Organic light-emitting device, its manufacturing method, and composition for organic layer

Abstract

The present specification relates to an organic light-emitting device containing a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2, a method for producing the same, and a composition for an organic layer, which can reduce the driving voltage of the device, improve the light efficiency, and particularly improve the life characteristics of the device due to the thermal stability of the compound.

Description

[Technical field]

[0001] The present specification relates to an organic light-emitting device, a method for producing the same, and a composition for an organic layer.

[0002] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0028918, filed with the Korean Intellectual Property Office on March 7, 2022, the entire contents of which are incorporated herein by reference. [Background technology]

[0003] An organic electroluminescent device is a type of self-luminous display device, and has the advantages of a wide viewing angle, excellent contrast, and fast response speed.

[0004] An organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light emitting device having such a 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 configured as a single layer or multiple layers as necessary.

[0005] The material of the organic thin film may have a light-emitting function as necessary. For example, the material of the organic thin film may be a compound that can form a light-emitting layer by itself, 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 inject holes, transport holes, block electrons, transport electrons, inject electrons, etc.

[0006] There is a continuing need to develop materials for organic thin films to improve the performance, lifetime, or efficiency of organic light-emitting devices.

[0007] There is a need for research into organic light-emitting devices that contain compounds having chemical structures that can satisfy the requirements for materials that can be used in organic light-emitting devices, such as suitable energy levels, electrochemical stability, and thermal stability, and that can perform the various roles required of organic light-emitting devices depending on the substituents. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] U.S. Patent No. 4,356,429 Summary of the Invention [Problem to be solved by the invention]

[0009] An object of the present invention is to provide an organic light-emitting device, a method for producing the same, and a composition for an organic layer. [Means for solving the problem]

[0010] The present invention provides an organic light-emitting device including a first electrode, a second electrode, and one or more organic layers provided between the first electrode and the second electrode, the organic layer including a heterocyclic compound represented by the following chemical formula 1 and a heterocyclic compound represented by the following chemical formula 2:

[0011] [ka] [ka] In the above Chemical Formula 1 and Chemical Formula 2, X is O; or S; One of R1 to R6 is [ka] and the remaining one is [ka] and the remaining groups are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'; [ka] are the positions at which they are bonded to R1 to R6, L1 to L6 are the same or different 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; a, b, m, n, m1, and m2 are each an integer of 0 to 3; and when a, b, m, n, m1, and m2 are each 2 or more, the substituents in the parentheses are the same or different, N-Het1 and N-Het2 are each independently a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N; Ar1 is a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; Y is O; or S; Ar2 and Ar3 are the same or different, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or -NRR'; Adjacent substituents of L3, L5, L6, Ar2, and Ar3 may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic or aromatic heterocycle; Rr, Rp, and Rq are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR', where r is an integer of 0 to 4, p and q are each an integer of 0 to 3, and when r, p, and q are each 2 or more, the substituents in the parentheses are the same or different, The R, R', and R'' are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0012] In addition, another embodiment of the present application provides a composition for an organic layer of an organic light-emitting device, comprising: a heterocyclic compound represented by Chemical Formula 1; and a heterocyclic compound represented by Chemical Formula 2.

[0013] 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 material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers comprises forming one or more organic material layers using a composition for an organic material layer according to one embodiment of the present application. Effect of the Invention

[0014] The compounds described herein can be used as materials for the organic layers of organic light-emitting devices. The compounds can act as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, etc. in the organic light-emitting devices. In particular, the compounds can be used as light-emitting materials for the organic light-emitting devices.

[0015] In addition, the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 can be simultaneously used as materials for the light-emitting layer of an organic light-emitting device. In this case, the driving voltage of the device can be reduced, the light efficiency can be improved, and the life characteristics of the device can be particularly improved due to the thermal stability of the compound. [Brief description of the drawings]

[0016] [Figure 1] 1 is a diagram illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Diagram 2] 1 is a diagram illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Diagram 3] 1 is a diagram illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Figure 4] 1 is a diagram illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Explanation of symbols]

[0017] 100 ···Substrate 200...Anode 300...organic layer 301 Hole injection layer 302 Hole transport layer 303 Light-emitting layer 304 Hole blocking layer 305...electron transport layer 306...electron injection layer 400...Cathode DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0018] The present application will be described in detail below.

[0019] The present invention provides an organic light-emitting device including a first electrode, a second electrode, and one or more organic layers provided between the first electrode and the second electrode, the organic layer including a heterocyclic compound represented by the following chemical formula 1 and a heterocyclic compound represented by the following chemical formula 2:

[0020] [ka] [ka] In the above Chemical Formula 1 and Chemical Formula 2, X is O; or S; One of R1 to R6 is [ka] and the remaining one is [ka] and the remaining groups are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'; [ka] are the positions at which they are bonded to R1 to R6, L1 to L6 are the same or different 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; a, b, m, n, m1, and m2 are each an integer of 0 to 3; and when a, b, m, n, m1, and m2 are each 2 or more, the substituents in the parentheses are the same or different, N-Het1 and N-Het2 are each independently a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N; Ar1 is a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; Y is O; or S; Ar2 and Ar3 are the same or different, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or -NRR'; Adjacent substituents of L3, L5, L6, Ar2, and Ar3 may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic or aromatic heterocycle; Rr, Rp, and Rq are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR', where r is an integer of 0 to 4, p and q are each an integer of 0 to 3, and when r, p, and q are each 2 or more, the substituents in the parentheses are the same or different, The R, R', and R'' are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0021] The heterocyclic compound of the present invention represented by Formula 1 has excellent electron transporting ability, high thermal stability, and suitable molecular weight and band gap, which provides good hole transporting ability, prevents electron loss, and allows for the formation of an effective recombination zone.

[0022] In addition, the heterocyclic compound represented by Formula 2 of the present invention has excellent hole mobility, reduces current leakage due to electron block, and facilitates electron confinement.

[0023] Therefore, when the organic material layer of the organic light emitting device contains the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, the efficiency and life of the device can be improved. In particular, when the organic material layer is a light emitting layer, the efficiency and life of the device can be further improved.

[0024] In this specification, when a part "comprises" a certain component, it does not mean excluding other components, but means that the part may further include other components, unless otherwise specified.

[0025] In this specification, the chemical formula [ka] means the binding position.

[0026] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0027] In this specification, the term "substituted or unsubstituted" means deuterium; a halogen group; -CN; an alkyl group having 1 to 60 carbon atoms; an alkenyl group having 2 to 60 carbon atoms; an alkynyl group having 2 to 60 carbon atoms; a haloalkyl group having 1 to 60 carbon atoms; an alkoxy group having 1 to 60 carbon atoms; an aryloxy group having 6 to 60 carbon atoms; an alkylthio group having 1 to 60 carbon atoms; an arylthio group having 1 to 60 carbon atoms; an alkylsulfoxy group having 1 to 60 carbon atoms; an arylsulfoxy group having 6 to 60 carbon atoms; a cycloalkyl group having 3 to 60 carbon atoms; a heterocycloalkyl group having 2 to 60 carbon atoms; a heterocycloalkyl group having 2 to 60 carbon atoms; a aryloxy group having 6 to 60 carbon atoms; an alkylsulfoxy group having 1 to 60 carbon atoms; a heterocycloalkyl group having 2 ... "R" means that the alkyl group is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group; a C2-C60 heteroaryl group; -SiRR'R'', -P(=O)RR'; and -NRR', or with a substituent in which two or more substituents selected from the above-listed substituents are linked, and R, R', and R'' are each independently at least one substituent selected from the group consisting 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.

[0028] As used herein, "Cn" means that the number of carbon atoms is n. For example, C6 means that the number of carbon atoms is 6, and C60 means that the number of carbon atoms is 60.

[0029] In this specification, when "no substituent is shown in the chemical formula or compound structure," it means that a hydrogen atom is bonded to the carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0030] In one embodiment of the present application, "when no substituent is shown in the chemical formula or compound structure", it may mean that all positions available as a substituent are hydrogen or deuterium. That is, in the case of deuterium, which is an isotope of hydrogen, some hydrogen atoms may be deuterium, which is an isotope of hydrogen, and in this case, the content of deuterium may be 0% to 100%.

[0031] In one embodiment of the present application, in the case where "substituents are not shown in the chemical formula or compound structure", when deuterium is not explicitly excluded, such as when the deuterium content is 0%, the hydrogen content is 100%, or all substituents are hydrogen, hydrogen and deuterium may be used together in the compound.

[0032] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, and is an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, and may be represented as hydrogen-2, and the atomic symbol is D or 2 It may also be written as H.

[0033] In one embodiment of the present application, isotopes, meaning atoms with the same atomic number (Z) but different mass numbers (A), can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0034] In one embodiment of the present application, the content T% of a specific substituent can be defined as T2 / T1×100=T%, where T1 is the total number of substituents that the base compound may have and T2 is the number of specific substituents among the total number of substituents.

[0035] That is, in one example, [ka] In a phenyl group represented by the formula, the deuterium content is 20% when the total number of substituents that the phenyl group may have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula). In other words, a phenyl group with a deuterium content of 20% may be represented by the following structural formula.

[0036] [ka] In addition, in one embodiment of the present application, a "phenyl group having a deuterium content of 0%" may mean a phenyl group that does not contain a deuterium atom, that is, a phenyl group that has five hydrogen atoms.

[0037] As used herein, halogen may be fluorine, chlorine, bromine, or iodine.

[0038] In this specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. 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, and a 3,3-dimethylbutyl group. , 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

[0039] In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include 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, but are not limited thereto.

[0040] In this specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically 2 to 20.

[0041] In the present specification, a haloalkyl group means an alkyl group substituted with a halogen group, and a specific example is -CF 3 , -CF 2 CF 3 These include, but are not limited to:

[0042] In this specification, the alkoxy group is represented by -O(R101), and R101 may be any of the alkyl groups exemplified above.

[0043] In this specification, the aryloxy group is represented by -O(R102), and R102 may be any of the examples of the aryl group mentioned above.

[0044] In this specification, an alkylthio group is represented by -S(R103), and R103 may be any of the alkyl groups exemplified above.

[0045] In this specification, an arylthioxy group is represented by -S(R104), and R104 may be any of the examples of aryl groups mentioned above.

[0046] As used herein, an alkylsulfoxy group is defined as -S(=O) 2 (R105), where R105 may be any of the alkyl groups exemplified above.

[0047] As used herein, an arylsulfoxy group is defined as -S(=O) 2 (R106), where R106 may be any of the examples of the aryl group mentioned above.

[0048] In the present specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic group means a group in which the cycloalkyl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but may also be other types of cyclic groups, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of the cycloalkyl group 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.

[0049] In the present specification, the heterocycloalkyl group includes O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic group means a group in which the heterocycloalkyl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be other types of cyclic groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.

[0050] In this specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, which may be further substituted with other substituents. Here, the polycyclic ring means a group in which the aryl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be an aryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The aryl group includes a spiro group. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the 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.

[0051] As used herein, the terphenyl group may be selected from the following structures:

[0052] [ka] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0053] When the fluorenyl group is substituted, it may have the following structural formula, but is not limited to these:

[0054] [ka]

[0055] In the present specification, the heteroaryl group includes S, O, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring means a group in which the heteroaryl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a heteroaryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25.Specific examples of the 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 dioxine 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, a benzoxazole group, a benzimidazole group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a benzocarbazole group, a 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, phenothiazine group, phthalazine group, phenanthroline group, naphthobenzofuran group, naphthobenzo Examples of such groups include, but are not limited to, a thiophene group, a benzo[c][1,2,5]thiadiazole group, a 2,3-dihydrobenzo[b]thiophene group, a 2,3-dihydrobenzofuran group, a 5,10-dihydrodibenzo[b,e][1,4]azasiline group, a pyrazolo[1,5-c]quinazoline group, a pyrido[1,2-b]indazole group, a pyrido[1,2-a]imidazo[1,2-e]indoline group, and a 5,11-dihydroindeno[1,2-b]carbazole group.

[0056] In this specification, when a substituent is a carbazole group, it is meant to be bonded to the nitrogen or carbon of the carbazole.

[0057] As used herein, when the carbazole group is substituted, additional substituents may be substituted on the nitrogen or carbon of the carbazole.

[0058] As used herein, a benzocarbazole group may have any one of the following structures: [ka]

[0059] As used herein, a dibenzocarbazole group may have any one of the following structures: [ka]

[0060] As used herein, a naphthobenzofuran group may have any one of the following structures: [ka]

[0061] As used herein, a naphthobenzothiophene group may have any one of the following structures: [ka]

[0062] In this specification, a silyl group is a substituent that contains Si and is directly linked to the Si atom as a radical, and is represented by -Si(R107)(R108)(R109), where R107 to R109 may be the same or different and each independently represent 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.

[0063] Specific examples of the silyl group include: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] These include, but are not limited to:

[0064] In the present specification, the phosphine oxide group is represented by -P(=O)(R110)(R111), where R110 and R111 are the same or different and each may be independently a substituent consisting 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 above-mentioned examples of the alkyl group and the aryl group may be applied. For example, the phosphine oxide group may include, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, and a dinaphthylphosphine oxide group.

[0065] In the present specification, the amine group is represented by -N(R112)(R113), where R112 and R113 may be the same or different and each independently may be a substituent consisting 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 is represented by -NH 2 The amine group may be selected from the group consisting of 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 amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an 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, but are not limited thereto.

[0066] In this specification, the arylene group may be any of the examples of the aryl group described above, except that the arylene group is a divalent group.

[0067] In this specification, the heteroarylene group may be the same as the examples of the heteroaryl group described above, except that the heteroarylene group is a divalent group.

[0068] In this specification, the term "adjacent" groups may refer to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0069] The hydrocarbon ring and hetero ring which can form the adjacent group include an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aliphatic hetero ring, and an aromatic hetero ring, and the structures exemplified as the above-mentioned cycloalkyl group, aryl group, heterocycloalkyl group, and heteroaryl group, respectively, may be applied, except that the ring is not a monovalent group.

[0070] In one embodiment of the present application, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0% or more and 100% or less, preferably 20% or more and 100% or less, and more preferably 40% or more and 100% or less.

[0071] In particular, in the above Chemical Formula 1, any substituent not shown may be hydrogen or deuterium.

[0072] The heterocyclic compound represented by Chemical Formula 1 of the present invention has an easily adjustable band gap and T1 value, an improved hole transport ability, an easily adjustable decomposition temperature, excellent thermal stability, and high molecular stability, thereby reducing the driving voltage of a device and improving the light efficiency, and the thermal stability of the compound can improve the life characteristics of the device.

[0073] In one embodiment of the present application, X in the above formula 1 is O; or S.

[0074] In one embodiment of the present application, said X is O.

[0075] In one embodiment of the present application, said X is S.

[0076] In one embodiment of the present application, one of R1 to R6 in the above-mentioned Chemical Formula 1 is [ka] and the remaining one is [ka] and the remaining groups are the same or different and may each be independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C2-C60 alkenyl group; a substituted or unsubstituted C2-C60 alkynyl group; a substituted or unsubstituted C1-C60 alkoxy group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'.

[0077] In one embodiment of the present application, one of R1 to R6 is [ka] and the remaining one is [ka] and the remaining groups may be the same or different and each may be independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.

[0078] In another embodiment, one of R1 to R6 is [ka] and the remaining one is [ka] and the remaining groups may be the same or different and each independently selected from the group consisting of hydrogen; deuterium; a C1 to C60 alkyl group; a C6 to C60 aryl group; and a C2 to C60 heteroaryl group.

[0079] In another embodiment, one of R1 to R6 is [ka] and the remaining one is [ka] and the remaining groups may be the same or different and each independently selected from the group consisting of hydrogen; deuterium; a C1 to C40 alkyl group; a C6 to C40 aryl group; and a C2 to C40 heteroaryl group.

[0080] In yet another embodiment, one of R1 to R6 is [ka] and the remaining one is [ka] and the remaining groups may be the same or different and each independently selected from the group consisting of hydrogen; deuterium; a C1 to C30 alkyl group; a C6 to C30 aryl group; and a C2 to C30 heteroaryl group.

[0081] In yet another embodiment, one of R1 to R6 is [ka] and the remaining one is [ka] and the remaining remainders may be the same or different from one another and may each independently be hydrogen; or deuterium.

[0082] In one embodiment of the present application, R1 is [ka] wherein R2 is [ka] wherein R3 to R6 are the same or different and may each be independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy 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; and a substituted or unsubstituted C2 to C60 heteroaryl group.

[0083] In one embodiment of the present application, R1 is [ka] wherein R2 is [ka] wherein R3 to R6 may be the same or different and each independently represent hydrogen or deuterium.

[0084] In one embodiment of the present application, R1 is [ka] wherein R3 is [ka] wherein R2 and R4 to R6 are the same or different and may each be independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy 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; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'.

[0085] In one embodiment of the present application, R1 is [ka] wherein R3 is [ka] wherein R2 and R4 to R6 may be the same or different, and each independently may be hydrogen or deuterium.

[0086] In one embodiment of the present application, R1 is [ka] wherein R4 is [ka] wherein R2, R3, R5, and R6 are the same or different and may each be independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'.

[0087] In one embodiment of the present application, R1 is [ka] wherein R4 is [ka] wherein R2, R3, R5, and R6 are the same or different from each other, and each independently, R2 and R4 to R6 are the same or different from each other, and each independently, R2, R3, R5, and R6 are the same or different from each other, and each independently, R2, R4, R5, R6, and R6 may be hydrogen or deuterium.

[0088] In one embodiment of the present application, R1 is [ka] wherein R5 is [ka] wherein R2 to R4 and R6 are the same or different and may each be independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy 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; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'.

[0089] In one embodiment of the present application, R1 is [ka] wherein R5 is [ka] wherein R2 to R4 and R6 may be the same or different and each independently may be hydrogen or deuterium.

[0090] In one embodiment of the present application, R1 is [ka] wherein R6 is [ka] wherein R2 to R5 are the same or different and may each be independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy 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; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'.

[0091] In one embodiment of the present application, R1 is [ka] wherein R6 is [ka] wherein R2 to R5 may be the same or different and each independently may be hydrogen or deuterium.

[0092] In one embodiment of the present application, R1 is [ka] wherein R2 is [ka] wherein R3 to R6 are the same or different and may each be independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy 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; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'.

[0093] In one embodiment of the present application, R1 is [ka] wherein R2 is [ka] wherein R3 to R6 may be the same or different and each independently represent hydrogen or deuterium.

[0094] In one embodiment of the present application, R1 is [ka] wherein R3 is [ka] wherein R2 and R4 to R6 are the same or different and may each be independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy 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; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'.

[0095] In one embodiment of the present application, R1 is [ka] wherein R3 is [ka] wherein R2 and R4 to R6 may be the same or different, and each independently may be hydrogen or deuterium.

[0096] In one embodiment of the present application, R1 is [ka] wherein R4 is [ka] wherein R2, R3, R5, and R6 are the same or different and may each be independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'.

[0097] In one embodiment of the present application, R1 is [ka] wherein R4 is [ka] wherein R2, R3, R5, and R6 are the same or different and may each independently be hydrogen or deuterium.

[0098] In one embodiment of the present application, R1 is [ka] wherein R5 is [ka] wherein R2 to R4 and R6 are the same or different and may each be independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy 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; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'.

[0099] In one embodiment of the present application, R1 is [ka] wherein R5 is [ka] wherein R2 to R4 and R6 may be the same or different and each independently may be hydrogen or deuterium.

[0100] In one embodiment of the present application, R1 is [ka] wherein R6 is [ka] wherein R2 to R5 are the same or different and may each be independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy 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; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'.

[0101] In one embodiment of the present application, R1 is [ka] wherein R6 is [ka] wherein R2 to R5 may be the same or different and each independently may be hydrogen or deuterium.

[0102] In one embodiment of the present application, L1 and L2 in the above Chemical Formula 1 may be the same or different, and each may independently be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0103] In another embodiment, L1 and L2 are the same or different 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.

[0104] In still another embodiment, L1 and L2 may be the same or different and each independently represent a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0105] In still another embodiment, L1 and L2 may be the same or different and each independently represent a direct bond; or a substituted or unsubstituted C6 to C40 monocyclic or polycyclic arylene group.

[0106] In yet another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted C6 to C10 monocyclic arylene group; or a substituted or unsubstituted C10 to C40 polycyclic arylene group.

[0107] In yet another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted anthracenylene group.

[0108] The phenylene group, biphenylene group, naphthylene group, and anthracenylene group are divalent groups of a phenyl group, a biphenyl group, a naphthyl group, and an anthracenyl group, respectively.

[0109] In one embodiment of the present application, said L1 and L2 may be deuterium substituted or unsubstituted.

[0110] In one embodiment of the present application, the deuterium content of L1 and L2 may be 0% or more and 100% or less, preferably 20% or more and 100% or less, and more preferably 40% or more and 100% or less.

[0111] In one embodiment of the present application, the a and b are each an integer of 0 to 3, and when a and b are each 2 or more, the substituents in the parentheses are the same or different.

[0112] In one embodiment of the present application, a is 0. a is 1. a is 2. a is 3. When a is 2 or more, L1 in the parentheses are the same or different.

[0113] In one embodiment of the present application, the b is 0. The b is 1. The b is 2. The b is 3. When the b is 2 or more, the L2 in the parentheses are the same or different.

[0114] In one embodiment of the present application, Ar1 may be a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0115] In one embodiment of the present application, Ar1 may be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0116] In one embodiment of the present application, Ar1 may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0117] In another embodiment, Ar1 may be a C6-C40 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a C6-C40 aryl group, and a C2-C40 heteroaryl group; or a C2-C40 heteroaryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a C6-C40 aryl group, and a C2-C40 heteroaryl group.

[0118] In yet another embodiment, Ar1 may be a C6 to C40 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group; or a C2 to C40 heteroaryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group.

[0119] In yet another embodiment, Ar1 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluoranthenyl group; a substituted or unsubstituted chrysenyl group; a substituted or unsubstituted dimethylfluorenyl group; a substituted or unsubstituted benzo[e]acephenanthrylene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted fluoranthenyl group fused with a substituted or unsubstituted benzene ring; a substituted or unsubstituted dibenzofuran group fused with a substituted or unsubstituted benzene ring; a substituted or unsubstituted dibenzothiophene group fused with a substituted or unsubstituted benzene ring; or a substituted or unsubstituted dimethylfluorenyl group fused with a substituted or unsubstituted benzene ring.

[0120] In yet another embodiment, the Ar1 are the same or different and each independently represent a phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group; a biphenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group; a terphenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group; a substituted or unsubstituted naphthyl group; a triphenylenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group; a phenanthrenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group; a fluoranthenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group; a chrysenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group; deuterium. a dimethylfluorenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, cyano, and halogen groups; a benzo[e]acephenanthrylene group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, cyano, and halogen groups; a dibenzofuran group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, cyano, and halogen groups; a dibenzothiophene group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, cyano, and halogen groups; a carbazole group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group; a fluoranthenyl group having a fused benzene ring substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group; a dibenzofuran group having a fused benzene ring substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group; a dibenzothiophene group having a fused benzene ring substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group;Or it may be a dimethylfluorenyl group condensed with a benzene ring substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a cyano group, and a halogen group.

[0121] In one embodiment of the present application, the deuterium content of Ar1 may be 0% or more and 100% or less, preferably 20% or more and 100% or less, and more preferably 40% or more and 100% or less.

[0122] In one embodiment of the present application, the N-Het1 is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N atoms.

[0123] In one embodiment of the present application, said N-Het1 is substituted or unsubstituted, and the monocyclic or polycyclic heterocyclic group containing one or more N may contain 1 to 3 N.

[0124] In one embodiment of the present application, L3 and L4 in the above Chemical Formula 2 may be the same or different, and each independently may be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0125] In another embodiment, L3 and L4 are the same or different 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.

[0126] In still another embodiment, L3 and L4 are the same or different 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.

[0127] In yet another embodiment, L3 and L4 are the same or different and may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted furanylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted anthracenylene group.

[0128] The phenylene group, furanylene group, naphthylene group, and anthracenylene group are divalent groups of a phenyl group, a furan group, a naphthyl group, and an anthracenyl group, respectively.

[0129] In one embodiment of the present application, said L3 and L4 may be deuterium substituted or unsubstituted.

[0130] In one embodiment of the present application, the deuterium content of L3 and L4 may be 0% or more and 100% or less, preferably 20% or more and 100% or less, and more preferably 40% or more and 100% or less.

[0131] In one embodiment of the present application, the above m and n are each an integer of 0 to 3, and when m and n are each 2 or more, the substituents in the parentheses are the same or different.

[0132] In one embodiment of the present application, m is 0. m is 1. m is 2. m is 3. When m is 2 or more, L3 in parentheses are the same or different.

[0133] In one embodiment of the present application, the n is 0. The n is 1. The n is 2. The n is 3. When the n is 2 or more, L4 in the parentheses are the same or different.

[0134] In one embodiment of the present application, the N-Het2 is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N atoms.

[0135] In one embodiment of the present application, said N-Het2 is substituted or unsubstituted, and the monocyclic or polycyclic heterocyclic group containing one or more N may contain 1 to 3 N.

[0136] In one embodiment of the present application, N-Het1 and N-Het2 may each independently be represented by the following chemical formula 3:

[0137] [ka] In the above Chemical Formula 3, X1 is CR101 or N, X2 is CR102 or N, X3 is CR103 or N, X4 is CR104 or N, X5 is CR105 or N, and at least one of X1 to X5 is N; R101 to R105 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy 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; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heterocycle, wherein [ka] is a moiety that is linked to Chemical Formula 1 or 2.

[0138] In one embodiment of the present application, the above-mentioned Chemical Formula 3 may be represented by any one of the following Chemical Formulas 4 to 8.

[0139] [ka] [ka] [ka] [ka] [ka] In Chemical Formula 4, one or more of X1, X3, and X5 is N, and the rest are the same as defined in Chemical Formula 3; In Chemical Formula 5, one or more of X1, X2, and X5 is N, and the rest are the same as defined in Chemical Formula 3; In Chemical Formula 6, at least one of X1 to X3 is N, and the rest are the same as defined in Chemical Formula 3; In Chemical Formula 7, one or more of X1, X4, and X5 is N, and the rest are the same as defined in Chemical Formula 3; In Chemical Formula 8, at least one of X1 to X3 is N, and the rest are the same as defined in Chemical Formula 3; Y1 and Y2 are each independently O; or S; R102, R104, and R203 to R206 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C20 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; substituted or unsubstituted phosphine oxide group; and substituted or unsubstituted amine group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heterocycle; [ka] The definition is the same as in Chemical Formula 3.

[0140] In one embodiment of the present application, the chemical formula 4 may be selected from any one of the structural formulas of Group A below.

[0141] [ka] The definition of the substituents in the structural formula of Group A is the same as that of Chemical Formula 4.

[0142] In one embodiment of the present application, the above-mentioned Chemical Formula 5 may be represented by the following Chemical Formula 5-1 or Chemical Formula 5-2.

[0143] [ka] [ka] The substituents in Chemical Formula 5-1 and Chemical Formula 5-2 are the same as those in Chemical Formula 5.

[0144] In one embodiment of the present application, the above-mentioned formula 6 may be represented by the following formula 6-1.

[0145] [ka] The substituents in the above Chemical Formula 6-1 are the same as those in the Chemical Formula 6.

[0146] In one embodiment of the present application, the above-mentioned formula 7 may be represented by the following formula 7-1:

[0147] [ka] The substituents in the above Chemical Formula 7-1 are the same as those in the Chemical Formula 7.

[0148] In one embodiment of the present application, the formula 8 may be represented by the following formula 8-1:

[0149] [ka] The substituents in the above Chemical Formula 8-1 are the same as those in the Chemical Formula 8.

[0150] In one embodiment of the present application, R101 to R105 and R203 to R206 may be the same or different and each independently represent hydrogen; deuterium; a halogen; 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.

[0151] In one embodiment of the present application, R101 to R105 and R203 to R206 may be the same or different, and each independently may be hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0152] In one embodiment of the present application, R101 to R105 and R203 to R206 may be the same or different, and each independently may be hydrogen; deuterium; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0153] In one embodiment of the present application, R101 to R105 and R203 to R206 may be the same or different, and each independently may be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0154] In one embodiment of the present application, L5 and L6 in the above Chemical Formula 2 may be the same or different, and each may independently be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0155] In another embodiment, L5 and L6 are the same or different 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.

[0156] In still another embodiment, L5 and L6 are the same or different 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.

[0157] In yet another embodiment, L5 and L6 are the same or different and may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted anthracenylene group; a substituted or unsubstituted carbazolene group; a substituted or unsubstituted fused carbazolene group; a substituted or unsubstituted furanylene group; or a substituted or unsubstituted thiophenylene group.

[0158] The phenylene group, biphenylene group, naphthylene group, anthracenylene group, carbazolene group, condensed carbazole group, furanylene group, and thiophenylene group are divalent groups of a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a carbazole group, a condensed carbazole group, a furan group, and a thiophene group, respectively.

[0159] In one embodiment of the present application, said L5 and L6 may be unsubstituted or substituted with deuterium.

[0160] In one embodiment of the present application, the deuterium content of L5 and L6 may be 0% or more and 100% or less, preferably 20% or more and 100% or less, and more preferably 40% or more and 100% or less.

[0161] In one embodiment of the present application, the m1 and m2 are each an integer of 0 to 3, and when m1 and m2 are each 2 or more, the substituents in the parentheses are the same or different.

[0162] In one embodiment of the present application, m1 is 0. m1 is 1. m1 is 2. m1 is 3. When m1 is 2 or more, L5 in the parentheses are the same or different.

[0163] In one embodiment of the present application, m2 is 0. m2 is 1. m2 is 2. m2 is 3. When m2 is 2 or more, L6 in parentheses are the same or different.

[0164] In one embodiment of the present application, Y in the above formula 2 is O; or S.

[0165] In one embodiment of the present application, said Y is O.

[0166] In one embodiment of the present application, said Y is S.

[0167] In one embodiment of the present application, Ar2 and Ar3 in the above Chemical Formula 2 are the same or different, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or -NRR'.

[0168] In one embodiment of the present application, Ar2 and Ar3 may be the same or different, and each independently may be a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or -NRR'.

[0169] In one embodiment of the present application, Ar2 and Ar3 may be the same or different, and each independently may be a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; or -NRR'.

[0170] In one embodiment of the present application, Ar2 and Ar3 are the same or different and each independently represent 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 phenanthrenyl group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted perylenyl group; a substituted or unsubstituted 4,5-diphenylbenzo[4,5]cyclohepta[1,2,3-de]naphthalenyl group; a substituted or unsubstituted dimethylfluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted diphenylfluorenyl group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted fused carbazole group; a substituted or unsubstituted fluoranthene group; a substituted or unsubstituted fused fluoranthene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted dibenzothiophene group; or -NRR'.

[0171] In one embodiment of the present application, adjacent substituents of L3, L5, L6, Ar2, and Ar3 may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic or aromatic heterocycle. The adjacent substituents of L3, L5, L6, Ar2, and Ar3 are bonded to each other, and include not only the case where Ar2 and Ar3 are bonded to each other, but also the case where L3, Ar2, and Ar3 are bonded to each other, the case where L5, L6, Ar2, and Ar3 are bonded to each other, and the case where L3, L5, and L6 are bonded to each other.

[0172] In one embodiment of the present application, Ar2 and Ar3 may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic or aromatic heterocycle.

[0173] In one embodiment of the present application, Ar2 and Ar3 are the same 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 -NRR', or Ar2 and Ar3 may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic or aromatic heterocycle.

[0174] In one embodiment of the present application, Ar2 and Ar3 are the same or different from each other, and each independently represent a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; or -NRR', or Ar2 and Ar3 may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic or aromatic heterocycle.

[0175] In one embodiment of the present application, Ar2, Ar3, and L3 may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic or aromatic heterocycle. In this case, L5 and L6 may be a direct bond. In the case where Ar2, Ar3, and L3 are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic or aromatic heterocycle, the following chemical formula A-9 may be mentioned as an example, but is not limited thereto.

[0176] In one embodiment of the present application, L5, L6, Ar2, and Ar3 may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic or aromatic heterocycle.

[0177] In one embodiment of the present application, L3, L5, and L6 may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic or aromatic heterocycle.

[0178] In one embodiment of the present application, R, R', and R'' are the same or different and may each independently be 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.

[0179] In another embodiment, the R, R', and R'' may be the same or different and each independently be a substituted or unsubstituted C6 to C60 aryl group.

[0180] In still another embodiment, the R, R', and R'' may be the same or different and each independently be a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group.

[0181] In still another embodiment, the R, R', and R'' may be the same or different and each independently be a substituted or unsubstituted C6 to C40 monocyclic aryl group.

[0182] In still another embodiment, the R, R', and R'' may be the same or different and each independently be a C6 to C20 monocyclic aryl group.

[0183] In yet another embodiment, R, R', and R'' may be phenyl groups.

[0184] In one embodiment of the present application, [ka] may be represented by any one of the following chemical formulas A-1 to A-12.

[0185] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] In the above Chemical Formulae A-1 to A-12, The definitions of L3 and m are the same as those in Chemical Formula 2. L'5 and L'6 are the same or different, and each independently represent a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; m'1 and m'2 are each independently an integer of 0 to 3, and when m'1 and m'2 are each 2 or greater, the substituents in the parentheses are the same or different, Ar'2 and Ar'3 are the same or different, and each independently represents NRR'; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; Z1 to Z3 are each independently O; S; CRaRb; or NRc; Y2 and Y3 are each independently O; or S; R, R', Ra, Rb, Rc, and Rd1 to Rd26 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; d1, d21, and d22 are each independently an integer of 0 to 8; d2, d4, d5, d9, and d26 are each independently an integer of 0 to 6; d3, d6, d8, d11, d12 to d14, d17, d18, d20, d23, and d24 are each independently an integer of 0 to 4; d7, d10, d19, and d25 are each independently an integer of 0 to 2; d15 is an integer from 0 to 5, d16 is an integer from 0 to 3, When d1 to d26 are each 2 or more, the substituents in the parentheses are the same or different.

[0186] In one embodiment of the present application, the definitions of the substituents of Ar2 and Ar3 may be applied to Ar'2 and Ar'3, except that in the definitions of the substituents of Ar2 and Ar3, Ar2 and Ar3 are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic or aromatic heterocycle.

[0187] In one embodiment of the present application, Rr, Rp, and Rq are the same or different and each independently represent hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy 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; a substituted or unsubstituted a C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR', where r is an integer of 0 to 4, p and q are each an integer of 0 to 3, and when r, p, and q are each 2 or more, the substituents in the parentheses are the same or different, and said R, R', and R'' are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0188] In one embodiment of the present application, Rr, Rp, and Rq are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0189] In one embodiment of the present application, Rr, Rp, and Rq are the same or different and each independently represent hydrogen; deuterium; halogen; or a cyano group.

[0190] In one embodiment of the present application, Rr, Rp, and Rq are the same or different and each independently is hydrogen; or deuterium.

[0191] In one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by the following Chemical Formula 1-1 or 1-2.

[0192] [ka] [ka] In the above Chemical Formula 1-1 and Chemical Formula 1-2, Rr1 and Rs are the same or different and each independently represents a hydrogen atom; a deuterium atom; a cyano group; a halogen group; or a substituted or unsubstituted C1 to C60 alkyl group; r1 is an integer of 0 to 5, and when r1 is 2 or more, Rr1 in the parentheses are the same or different, s is an integer of 0 to 3, and when s is 2 or more, Rs in the parentheses are the same or different, The definitions of X, L1, L2, Ar1, a, b, and N-Het1 are the same as those in Chemical Formula 1 above.

[0193] In one embodiment of the present application, the chemical formula 1-1 may be represented by any one of the following chemical formulas 1-1-1 to 1-1-4.

[0194] [ka] [ka] [ka] [ka] In the above Chemical Formulas 1-1-1 to 1-1-4, R11 to R15 are the same or different and each independently represents a hydrogen atom; a deuterium atom; a cyano group; a halogen group; or a substituted or unsubstituted C1 to C60 alkyl group. The definitions of X, Rs, L1, L2, Ar1, a, b, s, and N-Het1 are the same as those in Chemical Formula 1-1.

[0195] In one embodiment of the present application, the chemical formula 1-2 may be represented by any one of the following chemical formulas 1-2-1 to 1-2-4.

[0196] [ka] [ka] [ka] [ka] In the above Chemical Formulas 1-2-1 to 1-2-4, R11 to R15 are the same or different and each independently represents a hydrogen atom; a deuterium atom; a cyano group; a halogen group; or a substituted or unsubstituted C1 to C60 alkyl group. The definitions of X, Rs, L1, L2, Ar1, a, b, s, and N-Het1 are the same as those in Chemical Formula 1-2.

[0197] According to one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto: [ka] TIFF2025509247000119.tif215169 TIFF2025509247000120.tif213169 TIFF2025509247000121.tif217169 TIFF2025509247000122.tif225169 TIFF2025509247000123.tif202169 TIFF2025509247000124.tif202169 TIFF2025509247000125.tif201169 TIFF2025509247000126.tif205169 TIFF2025509247000127.tif202169 TIFF2025509247000128.tif198169 TIFF2025509247000129.tif210169 TIFF2025509247000130.tif214169 TIFF2025509247000131.tif216169 TIFF2025509247000132.tif218169 TIFF2025509247000133.tif205169 TIFF2025509247000134.tif213169 TIFF2025509247000135.tif221169 TIFF2025509247000136.tif230169 TIFF2025509247000137.tif227169 TIFF2025509247000138.tif196169 TIFF2025509247000139.tif212169 TIFF2025509247000140.tif192169 TIFF2025509247000141.tif186169 TIFF2025509247000142.tif193169 TIFF2025509247000143.tif204169 TIFF2025509247000144.tif225169 TIFF2025509247000145.tif229169 TIFF2025509247000146.tif230169 TIFF2025509247000147.tif217169 TIFF2025509247000148.tif201169 TIFF2025509247000149.tif204169 TIFF2025509247000150.tif217169 TIFF2025509247000151.tif217169 TIFF2025509247000152.tif213169 TIFF2025509247000153.tif198169 TIFF2025509247000154.tif224169 TIFF2025509247000155.tif218169 TIFF2025509247000156.tif225169 TIFF2025509247000157.tif221169 TIFF2025509247000158.tif212169 TIFF2025509247000159.tif217169 TIFF2025509247000160.tif214169 TIFF2025509247000161.tif217169 TIFF2025509247000162.tif213169 TIFF2025509247000163.tif209169 TIFF2025509247000164.tif224169 TIFF2025509247000165.tif197169 TIFF2025509247000166.tif192169 TIFF2025509247000167.tif225169 According to one embodiment of the present application, the formula 2 is represented by any one of the following compounds, but is not limited thereto: [Chemical] TIFF2025509247000169.tif192169 TIFF2025509247000170.tif213169 TIFF2025509247000171.tif208169 TIFF2025509247000172.tif220169 TIFF2025509247000173.tif198169 TIFF2025509247000174.tif209169 TIFF2025509247000175.tif193169 TIFF2025509247000176.tif196169 TIFF2025509247000177.tif209169 TIFF2025509247000178.tif214169 TIFF2025509247000179.tif225169 TIFF2025509247000180.tif202169 TIFF2025509247000181.tif214169 TIFF2025509247000182.tif225169 TIFF2025509247000183.tif218169 TIFF2025509247000184.tif233169 TIFF2025509247000185.tif218169 TIFF2025509247000186.tif216169 TIFF2025509247000187.tif222169 TIFF2025509247000188.tif198169 TIFF2025509247000189.tif198169 TIFF2025509247000190.tif201169 TIFF2025509247000191.tif214169 TIFF2025509247000192.tif225169 TIFF2025509247000193.tif216169 TIFF2025509247000194.tif213169 TIFF2025509247000195.tif214169 TIFF2025509247000196.tif213169 TIFF2025509247000197.tif214169

[0198] It is possible to synthesize compounds having the inherent properties of the introduced substituents by introducing various substituents into the structures of Chemical Formulae 1 and 2. For example, it is possible to synthesize materials that satisfy the requirements for each organic layer by introducing into the core structure substituents that are mainly used in hole injection layer materials, hole transport materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices.

[0199] In addition, by introducing various substituents into the structures of Chemical Formulas 1 and 2, the energy band gap can be finely adjusted, while the properties at the interface between organic materials can be improved, thereby diversifying the uses of the material.

[0200] On the other hand, the compound has a high glass transition temperature (Tg) and excellent thermal stability, which is an important factor in providing driving stability to the device.

[0201] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0202] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0203] 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 Chemical Formula 1 may be used as a material for the blue organic light emitting device.

[0204] In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the green organic light-emitting device.

[0205] In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the red organic light-emitting device.

[0206] 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 Chemical Formula 1 may be used as a material for the light emitting layer of the blue organic light emitting device.

[0207] In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the light-emitting layer of the green organic light-emitting device.

[0208] In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the light-emitting layer of the red organic light-emitting device.

[0209] The organic light-emitting device of the present invention may be manufactured by a typical manufacturing method and material for an organic light-emitting device, except that one or more organic layers are formed using the above-mentioned heterocyclic compound.

[0210] In manufacturing an organic light emitting device, the heterocyclic compound may be formed in an organic layer by a solution coating method as well as a vacuum deposition method, where the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0211] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have 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 layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0212] In the organic light-emitting device of the present invention, the organic layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound represented by Chemical Formula 1 above and the heterocyclic compound represented by Chemical Formula 2 above.

[0213] In another embodiment, the light-emitting layer may include a host material, and the host material may include the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2.

[0214] In the organic light-emitting device of the present invention, the organic layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 as hosts for the light-emitting layer.

[0215] In another embodiment, the host material may include two or more host materials, and among the two or more host materials, the heterocyclic compound represented by Chemical Formula 1 may be an N-type host material, and the heterocyclic compound represented by Chemical Formula 2 may be a P-type host material.

[0216] In this case, the exciplex phenomenon, which is emission due to the energy difference between the LUMO level of the acceptor (N-type host) and the HOMO level of the donor (P-type host), occurs more frequently due to electron exchange between the two molecules.

[0217] That is, when the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 are contained in the organic layer of the organic light emitting device, the organic light emitting device shows better efficiency and life effect. This result suggests that an exciplex phenomenon occurs when the two compounds are contained simultaneously.

[0218] The exciplex phenomenon is a phenomenon in which energy is released at the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) due to electron exchange between two molecules. When the exciplex phenomenon between two molecules occurs, reverse intersystem crossing (RISC) occurs, which can increase the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as the host of the emission layer, holes are injected into the p-host and electrons are injected into the n-host, which can reduce the driving voltage and thus help improve the lifetime.

[0219] In the organic light emitting device of the present invention, the host material may include two or more host materials, and the two or more host materials may be pre-mixed.

[0220] In addition, another embodiment of the present application provides a composition for an organic layer of an organic light-emitting device, comprising: a heterocyclic compound represented by Chemical Formula 1; and a heterocyclic compound represented by Chemical Formula 2.

[0221] The specific details regarding the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 are as described above.

[0222] The weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the heterocyclic compound represented by Chemical Formula 2 in the composition may be, but is not limited to, 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1.

[0223] The composition may be used when forming an organic material of an organic light-emitting device, and is particularly preferably used when forming a host for the light-emitting layer.

[0224] In one embodiment of the present application, the organic layer contains the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, and may be used together with a phosphorescent dopant.

[0225] In one embodiment of the present application, the organic layer contains the heterocyclic compound represented by Chemical Formula 1 above; and the heterocyclic compound represented by Chemical Formula 2 above, and may be used together with an iridium-based dopant.

[0226] The phosphorescent dopant material may be any material known in the art.

[0227] For example, phosphorescent dopant materials represented by LL'MX', LL'L''M, LMX'X'', L2MX', and L3M may be used, but the scope of the present invention is not limited to these examples.

[0228] Here, L, L', L'', X', and X'' are different bidentate ligands, and M is a metal that forms an octahedral complex.

[0229] M may be iridium, platinum, osmium, and the like.

[0230] L is an anionic bidentate ligand that coordinates to M as the iridium-based dopant through sp2 carbon and heteroatoms, and X can function to trap electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8-benzoquinoline), (thiophene group pyridine), phenylpyridine, benzothiophene group pyridine, 3-methoxy-2-phenylpyridine, thiophene group pyridine, tolylpyridine, and the like. Non-limiting examples of X' and X'' include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.

[0231] More specific examples are shown below, but the present invention is not limited to these examples.

[0232] [ka] In one embodiment of the present application, the iridium-based dopant is Ir(ppy) as a green phosphorescent dopant. 3 may also be used.

[0233] In one embodiment of the present application, the content of the dopant may be 1% to 15%, preferably 3% to 10%, and more preferably 5% to 10% based on the entire light-emitting layer. The content may mean a weight ratio.

[0234] The organic light-emitting device of the present invention may further include one or more layers selected from the group consisting of a light-emitting layer, a hole-injection layer, a hole-transport layer, an electron-injection layer, an electron-transport layer, an electron-blocking layer, and a hole-blocking layer.

[0235] 1 to 4 show examples of the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present application. However, these drawings do not limit the scope of the present application, and any structure of an organic light-emitting device known in the art may be applied to the present application.

[0236] 1 shows an organic light-emitting element in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the present invention is not limited to such a structure, and an organic light-emitting element in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate as shown in FIG.

[0237] Fig. 3 illustrates an example in which the organic layer is multi-layered. The organic light-emitting device according to Fig. 3 includes a hole injection layer 301, a hole transport layer 302, a light-emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, such a laminated structure does not limit the scope of the present application, and the remaining layers except for the light-emitting layer may be omitted as necessary, and other necessary functional layers may be further added.

[0238] Moreover, an organic light-emitting element 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.

[0239] In one embodiment of the present application, the first light-emitting layer and the second light-emitting layer may contain the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, respectively.

[0240] 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.

[0241] In this case, the first electron blocking layer, the first hole blocking layer, the second hole blocking layer, and the like shown in FIG. 4 may be omitted in some cases.

[0242] In one embodiment of the present application, an alkali metal or an alkaline earth metal may be doped into the compound of Chemical Formula 1. In this case, the driving voltage of the organic light emitting device may be reduced by forming a gap state, and the efficiency and lifespan may be further improved.

[0243] In one embodiment of the present application, there is provided a composition comprising an alkali metal or an alkaline earth metal in the compound of Chemical Formula 1. The content of the alkali metal or alkaline earth metal in the composition may be 0.01 wt% to 30 wt%, preferably 0.01 wt% to 25 wt%, more preferably 0.01 wt% to 20 wt%, based on the weight of the total composition.

[0244] In one embodiment of the present application, the alkali metal or alkaline earth metal may be, but is not limited to, lithium (Li), rubidium (Rb), cesium (Cs), or magnesium (Mg).

[0245] In one embodiment of the present application, there is provided 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 material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers comprises forming one or more organic material layers using a composition for an organic material layer according to one embodiment of the present application.

[0246] In one embodiment of the present application, there is provided a method for manufacturing an organic light-emitting device, wherein the step of forming the organic material layer comprises pre-mixing the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 and forming the organic material layer using a thermal vacuum deposition method.

[0247] The term "pre-mixed" refers to mixing the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 in one source before depositing them on an organic layer.

[0248] The premixed materials may be referred to as an organic layer composition according to one embodiment of the present application.

[0249] The organic layer containing the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 may further contain other substances, if necessary.

[0250] In an organic light-emitting device according to one embodiment of the present application, materials other than the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 are exemplified below, but these are merely illustrative and are not intended to limit the scope of the present application, and may be substituted with materials known in the art.

[0251] The anode material may be a material with a relatively large work function, such as a transparent conductive oxide, a metal, or a conductive polymer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al, or SnO 2 These include, but are not limited to: a combination of a metal and an oxide, such as Sb; and conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0252] The cathode material may be a material with a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF / Al or LiO 2 Examples of the material include, but are not limited to, multi-layered materials such as / Al.

[0253] The hole injection material may be a known hole injection material, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or a starburst type amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], for example, 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, polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid), etc. Alternatively, poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / Camphor sulfonic acid, or polyaniline / Poly(4-styrenesulfonate) may be used.

[0254] As the hole transport material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like may be used, and a low molecular weight or high molecular weight material may also be used.

[0255] As the electron transport material, oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and not only low molecular weight substances but also polymeric substances may be used.

[0256] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited thereto.

[0257] The light-emitting material may be a red, green, or blue light-emitting material, or may be a mixture of two or more light-emitting materials, if necessary. In this case, the two or more light-emitting materials may be evaporated as individual supply sources, or may be premixed and evaporated as one supply source. The light-emitting material may be a fluorescent material or a phosphorescent material. The light-emitting material may be a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, or a material in which both the host material and the dopant material are involved in light emission may be used.

[0258] When the hosts of the light-emitting materials are mixed, the hosts may be of the same type or different types. For example, two or more of n-type host materials or p-type host materials may be selected and used as the host material of the light-emitting layer.

[0259] The organic light emitting device according to one embodiment of the present application may be a top-emitting, bottom-emitting, or dual-sided emitting device depending on the materials used.

[0260] The heterocyclic compound according to one embodiment of the present application can also function in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors based on the same principles as those applied to organic light-emitting devices. EXAMPLES

[0261] The present specification will be described in more detail below with reference to examples. However, these are merely for illustrating the present application and are not intended to limit the scope of the present application.

[0262] <Production Example> <Production Example 1> Production of Compound 1 [ka]

[0263] 1) Preparation of Compound C1 Compound A1 (50.0g, 151mmol), Compound B1 (22.1g, 181mmol), Pd(PPh 3 ) 4 (8.72 g, 7.56 mmol), and K 2 CO 3 (41.7 g, 302 mmol) in distilled water / 1,4-dioxane (H 2 After dissolving in dichloromethane / distilled water (dichloromethane / H2O / 1,4-dioxane) (150 mL / 500 mL), the mixture was refluxed for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and cooled to room temperature. 2 The reaction mixture was extracted with 1:5 DCM:Hex. The reaction product was purified by column chromatography (DCM:Hex=1:5) and recrystallized from methanol to obtain compound C1 (45.1 g, 137 mmol, 91%).

[0264] The DCM means dichloromethane, and the Hex means hexane.

[0265] 2) Preparation of Compound D1 Compound C1 (45.1g, 137mmol), Pd 2 dba 3 (6.27 g, 6.85 mmol), Xphos (6.53 g, 13.7 mmol), and KOAc (26.9 g, 274 mmol) were dissolved in dioxane (450 mL) and refluxed for 4 hours. After completion of the reaction, the salt was filtered under reduced pressure and then concentrated. The concentrated reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain compound D1 (36.3 g, 86.4 mmol, 63%).

[0266] 3) Preparation of Compound 1 Compound D1 (7.0g, 16.7mmol), Compound E1 (4.34g, 16.3mmol), Pd(PPh 3 ) 4(0.96 g, 0.84 mmol), and K 2 CO 3 (4.62 g, 33.4 mmol) in distilled water / 1,4-dioxane (H 2 O / 1,4-dioxane (21 mL / 70 mL) was dissolved in 1,2-dioxane and refluxed for 2 hours. After completion of the reaction, the solid was obtained by washing with water and acetone. The dried solid was purified by column chromatography (DCB) and recrystallized from DCB to obtain compound 1 (8.16 g, 15.5 mmol, 93%).

[0267] The DCB stands for dichlorobenzene.

[0268] <Preparation Example 2> Preparation of Compounds 13, 37, 53, 57, 97, 133, 209, 237, 249, 253, 325, and 329 Compounds 13, 37, 53, 57, 97, 133, 209, 237, 249, 253, 325, and 329 were synthesized in the same manner as in Production Example 1, except that compounds A to E in Table 1 below were used in Production Example 2.

[0269] [Table 1] TIFF2025509247000201.tif208165 TIFF2025509247000202.tif47165

[0270] <Production Example 3> Production of Compound 22 [ka]

[0271] 1) Preparation of compound C8 Compound A2 (50.0g, 151mmol), Compound B1 (22.1g, 181mmol), Pd(PPh 3 ) 4 (8.72 g, 7.56 mmol), and K 2 CO 3(41.7 g, 302 mmol) in distilled water / 1,4-dioxane (H 2 After dissolving in dichloromethane / distilled water (dichloromethane / H2O / 1,4-dioxane) (150 mL / 500 mL), the mixture was refluxed for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and cooled to room temperature. 2 The reaction mixture was extracted with 1:5 DCM:Hex. The reaction mixture was purified by column chromatography (DCM:Hex=1:5) and recrystallized from methanol to obtain compound C8 (44.7 g, 136 mmol, 90%).

[0272] 2) Preparation of Compound D8 Compound C8 (44.7g, 136mmol), Pd 2 dba 3 (6.27 g, 6.80 mmol), Xphos (6.48 g, 13.6 mmol), and KOAc (26.7 g, 272 mmol) were dissolved in dioxane (450 mL) and then refluxed for 4 hours. After completion of the reaction, the salt was filtered under reduced pressure and then concentrated. The concentrated reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain compound D8 (37.2 g, 88.4 mmol, 65%).

[0273] 3) Preparation of Compound 22 Compound D8 (7.0g, 16.7mmol), Compound E17 (6.00g, 16.3mmol), Pd(PPh 3 ) 4 (0.96 g, 0.84 mmol), and K 2 CO 3 (4.62 g, 33.4 mmol) in distilled water / 1,4-dioxane (H 2 O / 1,4-dioxane (21 mL / 70 mL) was dissolved in 1,2-dioxane and refluxed for 2 hours. After completion of the reaction, the solid was obtained by washing with water and acetone. The dried solid was purified by column chromatography (DCB) and recrystallized from DCB to obtain compound 22 (10.0 g, 15.6 mmol, 96%).

[0274] <Production Example 4> Production of Compounds 39, 58, 115, 134, 226, 250, and 327 Compounds 39, 58, 115, 134, 226, 250, and 327 were synthesized in the same manner as in Production Example 3, except that compounds A to E in Table 2 below were used in Production Example 4.

[0275] [Table 2]

[0276] <Production Example 5> Production of Compound 511 [ka]

[0277] 1) Preparation of compound F3 Compound A3 (50.0g, 151mmol), B 2 pin 2 (60.0g, 158mmol), Pd(dppf)Cl 2 (5.52 g, 7.55 mmol), and KOAc (29.6 g, 302 mmol) were dissolved in dioxane (500 mL) and refluxed for 4 hours. After completion of the reaction, the salt was filtered under reduced pressure and then concentrated. The concentrated reaction product was purified by column chromatography (DCM:Hex=1:4) and recrystallized from methanol to obtain compound F3 (46.3 g, 122 mmol, 81%).

[0278] 2) Preparation of Compound G1 Compound F3 (46.3g, 122mmol), Compound E10 (38.0g, 120mmol), Pd(PPh 3 ) 4 (7.05 g, 6.10 mmol), and K 2 CO 3 (33.7 g, 244 mmol) in distilled water / 1,4-dioxane (H 2O / 1,4-dioxane (140 mL / 460 mL) was dissolved and refluxed for 2 hours. After completion of the reaction, the solid was obtained by washing with water and acetone. The dried solid was purified by column chromatography (DCB) and recrystallized from DCB to obtain compound G1 (59.3 g, 111 mmol, 91%).

[0279] 3) Preparation of Compound 511 Compound G1 (7.0g, 13.1mmol), Compound B1 (1.92g, 15.7mmol), Pd(PPh 3 ) 4 (0.76 g, 0.66 mmol), and K 2 CO 3 (3.62 g, 26.2 mmol) in distilled water / 1,4-dioxane (H 2 O / 1,4-dioxane (21 mL / 70 mL) was dissolved in 5,3-dioxane and refluxed for 4 hours. After completion of the reaction, the solid was obtained by washing with water and acetone. The dried solid was purified by column chromatography (DCB) and recrystallized from DCB to obtain compound 511 (7.09 g, 12.3 mmol, 94%).

[0280] <Production Example 6> Production of Compounds 523, 551, 635, 703, 711, 755, 827, 863, and 919 Compounds 523, 551, 635, 703, 711, 755, 827, 863, and 919 were synthesized in the same manner as in Preparation Example 5, except that compounds A, F, E, G, and B in Table 3 below were used in Preparation Example 6.

[0281] [Table 3] TIFF2025509247000207.tif77165

[0282] <Production Example 7> Production of Compound 521 [ka]

[0283] 1) Preparation of Compound F1 Compound A1 (50.0g, 151mmol), B 2 pin 2 (60.0g, 158mmol), Pd(dppf)Cl 2 (5.52 g, 7.55 mmol), and KOAc (29.6 g, 302 mmol) were dissolved in dioxane (500 mL) and refluxed for 4 hours. After completion of the reaction, the salt was filtered under reduced pressure and then concentrated. The concentrated reaction product was purified by column chromatography (DCM:Hex=1:4) and recrystallized from methanol to obtain compound F1 (47.5 g, 125 mmol, 83%).

[0284] 2) Preparation of Compound G2 Compound F1 (7.0g, 18.5mmol), Compound E17 (6.66g, 18.1mmol), Pd(PPh 3 ) 4 (1.07 g, 0.93 mmol), and K 2 CO 3 (5.11 g, 37.0 mmol) in distilled water / 1,4-dioxane (H 2 O / 1,4-dioxane (21 mL / 70 mL) was dissolved in 1,2-dioxane and refluxed for 2 hours. After completion of the reaction, the solid was obtained by washing with water and acetone. The dried solid was purified by column chromatography (DCB) and recrystallized from DCB to obtain compound G2 (10.1 g, 17.3 mmol, 94%).

[0285] 3) Preparation of Compound 521 Compound G2 (10.1g, 17.3mmol), Compound B1 (2.53g, 20.8mmol), Pd(PPh 3 ) 4 (1.01 g, 0.87 mmol), and K 2 CO 3 (4.78 g, 34.6 mmol) in distilled water / 1,4-dioxane (H 2O / 1,4-dioxane (30 mL / 100 mL) was dissolved and refluxed for 4 hours. After the reaction was completed, the solid was obtained by washing with water and acetone. The dried solid was purified by column chromatography (DCB) and recrystallized from DCB to obtain compound 521 (9.63 g, 15.4 mmol, 89%).

[0286] <Production Example 8> Production of Compounds 524, 597, 598, 633, 708, 724, 749, and 756 Compounds 524, 597, 598, 633, 708, 724, 749, and 756 were synthesized in the same manner as in Preparation Example 7, except that compounds A, F, E, G, and B in Table 4 below were used in Preparation Example 8.

[0287] [Table 4] TIFF2025509247000210.tif133165

[0288] <Production Example 9> Production of Compound 1002 [ka] Compound H1 (7.0g, 16.1mmol), Compound I1 (3.96g, 16.1mmol), Pd 2 dba 3 (0.74g, 0.81mmol), Xphos (0.77g, 1.61mmol), and NaOtBu (3.10g, 32.2mmol) were dissolved in toluene (70mL) and refluxed for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through a Celite filter with DCM. After concentration, the mixture was separated on a column with DCM:Hex=1:2 to obtain compound 1002 (9.15g, 14.7mmol, 91%).

[0289] <Preparation Example 10> Preparation of Compounds 1005, 1011, 1015, 1021, 1050, 1054, 1056, 1057, 1064, 1065, 1073, 1097, 1100, 1123, 1124, 1142, 1146, 1157, 1158, 1174, 1175, 1176, 1186, and 1187 In Preparation 10, compounds 1005, 1011, 1015, 1021, 1050, 1054, 1056, 1057, 1064, 1065, 1073, 1097, 1100, 1123, 1124, 1142, 1146, 1157, 1158, 1174, 1175, 1176, 1186, and 1187 were synthesized in the same manner as in Preparation 9, except that compounds H and I in Table 5 below were used.

[0290] [Table 5] TIFF2025509247000213.tif213165 TIFF2025509247000214.tif204165 TIFF2025509247000215.tif213165 TIFF2025509247000216.tif213165 TIFF2025509247000217.tif116165

[0291] <Production Example 11> Production of Compound 1203 [ka]

[0292] 1) Preparation of compound F5 Compound A5 (50.0g, 178mmol), B 2 pin 2 (54.1g, 213mmol), Pd(dppf)Cl 2(6.51 g, 8.90 mmol), and KOAc (34.9 g, 356 mmol) were dissolved in dioxane (500 mL) and then refluxed for 4 hours. After completion of the reaction, the salt was filtered under reduced pressure and then concentrated. The concentrated reaction product was purified by column chromatography (DCM:Hex=1:4) and recrystallized from methanol to obtain compound F5 (44.0 g, 134 mmol, 75%).

[0293] 2) Preparation of compound H2 Compound F5 (7.0g, 21.3mmol), Compound E11 (7.18g, 20.9mmol), Pd(PPh 3 ) 4 (1.23 g, 1.07 mmol), and K 2 CO 3 (5.89 g, 42.6 mmol) in distilled water / 1,4-dioxane (H 2 After dissolving in O / 1,4-dioxane (21 mL / 70 mL), the mixture was refluxed for 2 h. After completion of the reaction, the mixture was washed with water and acetone to obtain a solid. The dried solid was purified by column chromatography (DCB) and recrystallized from DCB to obtain compound H2 (10.4 g, 20.4 mmol, 96%).

[0294] 3) Preparation of Compound 1203 Compound H2 (10.4g, 20.4mmol), Compound I1 (5.00g, 20.4mmol), Pd 2 dba 3 (0.93g, 1.02mmol), Xphos (0.97g, 2.04mmol), and NaOtBu (3.92g, 40.8mmol) were dissolved in toluene (100mL) and refluxed for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through a Celite filter with DCM. After concentration, the mixture was separated on a column with DCM:Hex=1:2 to obtain compound 1203 (11.6g, 16.1mmol, 76%).

[0295] <Production Example 12> Production of Compounds 1257, 1258, 1278, 1279, 1306, 1307, and 1365 Compounds 1257, 1258, 1278, 1279, 1306, 1307, and 1365 were synthesized in the same manner as in Preparation Example 11, except that compounds A, F, E, H, and I in Table 6 below were used in Preparation Example 12.

[0296] [Table 6] TIFF2025509247000220.tif71165

[0297] <Production Example 13> Production of Compound 1403 [ka] Compound H1 (7.0g, 16.1mmol), Compound J1 (6.50g, 16.9mmol), Pd 2 dba 3 (0.74 g, 0.81 mmol), Xphos (0.77 g, 1.61 mmol), and NaOH (1.29 g, 32.2 mmol) were dissolved in distilled water / 1,4-dioxane (H 2 After dissolving in O / 1,4-dioxane (21 mL / 70 mL), the mixture was refluxed for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through a Celite filter with DCM. After concentration, the mixture was separated through a column with DCM:Hex=1:3 to obtain compound 1403 (9.95 g, 13.8 mmol, 86%).

[0298] <Production Example 14> Production of Compounds 1404, 1413, 1417, 1437, and 1439 Compounds 1404, 1413, 1417, 1437, and 1439 were synthesized in the same manner as in Preparation Example 13, except that compounds H and J in Table 7 below were used in Preparation Example 14.

[0299] [Table 7]

[0300] <Production Example 15> Production of Compound 1405 [ka]

[0301] 1) Preparation of compound H7 Compound F5 (7.0g, 21.3mmol), Compound E19 (7.18g, 20.9mmol), Pd(PPh 3 ) 4 (1.23 g, 1.07 mmol), and K 2 CO 3 (5.89 g, 42.6 mmol) in distilled water / 1,4-dioxane (H 2 O / 1,4-dioxane (21 mL / 70 mL) was dissolved and refluxed for 2 hours. After completion of the reaction, the solid was obtained by washing with water and acetone. The dried solid was purified by column chromatography (DCB) and recrystallized from DCB to obtain compound H7 (10.2 g, 20.0 mmol, 94%).

[0302] 2) Preparation of Compound 1405 Compound H7 (10.2g, 20.0mmol), Compound J3 (6.07g, 21.0mmol), Pd 2 dba 3 (0.92 g, 1.00 mmol), Xphos (0.95 g, 2.00 mmol), and NaOH (1.60 g, 40.0 mmol) were dissolved in distilled water / 1,4-dioxane (H 2 After dissolving in 1,2-hexanediol (21 mL / 70 mL), the mixture was refluxed for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through a Celite filter with DCM. After concentration, the mixture was separated on a column with DCM:Hex=1:3 to obtain compound 1405 (11.8 g, 16.4 mmol, 82%).

[0303] <Production Example 16> Production of Compounds 1444, 1453, 1488, 1489, 1585, 1587, and 1595 Compounds 1444, 1453, 1488, 1489, 1585, 1587, and 1595 were synthesized in the same manner as in Preparation Example 15, except that compounds F, E, H, and J in Table 8 below were used in Preparation Example 16.

[0304] [Table 8] TIFF2025509247000225.tif75165

[0305] <Production Example 17> Production of Compound 1505 [ka]

[0306] 1) Preparation of compound H8 Compound F5 (7.0g, 21.3mmol), Compound E20 (5.86g, 20.9mmol), Pd(PPh 3 ) 4 (1.23g, 1.07mmol), K 2 CO 3 (5.89 g, 42.6 mmol) in distilled water / 1,4-dioxane (H 2 O / 1,4-dioxane (21 mL / 70 mL) was dissolved and refluxed for 2 hours. After completion of the reaction, the solid was obtained by washing with water and acetone. The dried solid was purified by column chromatography (DCB) and recrystallized from DCB to obtain compound H8 (8.47 g, 19.0 mmol, 89%).

[0307] 2) Preparation of Compound 1505 Compound H8 (8.47g, 19.0mmol), Compound I1 (4.66g, 19.0mmol), Pd 2 dba 3 (0.87 g, 0.95 mmol), Xphos (0.91 g, 1.90 mmol), and NaOH (1.52 g, 38.0 mmol) were dissolved in distilled water / 1,4-dioxane (H 2After dissolving in 1,2-hexanediol (25 mL / 1,4-dioxane), the mixture was refluxed for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through a Celite filter with DCM. After concentration, the mixture was separated through a column with DCM:Hex=1:2 to obtain compound 1505 (10.1 g, 15.4 mmol, 81%).

[0308] <Production Example 18> Production of Compounds 1506, 1559, 1570, and 1579 Compounds 1506, 1559, 1570, and 1579 were synthesized in the same manner as in Preparation Example 17, except that in Preparation Example 18, compounds F, E, H, and I in Table 9 below were used.

[0309] [Table 9] The synthesis results of the compounds described in the above Production Examples 1 to 18 and Tables 1 to 9 are shown in the following Tables 10 and 11. 1 H NMR (CDCl 3 The values ​​are measured by a 300 MHz (300 MHz) frequency band, and Table 11 below shows the values ​​measured by FD-MS (Field desorption mass spectrometry).

[0310] [Table 10] TIFF2025509247000229.tif210165 TIFF2025509247000230.tif210165 TIFF2025509247000231.tif210165 TIFF2025509247000232.tif210165 TIFF2025509247000233.tif210165 TIFF2025509247000234.tif210165 TIFF2025509247000235.tif210165 TIFF2025509247000236.tif210165 TIFF2025509247000237.tif210165 TIFF2025509247000238.tif210165 TIFF2025509247000239.tif210165 TIFF2025509247000240.tif210165 TIFF2025509247000241.tif210165 TIFF2025509247000242.tif210165 TIFF2025509247000243.tif210165 TIFF2025509247000244.tif210165 TIFF2025509247000245.tif210165 TIFF2025509247000246.tif210165 TIFF2025509247000247.tif210165 TIFF2025509247000248.tif122165

[0311] [Table 11] TIFF2025509247000250.tif216165 TIFF2025509247000251.tif216165 TIFF2025509247000252.tif216165 TIFF2025509247000253.tif217165 TIFF2025509247000254.tif217165 TIFF2025509247000255.tif156165

[0312] <Experimental Example 1> 1) Preparation of organic light-emitting device (red host, single) A glass substrate coated with a thin ITO film to a thickness of 1,500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then UVO treatment was performed using UV in a UV cleaner for 5 minutes. The substrate was then transferred to a plasma cleaner (PT) and plasma treatment was performed in a vacuum state to treat the ITO surface and remove residual film, and then transferred to a thermal evaporation device for organic deposition.

[0313] On the ITO transparent electrode (anode), a hole injection layer made of 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer made of NPB (N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed as common layers.

[0314] An emitting layer was then thermally vacuum deposited thereon as follows: The emitting layer was formed by depositing a compound shown in Table 12 below as a red host from a single source, and (piq) as a red phosphorescent dopant. 2 Using (Ir)(acac), the host was doped with 3 wt% Ir compound and evaporated to a thickness of 400 Å. Then, bathophenanthroline (hereinafter Bphen) was evaporated to a thickness of 30 Å as a hole blocking layer, and Alq was evaporated on top of it as an electron transport layer. 3 Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode, thereby manufacturing an organic electroluminescent device.

[0315] On the other hand, all the organic compounds required for the production of OLED elements are about 10 -6 ~10 -8 The resulting material was purified by vacuum sublimation under torr and used to fabricate OLEDs.

[0316] 2) Performance evaluation of organic light-emitting device (red host, single) The electroluminescence (EL) characteristics of the organic electroluminescent device prepared as described above were measured using a Mac Science M7000. Using the measurement results, a reference luminance of 6,000 cd / m was measured using a Mac Science M6000 lifespan measurement device. 2 When T 90 was measured.

[0317] The measurement results are shown in Table 12 below.

[0318] [Table 12] TIFF2025509247000257.tif209165 TIFF2025509247000258.tif209165 TIFF2025509247000259.tif163165

[0319] In Table 12, compounds A to I are as follows. [ka]

[0320] <Experimental Example 2> 1) Preparation of organic light-emitting devices (pre-mixed, red host) A glass substrate coated with a thin ITO film to a thickness of 1,500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then UVO treatment was performed for 5 minutes using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treatment was performed in a vacuum state to determine the work function of the ITO and remove residual film, and then transferred to a thermal evaporation device for organic deposition.

[0321] On the ITO transparent electrode (anode), a hole injection layer 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine), a hole transport layer NPB (N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), and an electron blocking layer TAPC (cyclohexylidenebis[N,N-bis(4-methylphenyl)benzoamine] or an exciton blocking layer TCTA (Tris(4-carbazoyl-9-ylphenyl)amine) were formed as a common layer.

[0322] An emitting layer was formed thereon by thermal vacuum deposition as follows. The emitting layer was formed by depositing two compounds shown in Table 13 below as a red host from one source, and (piq) as a red phosphorescent dopant. 2 Using (Ir)(acac), the host was doped with 3 wt% Ir compound and evaporated to a thickness of 400 Å. Then, Bphen was evaporated to a thickness of 30 Å as a hole blocking layer, and TPBI (1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene) was evaporated to a thickness of 250 Å as an electron transport layer on top of that. Finally, lithium fluoride (LiF) was evaporated to a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was evaporated to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing an organic electroluminescent device.

[0323] On the other hand, all the organic compounds required for the production of OLED elements are about 10 -6 ~10 -8 The resulting material was purified by vacuum sublimation under torr and used to fabricate OLEDs.

[0324] 2) Preparation of organic light-emitting devices (pre-mixed, red host) and performance evaluation The electroluminescence (EL) characteristics of the organic electroluminescent device prepared as described above were measured using a Mac Science M7000. Using the measurement results, a reference luminance of 6,000 cd / m was measured using a Mac Science M6000 lifespan measurement device.2 When T 90 was measured.

[0325] The measurement results are shown in Table 13 below.

[0326] [Table 13] TIFF2025509247000262.tif200165 TIFF2025509247000263.tif187165 TIFF2025509247000264.tif200165 TIFF2025509247000265.tif173165 TIFF2025509247000266.tif200165 TIFF2025509247000267.tif187165 TIFF2025509247000268.tif42165

[0327] As can be seen from the results of Tables 12 and 13, in the case of Examples 1 to 86 in which the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 of the present invention are used as a host in the organic layer, particularly the light-emitting layer, of the organic light-emitting device, the driving voltage, efficiency, and lifetime were improved compared to the organic light-emitting device of the comparative example.

[0328] The heterocyclic compound of the present invention represented by Chemical Formula 1 has high thermal stability and suitable molecular weight and band gap. The suitable band gap of the light-emitting layer provides good hole transport ability, prevents electron loss, and helps to form an effective recombination zone.

[0329] It was confirmed that the compound represented by Formula 2 of the present invention is contained in the organic layer of the organic light emitting device, and thus the driving voltage and lifespan can be significantly improved due to the increase in hole mobility.In addition, it was confirmed that the efficiency is improved due to the reduction in current leakage and the electron confinement caused by the electron block.

[0330] In the case of a combination of Chemical Formula 1 and Chemical Formula 2 in the light-emitting layer, the driving, efficiency, and lifespan are improved. This is because when a donor with good hole transporting ability (p-host, heterocyclic compound represented by Chemical Formula 2) and an acceptor with good electron transporting ability (n-host, heterocyclic compound represented by Chemical Formula 1) are used as the host of the light-emitting layer, the driving voltage at which electrons and holes are injected can be reduced, and the efficiency and lifespan are improved due to the formation of an effective recombination zone.

[0331] This result is due to the more frequent occurrence of the exciplex phenomenon, which is a phenomenon in which electrons are emitted due to the energy difference between the LUMO level of the acceptor (N-type host) and the HOMO level of the donor (P-type host) as a result of electron exchange between two molecules.When a donor (P-type host) with good hole transporting ability and an acceptor (N-type host) with good electron transporting ability are used as the host of the light-emitting layer due to the exciplex phenomenon, holes are injected into the P-type host and electrons are injected into the N-type host, facilitating the combination of electrons and holes in the light-emitting layer.

Claims

1. An organic light-emitting device including a first electrode, a second electrode, and one or more organic layers provided between the first electrode and the second electrode, the organic layer including a heterocyclic compound represented by the following chemical formula 1 and a heterocyclic compound represented by the following chemical formula 2: 【Chemistry 130】 【Chemistry 131】 In the above Chemical Formula 1 and Chemical Formula 2, X is O; or S; One of R1 to R6 is 【Chemistry 132】 and the remaining one is 【Chemistry 133】 and the remaining groups are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'; 【Chemistry 134】 are the positions at which the groups bond to R1 to R6, L1 to L6 are the same or different, 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; a, b, m, n, m1, and m2 are each an integer of 0 to 3, and when a, b, m, n, m1, and m2 are each 2 or more, the substituents in the brackets are the same or different, N-Het1 and N-Het2 are each independently a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N; Ar1 is a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; Y is O; or S; Ar2 and Ar3 are the same or different, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or -NRR'; Adjacent substituents of L, L, L, Ar, and Ar may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic or aromatic heterocycle; Rr, Rp, and Rq are the same or different, and each independently is selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR', where r is an integer of 0 to 4, p and q are each an integer of 0 to 3, and when r, p, and q are each 2 or more, the substituents in the brackets are the same or different, The R, R', and R'' are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

2. The organic light-emitting device according to claim 1 , wherein N-Het1 and N-Het2 are each independently represented by the following formula 3: 【Chemistry 135】 In the above Chemical Formula 3, X1 is CR101 or N, X2 is CR102 or N, X3 is CR103 or N, X4 is CR104 or N, X5 is CR105 or N, and at least one of X1 to X5 is N; R101 to R105 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy 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; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heterocycle, wherein 【Chemistry 136】 is a moiety that is linked to Formula 1 or 2.

3. The organic light-emitting device according to claim 1, wherein the chemical formula 1 is a heterocyclic compound represented by the following chemical formula 1-1 or 1-2: 【Chemistry 137】 【Chemistry 138】 In the above Chemical Formula 1-1 and Chemical Formula 1-2, Rr1 and Rs are the same or different and each independently represents hydrogen; deuterium; a cyano group; a halogen group; or a substituted or unsubstituted C1 to C60 alkyl group; r1 is an integer of 0 to 5, and when r1 is 2 or more, Rr1 in the parentheses are the same or different, s is an integer of 0 to 3, and when s is 2 or more, Rs in the parentheses are the same or different, The definitions of X, L1, L2, Ar1, a, b, and N-Het1 are the same as those in Chemical Formula 1.

4. The organic light-emitting device according to claim 3, wherein the chemical formula 1-1 is represented by any one of the following chemical formulas 1-1-1 to 1-1-4: 【Chemistry 139】 【Chemistry 140】 【Chemistry 141】 【Chemistry 142】 In the above Chemical Formulas 1-1-1 to 1-1-4, R11 to R15 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a cyano group; a halogen group; or a substituted or unsubstituted C1 to C60 alkyl group; The definitions of X, Rs, L1, L2, Ar1, a, b, s, and N-Het1 are the same as those in Chemical Formula 1-1.

5. The organic light-emitting device according to claim 3, wherein the chemical formula 1-2 is represented by any one of the following chemical formulas 1-2-1 to 1-2-4: 【Chemistry 143】 【Chemistry 144】 【Chemistry 145】 【Chemistry 146】 In the above chemical formulas 1-2-1 to 1-2-4, R11 to R15 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a cyano group; a halogen group; or a substituted or unsubstituted C1 to C60 alkyl group; The definitions of X, Rs, L1, L2, Ar1, a, b, s, and N-Het1 are the same as those in Chemical Formula 1-2.

6. The above 【Chemistry 147】 The organic light-emitting device according to claim 1, wherein the organic light-emitting device is represented by any one of the following chemical formulas A-1 to A-12: 【Chemistry 148】 【Chemistry 149】 【Chemistry 150】 【Chemistry 151】 【Chemistry 152】 【Chemistry 153】 【Chemistry 154】 【Chemistry 155】 【Chemistry 156】 【Chemistry 157】 【Chemistry 158】 【Chemistry 159】 In the above Chemical Formulae A-1 to A-12, The definitions of L3 and m are the same as those in Chemical Formula 2. L'5 and L'6 are the same or different 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; m'1 and m'2 are each independently an integer of 0 to 3, and when m'1 and m'2 are each 2 or more, the substituents in the parentheses are the same or different; Ar'2 and Ar'3 are the same or different, and each independently represents NRR'; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; Z1 to Z3 are each independently O; S; CRaRb; or NRc; Y2 and Y3 are each independently O; or S; R, R', Ra, Rb, Rc, and Rd1 to Rd26 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; d1, d21, and d22 each independently represent an integer of 0 to 8; d2, d4, d5, d9, and d26 each independently represent an integer of 0 to 6; d3, d6, d8, d11, d12 to d14, d17, d18, d20, d23, and d24 each independently represent an integer of 0 to 4; d7, d10, d19, and d25 each independently represent an integer of 0 to 2; d15 is an integer from 0 to 5; d16 is an integer from 0 to 3, When each of d1 to d26 is 2 or more, the substituents in the brackets are the same or different.

7. The organic light-emitting device according to claim 1 , wherein the formula 1 is represented by any one of the following compounds: 【Chemistry 160】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

8. The organic light-emitting device according to claim 1 , wherein the formula 2 is represented by any one of the following compounds: 【Chemistry 161】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

9. The organic light-emitting device according to claim 1 , wherein the organic layer includes a light-emitting layer, the light-emitting layer including the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2.

10. The 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 represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2.

11. 11. The organic light-emitting device according to claim 10, wherein the host material includes two or more host materials, and among the two or more host materials, the heterocyclic compound represented by Chemical Formula 1 is an N-type host material, and the heterocyclic compound represented by Chemical Formula 2 is a P-type host material.

12. The organic light emitting device according to claim 10, wherein the host material includes two or more host materials, and the two or more host materials are pre-mixed.

13. A composition for an organic layer of an organic light-emitting device, comprising the heterocyclic compound represented by Chemical Formula 1 according to claim 1 and the compound represented by Chemical Formula 2.

14. The composition for an organic layer of an organic light-emitting device according to claim 13, wherein the weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the compound represented by Chemical Formula 2 in the composition is 1:10 to 10:

1.

15. Providing 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; Including, The method for manufacturing an organic light emitting device, wherein the forming of the organic layer comprises forming one or more organic layers using the composition for an organic layer according to claim 13 .

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