035 : 652.18259.4Green364 Example 28130 : 702.19258.4Green369 Example 282290 : 2-5440 : 605.5287.9Green152 Example 28335 : 655.5587.1Green155 Example 28430 : 705.5885.8Green156 Example 285293 : 2-5440 : 605.5189.3Green155 Example 28635 : 655.5388.1 Green158 Example 28730 : 705.5687.6 Green160 Example 288300 : 2-2740 : 605.5988.7 Green151 Example 28935 : 655.6287.6 Green153 Example 29030 : 705.6387.4 Green157 Example 291302 : 2-640 : 605.5789.3 Green152 Example 29235 : 655.5988.1 Green156 Example 29330 : 705.6187.4 Green159 Example 294305 : 3-4340 : 605.8783.2Green140 Example 29535 : 655.9382.4Green143 Example 29630 : 705.9981.1Green144 Example 297306 : 3-3840 : 605.8284.6Green142 Example 29835 : 655.8483.2Green144 Example 29930 : 705.8582.6Green148 Example 300318 : 3-5440 : 605.8582.9Green142 Example 30135 : 655.8781.6Green146 Example 30230 : 705.9180.3Green149 Example 303320 : 3-3840 : 605.8183.3Green141 Example 30435 : 655.8382.1Green143 Example 30530 : 705.8881.9Green147 Example 306323 : 2-2740 : 605.6185.3Green150 Example 30735 : 655.6384.1Green153 Example 30830 : 705.6682.6Green155 Example 309331 : 2-4340 : 605.7286.4Green149 Example 31035 : 655.7485.6Green151 Example 31130 : 705.7984.1Green153 Example 312334 : 2-640 : 605.6485.6Green147 Example 31335 : 655.6784.4Green150 Example 31430 : 705.6983.2Green152 Example 315340 : 3-4340 : 605.2398.7Green182 Example 31635 : 655.2597.6 Green185 Example 31730 : 705.2996.3 Green189 Example 318348 : 3-5440 : 605.2099.4 Green180 Example 31935 : 655.2298.7 Green183 Example 32030 : 705.2397.1 Green186 Example 321351 : 3-4340 : 605.2498.5 Green181 Example 32235 : 655.2698.2 Green185 Example 32330 : 705.2997.1 Green187 Example 324353 : 2-1140 : 605.3292.1Green161 Example 32535 ​​: 655.3491.3Green164 Example 32630 : 705.3691.0Green166 Example 327360 : 2-2740 : 605.3393.4Green165 Example 32835 : 655.3892.6Green167 Example 32930 : 705.4091.1Green170 Example 330361 : 2-440 : 605.3193.5Green163 Example 33135 : 655.3492.7Green164 Example 33230 : 705.3791.5Green166 Example 333365 : 2-4340 : 605.3294.4Green161 Example 33435 : 655.3693.7Green162 Example 33530 : 705.3992.5Green165 Example 336370 : 3-4340 : 605.2895.5Green172 Example 33735 : 655.3094.7Green174 Example 33830 : 705.3293.5Green177 Example 339375 : 3-5440 : 605.2796.9Green175 Example 34035 : 655.2995.3Green178 Example 34130 : 705.3194.7Green180 Example 342379 : 3-3840 : 605.2997.4Green171 Example 34335 : 655.3296.2Green174 Example 34430 : 705.3395.1Green176 Example 345382 : 3-2040 : 605.2796.2Green172 Example 34635 : 655.3095.1 Green175 Example 34730 : 705.3294.6 Green180 Example 348391 : 2-2740 : 604.51129.5 Green210 Example 34935 : 654.53128.7 Green213 Example 35030 : 704.55127.4 Green218 Example 351394 : 2-4340 : 604.52128.1 Green212 Example 35235 : 654.54127.7 Green214 Example 35330 : 704.56126.6 Green219 Example 354400 : 2-640 : 604.50127.6Green211 Example 35535 : 654.52126.3Green213 Example 35630 : 704.55125.5Green215 Example 357402 : 3-5440 : 605.01110.3Green193 Example 35835 : 655.05109.8Green195 Example 35930 : 705.10108.7Green198 Example 360409 : 3-2040 : 604.98108.5Green191 Example 36135 : 655.02107.3Green194 Example 36230 : 705.05106.9Green196 Example 363416 : 3-5440 : 604.89105.3Green193 Example 36435 : 654.92104.6Green195 Example 36530 : 704.99103.3Green197 Example 366418 : 3-2040 : 604.62123.5Green200 Example 36735 : 654.66122.1Green205 Example 36830 : 704.68121.9Green209 Example 369427 : 3-4340 : 604.65125.4Green203 Example 37035 : 654.68124.1Green206 Example 37130 : 704.71123.6Green207 Example 372431 : 3-2940 : 604.68126.8Green201 Example 37335 : 654.72125.1Green203 Example 37430 : 704.75124.3Green208 Example 375436 : 3-2940 : 605.5288.7 Green143 Example 37635 : 655.5587.1 Green147 Example 37730 : 705.5885.9 Green150 Example 378438 : 3-5440 : 605.6386.3 Green146 Example 37935 : 655.6685.1 Green152 Example 38030 : 705.6884.9 Green160 Example 381448 : 3-5440 : 605.2393.2 Green182 Example 38235 : 655.2892.1 Green185 Example 38330 : 705.3191.6Green188 Example 384449 : 3-2940 : 605.2295.3Green181 Example 38535 : 655.2594.2Green183 Example 38630 : 705.2993.8Green187 Example 387450 : 3-2040 : 605.3192.2Green162 Example 38835 : 655.3391.1Green166 Example 38930 : 705.3791.0Green170 Example 390455 : 3-2940 : 605.2993.7Green172 Example 39135 : 655.3292.5Green177 Example 39230 : 705.3691.2Green179 Example 393459 : 3-4340 : 606.3276.3Green135 Example 39435 : 656.3475.2Green137 Example 39530 : 706.3674.8Green140 Example 396464 : 3-5440 : 605.5385.2Green142 Example 39735 : 655.5583.8Green144 Example 39830 : 705.5982.1Green149 Example 399465 : 3-3840 : 605.6287.7Green143 Example 40035 : 655.6686.4Green149 Example 40130 : 705.6985.5Green152 Example 402467 : 3-5440 : 605.3295.3Green161 Example 40335 : 655.3593.2Green165 Example 40430 : 705.3892.1Green168.

[0463] When comparing the results of Table 10 above with the results of Table 9 above, it was confirmed that when the compound of the present invention is used together with the heterocyclic compound of Formula 2, it provides a superior effect in terms of efficiency and lifespan.

[0464] This is due to the exciplex phenomenon, which is a phenomenon in which electron exchange between two molecules releases energy equivalent to the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host). When the exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) takes place, which can increase the internal quantum efficiency of fluorescence emission to 100%.

[0465] 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.

[0466] When a compound of Chemical Formula 1 and a heterocyclic compound of Chemical Formula 2 are mixed and used as a material for the light-emitting layer, it is possible to obtain the effect of partially improving the current efficiency of the light-emitting layer and construct a device with long lifespan characteristics. 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

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 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, 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 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 combined deuterium content of the above structural formulas A and B; or the combined deuterium content of the above structural formulas C and B; is 50% or more and 100% or less. In claim 1, The combined deuterium content of the above structural formulas A and B is 50% or more and 100% or less, and A heterocyclic compound having a deuterium content of 10% or less of the above structural formula C. In claim 1, The combined deuterium content of the above structural formulas B and C is 50% or more and 100% or less, and A heterocyclic compound having a deuterium content of 10% or less of the above structural formula A. 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. Claim 1, wherein A is a heterocyclic compound represented by the following structural formula A-1 or A-2: [Structural Formula A-1] [Structural Formula A-2] 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. A heterocyclic compound according to claim 1, wherein L is represented by one of the following linkers: In the above connector, means the position where they combine with each other. A heterocyclic compound according to claim 1, wherein the deuterium substitution rate of the compound of formula 1 is 20% or more and 95% or less. In claim 1, The above chemical formula 1 is a heterocyclic compound represented by any one of the following compounds: 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 8. An organic light-emitting device according to claim 9, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the heterocyclic compound. An organic light-emitting device according to claim 10, wherein the light-emitting layer comprises a host material, and the host material comprises the heterocyclic compound. An organic light-emitting device according to claim 11, wherein the host material further comprises a heterocyclic compound represented by the following chemical formula 2: [Chemical Formula 2] In the above chemical formula 2, 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; Selected from the group consisting of substituted or unsubstituted amine groups, or two or more adjacent groups are combined 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, and when d is an integer of 2, R9 are the same or different from each other, and 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; and Ar3 and Ar4 are the same or different from each other and each independently are 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 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. An organic light-emitting device according to claim 12, wherein the chemical formula 2 is represented by any one of the following compounds: A composition for an organic layer of an organic light-emitting device comprising: a heterocyclic compound represented by Formula 1 according to any one of claims 1 to 8; and a heterocyclic compound represented by Formula 2 below: [Chemical Formula 2] In the above chemical formula 2, 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; Selected from the group consisting of substituted or unsubstituted amine groups, or two or more adjacent groups are combined 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, and when d is an integer of 2, R9 are the same or different from each other, and 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; and Ar3 and Ar4 are the same or different from each other and each independently are 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 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. In claim 14, A composition for an organic layer of an organic light-emitting device, wherein the weight ratio of the heterocyclic compound represented by Chemical Formula 2 in the composition is higher than the weight ratio of the heterocyclic compound represented by Chemical Formula 1.

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