KR102734915B1 - Heterocyclic compound, organic light-emitting device comprising same, composition for organic material layer of organic light-emitting device comprising same and manufacturing method for organic light-emitting device - Google Patents

Abstract

The present specification provides a heterocyclic compound, an organic light-emitting device comprising the same, a composition for an organic layer of an organic light-emitting device, and a method for producing an organic light-emitting device.

Description

Heterocyclic compound, organic light-emitting device comprising the same, composition for organic material layer of organic light-emitting device, and manufacturing method for organic light-emitting device {HETEROCYCLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME, COMPOSITION FOR ORGANIC MATERIAL LAYER OF ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME AND MANUFACTURING METHOD FOR ORGANIC LIGHT-EMITTING DEVICE}

The present invention relates to a heterocyclic compound, an organic light-emitting device comprising the same, a composition for an organic layer of an organic light-emitting device, and a method for manufacturing an organic light-emitting device.

Organic electroluminescent devices are a type of self-luminous display device that have the advantages of a wide viewing angle, excellent contrast, and fast response speed.

The organic light-emitting device has a structure in which an organic thin film is placed 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.

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

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

U.S. Patent No. 4,356,429

The present invention provides a heterocyclic compound, an organic light-emitting device comprising the same, a composition for an organic layer of an organic light-emitting device, and a method for manufacturing an organic light-emitting device.

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

[Chemical Formula 1]

In the above chemical formula 1,

L1 and L2 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and m1 and m2 are integers of 0 to 3, and when m1 is 2 or more, L1 in the parentheses are the same or different from each other, and when m2 is 2 or more, L2 in the parentheses are the same or different from each other,

R1 to R3 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

a is an integer from 0 to 3, b and c are each an integer from 0 to 4, and when a is 2 or greater, R1 within the parentheses are identical or different from each other, when b is 2 or greater, R2 within the parentheses are identical or different from each other, when c is 2 or greater, R3 within the parentheses are identical or different from each other,

A1 and A2 are the same or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a group represented by the following chemical formula A,

[Chemical Formula A]

In the above chemical formula A,

Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

is a position that binds to L1 or L2 of the above chemical formula 1,

At least one of the above A1 and A2 is a group represented by the above chemical formula A.

In addition, in one embodiment of the present application, an organic light-emitting device is provided, which includes a first electrode; a second 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 a heterocyclic compound represented by the chemical formula 1.

In addition, one embodiment of the present application provides a composition for an organic layer of an organic light-emitting device including a heterocyclic compound represented by the chemical formula 1.

Finally, one embodiment of the present application provides a method for manufacturing an organic light-emitting device, 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 the present application.

The heterocyclic compound according to one embodiment of the present application can be used as an organic layer material of an organic light-emitting device. The heterocyclic compound can be used as a material of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. in an organic light-emitting device. In particular, the heterocyclic compound represented by the chemical formula 1 can be used as a material of an electron transport layer or a charge generation layer of an organic light-emitting device.

Specifically, when the heterocyclic compound represented by the above chemical formula 1 is used in an organic light-emitting device, the driving voltage of the device can be lowered, the light efficiency can be improved, and the life characteristics of the device can be improved due to the thermal stability of the compound.

Figures 1 to 4 are drawings schematically showing a laminated structure of an organic light-emitting device according to one embodiment of the present application, respectively.

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

In this specification, when a part is said to "include" a component, this does not mean that other components are excluded, but rather that other components may be included, unless otherwise specifically stated.

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

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

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 substituted, i.e., a position where a substituent can be substituted, and when two or more are substituted, the two or more substituents may be the same or different from each other.

In this specification, "substituted or unsubstituted" means deuterium; a halogen group; -CN; a C1 to C60 alkyl group; a C2 to C60 alkenyl group; a C2 to C60 alkynyl group; a C1 to C60 haloalkyl group; a C1 to C60 alkoxy group; a C6 to C60 aryloxy group; a C1 to C60 alkylthioxy group; a C6 to C60 arylthioxy group; a C1 to C60 alkylsulfoxy group; a C6 to C60 arylsulfoxy group; a C3 to C60 cycloalkyl group; a C2 to C60 heterocycloalkyl group; a C6 to C60 aryl group; a C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'; or a substituent in which two or more substituents are linked to each other, 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.

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, since deuterium ( ² H, Deuterium) is an isotope of hydrogen, some of the hydrogen atoms may be deuterium.

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

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.

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

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

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

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%. That is, the content of deuterium of 20% in the phenyl group can be expressed by the structural formula below.

In addition, 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 a deuterium atom, i.e., has 5 hydrogen atoms.

In this specification, halogen can be fluorine, chlorine, bromine or iodine.

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 a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, an n-heptyl group, a 1-methylhexyl group, an octyl group, an n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, a n-nonyl group, a 2,2-dimethylheptyl group, Examples thereof include, but are not limited to, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

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.

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.

In this specification, a haloalkyl group means an alkyl group substituted with a halogen group, and specific examples include, but are not limited to, -CF ₃ , -CF ₂ CF ₃ .

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

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.

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

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

In this specification, an alkylsulfoxy group is represented as -S(=0) ₂ (R105), and R105 can be applied as an example of the above-mentioned alkyl group.

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

In the present specification, a cycloalkyl group includes a monocyclic or polycyclic ring 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, and more specifically 5 to 20. Specifically, examples thereof include, 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, and a cyclooctyl group.

In the present specification, a heterocycloalkyl group includes O, S, 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, 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, and more specifically 3 to 20.

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.

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

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

When the above fluorenyl group is substituted, , , , , , This may include, but is not limited to, the following.

In the present specification, a heteroaryl group includes S, O, Se, N or Si as a heteroatom, a monocyclic ring 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, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40, and more specifically 3 to 25. 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, a 2,3-dihydrobenzo[b]thiophene group, a 2,3-dihydrobenzofuran group, a 5,10-dihydrodibenzo[b,e][1,4]azacillin group, a pyrazolo[1,5-c]quinazoline group, a pyrido[1,2-b]indazole group, a pyrido[1,2-a]imidazo[1,2-e]indolin group, and a 5,11-dihydroindeno[1,2-b]carbazole group.

In this specification, when the substituent is a carbazole group, it means bonding with the nitrogen or carbon of the carbazole.

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

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

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

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

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

In the present specification, a silyl group is a substituent that contains Si and in which the Si atom is directly connected 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 be a substituent independently 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. Specific examples of the silyl group include (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), but is not limited thereto.

In the present specification, a phosphine oxide group is represented by -P(=O)(R110)(R111), wherein R110 and R111 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. Specifically, it may be substituted with an alkyl group or an aryl group, and the alkyl group and aryl group may be applied with the examples described above. For example, the phosphine oxide group may include, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like.

In the present specification, an amine group is represented by -N(R112)(R113), wherein R112 and R113 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. The amine group may be selected from the group consisting of -NH ₂ ; 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, a biphenyltriphenylenylamine group, and the like.

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.

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

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 stereostructurally closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

The hydrocarbon rings and heterocycles that adjacent groups can form include an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aliphatic heterocycle, and an aromatic heterocycle, and the structures exemplified by the above-mentioned cycloalkyl group, aryl group, heterocycloalkyl group, and heteroaryl group can be applied to each of the rings, except that they are not monovalent groups.

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

The heterocyclic compound represented by the above chemical formula 1 is a compound containing a phosphine oxide group and a phenanthroline group, and can efficiently transfer electrons due to stable bonding with metals used in the cathode. Through this, when the heterocyclic compound represented by the above chemical formula 1 is used in an organic light-emitting device, it is possible to manufacture an organic light-emitting device with excellent operation, efficiency, and lifespan.

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.

In one embodiment of the present application, the deuterium content of the heterocyclic compound represented by the chemical formula 1 may be 0% to 100%.

In one embodiment of the present application, the deuterium content of the heterocyclic compound represented by the chemical formula 1 may be 10% to 100%.

In one embodiment of the present application, the deuterium content of the heterocyclic compound represented by the chemical formula 1 may be 20% to 100%.

In general, compounds bonded with hydrogen and compounds substituted with deuterium show differences in thermodynamic behavior. This is because the mass of a deuterium atom is twice that of hydrogen, and because of the difference in atomic mass, deuterium has the characteristic of having lower vibrational energy. In addition, the bond length between carbon and deuterium is shorter than that of the bond with hydrogen, and the dissociation energy used to break the bond is also stronger. This is because the van der Waals radius of deuterium is smaller than that of hydrogen, so the elongation amplitude of the bond between carbon and deuterium is narrower.

Among the heterocyclic compounds represented by the chemical formula 1 of the present invention, a compound substituted with deuterium has a characteristic of lowering the energy of the ground state compared to a hydrogen-substituted compound, and as the bond length between carbon and deuterium becomes shorter, the molecular hardcore volume decreases. This can reduce the electrical polarizability and make the intermolecular interaction weaker, thereby increasing the volume of the device thin film. This characteristic induces the effect of lowering the crystallinity by creating an amorphous state of the thin film. Therefore, among the heterocyclic compounds represented by the chemical formula 1, a compound substituted with deuterium can be effective in improving the heat resistance of an OLED (Organic Light Emitting Diodes) device, and thus the lifespan and operating characteristics can be improved.

In this specification, the 'OLED device' may be expressed by terms such as 'organic light emitting diode', 'OLED (Organic Light Emitting Diodes)', 'organic light emitting device', and 'organic electroluminescent device'.

In one embodiment of the present application, L1 and L2 of the chemical formula 1 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and m1 and m2 are integers of 0 to 3, and when m1 is 2 or more, L1 in the parentheses may be the same as or different from each other, and when m2 is 2 or more, L2 in the parentheses may be the same as or different from each other.

In one embodiment of the present application, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

In one embodiment of the present application, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

In one embodiment of the present application, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

In one embodiment of the present application, L1 and L2 are the same as or different from each other, and can each independently be a direct bond; a phenylene group; or a biphenylene group.

In one embodiment of the present application, L1 is a direct bond.

In one embodiment of the present application, L1 is a phenylene group unsubstituted or substituted with one or more deuterium atoms.

In one embodiment of the present application, L1 is a biphenylene group unsubstituted or substituted with one or more deuterium atoms.

In one embodiment of the present application, L2 is a direct bond.

In one embodiment of the present application, L2 is a phenylene group unsubstituted or substituted with one or more deuterium atoms.

In one embodiment of the present application, L2 is a biphenylene group unsubstituted or substituted with one or more deuterium atoms.

In one embodiment of the present application, the m1 is 0. In one embodiment of the present application, the m1 is 1. In one embodiment of the present application, the m1 is 2. In one embodiment of the present application, the m1 is 3. In addition, when the m1 is 2 or more, the L1 in the parentheses are the same as or different from each other.

In one embodiment of the present application, the m2 is 0. In one embodiment of the present application, the m2 is 1. In one embodiment of the present application, the m2 is 2. In one embodiment of the present application, the m2 is 3. In addition, when the m2 is 2 or more, L2 in the parentheses are the same as or different from each other.

In one embodiment of the present application, R1 to R3 of the chemical formula 1 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and a is an integer from 0 to 3, b and c are each an integer from 0 to 4, and when a is 2 or more, R1 in the parentheses may be the same as or different from each other, when b is 2 or more, R2 in the parentheses may be the same as or different from each other, and when c is 2 or more, R3 in the parentheses may be the same as or different from each other.

In one embodiment of the present application, R1 to R3 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In one embodiment of the present application, R1 to R3 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

In one embodiment of the present application, R1 to R3 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

In one embodiment of the present application, R1 to R3 are the same as or different from each other, and may each independently be hydrogen or deuterium.

In one embodiment of the present application, a is 0. In one embodiment of the present application, a is 1. In one embodiment of the present application, a is 2. In one embodiment of the present application, a is 3. When a is 2 or more, R1 in the parentheses are the same as or different from each other.

In one embodiment of the present application, b is 0. In one embodiment of the present application, b is 1. In one embodiment of the present application, b is 2. In one embodiment of the present application, b is 3. In one embodiment of the present application, b is 4. When b is 2 or more, R2 in parentheses are the same as or different from each other.

In one embodiment of the present application, c is 0. In one embodiment of the present application, c is 1. In one embodiment of the present application, c is 2. In one embodiment of the present application, c is 3. In one embodiment of the present application, c is 4. When c is 2 or more, R3 in the parentheses are the same as or different from each other.

In one embodiment of the present application, A1 and A2 are the same as or different from each other, and each independently represent a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a group represented by the following chemical formula A, and at least one of A1 and A2 may be a group represented by the following chemical formula A.

[Chemical Formula A]

In the above chemical formula A,

Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

is a position that binds to L1 or L2 of the above chemical formula 1.

In one embodiment of the present application, A1 and A2 are the same as or different from each other, and each independently represent a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or a group represented by the chemical formula A, and at least one of A1 and A2 may be a group represented by the chemical formula A.

In one embodiment of the present application, A1 and A2 are the same as or different from each other, and each independently represent a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or a group represented by the chemical formula A, and at least one of A1 and A2 may be a group represented by the chemical formula A.

In one embodiment of the present application, A1 and A2 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; or a group represented by the chemical formula A, and at least one of A1 and A2 may be a group represented by the chemical formula A.

In one embodiment of the present application, A1 and A2 may be the same as or different from each other, and may each independently be a group represented by the following chemical formula B; or a group represented by the above chemical formula A.

[Chemical Formula B]

In the above chemical formula B,

R4 and R5 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

d is an integer from 0 to 2, e is an integer from 0 to 5, and when d is 2, R4 within the parentheses are identical or different from each other, and when e is 2 or greater, R5 within the parentheses are identical or different from each other,

is a position that binds to L1 or L2 of the above chemical formula 1.

In this case, at least one of A1 and A2 may be a group represented by the chemical formula A.

In one embodiment of the present application, Ar1 and Ar2 of the chemical formula A may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In one embodiment of the present application, Ar1 and Ar2 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.

In one embodiment of the present application, Ar1 and Ar2 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.

In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and can each independently be a substituted or unsubstituted phenyl group; or a substituted or unsubstituted pyridine group.

In one embodiment of the present application, Ar1 and Ar2 may be the same as or different from each other, and may each independently be a phenyl group substituted or unsubstituted with one or more deuterium atoms; or a pyridine group substituted or unsubstituted with one or more deuterium atoms.

In one embodiment of the present application, Ar1 and Ar2 are identical to each other.

In one embodiment of the present application, R4 and R5 of the chemical formula B are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and d is an integer from 0 to 2, e is an integer from 0 to 5, and when d is 2, R4 in the parentheses may be the same as or different from each other, and when e is 2 or more, R5 in the parentheses may be the same as or different from each other.

In one embodiment of the present application, R4 and R5 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

In one embodiment of the present application, R4 and R5 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

In one embodiment of the present application, R4 and R5 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted pyridine group.

In one embodiment of the present application, R4 and R5 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a phenyl group unsubstituted or substituted with one or more deuteriums; a naphthyl group unsubstituted or substituted with one or more deuteriums; or a pyridine group unsubstituted or substituted with one or more deuteriums.

In one embodiment of the present application, d is 0. In one embodiment of the present application, d is 1. In one embodiment of the present application, d is 2. When d is 2, R4 in the parentheses are the same as or different from each other.

In one embodiment of the present application, e is 0. In one embodiment of the present application, e is 1. In one embodiment of the present application, e is 2. In one embodiment of the present application, e is 3. In one embodiment of the present application, e is 4. In one embodiment of the present application, e is 5. When e is 2 or more, R5 in the parentheses are the same as or different from each other.

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

[Chemical Formula 1-1]

[Chemical Formula 1-2]

In the above chemical formulas 1-1 and 1-2,

The definitions of L1, L2, Ar1, Ar2, R1 to R3, m1, m2 and a to e are the same as those in the chemical formula 1 above,

R4 and R5 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

d is an integer from 0 to 2, e is an integer from 0 to 5, and when d is 2, R4 within the parentheses are the same or different, and when e is 2 or greater, R5 within the parentheses are the same or different.

In one embodiment of the present application, the chemical formula 1-1 can be represented by any one of the following chemical formulas 1-1-1 to 1-1-3.

[Chemical Formula 1-1-1]

[Chemical Formula 1-1-2]

[Chemical Formula 1-1-3]

In the chemical formulas 1-1-1 to 1-1-3 above,

The definitions of L1, L2, Ar1, Ar2, R1 to R5, m1, m2, and a to e are the same as those in the chemical formula 1-1.

In one embodiment of the present application, the chemical formula 1-2 can be represented by any one of the following chemical formulas 1-2-1 to 1-2-3.

[Chemical Formula 1-2-1]

[Chemical formula 1-2-2]

[Chemical formula 1-2-3]

In the chemical formulas 1-2-1 to 1-2-3 above,

The definitions of L1, L2, Ar1, Ar2, R1 to R5, m1, m2, and a to e are the same as those in the chemical formula 1-2.

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

In addition, by introducing various substituents into the structure of the above chemical formula 1, it is possible to synthesize a compound having the unique characteristics of the introduced substituent. For example, by introducing a substituent 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 above core structure, it is possible to synthesize a material that satisfies the conditions required in each organic layer.

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.

In one embodiment of the present application, an organic light-emitting device is provided, comprising: a first electrode; a second 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 a heterocyclic compound represented by the chemical formula 1.

In another embodiment, an organic light-emitting device is provided, wherein the organic layer includes an electron transport layer, and the electron transport layer includes a heterocyclic compound represented by the chemical formula 1.

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

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

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.

The stacking order of the electrodes and organic layers of the organic light-emitting device according to one embodiment of the present application is exemplified in FIGS. 1 to 3. However, the scope of the present application is not intended to be limited by these drawings, and the structure of the organic light-emitting device known in the art can also be applied to the present application.

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, it 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 in FIG. 2, may be implemented.

Fig. 3 is an example of a case where the organic layer is multilayer. The organic light-emitting element according to Fig. 3 includes a hole injection layer (301), a hole transport layer (302), a light-emitting layer (303), a hole blocking layer (304), an electron transport layer (305), and an electron injection layer (306). However, the scope of the present application is not limited by such a laminated structure, and, if necessary, the remaining layers except for the light-emitting layer may be omitted, and other necessary functional layers may be further added.

In addition, an organic light-emitting device according to one embodiment of the present application includes: a first electrode; a first stack provided on the first electrode and including a first light-emitting layer; a charge generation layer provided on the first stack; a second stack provided on the charge generation layer and including a second light-emitting layer; and a second electrode provided on the second stack.

At this time, the charge generation layer may include a heterocyclic compound represented by the chemical formula 1. When the heterocyclic compound is used in the charge generation layer, the operation, efficiency, and lifespan of the organic light-emitting device may be improved.

In one embodiment of the present application, the charge generation layer may be an N-type charge generation layer.

When the heterocyclic compound represented by the above chemical formula 1 is used as an N-type charge generation layer, a gap state is formed in the N-type charge generation layer, and electrons generated from the P-type charge generation layer are injected into the electron transport layer through the gap state generated in the N-type charge generation layer. Therefore, a stable gap state is formed through the stable bonding of the material and the metal, and the electron transfer efficiency from the P-type charge generation layer to the N-type charge generation layer is increased. This has the effect of lowering the operating voltage of the organic light-emitting device and improving the efficiency and lifespan of the device.

In addition, the first stack and the second stack may each independently additionally include one or more of the aforementioned hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer, etc.

As an organic light-emitting device according to one embodiment of the present application, an organic light-emitting device having a 2-stack tandem structure is exemplarily shown in FIG. 4 below.

At this time, the first electron blocking layer, the first hole blocking layer, and the second hole blocking layer described in FIG. 4 below may be omitted depending on the case.

In one embodiment of the present application, a composition for an organic layer of an organic light-emitting device comprising a heterocyclic compound represented by the chemical formula 1 is provided.

The above composition can be used when forming an organic layer of an organic light-emitting device, and can be particularly preferably used as a material for an electron transport layer or a charge generation layer.

The above composition is in the form of a simple mixture of two or more compounds, and powder-state materials may be mixed before forming an organic layer of an organic light-emitting device, or compounds that are in a liquid state at an appropriate temperature or higher may be mixed. The above composition is in a solid state below the melting point of each material, and can be maintained in a liquid state by adjusting the temperature.

The above composition may additionally contain materials known in the art, such as solvents and additives.

In one embodiment of the present application, a method for manufacturing an organic light-emitting device is provided, comprising: a step of preparing a substrate; a step of forming a first electrode on the substrate; a step of forming one or more organic layers on the first electrode; and a step of forming a second electrode on the organic layer, wherein the step of forming the organic layer includes a step of forming one or more organic layers using an organic layer composition according to one embodiment of the present application.

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 forming a heterocyclic compound represented by the chemical formula 1 using a thermal vacuum deposition method.

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 compound described above.

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.

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.

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.

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.

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 spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

The organic layer of the organic light-emitting device of the present invention may be formed as a single-layer structure, but may be formed as a multilayer 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.

In one embodiment of the present application, the organic layer may include an iridium-based dopant.

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

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

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 above-described heterocyclic compound.

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, etc. 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 SnO ₂ :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

Materials having 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 LiO ₂ /Al.

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-type 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.

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.

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.

LiF is typically used as an electron injection material in the art, but the present application is not limited thereto.

As the light-emitting material, a red, green or blue light-emitting material can be used, and if necessary, two or more light-emitting materials can be mixed and used. At this time, two or more light-emitting materials can be deposited and used as individual sources, or can be premixed and deposited and used as one source. In addition, a fluorescent material can be used as the light-emitting material, but it can also be used as a phosphorescent material. As the light-emitting material, a material that emits light by combining holes and electrons injected from the anode and cathode respectively can be used alone, but materials in which the host material and the dopant material participate in light emission together can also be used.

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

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

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., by a similar principle to that applied to organic light-emitting devices.

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.

<Example>

[Manufacturing Example 1] Manufacturing of compound 1

1) Preparation of compound 1-1

In a reaction flask, compound 3-bromo-[1,1'-biphenyl]-2-amine (A) (40 g, 0.161 mol, 1 eq), dichloromethane (DCM) (510 ml), and triethylamine (Et ₃ N) (16.3 g, 0.161 mol, 1 eq) were added and cooled to 0°C with stirring. Then, 2-chlorobenzoyl chloride (B) (31.0 g 0.177 mol, 1.1 eq) diluted in DCM (90 ml) was slowly added and stirred at room temperature for 1 hour (h). After quenching the reaction by adding water, extraction was performed using DCM and water. Then, moisture was removed with MgSO ₄ . Compound 1-1 (50.6 g) was obtained with a yield of 81% by separation using a silica gel column.

2) Preparation of compound 1-2

Compound 1-1 (50 g, 0.129 mol, 1 eq), nitrobenzene (500 ml), triphenylphosphine (33.0 g, 0.126 mol, 2.0 eq), and phosphoryl chloride (29.0 g, 0.189 mol, 1.5 eq) were added to a reaction flask and stirred at 150°C for 3 hours (h). After the reaction was completed, the mixture was cooled to room temperature and NaHCO ₃ aqueous solution was added to adjust the pH to 7. The formed crystals were filtered and washed with purified water. The filtered crystals were then slurried under DCM/acetone conditions, filtered, washed with acetone, and dried to obtain compound 1-2, 37.6 g, in a yield of 79%.

3) Preparation of compounds 1-3

A reaction flask was charged with compound 1-2 (35 g, 0.095 mol, 1 eq), diphenylphosphine oxide (C) (21.2 g, 0.105 mol, 1.1 eq), Pd(PPh ₃ ) ₄ (5.8 g, 0.005 mol, 0.05 eq), Et ₃ N (19.2 g, 0.190 mol, 2.0 eq), and toluene (350 ml) and stirred at 110°C for 3 hours (h). After quenching the reaction by adding water, extraction was performed using DCM and water. Thereafter, moisture was removed with MgSO ₄ . After separation using a silica gel column, compound 1-3, 25.0 g, was obtained in a yield of 54%.

4) Preparation of compounds 1-4

In a reaction flask, compounds 1-3 (25 g, 0.051 mol, 1 eq), B ₂ pin ₂ (19.6 g, 0.077 mol, 1.5 eq), Pd(dba) ₂ (2.9 g, 0.005 mol, 0.1 eq), XPhos (4.8 g, 0.010 mol, 0.2 eq), and KOAc (15.0 g, 0.153 mol, 3.0 eq) were added to 1,4-dioxane (250 ml), and stirred under reflux for 3 h. After the reaction was completed, the mixture was cooled to room temperature, the solvent was removed, and then slurry was prepared under DCM/isopropylether conditions. After filtration and washing with isopropyl ether and water, the residue was dried to obtain 27 g of compound 1-4 in a yield of 94%.

5) Preparation of compound 1

Compounds 1-4 (10 g, 0.017 mol, 1 eq), 2-bromo-1,10-phenanthroline (D) (4.4 g, 0.017 mol, 1.0 eq), Pd(PPh ₃ ) ₄ (1.2 g, 0.001 mol, 0.05 eq), K ₃ PO ₄ (7.9 g, 0.037 mol, 2.2 eq), 1,4-dioxane (120 ml), and water (30 ml) were added to a reaction flask and stirred under reflux for 3 h. After the reaction was completed, the mixture was cooled to room temperature and water was added to crystallize. The mixture was filtered and washed with methanol and water. Afterwards, silica gel filtration was performed to obtain compound 1, 8.2 g with a yield of 79%.

Except that Intermediate A of Table 1 below was used instead of 3-bromo-[1,1'-biphenyl]-2-amine (A) in Manufacturing Example 1, Intermediate B of Table 1 below was used instead of 2-chlorobenzoyl chloride (B), Intermediate C of Table 1 below was used instead of diphenylphosphine oxide (C), and Intermediate D of Table 1 below was used instead of 2-bromo-1,10-phenanthroline (D), the compound of Table 1 below was synthesized in the same manner as Manufacturing Example 1.

[Manufacturing Example 2] Preparation of compound 92

1) Preparation of compound 92-1

Compound 92-1 was synthesized in the same manner as in the preparation of compound 1-1 of Preparation Example 1, except that 4-chlorobenzoyl chloride was used instead of 2-chlorobenzoyl chloride (B) in the preparation of compound 1-1 of Preparation Example 1.

2) Preparation of compound 92-2

Compound 92-2 was synthesized in the same manner as in the preparation of compound 1-2 of Manufacturing Example 1, except that compound 92-1 was used instead of compound 1-1 in the preparation of compound 1-2 of Manufacturing Example 1.

3) Preparation of compound 92-3

Compound 92-2 (20 g, 0.054 mol, 1 eq), diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide (C) (21.8 g, 0.054 mol, 1.0 eq), Pd(PPh ₃ ) ₄ (3.5 g, 0.003 mol, 0.05 eq), K ₃ PO ₄ (25.3 g, 0.119 mol, 2.2 eq), 1,4-dioxane (240 ml) and water (60 ml) were added to a reaction flask and stirred under reflux. Stirred for 3 hours (h). After adding water to stop the reaction, extraction was performed using DCM and water. After that, moisture was removed with MgSO ₄ . After separation with a silica gel column, 25.5 g of compound 92-3 was obtained with a yield of 83%.

4) Preparation of compound 92-4

Compound 92-4 was synthesized in the same manner as in the preparation of compound 1-4 of Manufacturing Example 1, except that compound 92-3 was used instead of compound 1-3 in the preparation of compound 1-4 of Manufacturing Example 1.

5) Preparation of compound 92

Compound 92 was synthesized in the same manner as in the preparation of compound 1 in Preparation Example 1, except that compound 92-4 was used instead of compound 1-4 in the preparation of compound 1 in Preparation Example 1.

Except that in the above Preparation Example 2, Intermediate A of Table 2 below was used instead of 3-bromo-[1,1'-biphenyl]-2-amine (A), Intermediate B of Table 2 below was used instead of 2-chlorobenzoyl chloride (B), Intermediate C of Table 2 below was used instead of diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide (C), and Intermediate D of Table 2 below was used instead of 2-bromo-1,10-phenanthroline (D). The compounds in Table 2 below were synthesized using the same method as Manufacturing Example 2.

[Manufacturing Example 3] Preparation of compound 145

1) Preparation of compound 145-1

Compound 145-1 was synthesized in the same manner as in the preparation of compound 1-1 of Preparation Example 1, except that 4-chloro-[1,1'-biphenyl]-2-amine was used instead of 3-bromo-[1,1'-biphenyl]-2-amine (A), and 2-bromobenzoyl chloride was used instead of 2-chlorobenzoyl chloride (B).

2) Preparation of compound 145-2

Compound 145-2 was synthesized in the same manner as in the preparation of compound 1-2 of Manufacturing Example 1, except that compound 145-1 was used instead of compound 1-1 in the preparation of compound 1-2 of Manufacturing Example 1.

3) Preparation of compound 145-3

Compound 145-3 was synthesized in the same manner as in the preparation of compound 1-3 of Manufacturing Example 1, except that compound 145-2 was used instead of compound 1-1 in the preparation of compound 1-3 of Manufacturing Example 1.

4) Preparation of compound 145-4

Compound 145-4 was synthesized in the same manner as in the preparation of compound 1-4 of Preparation Example 1, except that compound 145-3 was used instead of compound 1-3 in the preparation of compound 1-4 of Preparation Example 1.

5) Preparation of compound 145

Compound 145 was synthesized in the same manner as in the preparation of compound 1 of Preparation Example 1, except that compound 145-4 was used instead of compound 1-4, and 2-bromo-9-phenyl-1,10-phenanthroline was used instead of 2-bromo-1,10-phenanthroline (D).

Except that intermediate A of Table 3 was used instead of 4-chloro-[1,1'-biphenyl]-2-amine (A) in Manufacturing Example 3, intermediate B of Table 3 was used instead of 2-bromobenzoyl chloride (B), intermediate C of Table 3 was used instead of diphenylphosphine oxide (C), and intermediate D of Table 3 was used instead of 2-bromo-9-phenyl-1,10-phenanthroline (D), the compound of Table 3 was synthesized in the same manner as Manufacturing Example 3.

Compounds were manufactured using the same method as the above manufacturing examples, and the results of their synthesis are shown in Table 4 and Table 4. Table 4 shows the measured values of ¹ H NMR (CDCl ₃ , 200 MHz), and Table 5 shows the measured values of FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[Experimental example]

<Experimental Example 1>

1) Fabrication of organic light-emitting devices

An indium tin oxide (ITO) thin film as a transparent electrode obtained from glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned sequentially using trichloroethylene, acetone, ethanol, and distilled water for 5 minutes each, and then stored in isopropanol before use. Next, the ITO substrate was installed in the substrate folder of the vacuum deposition equipment, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was placed in the cell in the vacuum deposition equipment.

Subsequently, the chamber was evacuated until the vacuum level inside the chamber reached 10 ^-6 torr, and then current was applied to the cell to evaporate 2-TNATA and deposit a hole injection layer with a thickness of 600 Å on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell inside the vacuum deposition equipment, and current was applied to the cell to evaporate it and deposit a hole transport layer with a thickness of 300 Å on the hole injection layer.

After forming the hole injection layer and the hole transport layer in this manner, a blue emitting material having the following structure was deposited as an emitting layer thereon. Specifically, a blue emitting host material, H1, was vacuum-deposited to a thickness of 200Å in one cell within a vacuum deposition device, and a blue emitting dopant material, D1, was vacuum-deposited thereon at a thickness of 5% relative to the host material.

Next, a compound of the following structural formula E1 was deposited as an electron transport layer with a thickness of 300 Å.

OLED devices were fabricated by depositing lithium fluoride (LiF) as an electron injection layer with a thickness of 10Å and using an Al cathode with a thickness of 1,000Å. Meanwhile, all organic compounds necessary for OLED device fabrication were purified by vacuum sublimation under 10 ^{-8 torr} to 10 ^-6 torr for each material and used in OLED fabrication.

Organic electroluminescent devices (Examples 1 to 36 and Comparative Examples 2 to 4) were manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 6 below were used instead of E1 used in forming the electron transport layer in Comparative Example 1.

2) Driving voltage and luminous efficiency of organic electroluminescent devices

The electroluminescence (EL) characteristics of the organic electroluminescent devices of Examples 1 to 36 and Comparative Examples 1 to 4 manufactured as described above were measured using M7000 of Maxscience, and the T ₉₅ was measured using the lifespan measuring equipment (M6000) manufactured by Maxscience when the standard luminance was 3,500 cd/m ² based on the measurement results. The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan (T ₉₅ , unit: h) of the blue organic electroluminescent devices manufactured according to the present invention were as shown in Table 6.

compound Driving voltage
(V) Luminous Efficiency
(cd/A) CIE
(x, y) life
(T ₉₅ ) Example 1 1 5.13 6.83 (0.134, 0.100) 83 Example 2 2 5.20 6.83 (0.133, 0.100) 88 Example 3 18 5.21 6.80 (0.133, 0.102) 89 Example 4 24 5.18 6.80 (0.133, 0.100) 85 Example 5 35 5.20 6.79 (0.133, 0.101) 88 Example 6 50 5.21 6.79 (0.133, 0.101) 87 Example 7 64 5.15 6.78 (0.134, 0.101) 84 Example 8 68 5.28 6.90 (0.133, 0.101) 86 Example 9 78 5.30 6.85 (0.133, 0.102) 86 Example 10 92 5.24 6.93 (0.132, 0.100) 88 Example 11 93 5.20 6.95 (0.133, 0.101) 89 Example 12 100 5.22 6.81 (0.134, 0.100) 90 Example 13 101 5.34 6.88 (0.133, 0.100) 88 Example 14 113 5.32 6.80 (0.134, 0.101) 87 Example 15 127 5.32 6.81 (0.133, 0.100) 85 Example 16 133 5.28 6.82 (0.132, 0.100) 83 Example 17 135 5.18 6.85 (0.133, 0.101) 88 Example 18 145 5.25 6.88 (0.133, 0.100) 84 Example 19 160 5.23 6.82 (0.134, 0.101) 84 Example 20 171 5.25 6.82 (0.132, 0.100) 85 Example 21 186 5.22 6.89 (0.133, 0.103) 87 Example 22 188 5.29 6.84 (0.133, 0.102) 85 Example 23 189 5.29 6.81 (0.134, 0.101) 84 Example 24 197 5.25 6.88 (0.134, 0.102) 88 Example 25 200 5.25 6.90 (0.133, 0.102) 83 Example 26 219 5.19 6.81 (0.133, 0.102) 87 Example 27 227 5.20 6.83 (0.133, 0.102) 85 Example 28 233 5.18 6.86 (0.133, 0.100) 87 Example 29 238 5.30 6.80 (0.133, 0.102) 88 Example 30 248 5.30 6.83 (0.133, 0.102) 85 Example 31 255 5.31 6.81 (0.133, 0.101) 88 Example 32 257 5.29 6.75 (0.134, 0.100) 83 Example 33 265 5.13 6.78 (0.134, 0.101) 91 Example 34 268 5.15 6.86 (0.133, 0.101) 90 Example 35 270 5.19 6.83 (0.133, 0.101) 99 Example 36 272 5.25 6.84 (0.134, 0.100) 98 Comparative Example 1 E1 5.88 6.15 (0.134, 0.100) 35 Comparative Example 2 Comparative compound A 5.75 6.23 (0.133, 0.102) 56 Comparative Example 3 Comparative compound B 5.78 6.28 (0.132, 0.100) 58 Comparative Example 4 Comparative compound C 5.68 6.327 (0.134, 0.101) 58

Comparative compounds A to C used in Table 6 above were as follows.

As can be seen from the results in Table 6 above, it was confirmed that the organic light-emitting devices of Examples 1 to 36 using the heterocyclic compound according to the present application as an electron transport layer material of a blue organic light-emitting device had lower driving voltage and significantly improved luminous efficiency and lifespan compared to Comparative Examples 1 to 4.

The reason for these results is believed to be that when the heterocyclic compound according to the present application is used as a material for an organic layer of an organic light-emitting device, particularly an electron transport layer, the phosphine oxide functional group and phenanthroline functional group of the heterocyclic compound according to the present application can efficiently transfer electrons due to stable bonding with metals used in the cathode.

That is, when the heterocyclic compound according to the present application is used as a material for an electron transport layer of an organic light-emitting device, the electron transport characteristics and stability within the device are improved, thereby demonstrating excellence in all aspects of the device's operation, efficiency, and lifespan.

<Experimental Example 2> Fabrication of Organic Light-Emitting Devices

1) Fabrication of organic light-emitting devices

A glass substrate coated with a thin film of ITO with a thickness of 1500Å was ultrasonically washed in distilled water. After washing with distilled water, it was ultrasonically washed with a solvent such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes using UV in a UV cleaner. After that, the substrate was transferred to a plasma cleaner (PT), and 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.

On the above ITO transparent electrode (anode), an organic material was formed in a 2-stack WOLED (White Organic Light Device) structure. For the first stack, TAPC was first thermally vacuum deposited to a thickness of 300Å to form a hole transport layer. After the hole transport layer was formed, an emitting layer was thermally vacuum deposited thereon as follows. The emitting layer was deposited to 300Å by doping 8% of FIrpic as a blue phosphorescent dopant into TCz1 as a host. The electron transport layer was formed to 400Å using TmPyPB, and then the charge generation layer was formed to 100Å by doping 20% of Cs ₂ CO ₃ in the compound described in Table 6 below.

The second stack was first formed by thermal vacuum depositing MoO ₃ to a thickness of 50 Å to form a hole injection layer. The common layer, the hole transport layer, was formed by doping TAPC with 20% MoO ₃ to 100 Å, and then depositing TAPC to 300 Å. On top of that, the emitting layer was formed by doping TCz1, the host, with 8% green phosphorescent topant Ir(ppy) ₃ to 300 Å, and then using TmPyPB as the electron transport layer to form 600 Å. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing organic electroluminescent devices (Examples 37 to 72 and Comparative Examples 5 to 8).

Meanwhile, all organic compounds required for OLED device production were purified by vacuum sublimation under 10 ^-8 to 10 ^-6 torr for each material and used in OLED production.

2) Driving voltage and luminous efficiency of organic electroluminescent devices

The electroluminescence (EL) characteristics of the organic electroluminescent devices manufactured as described above in Examples 37 to 72 and Comparative Examples 5 to 8 were measured using M7000 from Maxscience, and the T ₉₅ was measured using the life measurement equipment (M6000) manufactured by Maxscience with the measurement results when the reference luminance was 3,500 cd/m ² .

The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan (T ₉₅ , unit: h) of the white organic electroluminescent device manufactured according to the present invention were as shown in Table 7 below.

compound Driving voltage
(V) Luminous Efficiency
(cd/A) CIE
(x, y) life
(T ₉₅ ) Example 37 1 7.13 65.45 (0.210, 0.430) 87 Example 38 2 7.15 68.76 (0.211, 0.428) 82 Example 39 18 7.23 68.90 (0.213, 0.425) 88 Example 40 24 7.18 69.05 (0.212, 0.425) 87 Example 41 35 7.20 70.33 (0.212, 0.425) 85 Example 42 50 7.20 70.03 (0.213, 0.425) 85 Example 43 64 7.25 69.13 (0.208, 0.430) 84 Example 44 78 7.20 69.82 (0.213, 0.425) 85 Example 45 68 7.18 68.88 (0.208, 0.430) 88 Example 46 92 7.19 69.85 (0.213, 0.430) 85 Example 47 93 7.20 70.05 (0.214, 0.430) 89 Example 48 100 7.14 69.53 (0.210, 0.430) 90 Example 49 101 7.15 69.03 (0.211, 0.429) 89 Example 50 113 7.23 69.55 (0.212, 0.429) 85 Example 51 127 7.15 69.00 (0.213, 0.425) 88 Example 52 133 7.22 68.77 (0.212, 0.430) 85 Example 53 135 7.18 66.47 (0.215, 0.425) 82 Example 54 145 7.20 67.75 (0.212, 0.423) 83 Example 55 160 7.19 67.83 (0.213, 0.425) 83 Example 56 171 7.20 67.77 (0.212, 0.425) 82 Example 57 186 7.18 67.53 (0.218, 0.428) 85 Example 58 188 7.15 67.72 (0.209, 0.429) 87 Example 59 189 7.19 69.58 (0.213, 0.428) 88 Example 60 197 7.23 69.23 (0.212, 0.430) 88 Example 61 200 7.20 70.13 (0.213, 0.425) 84 Example 62 219 7.18 68.93 (0.212, 0.425) 83 Example 63 227 7.20 69.05 (0.212, 0.425) 83 Example 64 233 7.17 68.66 (0.214, 0.425) 84 Example 65 238 7.18 69.83 (0.214, 0.428) 84 Example 66 248 7.18 69.90 (0.213, 0.425) 83 Example 67 255 7.20 68.84 (0.218, 0.427) 85 Example 68 257 7.22 67.32 (0.210, 0.425) 90 Example 69 265 7.20 70.32 (0.213, 0.429) 98 Example 70 268 7.24 70.13 (0.210, 0.429) 101 Example 71 270 7.19 69.87 (0.214, 0.430) 96 Example 72 272 7.18 69.67 (0.213, 0.425) 98 Comparative Example 5 TmPyPB 8.20 47.71 (0.210, 0.430) 46 Comparative Example 6 Comparative compound A 7.85 54.22 (0.213, 0.430) 57 Comparative Example 7 Comparative compound B 7.84 58.47 (0.209, 0.428) 53 Comparative Example 8 Comparative compound C 7.88 58.62 (0.210, 0.428) 56

Comparative compounds A to C used in Table 7 above are identical to the compounds used in Experimental Example 1.

As can be seen from the results in Table 7 above, it was confirmed that the organic electroluminescent devices of Examples 37 to 72 using the heterocyclic compound according to the present application as a charge generation layer material of a 2-stack white organic electroluminescent device had lower driving voltage and improved lifespan and luminous efficiency compared to Comparative Examples 5 to 8.

The reason for these results is believed to be that when the heterocyclic compound according to the present application of the material is used as a material for an organic layer of an organic light-emitting device, among which, a charge generating layer, the phosphine oxide functional group and phenanthroline functional group of the heterocyclic compound according to the present application enable stable bonding with metals used as electrodes.

More specifically, when the heterocyclic compound according to the present application is used as an N-type charge generation layer, a stable gap state is formed within the N-type charge generation layer. This is thought to be because electrons generated from the P-type charge generation layer are injected into the electron transport layer through the gap state generated within the N-type charge generation layer.

When the gap state is stably formed within the charge generation layer in this way, electron transfer occurs efficiently from the P-type charge generation layer to the N-type charge generation layer.

That is, when the heterocyclic compound according to the present application is used as an N-type charge generation layer, the driving voltage of the organic light-emitting device is lowered and the efficiency and lifespan are improved.

100: Substrate
200: Bipolar
300: Organic layer
301: Hole injection layer
302: Hole transport layer
303: Emitting layer
304: The static low layer
305: Electron transport layer
306: Electron injection layer
400: Negative

Claims (15)

A heterocyclic compound represented by the following chemical formula 1:
[Chemical Formula 1]

In the above chemical formula 1,
L1 and L2 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted C6 to C60 arylene group, m1 and m2 are integers of 0 to 3, and when m1 is 2 or more, L1 in the parentheses are the same or different from each other, and when m2 is 2 or more, L2 in the parentheses are the same or different from each other,
R1 to R3 are the same or different from each other, and are each independently hydrogen; or deuterium,
a is an integer from 0 to 3, b and c are each an integer from 0 to 4, and when a is 2 or greater, R1 within the parentheses are identical or different from each other, when b is 2 or greater, R2 within the parentheses are identical or different from each other, when c is 2 or greater, R3 within the parentheses are identical or different from each other,
One of A1 and A2 is a group represented by the following chemical formula A, and the other of A1 and A2 is a group represented by the following chemical formula B,
[Chemical Formula A]

In the above chemical formula A,
Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
is a position that binds to L1 or L2 of the above chemical formula 1,
[Chemical Formula B]

In the above chemical formula B,
R4 and R5 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
d is an integer from 0 to 2, e is an integer from 0 to 5, and when d is 2, R4 within the parentheses are identical or different from each other, and when e is 2 or greater, R5 within the parentheses are identical or different from each other,
is a position that binds to L1 or L2 of the above chemical formula 1. delete 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 the above chemical formulas 1-1 and 1-2,
The definitions of L1, L2, Ar1, Ar2, R1 to R3, m1, m2 and a to e are the same as those in the chemical formula 1 above,
R4 and R5 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,
d is an integer from 0 to 2, e is an integer from 0 to 5, and when d is 2, R4 within the parentheses are the same or different, and when e is 2 or greater, R5 within the parentheses are the same or different. In claim 3, the chemical formula 1-1 is a heterocyclic compound represented by any one of the following chemical formulas 1-1-1 to 1-1-3:
[Chemical Formula 1-1-1]

[Chemical Formula 1-1-2]

[Chemical Formula 1-1-3]

In the chemical formulas 1-1-1 to 1-1-3 above,
The definitions of L1, L2, Ar1, Ar2, R1 to R5, m1, m2, and a to e are the same as those in the chemical formula 1-1. In claim 3, the chemical formula 1-2 is a heterocyclic compound represented by any one of the following chemical formulas 1-2-1 to 1-2-3:
[Chemical Formula 1-2-1]

[Chemical formula 1-2-2]

[Chemical formula 1-2-3]

In the chemical formulas 1-2-1 to 1-2-3 above,
The definitions of L1, L2, Ar1, Ar2, R1 to R5, m1, m2, and a to e are the same as those in the chemical formula 1-2. In claim 1, a heterocyclic compound represented by the chemical formula 1 has a deuterium content of 0% to 100%. In claim 1, the chemical formula 1 is a heterocyclic compound represented by any one of the following compounds:













An organic light-emitting device comprising a first electrode; a second electrode, and at least one organic layer 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 and 3 to 7. An organic light-emitting device according to claim 8, wherein the organic layer includes an electron transport layer, and the electron transport layer includes the heterocyclic compound. An organic light-emitting device according to claim 8, wherein the organic light-emitting device further comprises one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer. In claim 8, the organic light-emitting device comprises: a first electrode; a first stack provided on the first electrode and including a first light-emitting layer; a charge generation layer provided on the first stack; a second stack provided on the charge generation layer and including a second light-emitting layer; and a second electrode provided on the second stack. An organic light-emitting device according to claim 11, wherein the charge generation layer comprises the heterocyclic compound. An organic light-emitting device according to claim 12, wherein the charge generation layer is an N-type charge generation layer. A composition for an organic layer of an organic light-emitting device comprising a heterocyclic compound according to any one of claims 1 and 3 to 7. Steps to prepare the substrate;
A step of forming a first electrode on the above substrate;
A step of forming one or more organic layers on the first electrode; and
Comprising a step of forming a second electrode on the organic layer,
A method for manufacturing an organic light-emitting device, wherein the step of forming the organic layer includes the step of forming one or more organic layers using the composition for an organic layer according to claim 14.