Heterocyclic compound and organic light-emitting device comprising same

Abstract

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

Description

Heterocyclic compound and organic light-emitting device containing the same

[0001] The present invention relates to a heterocyclic compound and an organic light-emitting device comprising the same.

[0002] This application claims the benefit of Korean Patent Application No. 10-2023-0149112, filed with the Korean Intellectual Property Office on November 1, 2023, the entire contents of which are incorporated herein by reference.

[0003] Electroluminescent elements are a type of self-luminous display element that have the advantages of a wide viewing angle, excellent contrast, and a fast response speed.

[0004] Organic light-emitting devices are structured by placing an organic thin film between two electrodes. When voltage is applied to an organic light-emitting device of this structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, and then disappear, emitting light. The organic thin film may be composed of a single layer or multiple layers, as needed.

[0005] The material of the organic thin film may have a light-emitting function as needed. For example, the organic thin film material may be a compound that can form a light-emitting layer on its own, or a compound that can act as a host or dopant in a host-dopant light-emitting layer. In addition, the material of the organic thin film may be a compound that can perform functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection.

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

[0007] The present invention seeks to provide a heterocyclic compound and an organic light-emitting device comprising the same.

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

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] X1 and X2 are the same or different, and are each independently O or S,

[0013] N-Het is a substituted or unsubstituted C2 to C60 heteroaryl group containing at least one N,

[0014] Ar1 is a substituted or unsubstituted carbazole group,

[0015] R1 to R4 are the same or different and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0016] r1 and r2 are each an integer from 0 to 3, and when r1 is 2 or more, R1 is equal to or different from each other, and when r2 is 2 or more, R2 is equal to or different from each other,

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

[0018] r4 is an integer from 0 to 2, and when r4 is 2, R4 are equal to or different from each other.

[0019] In addition, in one embodiment of the present application, an organic light-emitting device is provided, including a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes a heterocyclic compound represented by the above-described chemical formula 1.

[0020] The heterocyclic compound described herein can be used as an organic layer material of an organic light-emitting device. That is, it can function as a light-emitting layer in an organic light-emitting device.

[0021] Specifically, when used in the organic layer of an organic light-emitting device, the device can achieve significantly improved operation, efficiency, and lifespan.

[0022] Figures 1 to 3 are schematic drawings showing the laminated structure of an organic light-emitting device according to one embodiment of the present application.

[0023] [Explanation of symbols]

[0024] 100: Substrate

[0025] 200: Bipolar

[0026] 300: Organic layer

[0027] 301: Hole injection layer

[0028] 302: Hole transport layer

[0029] 303: Emissive layer

[0030] 304: Electron transport layer

[0031] 305: Electron injection layer

[0032] 307: Static low-level layer

[0033] 400: Cathode

[0034] Hereinafter, the present specification will be described in more detail.

[0035] In this specification, when a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components, unless specifically stated otherwise.

[0036] In this specification, the chemical formula means the position where it is combined.

[0037] In this specification, n in Cn means carbon number. That is, for example, C6 to C60 means carbon number 6 to carbon number 60.

[0038] 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 position of substitution is not limited as long as it is a position where a hydrogen atom is replaced, i.e., a position where a substituent can be replaced, and when two or more are replaced, the two or more substituents may be the same or different from each other.

[0039] 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 alkylsulfoxy group; C6 to C60 arylsulfoxy group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR', or a substituent in which two or more substituents selected from the above-mentioned substituents are connected, means substituted or unsubstituted, and R, R' and R" are each independently a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group.

[0040] In this specification, "when no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0041] In one embodiment of the present application, "when no substituent is indicated in the chemical formula or compound structure" may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the deuterium content may be 0% to 100%.

[0042] In one embodiment of the present application, in the case where "no substituent is indicated in the chemical formula or compound structure", if the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents are hydrogen, etc., and deuterium is not explicitly excluded, hydrogen and deuterium may be used in combination in the compound.

[0043] In one embodiment of the present application, deuterium is an element having a deuteron, which is one of the isotopes of hydrogen and is composed of one proton and one neutron, as its nucleus, and can be expressed as hydrogen-2, and its element symbol is D or 2 It can also be written as H.

[0044] In one embodiment of the present application, an isotope means an atom having the same atomic number (Z) but a different mass number (A). An isotope can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0045] In one embodiment of the present application, the meaning of the content T% of a specific substituent can be defined as T2 / T1Х100 = T% when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2.

[0046] That is, in one example, In the phenyl group represented by , the content of deuterium of 20% means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and if the number of deuterium among them is 1 (T2 in the formula), it can be expressed as 20%. In other words, the content of deuterium of 20% in the phenyl group can be expressed by the structural formula below.

[0047]

[0048] Additionally, in one embodiment of the present application, the term “phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, i.e., has 5 hydrogen atoms.

[0049] In this specification, halogen may be fluorine, chlorine, bromine or iodine.

[0050] In the present specification, an alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 40 carbon atoms, and more specifically 1 to 20 carbon atoms. 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, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, There are, but are not limited to, these.

[0051] In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0052] In the present specification, an alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0053] In this specification, a haloalkyl group means an alkyl group substituted with a halogen group, and specific examples include, but are not limited to, -CF3, -CF2CF3, etc.

[0054] In this specification, an alkoxy group is represented as -O(R101), and examples of the alkyl group described above can be applied to R101.

[0055] In this specification, the aryloxy group is represented as -O(R102), and R102 can be applied to the examples of the aryl group described above.

[0056] In this specification, the alkylthioxy group is represented as -S(R103), and examples of the alkyl group described above can be applied to R103.

[0057] In this specification, the arylthioxy group is represented as -S(R104), and R104 can be applied to the examples of the aryl group described above.

[0058] In this specification, an alkylsulfoxy group is represented as -S(=0)2(R105), and examples of the alkyl group described above can be applied to R105.

[0059] In this specification, an arylsulfoxy group is represented as -S(=0)2(R106), and examples of the aryl group described above can be applied to R106.

[0060] In the present specification, a cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a 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 another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The cycloalkyl group may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. Specifically, there are, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc.

[0061] In the present specification, a heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a 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 another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

[0062] In the present specification, an aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which an 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 another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. The aryl group includes a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the above aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof.

[0063] In this specification, the terphenyl group may be selected from the following structures.

[0064]

[0065] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0066] When the above fluorenyl group is substituted, , , , , , It can be, but is not limited to, the following.

[0067] In the present specification, a heteroaryl group includes S, O, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic ring means a group in which a 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 another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.Specific examples of the above heteroaryl group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, a triazole group, a furazan group, an oxadiazole group, a thiadiazole group, a dithiazole group, a tetrazolyl group, a pyran group, a thiopyran group, a diazine group, an oxazine group, a thiazine group, a dioxin group, a triazine group, a tetrazine group, a quinoline group, an isoquinoline group, a quinazoline group, an isoquinazoline group, a quinozoline group, a naphthyridine group, an acridine group, a phenanthridine group, an imidazopyridine group, a diazanaphthalene group, a triazaindene group, an indole group, an indolizine group, a benzothiazole group, Benzoxazole group, benzimidazole group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazole group, benzocarbazole group, dibenzocarbazole group, phenazine group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazine group, phenoxazine group, phenanthridine group, thienyl group, indolo[2,3-a]carbazole group, indolo[2,3-b]carbazole group, indoline 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 thereof include, but are not limited to, 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5,10-dihydrodibenzo[b,e][1,4]azacillin group, pyrazolo[1,5-c]quinazoline group, pyrido[1,2-b]indazole group, pyrido[1,2-a]imidazo[1,2-e]indolin group, and 5,11-dihydroindeno[1,2-b]carbazole group.

[0068] In the present specification, when the substituent is a carbazole group, it means that it is bonded to the nitrogen or carbon of the carbazole.

[0069] In the present specification, when a carbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole.

[0070] In the present specification, the benzocarbazole group may have any of the following structures.

[0071]

[0072] In the present specification, the dibenzocarbazole group may have any of the following structures.

[0073]

[0074] In the present specification, the naphthobenzofuran group may have any of the following structures.

[0075]

[0076] In the present specification, the naphthobenzothiophene group may have any of the following structures.

[0077]

[0078] In the present specification, a silyl group is a substituent that includes Si and is directly connected to the Si atom as a radical, and is represented by -Si(R107)(R108)(R109), and R107 to R109 are the same as or different from each other, and may each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group.

[0079] A specific example of a cylinder is (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), but is not limited thereto.

[0080] In the present specification, a phosphine oxide group is represented by -P(=O)(R110)(R111), and R110 and R111 are the same as or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. Specifically, it can be substituted with an alkyl group or an aryl group, and the above-described examples can be applied to the alkyl group and the aryl group. For example, the phosphine oxide group includes, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, and dinaphthylphosphine oxide.

[0081] In the present specification, an amine group is represented by -N(R112)(R113), and R112 and R113 are the same as or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. The amine group can be selected from the group consisting of -NH2; a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group.

[0082] In the present specification, the arylene group may be applied to the examples of the aryl group described above, except that it is a divalent group.

[0083] In the present specification, the heteroarylene group may be applied to the examples of the heteroaryl group described above, except that it is a divalent group.

[0084] As used herein, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. 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" to each other.

[0085] Hydrocarbon rings and heterocycles that adjacent groups can form include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles, and structures exemplified by the aforementioned cycloalkyl groups, aryl groups, heterocycloalkyl groups, and heteroaryl groups can be applied to the rings, except that they are not monovalent groups.

[0086] In one embodiment of the present application, a group not indicated as a substituent; or a group indicated as hydrogen may all mean that it can be substituted with deuterium. That is, hydrogen; or deuterium may indicate that they are mutually substitutable.

[0087] Compounds bonded with hydrogen and those substituted with deuterium generally exhibit different thermodynamic behaviors. This is because the mass of a deuterium atom is twice that of hydrogen. This difference in atomic mass gives deuterium the characteristic of having lower vibrational energy.

[0088] Additionally, the single bond dissociation energy (BDE) of carbon and deuterium is higher than that of carbon and hydrogen. Therefore, structures substituted with deuterium have increased thermal stability of the molecule, which has the effect of improving the lifespan of devices utilizing them.

[0089] When compounds are deposited on silicon wafers, substances containing deuterium tend to pack more tightly between molecules. Furthermore, observing the thin film surface with an atomic force microscope (AFM) reveals that thin films made with deuterium-containing compounds are deposited on a more uniform surface, with no aggregations.

[0090] In one embodiment of the present application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[0091] [Chemical Formula 1]

[0092]

[0093] In the above chemical formula 1,

[0094] X1 and X2 are the same or different, and are each independently O or S,

[0095] N-Het is a substituted or unsubstituted C2 to C60 heteroaryl group containing at least one N,

[0096] Ar1 is a substituted or unsubstituted carbazole group,

[0097] R1 to R4 are the same or different and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0098] r1 and r2 are each an integer from 0 to 3, and when r1 is 2 or more, R1 is equal to or different from each other, and when r2 is 2 or more, R2 is equal to or different from each other,

[0099] r3 is an integer from 0 to 4, and when r3 is 2 or greater, R3 are equal to or different from each other,

[0100] r4 is an integer from 0 to 2, and when r4 is 2, R4 are equal to or different from each other.

[0101] The heterocyclic compound represented by the above chemical formula 1 includes a dibenzofuran / dibenzothiophene linker (structural formula including X2) between a core dibenzofuran / dibenzothiophene (structural formula including X1) and a carbazole (represented by Ar1), and at this time, the structural formula including X1 and the carbazole are combined only in one benzene ring of the structural formula introduced as the linker, so that although it has a relatively high molecular weight, it has a structure that is characterized by a folded molecular structure and is proposed to facilitate tuning of the Td value.

[0102] By having these characteristics, the life and efficiency characteristics can be improved by increasing the steric hindrance within the molecule and minimizing molecular vibration.

[0103] O or S of the core dibenzofuran / dibenzothiophene is an electron donating group and can donate an unshared electron pair to the 2nd or 4th positions, which correspond to the ortho and para positions based on O or S, through the directing effect. Therefore, when electrons are injected into the N-Het Unit at the 2nd or 4th positions, which correspond to the ortho and para positions, during device operation, the stability of the molecular structure deteriorates.

[0104] In contrast, the N-Het Unit bonded to the 1st or 3rd position, which corresponds to the meta position based on O or S of dibenzofuran / dibenzothiophene, is relatively less affected by the unshared electron pair donation, so that the stability of the molecular structure can be secured when electrons are injected into the N-Het Unit during device operation. In particular, according to the results of molecular calculations (Gaussian 16 Program), when the N-Het Unit is bonded to the 3rd position of dibenzofuran / dibenzothiophene (Core), the dihedral angle is 0. o In close proximity, the Core and N-Het units exist on the same plane. This is a factor that can improve intermolecular interactions and is a form that can help intermolecular charge transfer.

[0105] On the other hand, when the N-Het Unit is bonded to position 1 of the Core, the dihedral angle is 20 o As confirmed above, since the Core and N-Het Unit do not exist on the same plane, the expression of the intermolecular interaction effect may be limited.

[0106] Additionally, Tg is one of the factors that can be used to predict the thermal stability of a host material during device operation. Generally, the more linear the structure, the higher the Tg of the molecule is observed at a higher temperature.

[0107] Therefore, the heterocyclic compound represented by the chemical formula 1 of the present invention can secure all of the mentioned strengths by combining the N-Het Unit at the 3rd position of the core.

[0108] In one embodiment of the present application, X1 and X2 may be O.

[0109] In another embodiment, X1 and X2 may be S.

[0110] In another embodiment, X1 may be O and X2 may be S.

[0111] In another embodiment, X1 may be S and X2 may be O.

[0112] In one embodiment of the present application, the N-Het may be a substituted or unsubstituted C2 to C40 heteroaryl group containing at least one N.

[0113] In another embodiment, the N-Het may be a substituted or unsubstituted C2 to C20 heteroaryl group containing at least one N.

[0114] In another embodiment, the N-Het may be a C2 to C20 heteroaryl group that contains two or more N and is substituted or unsubstituted with a substituted or unsubstituted C6 to C60 aryl group.

[0115] In another embodiment, the N-Het may be a C2 to C20 heteroaryl group having three N atoms and substituted with a substituted or unsubstituted C6 to C60 aryl group.

[0116] In one embodiment of the present application, Ar1 may be a carbazole group substituted or unsubstituted with deuterium or a substituted or unsubstituted C6 to C60 aryl group.

[0117] In another embodiment, Ar1 may be a carbazole group substituted or unsubstituted with deuterium or a substituted or unsubstituted C6 to C40 aryl group.

[0118] In another embodiment, Ar1 may be a carbazole group substituted or unsubstituted with deuterium or an aryl group having C6 to C20 substituted or unsubstituted with deuterium.

[0119] In another embodiment, Ar1 may be a carbazole group substituted or unsubstituted with deuterium or a phenyl group substituted or unsubstituted with deuterium.

[0120] In one embodiment of the present application, R1 to R4 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0121] In another embodiment, R1 to R4 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0122] In another embodiment, R1 to R4 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

[0123] In another embodiment, R1 to R4 are the same as or different from each other, and can each independently be hydrogen; deuterium; a methyl group; a phenyl group; or a biphenyl group.

[0124] In another embodiment, R1 to R4 are the same as or different from each other, and each independently may be hydrogen or deuterium.

[0125] In one embodiment of the present application, r1 and r2 are each an integer from 0 to 2, and when r1 is 2 or more, R1 may be the same as or different from each other, and when r2 is 2 or more, R2 may be the same as or different from each other.

[0126] In one embodiment of the present application, r3 is an integer from 0 to 3, and when r3 is 2 or more, R3 may be the same as or different from each other.

[0127] In another embodiment, the r3 is an integer from 0 to 2, and when the r3 is 2 or greater, R3 may be the same or different from each other.

[0128] In one embodiment of the present application, r4 is 0 or 1.

[0129] In one embodiment of the present application, the chemical formula 1 may be represented by the following chemical formula 1-1 or 1-2.

[0130] [Chemical Formula 1-1]

[0131]

[0132] [Chemical Formula 1-2]

[0133]

[0134] In Chemical Formula 1-1 and Chemical Formula 1-2,

[0135] The substituent definitions of X1, X2, N-Het, R1 to R4 and r1 to r4 are the same as those in the above chemical formula 1,

[0136] Ar2 is a substituted or unsubstituted C6 to C60 aryl group,

[0137] R5 and R6 are the same as or different from each other, and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0138] r5 is an integer from 0 to 8, and when r5 is 2 or greater, R5 are equal to or different from each other,

[0139] r6 is an integer from 0 to 7, and when r6 is 2 or greater, R6 are equal to or different from each other.

[0140] In one embodiment of the present application, Ar2 may be a substituted or unsubstituted C6 to C40 aryl group.

[0141] In another embodiment, Ar2 may be a substituted or unsubstituted C6 to C20 aryl group.

[0142] In another embodiment, Ar2 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0143] In another embodiment, Ar2 may be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium.

[0144] In another embodiment, Ar2 may be a phenyl group substituted or unsubstituted with deuterium.

[0145] In one embodiment of the present application, R5 and R6 may be the same as or different from each other, and each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0146] In another embodiment, R5 and R6 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0147] In another embodiment, R5 and R6 may be the same as or different from each other, and each independently be hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

[0148] In another embodiment, R5 and R6 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a methyl group; a phenyl group; or a biphenyl group.

[0149] In another embodiment, R5 and R6 are the same as or different from each other, and each independently may be hydrogen or deuterium.

[0150] In one embodiment of the present application, r5 is an integer from 0 to 7, and when r5 is 2 or more, R5 may be the same as or different from each other.

[0151] In another embodiment, the r5 is an integer from 0 to 6, and when the r5 is 2 or more, R5 may be the same or different from each other.

[0152] In another embodiment, the r5 is an integer from 0 to 5, and when the r5 is 2 or greater, R5 may be the same or different from each other.

[0153] In another embodiment, the r5 is an integer from 0 to 4, and when the r5 is 2 or greater, R5 may be the same or different from each other.

[0154] In another embodiment, the r5 is an integer from 0 to 3, and when the r5 is 2 or greater, R5 may be the same or different from each other.

[0155] In another embodiment, the r5 is an integer from 0 to 2, and when the r5 is 2 or greater, R5 may be the same as or different from each other.

[0156] In one embodiment of the present application, r6 is an integer from 0 to 6, and when r6 is 2 or more, R6 may be the same as or different from each other.

[0157] In another embodiment, the above r6 is an integer from 0 to 5, and when the above r6 is 2 or more, R6 may be the same or different from each other.

[0158] In another embodiment, the above r6 is an integer from 0 to 4, and when the above r6 is 2 or more, R6 may be the same or different from each other.

[0159] In another embodiment, the above r6 is an integer from 0 to 3, and when the above r6 is 2 or more, R6 may be the same or different from each other.

[0160] In another embodiment, the above r6 is an integer from 0 to 2, and when the above r6 is 2 or greater, R6 may be the same or different from each other.

[0161] In one embodiment of the present application, the N-Het may be represented by the following structural formula 1.

[0162] [Structural formula 1]

[0163]

[0164] In the above structural formula 1,

[0165] means a part that connects to another structure,

[0166] Y1 to Y5 are the same or different and are each independently CRa or N, but at least one is N,

[0167] The above Ra is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent Ra groups are bonded to each other to form a ring.

[0168] In one embodiment of the present application, Y1 to Y5 are the same as or different from each other and are each independently CRa or N, but two or more of them may be N.

[0169] In another embodiment, Y1 to Y5 are the same as or different from each other and are each independently CRa or N, and three or more of them may be N.

[0170] In another embodiment, Y1, Y3 and Y5 may be N, and Y2 and Y4 may be CRa.

[0171] In one embodiment of the present application, Ra is a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group; or two or more adjacent Ra groups may combine with each other to form a substituted or unsubstituted C2 to C40 aliphatic ring or a substituted or unsubstituted C2 to C40 aromatic ring.

[0172] In another embodiment, Ra is a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent Ra groups may be bonded to each other to form a substituted or unsubstituted C2 to C20 aliphatic ring or a substituted or unsubstituted C2 to C20 aromatic ring.

[0173] In another embodiment, Ra may be a substituted or unsubstituted C6 to C20 aryl group.

[0174] In another embodiment, Ra may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0175] In another embodiment, Ra may be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium.

[0176] In another embodiment, Ra may be a phenyl group substituted or unsubstituted with deuterium.

[0177] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 0% or 1% to 100%.

[0178] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 0% or 10% to 100%.

[0179] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 0% or 15% to 100%.

[0180] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 0% or 30% to 100%.

[0181] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 0% or 50% to 100%.

[0182] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 0% or 70% to 100%.

[0183] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 0% or 90% to 100%.

[0184] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 0%.

[0185] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 15% to 100%.

[0186] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 30% to 100%.

[0187] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 50% to 100%.

[0188] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 70% to 100%.

[0189] In one embodiment of the present application, the deuterium content of the compound of the chemical formula 1 may be 90% to 100%.

[0190] In one embodiment of the present application, the chemical formula 1 provides a compound represented by any one of the following compounds.

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] In one embodiment of the present application, the compound is an example and is not limited thereto, and may include other compounds included in the chemical formula 1 that include additional substituents. In addition, the substitution position of deuterium in the compound may exclude a specific position during the deuterium substitution and synthesis process, and hydrogen and deuterium may exist in a mixed state.

[0208] In addition, by introducing various substituents into the structure of the above 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, a material satisfying the conditions required for each organic layer can be synthesized.

[0209] In addition, by introducing various substituents into the structure of the above chemical formula 1 or changing the bonding position, the band gap can be finely controlled, and on the other hand, the properties at the interface between organic layers can be improved.

[0210] In addition, the compound of the above chemical formula 1 has excellent thermal stability, and this thermal stability provides operating stability to the organic light-emitting device and improves the life characteristics.

[0211] In one embodiment of the present application, an organic light-emitting device is provided, comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes a heterocyclic compound represented by the chemical formula 1.

[0212] In another embodiment, an organic light-emitting device is provided, comprising: a first electrode; a second electrode provided opposite the first electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes one type of heterocyclic compound represented by the chemical formula 1.

[0213] In another embodiment, an organic light-emitting device is provided, comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes two or more heterocyclic compounds represented by the chemical formula 1.

[0214] In another embodiment, the heterocyclic compound represented by the above chemical formula 1 can be used as a light-emitting material of a light-emitting layer of an organic light-emitting device.

[0215] In another embodiment, the heterocyclic compound represented by the above chemical formula 1 can be used as a host material of a light-emitting layer of an organic light-emitting device.

[0216] In one embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

[0217] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0218] 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 the chemical formula 1 may be used as a material of the blue organic light-emitting device.

[0219] 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 the chemical formula 1 may be used as a material of the green organic light-emitting device.

[0220] 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 the chemical formula 1 may be used as a material of the red organic light-emitting device.

[0221] 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 the chemical formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

[0222] 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 the chemical formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

[0223] 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 the chemical formula 1 may be used as a light-emitting layer material of the red organic light-emitting device.

[0224] In one embodiment of the present application, the specific details of the heterocyclic compound represented by the chemical formula 1 are the same as those described above.

[0225] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the aforementioned heterocyclic compound.

[0226] The above heterocyclic compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0227] 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 multi-layer structure in which two or more organic layers are laminated. 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 the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0228] In one embodiment of the present application, Ir(ppy)3, a green phosphorescent dopant, may be used as an iridium-based dopant.

[0229] In one embodiment of the present application, a red phosphorescent dopant, (piq)2(Ir)(acac), may be used as the iridium-based dopant.

[0230] In one embodiment of the present application, an organic light-emitting device is provided, wherein the organic material layer of the organic light-emitting device includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.

[0231] In one embodiment of the present application, an organic light-emitting device is provided, wherein the organic material layer of the organic light-emitting device includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the heterocyclic compound.

[0232] In the organic light-emitting device of the present invention, the organic layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound.

[0233] In another organic light-emitting device, the organic layer includes a hole-blocking layer, and the hole-blocking layer may include the heterocyclic compound.

[0234] In another organic light-emitting device, the organic layer includes an electron blocking layer, and the electron blocking layer may include the heterocyclic compound.

[0235] In another organic light-emitting device, the organic layer includes a hole transport layer, an emission layer, or an electron blocking layer, and the hole transport layer, the emission layer, or the electron blocking layer may include the heterocyclic compound.

[0236] In another organic light-emitting device, the organic layer includes a hole transport layer or a hole transport auxiliary layer, and the hole transport layer or the hole transport auxiliary layer may include the heterocyclic compound.

[0237] In the organic light-emitting device of the present application, materials having a relatively large work function can be used as the anode material, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the anode material include, but are not limited to, 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.

[0238] Materials with relatively low work functions can be used as cathode materials, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0239] As the hole injection material, a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a starburst amine derivative 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), a soluble conductive polymer such as polyaniline / dodecylbenzenesulfonic acid, or Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrene-sulfonate) can be used.

[0240] Pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport materials, and low molecular weight or high molecular weight materials can also be used.

[0241] As the electron transport material, metal complexes of oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, etc. can be used, and not only low molecular weight substances but also high molecular weight substances can be used.

[0242] For example, LiF is a representative material used in the art, but the present application is not limited thereto.

[0243] Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. At this time, two or more light-emitting materials may be deposited and used as individual sources, or may be premixed and deposited and used as a single source. In addition, a fluorescent material may be used as the light-emitting material, but it may also be used as a phosphorescent material. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used as the light-emitting material, but materials in which both the host material and the dopant material participate in light emission may also be used.

[0244] When using a mixture of hosts for light-emitting materials, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more types of materials, either n-type host materials or p-type host materials, may be selected and used as the host materials for the light-emitting layer.

[0245] An organic light-emitting device according to one embodiment of the present application may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0246] The heterocyclic compound according to one embodiment of the present application can function in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., using a principle similar to that applied to organic light-emitting devices.

[0247] The organic light-emitting device of the present invention may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0248] The organic light-emitting device of the present invention may further include one or two 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.

[0249] The stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present application is exemplified in Figures 1 to 4. However, the scope of the present application is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present application.

[0250] According to FIG. 1, an organic light-emitting device is illustrated in which an anode (200), an organic layer (300), and a cathode (400) are sequentially laminated on a substrate (100). However, the present invention is not limited to this structure, and an organic light-emitting device in which a cathode, an organic layer, and an anode are sequentially laminated on a substrate, as shown in FIG. 2, may also be implemented.

[0251] Figure 3 illustrates a case where the organic layer is multilayer.

[0252] The organic light-emitting device according to FIG. 3 includes a hole injection layer (301), a hole transport layer (302), a light-emitting layer (303), a hole blocking layer (307), an electron transport layer (304), and an electron injection layer (305).

[0253] However, the scope of the present application is not limited by such a laminated structure, and layers other than the light-emitting layer may be omitted as needed, and other necessary functional layers may be added.

[0254] The organic layer containing the above chemical formula 1 may additionally contain other substances as needed.

[0255] In one embodiment of the present application, an organic light-emitting device is provided in which the host material further includes a heterocyclic compound represented by the following chemical formula 2 or chemical formula 3.

[0256] [Chemical Formula 2]

[0257]

[0258] In chemical formula 2,

[0259] R21 and R22 are the same or different and each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0260] R7 and R8 are the same or different, and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0261] r7 and r8 are each an integer from 0 to 7, and when r7 is 2 or more, R7 are equal to or different from each other, and when r8 is 2 or more, R8 are equal to or different from each other,

[0262] [Chemical Formula 3]

[0263]

[0264] In chemical formula 3,

[0265] A is a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring,

[0266] R23 and R24 are the same or different and each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0267] R9 and R10 are the same as or different from each other, and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0268] r9 and r10 are each an integer from 0 to 4, and when r9 is 2 or more, R9 are the same as or different from each other, and when r10 is 2 or more, R10 are the same as or different from each other.

[0269] In one embodiment of the present application, R21 and R22 may be the same as or different from each other and may each independently be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0270] In another embodiment, R21 and R22 may be the same as or different from each other and may each independently be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0271] In another embodiment, R21 and R22 may be the same as 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 naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0272] In one embodiment of the present application, R7 and R8 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0273] In another embodiment, R7 and R8 may be the same as or different from each other, and each independently be hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0274] In another embodiment, R7 and R8 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

[0275] In another embodiment, R7 and R8 are the same or different from each other, and each independently may be hydrogen or deuterium.

[0276] In one embodiment of the present application, A may be a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring.

[0277] In another embodiment, A may be a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring.

[0278] In another embodiment, A may be a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring.

[0279] In another embodiment, A may be a substituted or unsubstituted benzene ring.

[0280] In another embodiment, A may be a benzene ring substituted or unsubstituted with deuterium.

[0281] In one embodiment of the present application, R23 and R24 may be the same as or different from each other and may each independently be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0282] In another embodiment, R23 and R24 may be the same as or different from each other and may each independently be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0283] In another embodiment, R23 and R24 may be the same as 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 naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0284] In one embodiment of the present application, R9 and R10 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0285] In another embodiment, R9 and R10 may be the same as or different from each other, and each independently be hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0286] In another embodiment, R9 and R10 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

[0287] In another embodiment, R9 and R10 are the same as or different from each other, and each independently may be hydrogen or deuterium.

[0288] In one embodiment of the present application, the deuterium content of the chemical formula 2 may be 0% to 100%.

[0289] In another embodiment, the deuterium content of the chemical formula 2 may be 0% or 20% to 100%.

[0290] In another embodiment, the deuterium content of the chemical formula 2 may be 0% or 40% to 100%.

[0291] In another embodiment, the deuterium content of the chemical formula 2 may be 0% or 60% to 100%.

[0292] In another embodiment, the deuterium content of the chemical formula 2 may be 0% or 80% to 100%.

[0293] In another embodiment, the deuterium content of the chemical formula 2 may be 0% or 100%.

[0294] In one embodiment of the present application, the deuterium content of the chemical formula 3 may be 0% to 100%.

[0295] In another embodiment, the deuterium content of the chemical formula 3 may be 0% or 20% to 100%.

[0296] In another embodiment, the deuterium content of the chemical formula 3 may be 0% or 40% to 100%.

[0297] In another embodiment, the deuterium content of the chemical formula 3 may be 0% or 60% to 100%.

[0298] In another embodiment, the deuterium content of the chemical formula 3 may be 0% or 80% to 100%.

[0299] In another embodiment, the deuterium content of the chemical formula 3 may be 0% or 100%.

[0300] In one embodiment of the present application, the chemical formula 2 provides an organic light-emitting device represented by any one of the following compounds.

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308] In one embodiment of the present application, the chemical formula 3 provides an organic light-emitting device represented by any one of the following compounds.

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316] The organic light-emitting device further comprising a heterocyclic compound represented by the above chemical formula 2 or 3 may be applied to the organic light-emitting device comprising a heterocyclic compound represented by the above chemical formula 1.

[0317] In another embodiment, the heterocyclic compound represented by the chemical formula 2 or 3 can be used as a light-emitting material of a light-emitting layer of an organic light-emitting device.

[0318] In another embodiment, the heterocyclic compound represented by the chemical formula 2 or 3 can be used as a light-emitting material of a light-emitting layer of an organic light-emitting device and can be used as a p-type host material.

[0319] In the organic light-emitting device of the present invention, the organic layer may include a heterocyclic compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 2 or 3. The organic layer may be formed by pre-mixing the heterocyclic compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 2 or 3 using a thermal vacuum deposition method.

[0320] In another organic light-emitting device, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include a heterocyclic compound represented by the chemical formula 1, and a heterocyclic compound represented by the chemical formula 2 or 3.

[0321] In another organic light-emitting device, the organic material layer may include a light-emitting layer, and may include a heterocyclic compound represented by the above chemical formula 1 as an n-type host material of the light-emitting layer, and may include a heterocyclic compound represented by the above chemical formula 2 or 3 as a p-type host material.

[0322] 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 layer, wherein the step of forming the organic layer includes the step of forming one or more organic layers using an organic layer composition according to one embodiment of the present application.

[0323] In one embodiment of the present application, the step of forming the organic layer provides a method for manufacturing an organic light-emitting device, wherein the heterocyclic compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 2 or 3 are supplied as separate sources, and then formed using a thermal vacuum deposition method.

[0324] 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 comprises pre-mixing a heterocyclic compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 2 or 3 and forming the organic layer using a thermal vacuum deposition method.

[0325] An organic light-emitting device according to one embodiment of the present application can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that an organic layer is formed using the aforementioned heterocyclic compound.

[0326] The organic light-emitting device of the present invention may further include one or two 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 auxiliary layer, and a hole blocking layer.

[0327] 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 chemical formula 1 and a heterocyclic compound represented by the chemical formula 2 or 3.

[0328] The weight ratio of the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 2 may be 1:10 to 10:1, or the weight ratio of the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 may be 1:10 to 10:1.

[0329] The weight ratio of the heterocyclic compound represented by the above chemical formula 1 in the above composition to the heterocyclic compound represented by the above chemical formula 2 may be 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1, but is not limited thereto.

[0330] The weight ratio of the heterocyclic compound represented by the above chemical formula 1 in the above composition to the heterocyclic compound represented by the above chemical formula 3 may be 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1, but is not limited thereto.

[0331] The above composition can be used in forming an organic layer of an organic light-emitting device, and can be particularly preferably used as a host material of a light-emitting layer.

[0332] The above composition is a simple mixture of two or more compounds, and powder-state materials may be mixed before forming the organic layer of the organic light-emitting device, or compounds that are in a liquid state at a suitable 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.

[0333] The above composition may additionally include materials known in the art, such as solvents and additives.

[0334] Hereinafter, the present specification will be described in more detail through examples, but these are only intended to illustrate the present application and are not intended to limit the scope of the present application.

[0335] <Manufacturing Example>

[0336] [Manufacturing Example 1] Preparation of compound 1-1[C]

[0337]

[0338] A mixture of 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-2-yl)-9H-carbazole (15.0 g, 0.033 mol) [A], 2-(9-bromodibenzo[b,d]furan-3-yl)-4,6-diphenyl-1,3,5-triazine (17.2 g, 0.036 mol) [B], K2CO3 (9 g, 0.065 mol), Pd(PPh3)4 (1.9 g, 0.002 mol), and 1,4-Dioxane (150 mL) / Water(H2O) (30 mL) was refluxed at 120°C in a one-neck round bottom flask.

[0339] After the reaction was completed, the precipitated solid was filtered, the obtained solid was dissolved in dichlorobenzene, and silica gel filtered. After concentration, it was treated with methanol to obtain compound [1-1]. (16.5 g, 69%) [C]

[0340] In the above Manufacturing Example 1, the target compound C was manufactured in the same manner as above, except that [A] and [B] were replaced with intermediates A and B of Table 1, respectively.

[0341] [Table 1]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348] [Manufacturing Example 2] Preparation of compound 1-101[F]

[0349] A mixture of 9-phenyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-1-yl)-9H-carbazole (15.0 g, 0.028 mol) [D], 2-(9-bromodibenzo[b,d]furan-3-yl)-4,6-diphenyl-1,3,5-triazine (14.7 g, 0.031 mol) [E], K2CO3 (7.7 g, 0.056 mol), Pd(PPh3)4 (1.6 g, 0.001 mol), and 1,4-Dioxane (150 mL) / Water(H2O) (30 mL) was refluxed at 120°C in a one-neck round bottom flask.

[0350] After the reaction was completed, the precipitated solid was filtered, the obtained solid was dissolved in dichlorobenzene, and silica gel filtered. After concentration, the solid was treated with methanol to obtain compound [1-101]. (16.7 g, 74%) [F]

[0351] In the above Manufacturing Example 2, the target compound F was manufactured in the same manner as above, except that [D] and [E] were replaced with intermediates D and E of Table 2, respectively.

[0352] [Table 2]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362] [Manufacturing Example 3] Preparation of Compound 2-1[C]

[0363]

[0364] Preparation of compound 2-1-i

[0365] 3-bromo-9H-carbazole (10.g, 49.59mmol), 2-bromobenzene-1-ylium (24.2g, 148.77mmol) [A], Pd2(dba)3 (2.27g, 2.48mmol), P(t-Bu)3 (2.42mL, 9.92mmol), NaOtBu (9.53g, 99.18mmol) were placed in a one-neck round bottom flask, then toluene (100mL) was added and heated at 135℃ for 15 hours.

[0366] After the reaction was completed, the mixture was extracted with MC and H2O and purified by column to obtain compound 2-1-i (14 g, 98%).

[0367] Preparation of compound 2-1[C]

[0368] In a one-neck round bottom flask, 2-[C]-1-i (14 g, 43.4 mmol), (9-phenyl-9H-carbazol-3-yl)boronic acid (14.9 g, 52 mmol) [B], Pd(PPh3)4 (2.5 g, 2.17 mmol), and K2CO3 (17.9 g, 130 mmol) were added, and a mixture of 1,4-dioxane / Water (140 ml / 35 ml) was heated at 120°C for 4 hours.

[0369] After the reaction was completed, the temperature was lowered to room temperature, and the resulting solid was washed sequentially with distilled water and MeOH to obtain the target compound 2-1[C] (17 g, 80%).

[0370] In the above manufacturing example 3, the target compound C was manufactured in the same manner as above except that [A] and [B] were replaced with intermediates A and B of Table 3 below, respectively.

[0371] [Table 3]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380] [Manufacturing Example 4] Preparation of compound 2-61[F]

[0381]

[0382] Preparation of compound 2-61-1-ii

[0383] 3-bromo-9H-carbazole (10 g, 40.23 mmol) and D6-benzene (1000 ml) were added to a one-neck round bottom flask, then CF3SO3H (170 g, 1075 mmol) was added and stirred at 50°C.

[0384] After the reaction was completed, the mixture was neutralized with D2O, extracted with MC and Na2CO3 aqueous solution, and purified by column to obtain compound 2-61-1-ii. (10 g, 98%)

[0385] Preparation of compound 2-61-1-i

[0386] 2 2-61-1-ii (10 g, 39.5 mmol), Bromobenzene (12.4 g, 79 mmol) [D], Pd2(dba)3 (1.81 g, 1.98 mmol), P(t-Bu)3 (1.93 mL, 7.9 mmol), NaOtBu (11.4 g, 118.51 mmol) were added to a one-neck round bottom flask, and then toluene (100 mL) was added and heated at 135°C for 10 hours.

[0387] After the reaction was completed, the mixture was extracted with MC and H2O and purified by column to obtain compound 2-61-1-i (11 g, 84%).

[0388] Preparation of compound 2-61-2-ii

[0389] 9H-carbazol-3-ylboronic acid (10 g, 47.3 mmol) and D6-benzene (1000 ml) were added to a one-neck round bottom flask, then CF3SO3H (170 g, 1075 mmol) was added and stirred at 50°C.

[0390] After the reaction was completed, neutralization with D2O was performed, followed by extraction with MC and Na2CO3 aqueous solution and column purification to obtain 2-61-2-ii. (9g, 87%)

[0391] Preparation of compound 2-61-2-i

[0392] 2-61-2-ii (9 g, 41.3 mmol), Bromobenzene (12.9 g, 82.5 mmol) [E], Pd2(dba)3 (1.89 g, 2.06 mmol), P(t-Bu)3 (2 mL, 8.25 mmol), NaOtBu (7.93 g, 82.54 mmol) were added to a one-neck round bottom flask, and then toluene (100 mL) was added and heated at 135°C for 10 hours.

[0393] After the reaction was completed, the product was extracted with MC and H2O and purified by column to obtain 2-61-2-i (10 g, 82%).

[0394] Preparation of compound 2-61[F]

[0395] 2-[F]-61-i (10 g, 30.37 mmol), 2-61-2-ii (17.87 g, 60.75 mmol), Pd(PPh3)4 (1.39, 1.52 mmol), K2CO3 (12.59 g, 91.13 mmol) were added to a one-neck round bottom flask, and the mixture of 1,4-dioxane / Water (140 ml / 35 ml) was heated at 120°C for 4 hours.

[0396] After the reaction was completed, the temperature was lowered to room temperature, and the resulting solid was washed with distilled water and MeOH to obtain the target compound 2-61 [F] (13 g, 85%).

[0397] In the above manufacturing example 4, the target compound F was manufactured in the same manner as above except that [D] and [E] were replaced with intermediates D and E of Table 6 below, respectively.

[0398] [Table 6]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404] [Manufacturing Example 5] Preparation of compound 3-78[D]

[0405]

[0406]

[0407] Preparation of compound 3-1-1

[0408] 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindolo[2,3-c]carbazole (10.g, 24.48mmol) [A], 3-Bromobiphenyl (5.82 g, 24.48mmol) [B], Pd2(dba)3 (1.12 g, 1.22mmol), XPhos (1.17 g, 2.45 mmol), NaOtBu (7.06 g, 73.44 mmol) were added to a one-neck round bottom flask, and then toluene (100mL) was added and heated at 135℃ for 15 hours.

[0409] After the reaction was completed, the target compound 3-1-1[C] was obtained by extracting with MC and H2O and purifying by column. (12g, 87%)

[0410] Preparation of compound 3-78 [D]

[0411] 5-([1,1'-biphenyl]-3-yl)-8-([1,1'-biphenyl]-4-yl)-5,8-dihydroindolo[2,3-c]carbazole (12 g, 21.4 mmol) 3-1-1 [C] and 100 mL of D6-Benzene were added to a one-neck round bottom flask and stirred in an ice bath.

[0412] After adding triflic acid (18.89 mL, 214.02 mmol) dropwise, the mixture was stirred at 50°C for 1 hr. After completion of the reaction, the reactor was transferred to an ice bath, and a supersaturated aqueous solution of K3PO4 (45.43 g, 214.02 mmol) dissolved in 300 mL of D2O was added dropwise to the reactor to neutralize. After extraction with MC and H2O, the target compound 3-78 [D] was obtained through column purification. (10 g, 79%)

[0413] In the above Manufacturing Example 5, the target compound C was manufactured in the same manner as above, except that [A] and [B] were replaced with intermediates A and B of Table 5 below, respectively.

[0414] [Table 5]

[0415] [Correction pursuant to Rule 91, January 15, 2024]

[0416] Compounds were prepared using the same method as the above manufacturing examples, and the results of their synthesis are shown in Tables 6 and 7 below. Table 6 below shows the measured values ​​from FD-mass spectrometry (FD-MS), and Table 7 below shows the NMR values.

[0417] [Table 6]

[0418]

[0419]

[0420]

[0421]

[0422] [Table 7]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428] Experimental Example 1

[0429] 1) Fabrication of organic light-emitting devices

[0430] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT), where it was plasma-treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0431] A common layer, a hole injection layer 2-TNATA (4,4′,4′′-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N′-Di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine), were formed on the ITO transparent electrode (anode).

[0432] On top of that, a light-emitting layer was thermally vacuum deposited as follows. The light-emitting layer used the compound described in Table 5 below as a host, and Ir(ppy)3(tris(2-phenylpyridine)iridium) as a green phosphorescent dopant, and the host was doped with 7% Ir(ppy)3 and deposited to 400Å. Then, BCP(Bathocuproine) was deposited to 60Å as a hole-blocking layer, and Alq3 was deposited to 200Å as an electron-transporting layer thereon. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron-transporting layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1200Å on the electron injection layer to form a cathode, thereby manufacturing an organic light-emitting device.

[0433] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0434] 2) Driving voltage and luminous efficiency of organic light-emitting devices

[0435] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using M7000 from MaxScience, and the standard luminance was determined to be 6,000 cd / m using the life measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 When, T 90 was measured.

[0436] The driving voltage, luminous efficiency, color coordinates (CIE) and lifespan (T) of the organic light-emitting device manufactured according to the present invention 90 ) are measured as shown in Table 8 below.

[0437] [Table 8]

[0438]

[0439]

[0440]

[0441]

[0442] [Comparative example compound]

[0443]

[0444] As can be seen from the results in Table 8 above, Examples 1 to 74 using the compound represented by Chemical Formula 1 of the present invention as a light-emitting layer material had lower driving voltages and significantly improved luminous efficiency and lifespans compared to Comparative Examples 1 to 14 using compounds A to K as light-emitting layer materials.

[0445] When the N-Het unit is bonded to the 3rd position of the dibenzofuran / dibenzothiophene used as the core, the dihedral angle approaches 0°, so the core and the N-Het unit exist on the same plane. This is a factor that can enhance intermolecular interactions and helps intermolecular charge transfer.

[0446] When N-Het aryl is bonded to position 1 of Dibenzofuran as in Comparative Examples 1 and 2, the dihedral angle is confirmed to be 20° or more, so the Core and N-Het Unit do not exist in the same plane, and thus the intermolecular charge transfer ability is inferior to that of the compounds of the above-described examples.

[0447] In Comparative Examples 3, 4, 5, 7, 8 and Comparative Example 10, the Core and the HT Unit (carbazole, benzocarbazole, aryl amine) are bonded directly or through a phenylene linker, and the HOMO region is limited to a narrow region, resulting in relatively poor device characteristics compared to the exemplary structure.

[0448] In the case of Comparative Examples 6 to 9, the Td value is high due to the high molecular weight and linear molecular structure, making it difficult to stably express the device performance.

[0449] In the case of Comparative Example 11, it can be confirmed that the device characteristics are insufficient because the charge balance is not maintained during operation due to the unit not including Aryl amine or Carbazole, which are classified as representative HT units.

[0450] In the case of Comparative Example 12, since carbazole and dibenzothiophene are bonded together to the same benzene ring of the dibenzofuran core, the expansion of HOMO and LUMO is limited compared to the compounds of the examples described above.

[0451] In the case of Comparative Example 13, it can be confirmed that the device characteristics are insufficient because the charge balance is not maintained during operation due to the unit such as Triazine, which is classified as a representative ET unit, not being included.

[0452] In the case of Comparative Example 14, the structure is a dibenzofuran linker bonded with carbazole to a dibenzothiophenoxide core with strong HT characteristics, and a triazine is bonded. Unlike the compound of the specific example of the chemical formula of the present invention, it is designed with a structure in which the expansion of HOMO and LUMO is limited, and thus exhibits relatively poor device characteristics.

[0453] Experimental Example 2

[0454] 1) Fabrication of organic light-emitting devices

[0455] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), where it was plasma-treated in a vacuum to remove the ITO work function and residual film, and then 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′-Di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine), were formed on the ITO transparent electrode (anode). A light-emitting layer was thermally vacuum-deposited thereon as follows.

[0457] The light-emitting layer was pre-mixed with one heterocyclic compound having the structure of chemical formula 1 as a host and one compound having the structure of chemical formula 2 or 3 in the ratio (weight ratio) of Table 9 below, and deposited at 400 Å in one park, and the green phosphorescent dopant was deposited by doping Ir(ppy)3 at 7% of the thickness of the light-emitting layer deposition.

[0458] Afterwards, BCP was deposited to a thickness of 60Å as a hole blocking layer, and Alq3 was deposited to a thickness of 200Å as an electron transport layer on top of it. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200Å on the electron injection layer to form a cathode, thereby manufacturing an organic light-emitting device.

[0459] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0460] 2) Driving voltage and luminous efficiency of organic light-emitting devices

[0461] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using MacScience's M7000, and the standard luminance was determined to be 6,000 cd / m using the lifespan measuring equipment (M6000) manufactured by MacScience based on the measurement results. 2 When, T 90 was measured.

[0462] The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention are as shown in Table 9 below.

[0463] [Table 9]

[0464]

[0465]

[0466]

[0467]

[0468] As can be seen from the results in Table 9 above, Examples 75 to 98, which are organic light-emitting devices using the compound represented by Chemical Formula 1 of the present invention and the compound of Chemical Formula 2 or 3 as light-emitting layer materials, have lower driving voltages and significantly improved luminous efficiency and lifespans compared to Comparative Examples 15 to 20, which are organic light-emitting devices using the comparative compound of A, C or I and the compound of Chemical Formula 2 or 3 of the present invention as light-emitting layer materials.

[0469] This result is due to exciplex, which occurs when two compounds are included simultaneously.

[0470] The above exciplex phenomenon is a phenomenon in which energy of the size of the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) is released through electron exchange between two molecules. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as hosts for the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host, so the driving voltage can be lowered, which can help improve the lifespan.

[0471] Specifically, the donor role is performed by the compound of the above chemical formula A or B, and the acceptor role is performed by the heterocyclic compound of the above chemical formula 1, whereas in Comparative Examples 15 to 20, although the donor is the same, the acceptor uses a compound that exhibits poor device characteristics as a light-emitting layer host as reviewed in Table 9, so it can be confirmed that a significant difference in device characteristics appears between the example group and the comparative example group.

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X1 and X2 are the same or different, and are each independently O or S, N-Het is a substituted or unsubstituted C2 to C60 heteroaryl group containing at least one N, Ar1 is a substituted or unsubstituted carbazole group, R1 to R4 are the same or different and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, r1 and r2 are each an integer from 0 to 3, and when r1 is 2 or more, R1 is equal to or different from each other, and when r2 is 2 or more, R2 is equal to or different from each other, r3 is an integer from 0 to 4, and when r3 is 2 or greater, R3 are equal to or different from each other, r4 is an integer from 0 to 2, and when r4 is 2, R4 are equal to or different from each other.

2. In claim 1, the chemical formula 1 is a heterocyclic compound represented by the following chemical formula 1-1 or chemical formula 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In Chemical Formula 1-1 and Chemical Formula 1-2, The substituent definitions of X1, X2, N-Het, R1 to R4 and r1 to r4 are the same as those in the above chemical formula 1, Ar2 is a substituted or unsubstituted C6 to C60 aryl group, R5 and R6 are the same as or different from each other, and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, r5 is an integer from 0 to 8, and when r5 is 2 or greater, R5 are equal to or different from each other, r6 is an integer from 0 to 7, and when r6 is 2 or greater, R6 are equal to or different from each other.

3. In claim 1, The above N-Het is a heterocyclic compound represented by the following structural formula 1: [Structural formula 1] In the above structural formula 1, means a part that connects to another structure, Y1 to Y5 are the same or different and are each independently CRa or N, but at least one is N, The above Ra is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent Ra groups are bonded to each other to form a ring.

4. In claim 3, A heterocyclic compound wherein the above Ra is a substituted or unsubstituted C6 to C20 aryl group.

5. In claim 1, A heterocyclic compound wherein the above Ar1 is a carbazole group substituted or unsubstituted with deuterium or an aryl group having C6 to C20 substituted or unsubstituted with deuterium.

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

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

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

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

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

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

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

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

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

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