Heterocyclic compound and organic light-emitting device comprising same

Abstract

The present invention relates to: a heterocyclic compound represented by chemical formula 1; and an organic light-emitting device comprising same.

Description

Heterocyclic compound and organic light-emitting device containing the same

[0001] This application claims the benefit of priority to Korean Patent Application No. 10-2023-0167818, dated November 28, 2023, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a heterocyclic compound and an organic light-emitting device comprising the same.

[0003]

[0004] Organic light-emitting diodes are a type of self-luminous display device that have the advantages of a wide viewing angle, excellent contrast, and fast response speed.

[0005] Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting device of this structure, electrons and holes injected from the two electrodes combine in the organic thin film, forming pairs and then disappearing, emitting light. The organic thin film may be composed of a single layer or multiple layers, as needed.

[0006] The material of the organic thin film may have a light-emitting function as needed. For example, the organic thin film material may be a compound that can form a light-emitting layer on its own, or a compound that can act as a host or dopant in a host-dopant light-emitting layer. In addition, the material of the organic thin film may be a compound that can perform roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection.

[0007] To improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of materials for organic thin films is continuously required.

[0008] There is a need for research on organic light-emitting devices that include compounds having chemical structures that can satisfy the conditions required for materials usable in organic light-emitting devices, such as appropriate energy levels, electrochemical stability, and thermal stability, and that can play various roles required in organic light-emitting devices depending on substituents.

[0009]

[0010] [Previous literature]

[0011] [Patent Document]

[0012] U.S. Patent No. 4,356,429

[0013]

[0014] The present invention seeks to provide a heterocyclic compound and an organic light-emitting device comprising the same.

[0015]

[0016] To achieve the above purpose,

[0017] The present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0018] [Chemical Formula 1]

[0019]

[0020] In the above chemical formula 1,

[0021] wherein R1 to R10 are the same as or different from each other, and each independently represent hydrogen; deuterium; 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; -SiR101R102R103; -NR101R102; selected from the group consisting of the following chemical formula 2; and the following chemical formula 3, or a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring in which two or more adjacent groups are bonded to each other; Or forms a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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,

[0022] Any one of the above R1 to R10 is the following chemical formula 2; or the following chemical formula 3,

[0023] [Chemical Formula 2]

[0024]

[0025] [Chemical Formula 3]

[0026]

[0027] In the above chemical formulas 2 and 3,

[0028] wherein R11 to R14 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; 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; -SiR101R102R103; and -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; Or forms a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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,

[0029] The above a is an integer from 0 to 6, and when a is 2 or more, R12 are equal to or different from each other,

[0030] The above L1 and L2 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0031] The above b is an integer from 0 to 5, and when b is 2 or greater, L1 is equal to or different from each other,

[0032] The above c is an integer from 0 to 5, and when c is 2 or greater, L2 are equal to or different from each other.

[0033]

[0034] In addition, the present invention

[0035] First electrode;

[0036] A second electrode provided opposite to the first electrode; and

[0037] An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode,

[0038] An organic light-emitting device is provided, wherein at least one of the organic layers comprises a heterocyclic compound represented by the chemical formula 1.

[0039]

[0040] The heterocyclic compound of the present invention can be used as an organic layer material of an organic light-emitting device. In particular, it can be used as an electron transport layer, charge generation layer, electron injection layer, electron blocking layer, or hole blocking layer material, thereby providing remarkable effects of lowering the operating voltage of the organic light-emitting device, improving the luminous efficiency, and enhancing the lifespan characteristics.

[0041]

[0042] Figures 1 to 4 are drawings schematically showing the laminated structure of an organic light-emitting device according to one embodiment of the present application.

[0043]

[0044] Hereinafter, the present invention will be described in more detail.

[0045]

[0046] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is replaced, i.e., a position where a substituent can be replaced, and when two or more are replaced, the two or more substituents may be the same or different from each other.

[0047] In this specification, "substituted or unsubstituted" means deuterium; halogen; cyano group; straight or branched chain alkyl group having a carbon atom ... -SiRR'R"; -P(=O)RR'; is unsubstituted or substituted with one or more substituents selected from the group consisting of a C1 to C20 alkylamine group; a C6 to C60 monocyclic or polycyclic arylamine group; and a C2 to C60 monocyclic or polycyclic heteroarylamine group, or is unsubstituted or substituted with a substituent in which two or more substituents selected from the above-mentioned substituents are linked, wherein R, R' and R" are a C6 to C60 monocyclic or polycyclic aryl group; or a C2 to C60 monocyclic or polycyclic heteroaryl group.

[0048] In this specification, halogen may be fluorine; chlorine; bromine; or iodine.

[0049] In the present specification, an alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 40 carbon atoms, and more specifically 1 to 20 carbon atoms. Specific examples include a methyl group; an ethyl group; an n-propyl group; an isopropyl 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; an n-pentyl group; an isopentyl group; a neopentyl group; a tert-pentyl group; an n-hexyl group; a 1-methylpentyl group; a 2-methylpentyl group; a 4-methyl-2-pentyl group; a 3,3-dimethylbutyl group; a 2-ethylbutyl group; a n-heptyl group; a 1-methylhexyl group; a cyclopentylmethyl group; a cyclohexylmethyl group; n-octyl group; tert-octyl group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethyl-propyl group; 1,1-dimethyl-propyl group; isohexyl group; 4-methylhexyl group; 5-methylhexyl group, etc., but are not limited thereto.

[0050] In the present specification, an alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include 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; 2,2-bis(diphenyl-1-yl)vinyl-1-yl group; stilbenyl group; styrenyl group, etc., but are not limited thereto.

[0051] In the present specification, an alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0052] In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, examples thereof include, but are not limited to, a methoxy group; an ethoxy group; an n-propoxy group; an isopropoxy group; an n-butoxy group; an isobutoxy group; a tert-butoxy group; a sec-butoxy group; an n-pentyloxy group; a neopentyloxy group; an isopentyloxy group; an n-hexyloxy group; a 3,3-dimethylbutyloxy group; a 2-ethylbutyloxy group; an n-octyloxy group; an n-nonyloxy group; an n-decyloxy group; a benzyloxy group; and a p-methylbenzyloxy group.

[0053] In the present specification, a cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group; for example, a heterocycloalkyl group; an aryl group; a heteroaryl group, etc. The cycloalkyl group may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. Specifically, 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; 4-tert-butylcyclohexyl group; cycloheptyl group; cyclooctyl group, etc., but are not limited thereto.

[0054] In the present specification, a heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group; for example, a cycloalkyl group; an aryl group; a heteroaryl group, etc. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

[0055] In the present specification, an aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group; for example, a cycloalkyl group; a heterocycloalkyl group; a heteroaryl group, etc. The aryl group may include a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 20 carbon atoms. Specific examples of the aryl group include a phenyl group; a biphenyl group; a triphenyl group; a naphthyl group; 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; Acenaphthylenyl group; benzofluorenyl group; spirobifluorenyl group; 2,3-dihydro-1H-indenyl group; and condensed ring groups thereof, but are not limited thereto.

[0056] In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 are the same or different from each other, and each independently may be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specifically, it may be substituted with an aryl group, and the above-described examples may be applied to the aryl group. For example, the phosphine oxide group includes, but is not limited to, a diphenylphosphine oxide group; a dinaphthylphosphine oxide group, and the like.

[0057] In the present specification, a silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -SiR101R102R103, wherein R101 to R103 are the same as or different from each other, and may each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group; a triethylsilyl group; a t-butyldimethylsilyl group; a vinyldimethylsilyl group; a propyldimethylsilyl group; a triphenylsilyl group; a diphenylsilyl group; and a phenylsilyl group.

[0058] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0059] When the above fluorenyl group is substituted, It can be, but is not limited to, the following.

[0060] In the present specification, a spiro group is a group including a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the following spiro group may include any one of the groups having the following structural formula.

[0061]

[0062] In the present specification, a heteroaryl group includes S; O; Se; N; or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic ring means a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, for example, a cycloalkyl group; a heterocycloalkyl group; an aryl group, etc. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.Specific examples of the above heteroaryl group include a pyridyl group; a pyrrolyl group; a pyrimidyl group; a pyridazinyl group; a furanyl group; a thiophenyl group; an imidazolyl group; a pyrazolyl group; an oxazolyl group; an isoxazolyl group; a thiazolyl group; an isothiazolyl group; a triazolyl group; a furazanyl group; an oxadiazolyl group; a thiadiazolyl group; a dithiazolyl group; a tetrazolyl group; a pyranyl group; a thiopyranyl group; a diazinyl group; an oxazinyl group; a thiazinyl group; a dioxynyl group; a triazinyl group; a tetrazinyl group; a quinolyl group; an isoquinolyl group; a quinazolinyl group; an isoquinazolinyl group; a quinozolinyl group; a naphthyridyl group; an acridinyl group; a phenanthridinyl group; an imidazopyridinyl group; a diazanaphthalenyl group; Triazaindenyl group; 2-indolyl group; indolizinyl group; benzothiazolyl group; benzoxazolyl group; benzimidazolyl group; benzothiophenyl group; benzofuranyl group; dibenzothiophenyl group; dibenzofuranyl group; carbazolyl group; benzocarbazolyl group; dibenzocarbazolyl group; phenazinyl group; dibenzosilole group; spirobi(dibenzosilole) group; dihydrophenazinyl group; phenoxazinyl group; phenanthridyl group; thienyl group; indolo[2,3-a]carbazolyl group; indolo[2,3-b]carbazolyl group; indolinyl group; 10,11-dihydro-dibenzo[b,f]azepinyl group; 9,10-dihydroacridinyl group; phenanthrazinyl group; phenothiazinyl group; Examples thereof include, but are not limited to, a phthalazinyl group; a naphthyridinyl group; a phenanthrolinyl group; a benzo[c][1,2,5]thiadiazolyl group; a 5,10-dihydrodibenzo[b,e][1,4]azacylinyl group; a pyrazolo[1,5-c]quinazolinyl group; a pyrido[1,2-b]indazolyl group; a pyrido[1,2-a]imidazo[1,2-e]indolinyl group; and a 5,11-dihydroindeno[1,2-b]carbazolyl group.

[0063] In the present specification, the amine group may be selected from the group consisting of a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; -NH2; 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; 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; Biphenyltriphenylenylamine groups, etc. are included, but are not limited thereto.

[0064] In this specification, an arylene group means a group having two bonding positions to an aryl group, i.e., a divalent group. The description of the aryl group described above may be applied to these groups, except that each group is divalent. In addition, a heteroarylene group means a group having two bonding positions to a heteroaryl group, i.e., a divalent group. The description of the heteroaryl group described above may be applied to these groups, except that each group is divalent.

[0065] As used herein, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent; a substituent that is sterically closest to the substituent; or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

[0066] In the present invention, "when no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2Since H, Deuterium (D)) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0067] In one embodiment of the present invention, "when no substituent is indicated in the chemical formula or compound structure" may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the deuterium content may be 0% to 100%.

[0068] In one embodiment of the present invention, in cases where “no substituent is indicated in the chemical formula or compound structure,” hydrogen and deuterium may be used in combination in the compound, unless deuterium is explicitly excluded, such as “the content of deuterium is 0%,” “the content of hydrogen is 100%,” or “all substituents are hydrogen.”

[0069] In one embodiment of the present invention, deuterium is an element having a deuteron, which is one of the isotopes of hydrogen and is composed of one proton and one neutron, as its nucleus. -2 It can be expressed as , and the element symbol is D or 2 It can also be written as H.

[0070] In one embodiment of the present invention, an isotope means an atom having the same atomic number (Z) but a different mass number (A). An isotope can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0071] In one embodiment of the present invention, the meaning of the content T% of a specific substituent can be defined as T2 / T1Х100 = T%, where the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2.

[0072] That is, there is an example, In the phenyl group represented by , the content of deuterium of 20% can mean that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and among them, the number of deuterium is 1 (T2 in the formula). That is, the content of deuterium of 20% in the phenyl group can be expressed by the structural formula below.

[0073]

[0074]

[0075] Additionally, in one embodiment of the present invention, the term “phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, i.e., has 5 hydrogen atoms.

[0076] In the present invention, the C6 to C60 aromatic hydrocarbon ring means a compound including an aromatic ring composed of C6 to C60 carbons and hydrogen, and examples thereof include, but are not limited to, a phenyl group; a biphenyl group; a terphenyl group; a triphenylenyl group; a naphthyl group; anthracenyl group; a phenalenyl group; a phenanthrenyl group; a fluorenyl group; a pyrenyl group; a chrysenyl group; a perylenyl group; an azulenyl group, and the like. All aromatic hydrocarbon ring compounds known in the art that satisfy the above carbon number are included.

[0077]

[0078] The present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0079] [Chemical Formula 1]

[0080]

[0081] In the above chemical formula 1,

[0082] wherein R1 to R10 are the same as or different from each other, and each independently represent hydrogen; deuterium; 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; -SiR101R102R103; -NR101R102; selected from the group consisting of the following chemical formula 2; and the following chemical formula 3, or a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring in which two or more adjacent groups are bonded to each other; Or forms a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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,

[0083] Any one of the above R1 to R10 is the following chemical formula 2; or the following chemical formula 3,

[0084] [Chemical Formula 2]

[0085]

[0086] [Chemical Formula 3]

[0087]

[0088] In the above chemical formulas 2 and 3,

[0089] wherein R11 to R14 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; 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; -SiR101R102R103; and -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; Or forms a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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,

[0090] The above a is an integer from 0 to 6, and when a is 2 or more, R12 are equal to or different from each other,

[0091] The above L1 and L2 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0092] The above b is an integer from 0 to 5, and when b is 2 or greater, L1 is equal to or different from each other,

[0093] The above c is an integer from 0 to 5, and when c is 2 or greater, L2 are equal to or different from each other.

[0094]

[0095] In one embodiment of the present invention, R1 to R10 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -SiR101R102R103; -NR101R102; or the above formula 2; or the above formula 3, or two or more adjacent groups bond to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; Or form a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represent a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group, and any one of R1 to R10 may be represented by the above chemical formula 2; or the above chemical formula 3.

[0096] In another embodiment of the present invention, R1 to R10 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -SiR101R102R103; -NR101R102; the above chemical formula 2; Or the above chemical formula 3, or two or more adjacent groups combine with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, and any one of the R1 to R10 may be the above chemical formula 2; or the above chemical formula 3.

[0097] In another embodiment of the present invention, R1 to R10 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -SiR101R102R103; -NR101R102; the above chemical formula 2; Or, the chemical formula 3 is as above, and R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, and any one of R1 to R10 may be the chemical formula 2; or the chemical formula 3.

[0098] In another embodiment of the present invention, R1 to R10 are the same as or different from each other, and each independently represent hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; the above formula 2; or the above formula 3, and any one of R1 to R10 may be the above formula 2; or the above formula 3.

[0099] In another embodiment of the present invention, R1 to R4 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0100] In another embodiment of the present invention, R5 to R10 are different from each other and each independently represent hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; the above formula 2; or formula 3, and any one of R5 to R10 may be the above formula 2; or formula 3.

[0101] In another embodiment of the present invention, R5 to R10 are different from each other and each independently represent hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; the above formula 2; or formula 3, and any one of R5 to R10 may be the above formula 2; or formula 3.

[0102] In another embodiment of the present invention, R5 to R10 are different from each other and each independently represent hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; the above formula 2; or formula 3, and any one of R5 to R10 may be the above formula 2; or formula 3.

[0103] In another embodiment of the present invention, R5 to R10 are different from each other and each independently represent hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted pyridinyl group; the above formula 2; or the above formula 3, and any one of R5 to R10 may be the above formula 2; or the above formula 3.

[0104] In another embodiment of the present invention, R5 to R10 are different from each other and can each independently be hydrogen; deuterium; a phenyl group; a naphthyl group; a pyridinyl group; the above chemical formula 2; or chemical formula 3, and any one of R5 to R10 can be the above chemical formula 2; or chemical formula 3.

[0105]

[0106] In one embodiment of the present invention, R11 to R14 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -SiR101R102R103; or -NR101R102, or two or more adjacent groups bond to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; Or form a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0107] In another embodiment of the present invention, R11 to R14 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -SiR101R102R103; or -NR101R102, or two or more adjacent groups bond to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; Or form a substituted or unsubstituted C2 to C20 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0108] In another embodiment of the present invention, R11 to R14 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -SiR101R102R103; Or -NR101R102, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0109] In another embodiment of the present invention, R11 to R14 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0110] In another embodiment of the present invention, R11 may be hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0111] In another embodiment of the present invention, R11 may be hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0112] In another embodiment of the present invention, R11 may be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0113] In another embodiment of the present invention, R11 may be hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted pyridinyl group.

[0114] In another embodiment of the present invention, R12 may be hydrogen or deuterium.

[0115] In another embodiment of the present invention, R13 and R14 may be the same as or different from each other, and may each independently be 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.

[0116] In another embodiment of the present invention, R13 and R14 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0117] In another embodiment of the present invention, R13 and R14 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0118] In another embodiment of the present invention, R13 and R14 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted pyridinyl group.

[0119] In another embodiment of the present invention, R13 and R14 may be the same as or different from each other, and may each independently be a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted pyridinyl group.

[0120]

[0121] In one embodiment of the present invention, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0122] In another embodiment of the present invention, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0123] In another embodiment of the present invention, L1 may 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 pyridinylene group.

[0124] In another embodiment of the present invention, L2 may 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 pyridinylene group; a substituted or unsubstituted pyrimidylene group; a substituted or unsubstituted furanylene group; or a substituted or unsubstituted thiophenylene group.

[0125]

[0126] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-3.

[0127] [Chemical Formula 1-1]

[0128]

[0129] [Chemical Formula 1-2]

[0130]

[0131] [Chemical Formula 1-3]

[0132]

[0133] In the above chemical formulas 1-1 to 1-3,

[0134] wherein R21 and R22 are the same as or different from each other, and each independently represent hydrogen; deuterium; 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; -SiR101R102R103; and -NR101R102, or are selected from the group consisting of two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; Or forms a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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,

[0135] The above d1 is an integer from 0 to 2, and when the above d1 is 2 or greater, R21 are equal to or different from each other,

[0136] The above d2 is an integer from 0 to 1,

[0137] The above e1 is an integer from 0 to 4, and when the above e1 is 2 or more, R22 are equal to or different from each other,

[0138] The above e2 is an integer from 0 to 3, and when the above e2 is 2 or greater, R22 are equal to or different from each other,

[0139] The above Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0140] The above R1 to R4 are the same as the definition of the above chemical formula 1,

[0141] The above L1, R11, R12, a and b are the same as defined in the above chemical formula 2.

[0142]

[0143] In one embodiment of the present invention, R21 and R22 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; -SiR101R102R103; or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; Or form a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0144] In another embodiment of the present invention, R21 and R22 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; -SiR101R102R103; or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; Or form a substituted or unsubstituted C2 to C20 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0145] In another embodiment of the present invention, R21 and R22 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; -SiR101R102R103; or -NR101R102, and R101, R102, and R103 are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.

[0146] In another embodiment of the present invention, R21 and R22 may be the same as or different from each other, and may each independently be hydrogen or deuterium.

[0147]

[0148] In one embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0149] In another embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0150] In another embodiment of the present invention, Ar1 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted pyridinyl group.

[0151] In another embodiment of the present invention, Ar1 may be a phenyl group; a naphthyl group; or a pyridinyl group.

[0152]

[0153] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-1 may be represented by the following chemical formula 1-1a or chemical formula 1-1b, the heterocyclic compound represented by the chemical formula 1-2 may be represented by the following chemical formula 1-2a, and the heterocyclic compound represented by the chemical formula 1-3 may be represented by the following chemical formula 1-3a.

[0154] [Chemical Formula 1-1a]

[0155]

[0156] [Chemical Formula 1-1b]

[0157]

[0158] [Chemical Formula 1-2a]

[0159]

[0160] [Chemical Formula 1-3a]

[0161]

[0162] In the above chemical formulas 1-1a, 1-1b, 1-2a and 1-3a,

[0163] The above R1 to R4 are the same as the definition of the above chemical formula 1,

[0164] The above L1, R11, R12, a and b are the same as the definitions in the above chemical formula 2,

[0165] The above R21, R22, Ar1, d1, e1 and e2 are the same as the definitions of the above chemical formulas 1-1 to 1-3.

[0166]

[0167] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be represented by any one of the following chemical formulas 1-4 to 1-6.

[0168] [Chemical Formula 1-4]

[0169]

[0170] [Chemical Formula 1-5]

[0171]

[0172] [Chemical Formula 1-6]

[0173]

[0174] In the above chemical formulas 1-4 to 1-6,

[0175] wherein R31 and R32 are the same as or different from each other, and each independently represent hydrogen; deuterium; 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; -SiR101R102R103; and -NR101R102, or are selected from the group consisting of two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; Or forms a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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,

[0176] The above f1 is an integer from 0 to 2, and when the above f1 is 2 or greater, R31 are equal to or different from each other,

[0177] The above f2 is an integer from 0 to 1,

[0178] The above g1 is an integer from 0 to 4, and when the above g1 is 2 or more, R32 are equal to or different from each other,

[0179] The above g2 is an integer from 0 to 3, and when the above g2 is 2 or more, R32 are equal to or different from each other,

[0180] The above Ar2 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0181] The above R1 to R4 are the same as the definition of the above chemical formula 1,

[0182] The above L2, R13, R14 and c are the same as defined in the above chemical formula 3.

[0183]

[0184] In one embodiment of the present invention, R31 and R32 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; -SiR101R102R103; or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; Or form a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0185] In another embodiment of the present invention, R31 and R32 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; -SiR101R102R103; or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; Or form a substituted or unsubstituted C2 to C20 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0186] In another embodiment of the present invention, R31 and R32 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; -SiR101R102R103; or -NR101R102, and R101, R102, and R103 are the same as or different from each other, and each independently represent a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; Or it may be a substituted or unsubstituted C2 to C20 heteroaryl group.

[0187] In another embodiment of the present invention, R31 and R32 may be the same as or different from each other, and may each independently be hydrogen or deuterium.

[0188]

[0189] In one embodiment of the present invention, Ar2 may be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0190] In another embodiment of the present invention, Ar2 may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0191] In another embodiment of the present invention, Ar2 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted pyridinyl group.

[0192] In another embodiment of the present invention, Ar2 may be a phenyl group; a naphthyl group; or a pyridinyl group.

[0193]

[0194] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-4 may be represented by the following chemical formula 1-4a or chemical formula 1-4b, the heterocyclic compound represented by the chemical formula 1-5 may be represented by the following chemical formula 1-5a, and the heterocyclic compound represented by the chemical formula 1-6 may be represented by the following chemical formula 1-6a.

[0195] [Chemical Formula 1-4a]

[0196]

[0197] [Chemical Formula 1-4b]

[0198]

[0199] [Chemical Formula 1-5a]

[0200]

[0201] [Chemical Formula 1-6a]

[0202]

[0203] In the above chemical formulas 1-4a, 1-4b, 1-5a and 1-6a,

[0204] The above R1 to R4 are the same as the definition of the above chemical formula 1,

[0205] The above L2, R13, R14 and c are the same as the definitions in the above chemical formula 3,

[0206] The above R31, R32, Ar2, f1, g1 and g2 are the same as the definitions of the above chemical formulas 1-4 to 1-6.

[0207]

[0208] In one embodiment of the present invention, all of R1 to R14, R21, R22, R31, R32, L1, L2, Ar1 and Ar2 may include non-deuterated hydrogen (H).

[0209] In another embodiment of the present invention, at least one of R1 to R14, R21, R22, R31, R32, L1, L2, Ar1 and Ar2 may contain deuterium (D), and at least one of R1 to R14, R21, R22, R31, R32, L1, L2, Ar1 and Ar2 may contain non-deuterated hydrogen.

[0210] In another embodiment of the present invention, all of R1 to R14, R21, R22, R31, R32, L1, L2, Ar1 and Ar2 may contain deuterium.

[0211]

[0212] In one embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0213] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0214] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0215] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0216] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0217]

[0218] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be represented by any one of the following compounds.

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240] In addition, by introducing various substituents into the structure of the heterocyclic compound represented by the above chemical formula 1, it is possible to synthesize a compound having the unique characteristics of the introduced substituent. For example, by introducing a substituent mainly used in hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, electron blocking layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, it is possible to synthesize a material that satisfies the conditions required for each organic layer.

[0241] In addition, by introducing various substituents into the structure of the heterocyclic compound represented by the above chemical formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic substances and diversifying the uses of the material.

[0242] Meanwhile, the heterocyclic compound represented by the above chemical formula 1 has a high glass transition temperature (Tg) and thus excellent thermal stability. This increase in thermal stability is an important factor in providing operating stability to the device.

[0243] The heterocyclic compound represented by the above chemical formula 1 according to one embodiment of the present invention can be prepared through a multi-step chemical reaction. Some intermediate compounds are prepared first, and the heterocyclic compound represented by the above chemical formula 1 can be prepared from the intermediate compounds. More specifically, the heterocyclic compound represented by the above chemical formula 1 according to one embodiment of the present invention can be prepared based on the preparation example described below.

[0244]

[0245] Another embodiment of the present invention provides an organic light-emitting device comprising a heterocyclic compound represented by the above chemical formula 1. The “organic light-emitting device” may be expressed by terms such as “organic light-emitting diode”, “OLED (Organic Light Emitting Diodes)”, “OLED device”, and “organic electroluminescent device”.

[0246]

[0247] In addition, the present invention

[0248] First electrode;

[0249] A second electrode provided opposite to the first electrode; and

[0250] An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode,

[0251] An organic light-emitting device is provided, wherein at least one of the organic layers comprises a heterocyclic compound represented by the chemical formula 1.

[0252]

[0253] In one embodiment of the present invention, the first electrode may be an anode, and the second electrode may be a cathode.

[0254] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0255]

[0256] In one embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material for the blue organic light-emitting device. For example, the heterocyclic compound represented by the chemical formula 1 may be included in an electron transport layer or a charge generation layer of the blue organic light-emitting device.

[0257] In another embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material of the green organic light-emitting device. For example, the heterocyclic compound represented by the chemical formula 1 may be included in an electron transport layer or a charge generation layer of the green organic light-emitting device.

[0258] In another embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material of the red organic light-emitting device. For example, the heterocyclic compound represented by the chemical formula 1 may be included in an electron transport layer or a charge generation layer of the red organic light-emitting device.

[0259] The specific details of the heterocyclic compound represented by the above chemical formula 1 are the same as described above.

[0260]

[0261] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the heterocyclic compound represented by the above-described chemical formula 1.

[0262] The heterocyclic compound represented by the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0263] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, an electron blocking layer, a hole transport layer, a light-emitting layer, an electron transport layer, a hole blocking layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0264] 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 a heterocyclic compound represented by the chemical formula 1.

[0265] In the organic light-emitting device of the present invention, the organic layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include a heterocyclic compound represented by the chemical formula 1.

[0266] In the organic light-emitting device of the present invention, the organic layer includes an electron transport layer, and the electron transport layer may include a heterocyclic compound represented by the chemical formula 1.

[0267] In another organic light-emitting device, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound represented by the chemical formula 1.

[0268] In another organic light-emitting device, the organic layer includes an electron transport layer, an emission layer, or a hole blocking layer, and the electron transport layer, the emission layer, or the hole blocking layer may include a heterocyclic compound represented by the chemical formula 1.

[0269] The organic light-emitting device of the present invention may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole auxiliary layer, and a hole blocking layer.

[0270]

[0271] The stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present application is exemplified in Figures 1 to 3. However, the scope of the present application is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present application.

[0272] According to FIG. 1, an organic light-emitting device is illustrated in which an anode (200), an organic layer (300), and a cathode (400) are sequentially laminated on a substrate (100). However, the present invention is not limited to this structure, and an organic light-emitting device in which a cathode, an organic layer, and an anode are sequentially laminated on a substrate, as shown in FIG. 2, may also be implemented.

[0273] Fig. 3 illustrates a case where the organic layer is multilayered. 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, the scope of the present application is not limited by such a laminated structure, and, if necessary, the remaining layers except for the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0274]

[0275] In addition, in one embodiment of the present invention, the organic light-emitting element,

[0276] anode;

[0277] cathode; and

[0278] comprising two or more stacks provided between the positive and negative electrodes;

[0279] The above two or more stacks each independently include a light-emitting layer,

[0280] A charge generation layer is included between the two or more stacks,

[0281] The charge generation layer includes a heterocyclic compound represented by the chemical formula 1.

[0282]

[0283] In addition, in one embodiment of the present invention, the organic light-emitting element,

[0284] First electrode;

[0285] A first stack provided on the first electrode and including a first light-emitting layer;

[0286] A charge generation layer provided on the first stack;

[0287] A second stack provided on the charge generation layer and including a second light-emitting layer; and

[0288] It includes a second electrode provided on the second stack.

[0289] At this time, the charge generation layer may include a heterocyclic compound represented by the chemical formula 1. In addition, the first stack and the second stack may each independently additionally include one or more of the aforementioned hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer, etc.

[0290] The above charge generation layer may be an N-type charge generation layer, and the N-type charge generation layer may include a heterocyclic compound represented by the above chemical formula 1. In addition, the N-type charge generation layer may additionally include a dopant known in the art in addition to the heterocyclic compound represented by the above chemical formula 1.

[0291]

[0292] As an organic light-emitting device according to one embodiment of the present invention, an organic light-emitting device having a 2-stack tandem structure is schematically illustrated in FIG. 4.

[0293]

[0294] An organic light-emitting device according to the present specification can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes a heterocyclic compound represented by the chemical formula 1.

[0295] The organic layer including the heterocyclic compound represented by the above chemical formula 1 may additionally include other substances as needed.

[0296] The heterocyclic compound represented by the above chemical formula 1 can be used as a material of a charge generation layer in an organic light-emitting device.

[0297]

[0298] In addition, the present invention provides a composition for an organic layer of an organic light-emitting device comprising a heterocyclic compound represented by the above chemical formula 1.

[0299] The specific details of the heterocyclic compound represented by the above chemical formula 1 are the same as described above.

[0300] The composition for the organic layer of the above organic light-emitting device can be used when forming the organic layer of the organic light-emitting device, and in particular, can be more preferably used when forming an electron transport layer or a charge generation layer.

[0301]

[0302] In one embodiment of the present invention, the organic layer includes a heterocyclic compound represented by the chemical formula 1 and can be used together with a phosphorescent dopant.

[0303] As the above phosphorescent dopant material, those known in the art can be used. For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L2MX', and L3M can be used, but the scope of the present invention is not limited by these examples.

[0304] The above M can be iridium, platinum, osmium, etc.

[0305] The above L is sp 2 An anionic two-dentate ligand coordinated to M by carbon and heteroatoms, and X can perform the function of trapping electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothiophenylpyridine, 3-methoxy-2-phenylpyridine, thiophenylpyridine, tolylpyridine, etc. Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, etc.

[0306]

[0307] In one embodiment of the present invention, the organic layer includes a heterocyclic compound represented by the chemical formula 1, and can be used together with an iridium-based dopant.

[0308]

[0309] In one embodiment of the present invention, the iridium-based dopant may be (piq)2(Ir)(acac) as a red phosphorescent dopant, FIrpic as a blue phosphorescent dopant, or Ir(ppy)3 as a green phosphorescent dopant.

[0310]

[0311] In one embodiment of the present invention, the content of the dopant may be 1% to 15%, preferably 2% to 10%, and more preferably 3% to 7% based on the total weight of the light-emitting layer.

[0312]

[0313] The present invention,

[0314] Steps to prepare the substrate;

[0315] A step of forming a first electrode on the substrate;

[0316] A step of forming one or more organic layers on the first electrode; and

[0317] A method for manufacturing an organic light-emitting device, comprising: forming a second electrode on the organic layer of one or more layers; wherein the step of forming the organic layer of one or more layers includes forming the organic layer of one or more layers using a composition for an organic layer of an organic light-emitting device according to one embodiment of the present invention.

[0318]

[0319] In one embodiment of the present invention, the step of forming the organic layer may be to form the heterocyclic compound represented by the chemical formula 1 using a thermal vacuum deposition method.

[0320] The organic layer including the heterocyclic compound represented by the above chemical formula 1 may additionally include other substances as needed.

[0321]

[0322] In the organic light-emitting device according to one embodiment of the present invention, materials other than the heterocyclic compound represented by the above chemical formula 1 are exemplified below, but these are only for exemplification and are not intended to limit the scope of the present application, and may be replaced with materials known in the art.

[0323]

[0324] Materials having a relatively large work function can be used as the anode material, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0325]

[0326] Materials with relatively low work functions can be used as cathode materials, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0327]

[0328] As the hole injection layer material, a known hole injection layer material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a starburst amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), a soluble conductive polymer such as polyaniline / dodecylbenzenesulfonic acid, or Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate) can be used.

[0329]

[0330] Pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport layer materials, and low molecular weight or high molecular weight materials can also be used.

[0331]

[0332] As the electron transport layer material, metal complexes of oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, etc. can be used, and not only low molecular weight substances but also high molecular weight substances can be used.

[0333]

[0334] For example, LiF is typically used as an electron injection layer material in the art, but the present application is not limited thereto.

[0335]

[0336] Red, green, or blue light-emitting materials can be used as the light-emitting layer material, and if necessary, two or more light-emitting materials can be mixed and used. At this time, two or more light-emitting materials can be deposited and used as individual sources, or can be pre-mixed and deposited and used as a single source. In addition, a fluorescent material can be used as the light-emitting layer material, but a phosphorescent material can also be used. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, can be used as the light-emitting layer material, but materials in which both the host material and the dopant material participate in light emission can also be used.

[0337]

[0338] When using a mixture of host materials for the light-emitting layer, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more types of materials, either n-type host materials or p-type host materials, may be selected and used as the host material for the light-emitting layer.

[0339]

[0340] An organic light-emitting device according to one embodiment of the present invention may be a front-emitting, back-emitting, or double-sided emitting device depending on the material used.

[0341]

[0342] The heterocyclic compound according to one embodiment of the present invention can function in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.

[0343]

[0344] Hereinafter, preferred examples are presented to help understand the present invention, but the following examples are provided only to make it easier to understand the present invention and the present invention is not limited thereto.

[0345]

[0346] <Manufacturing Example>

[0347] Manufacturing Example 1. Preparation of Compound 1

[0348]

[0349]

[0350] Manufacturing Example 1-1. Manufacturing of Compound 1-1

[0351] 3-iodo-2-methoxydibenzo[b,d]furan (30 g, 0.093 mol, 1 eq), (2-fluorophenyl)boronic acid (14.3 g, 0.102 mol, 1.1 eq), Pd(dba)2 (1.7 g 0.003 mol, 0.03 eq), XPhos (2.9 g, 0.006 mol, 0.06 eq), K2CO3 (32.2 g, 0.233 mol, 2.5 eq), 1,4-dioxane (300 mL), and distilled water (60 mL) were added and stirred at 100°C for 4 hours.

[0352] After the reaction was terminated by adding distilled water, extraction was performed using dichloromethane and distilled water, and moisture was removed with MgSO4. Afterwards, separation was performed using a silica gel column to obtain 25.4 g (yield 93%) of compound 1-1.

[0353]

[0354] Manufacturing Example 1-2. Preparation of Compound 1-2

[0355] Compound 1-1 (25.4 g, 0.087 mol, 1 eq), tribromoborane (32.8 g, 0.131 mol, 1.5 eq) and dichloromethane (375 mL) were added and stirred at room temperature for 2 hours.

[0356] After the reaction was terminated by adding distilled water, extraction was performed using dichloromethane and distilled water, and moisture was removed with MgSO4. After separation using a silica gel column, 22.5 g (yield 93%) of compound 1-2 was obtained.

[0357]

[0358] Manufacturing Example 1-3. Preparation of Compound 1-3

[0359] Compound 1-2 (22.5 g, 0.081 mol, 1 eq) and chloroform (225 mL) were added and stirred, then N-bromosuccinimide (14.2 g, 0.089 mol, 1.1 eq) and chloroform (225 mL) were added and stirred at room temperature for 2 hours.

[0360] After the reaction was terminated by adding distilled water, extraction was performed using dichloromethane and distilled water, and moisture was removed with MgSO4. After separation using a silica gel column, 27.5 g (yield 95%) of compounds 1-3 were obtained.

[0361]

[0362] Manufacturing Example 1-4. Preparation of Compound 1-4

[0363] Compound 1-3 (27.5 g, 0.077 mol, 1 eq) and N,N-dimethylacetamide (275 mL) were added and stirred at 120°C. Then, Cs2CO3 (50.2 g 0.154 mol, 2.0 eq) was added and stirred for 2 hours under reflux.

[0364] After adding distilled water to terminate the reaction, filtration was performed to obtain 24.6 g (yield 95%) of crystallized compound 1-4.

[0365]

[0366] Manufacturing Example 1-5. Preparation of Compound 1-5

[0367] Compound 1-4 (24.6 g, 0.073 mol, 1 eq), B2pin2 (27.9 g, 0.110 mol, 1.5 eq), Pd(dppf)Cl2 (2.9 g, 0.004 mol, 0.05 eq), KOAc (21.5 g, 0.219 mol, 3.0 eq), and 1,4-dioxane (246 mL) were added and stirred at 100°C for 4 hours.

[0368] After the reaction was terminated by adding distilled water, extraction was performed using dichloromethane and distilled water, and moisture was removed with MgSO4. After separation using a silica gel column, 23.8 g (yield 85%) of compounds 1-5 were obtained.

[0369]

[0370] Manufacturing Example 1-6. Preparation of Compound 1

[0371] Compound 1-5 (10 g, 0.026 mol, 1 eq), 2-bromo-1,10-phenanthroline (7.5 g, 0.029 mol, 1.1 eq), Pd(PPh3)4 (1.2 g, 0.001 mol, 0.05 eq), K2CO3 (7.2 g, 0.052 mol, 2.0 eq), 1,4-dioxane (100 mL), and distilled water (20 mL) were added and stirred at 100°C for 4 hours.

[0372] After the reaction was terminated by adding distilled water, extraction was performed using dichloromethane and distilled water, and moisture was removed with MgSO4. After separation using a silica gel column, 9.2 g (80% yield) of compound 1 was obtained.

[0373]

[0374] The target compound of Table 1 was synthesized by the same method as in Manufacturing Example 1, except that Compound A of Table 1 was used instead of (2-fluorophenyl)boronic acid in Manufacturing Example 1, and Compound B of Table 1 was used instead of 2-bromo-1,10-phenanthroline.

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382] Manufacturing Example 2. Preparation of Compound 14

[0383]

[0384]

[0385] The preparation of compounds 1-1 to 1-4 was carried out in the same manner as in Preparation Example 1 above.

[0386] Compound 1-4 (10 g, 0.030 mol, 1 eq), diphenylphosphine oxide (6.7 g, 0.084 mol, 1.1 eq), Pd(PPh3)4 (2.3 g 0.002 mol, 0.05 eq), Et3N (16.5 g, 0.168 mol, 2.0 eq), and toluene (100 mL) were added and stirred under reflux conditions for 20 hours.

[0387] After the reaction was terminated by adding distilled water, extraction was performed using dichloromethane and distilled water, and moisture was removed with MgSO4. After separation using a silica gel column, 8.2 g (yield 60%) of compound 14 was obtained.

[0388]

[0389] The target compound of Table 2 was synthesized using the same method as in Manufacturing Example 2, except that Compound C of Table 2 was used instead of (2-fluorophenyl)boronic acid in Manufacturing Example 2, and Compound D of Table 2 was used instead of diphenylphosphine oxide.

[0390]

[0391]

[0392]

[0393] Manufacturing Example 3. Preparation of Compound 6

[0394]

[0395]

[0396] Compounds 6-1 and 6-2 were prepared in the same manner as in Preparation Examples 1-1 and 1-2, except that (4-bromo-2-fluorophenyl)boronic acid was used instead of (2-fluorophenyl)boronic acid.

[0397] In addition, compound 6-3 was prepared in the same manner as in Manufacturing Example 1-4, except that compound 6-2 was used instead of compound 1-3.

[0398] In addition, compound 6-4 was prepared in the same manner as in Manufacturing Example 1-5, except that compound 6-3 was used instead of compound 1-4.

[0399] In addition, compound 6-4 was prepared in the same manner as in Manufacturing Example 1-6, except that compound 6-4 was used instead of compound 1-5.

[0400]

[0401] The target compound of Table 3 was synthesized in the same manner as in Manufacturing Example 3, except that Compound E of Table 3 was used instead of (4-bromo-2-fluorophenyl)boronic acid in Manufacturing Example 3, and Compound F of Table 3 was used instead of 2-bromo-1,10-phenanthroline.

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408] Manufacturing Example 4. Preparation of Compound 18

[0409]

[0410]

[0411] Compounds 6-1 and 6-2 were prepared in the same manner as in Preparation Examples 1-1 and 1-2, except that (4-bromo-2-fluorophenyl)boronic acid was used instead of (2-fluorophenyl)boronic acid.

[0412] In addition, compound 6-3 was prepared in the same manner as in Manufacturing Example 1-4, except that compound 6-2 was used instead of compound 1-3.

[0413] In addition, compound 18 was prepared in the same manner as in Preparation Example 2, except that compound 6-3 was used instead of compound 1-4.

[0414]

[0415] The target compound of Table 4 was synthesized in the same manner as in Manufacturing Example 4, except that Compound G of Table 4 was used instead of (4-bromo-2-fluorophenyl)boronic acid in Manufacturing Example 4, and Compound H of Table 4 was used instead of diphenylphosphine oxide.

[0416]

[0417]

[0418]

[0419] Manufacturing Example 5. Preparation of Compound 225

[0420]

[0421]

[0422] Manufacturing Example 5-1. Manufacturing of Compound 225-2

[0423] Dibenzo[b,d]furan-2-ol (100 g, 0.543 mol, 1 eq) and acetic acid (400 mL) were added and stirred. Iodine monochloride (88.2 g, 0.543 mol, 1 eq), HCl (130 mL) and acetic acid (230 mL) were mixed and added to the solution, which was stirred at room temperature for 12 hours.

[0424] After the reaction was terminated by adding 3 L of distilled water, the resulting solid was filtered and separated using a silica gel column to obtain 102.6 g (yield 61%) of compound 225-1.

[0425] Compound 225-2 was obtained by performing the same procedure as in Manufacturing Example 1-1 except that phenyl boronic acid was used instead of (2-fluorophenyl) boronic acid.

[0426]

[0427] Manufacturing Example 5-2. Preparation of Compound 225-3

[0428] Compound 225-2 (65 g, 0.250 mol, 1 eq) and 4-bromo-2-fluoro-1-iodobenzene (90 g, 0.300 mol, 1.2 eq) were dissolved in N,N-dimethylacetamide (900 mL) and heated to 150°C. Cs2CO3 (162.9 g, 0.500 mol, 2.0 eq) was then added and stirred at 150°C for 2 hours.

[0429] After the reaction was terminated by adding distilled water, extraction was performed using dichloromethane and distilled water, and moisture was removed with MgSO4. After separation using a silica gel column, 115 g (yield 85%) of compound 225-3 was obtained.

[0430]

[0431] Manufacturing Example 5-3. Preparation of Compound 225

[0432] Compound 225-3 (40 g, 0.074 mol, 1 eq), Pd(PPh3)4 (4.6 g, 0.004 mol, 0.05 eq), KOAc (14.5 g, 0.148 mol, 1.2 eq) and N,N-dimethylformamide (400 mL) were added and stirred under reflux for 12 hours.

[0433] After the reaction was terminated by adding distilled water, extraction was performed using dichloromethane and distilled water, and moisture was removed with MgSO4. After separation using a silica gel column, 23.1 g (yield 75%) of compound 225-4 was obtained.

[0434] Compound 225-5 was prepared in the same manner as in Manufacturing Example 1-5, except that compound 225-4 was used instead of compound 1-4.

[0435] In addition, compound 225 was prepared in the same manner as in Preparation Example 1-6, except that compound 225-5 was used instead of compound 1-5, and 2-bromo-9-phenyl-1,10-phenanthroline was used instead of 2-bromo-1,10-phenanthroline.

[0436]

[0437] The target compound of Table 5 below was synthesized in the same manner as in Manufacturing Example 5, except that Compound I of Table 5 below was used instead of phenylboronic acid in Manufacturing Example 5, Compound J of Table 5 was used instead of 4-bromo-2-fluoro-1-iodobenzene, and Compound K of Table 5 was used instead of 2-bromo-9-phenyl-1,10-phenanthroline.

[0438]

[0439]

[0440]

[0441] Manufacturing Example 6. Preparation of Compound 238

[0442]

[0443]

[0444] Compounds 225-1 to 225-4 were manufactured in the same manner as in Manufacturing Example 5 above.

[0445] Additionally, compound 238 was prepared in the same manner as in Manufacturing Example 2, except that compound 225-4 was used instead of compound 1-4.

[0446]

[0447] The target compound of Table 6 was synthesized in the same manner as in Manufacturing Example 6, except that Compound L of Table 6 was used instead of phenylboronic acid, Compound M of Table 6 was used instead of 4-bromo-2-fluoro-1-iodobenzene, and Compound N of Table 6 was used instead of diphenylphosphine oxide.

[0448]

[0449]

[0450]

[0451] Manufacturing Example 7. Preparation of Compound 23

[0452]

[0453]

[0454] Compound 10 (8 g, 0.016 mol, 1 eq), D6-benzene (80 mL), and triflic acid (9.6 mL, 0.109 mol, 7.0 eq) were added and stirred at 60°C for 1 hour.

[0455] After the reaction was terminated by adding distilled water, extraction was performed using dichloromethane and distilled water, and moisture was removed with MgSO4. After separation using a silica gel column, 7.5 g (yield 90%) of compound 23 was obtained.

[0456]

[0457] The target compound of Table 7 below was synthesized by the same method as in Manufacturing Example 7 above, except that Compound O of Table 7 below was used instead of Compound 10 in Manufacturing Example 7 above.

[0458]

[0459]

[0460]

[0461] The results of the synthesis of the compounds described in Manufacturing Examples 1 to 7 and Tables 1 to 7 are shown in Tables 8 and 9 below.

[0462] Table 8 below 1 The values ​​are measured by H NMR (DMSO, 200 MHz), and Table 9 below is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469] Compound FD-MS Compound FD-MS 1 m / z = 436.12 (C 30 H 16 N2O2= 436.47)2m / z= 512.15 (C 36 H 20 N2O2= 512.57)4m / z= 513.15 (C 35 H 19 N3O2=513.56)6m / z= 436.12 (C 30 H 16 N2O2=436.47)7m / z= 512.15 (C 36 H 20 N2O2=512.57)8m / z= 513.15 (C 35 H 19 N3O2= 513.56)10m / z= 512.15 (C 36 H 20 N2O2=512.57)11m / z= 562.17 (C 40 H 22 N2O2=562.63)13m / z= 334.08 (C 20 H 15 O3P=334.31)14m / z= 458.11 (C 30 H 19 O3P=458.45)15m / z= 460.10 (C 28 H 17 N2O3P=460.43)18m / z= 458.11(C<h2 style=";text-align:left;direction:ltr"> 30 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 19 <h2 style=";text-align:left;direction:ltr"> O3P= 458.45)19m / z= 334.08(C<h2 style=";text-align:left;direction:ltr"> 20 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 15 <h2 style=";text-align:left;direction:ltr"> O3P= 334.31)23m / z= 531.27 (C<h2 style=";text-align:left;direction:ltr"> 36 <h2 style=";text-align:left;direction:ltr"> HD<h2 style=";text-align:left;direction:ltr"> 19 <h2 style=";text-align:left;direction:ltr"> N2O2 = 531.68)26m / z = 512.15 (C<h2 style=";text-align:left;direction:ltr"> 36 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 20 <h2 style=";text-align:left;direction:ltr"> N2O2 = 512.57)27m / z = 588.18 (C<h2 style=";text-align:left;direction:ltr"> 42 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> N2O2 = 588.67)29m / z = 664.22 (C<h2 style=";text-align:left;direction:ltr"> 48 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> N2O2 = 664.76)34m / z = 638.20 (C<h2 style=";text-align:left;direction:ltr"> 46 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> N2O2 = 638.73)37m / z = 512.15(C<h2 style=";text-align:left;direction:ltr"> 36 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 20 <h2 style=";text-align:left;direction:ltr"> N2O2 = 512.57)38m / z = 588.18 (C<h2 style=";text-align:left;direction:ltr"> 42 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> N2O2 = 588.67)44m / z = 589.18 (C<h2 style=";text-align:left;direction:ltr"> 41 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> N3O2 = 589.65)46m / z = 588.18 (C<h2 style=";text-align:left;direction:ltr"> 42 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> N2O2 = 588.67)52m / z = 588.18 (C<h2 style=";text-align:left;direction:ltr"> 42 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> N2O2 = 588.67)66 m / z = 512.15 (C<h2 style=";text-align:left;direction:ltr"> 36 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 20 <h2 style=";text-align:left;direction:ltr"> N2O2 = 512.57)67m / z = 588.18(C<h2 style=";text-align:left;direction:ltr"> 42 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> N2O2 = 588.67)68m / z = 666.23 (C<h2 style=";text-align:left;direction:ltr"> 48 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 30 <h2 style=";text-align:left;direction:ltr"> N2O2 = 666.78)73m / z = 588.18 (C<h2 style=";text-align:left;direction:ltr"> 42 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> N2O2 = 588.67)83m / z = 588.18 (C<h2 style=";text-align:left;direction:ltr"> 42 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> N2O2 = 588.67)87m / z = 638.20 (C<h2 style=";text-align:left;direction:ltr"> 46 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> N<h2 style=";text-align:left;direction:ltr"> 2O2= 638.73)89m / z= 588.18 (C 42 H 24 N2O2= 588.67)98m / z= 588.18 (C 42 H 24 N2O2= 588.67)114m / z= 410.11 (C 26 H 19 O3P= 410.41)115m / z= 534.14(C 36 H 23 O3P= 534.55)117m / z= 584.15 (C 40 H 25 O3P= 584.61)122m / z= 610.17 (C 42 H 27 O3P= 610.65)126m / z= 534.14 (C 36 H 23 O3P= 534.55)132m / z= 534.14(C 36 H 23 O3P= 534.55)137m / z= 534.14 (C 36 H 23 O3P= 534.55)150m / z= 410.11 (C 26 H 19 O3P= 410.41)151m / z= 534.14 (C 36 H 23 O3P= 534.55)152m / z= 535.13 (C 35 H 22 NO3P= 535.54)170m / z= 534.14 (C 36 H 23 O3P= 534.55)205m / z= 610.32(C 42 H2D 22 N2O2= 610.80)209m / z= 557.28 (C 36 D 23 O3P= 557.69)216m / z= 588.18 (C 42 H 24 N2O2= 588.67)217m / z= 589.18 (C 41 H 23 N3O2= 589.65)218m / z= 588.18 (C 42 H24 N2O2= 588.67)225m / z= 588.18 (C 42 H 24 N2O2= 588.67)227m / z= 588.18 (C 42 H 24 N2O2= 588.67)235m / z= 534.14 (C 36 H 23 O3P= 534.55)238m / z= 534.14 (C 36 H 23 O3P= 534.55)243m / z= 534.14 (C 36 H 23 O3P= 534.55)248m / z= 557.28 (C 36 D 23 O3P= 557.69)254m / z= 664.22 (C 48 H 28 N2O2= 664.76)282m / z= 664.22 (C 48 H 28 N2O2= 664.76)321m / z= 686.20 (C 48 H 31 O3P= 686.75)352m / z= 686.20 (C 48 H 31 O3P= 686.75)359m / z= 610.17 (C 42 H 27 O3P= 610.65)

[0470]

[0471] <Experimental Example>

[0472] Experimental Example 1.

[0473] Experimental Example 1-1. Fabrication of an Organic Light-Emitting Device

[0474] An indium tin oxide (ITO) thin film for a transparent electrode obtained from glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned sequentially using trichloroethylene, acetone, ethanol, and distilled water for 5 minutes each, and then stored in isopropanol before use. Next, the ITO substrate was installed in the substrate folder of the vacuum deposition equipment, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added to the cell in the vacuum deposition equipment.

[0475]

[0476] Then the vacuum level inside the chamber is 10 -6 After evacuating to reach 10 torr, a current was applied to the cell to evaporate 2-TNATA and deposit a 600 Å thick hole injection layer on an ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was added to another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it and deposit a 300 Å thick hole transport layer on the hole injection layer.

[0477]

[0478] After forming the hole injection layer and the hole transport layer in this way, a blue light-emitting material having the following structure was deposited as a light-emitting layer thereon. Specifically, a blue light-emitting host material, H1, was vacuum-deposited to a thickness of 200 Å in one cell within a vacuum deposition device, and a blue light-emitting dopant material, D1, was vacuum-deposited thereon at a thickness of 5% relative to the host material.

[0479]

[0480] Next, a compound of the following structural formula E1 was deposited as an electron transport layer with a thickness of 300 Å.

[0481]

[0482] An organic light-emitting device was fabricated by depositing lithium fluoride (LiF) to a thickness of 10 Å as an electron injection layer and depositing Al to a thickness of 1,000 Å to form a cathode.

[0483] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0484] Comparative Example 1 used E1 as an electron transport layer, and an organic light-emitting device was manufactured in the same manner as Comparative Example 1, except that the compound shown in Table 10 below was used instead of E1.

[0485]

[0486] Experimental Example 1-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0487] The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured using M7000 from Max Science, and the standard luminance was determined to be 3,500 cd / m using the lifespan measurement equipment (M6000) manufactured by Max Science based on the measurement results. 2 The lifespan T is the time it takes for the initial luminance to reach 95% of its original brightness. 95 was measured.

[0488] The driving voltage, luminous efficiency and lifespan (T) of the green organic light-emitting device manufactured according to the above manufacturing method 95 ) are measured as shown in Table 10.

[0489]

[0490] Compound number, driving voltage (V), luminous efficacy (cd / A), CIE (x, y), lifetime (T) 95) Example 1 15.45 7.73 (0.134, 0.100) 83 Example 2 25.43 7.78 (0.133, 0.100) 85 Example 3 45.54 7.62 (0.133, 0.101) 81 Example 4 65.50 7.75 (0.132, 0.101) 87 Example 5 75.57 7.63 (0.133, 0.101) 90 Example 6 85.44 7.55 (0.135, 0.098) 83 Example 7 105.55 7.73 (0.130, 0.100) 89 Example 8 115.53 7.74 (0.132, 0.102)84 Example 9135.557.88(0.131, 0.100)83 Example 10145.567.75(0.134, 0.100)85 Example 11155.887.60(0.133, 0.100)80 Example 12185.447.68(0.132, 0.101)85 Example 13195.537.85(0.131, 0.103)83 Example 14235.337.75(0.132, 0.101)95 Example 15265.357.66(0.134, 0.101)88 Example 16275.407.77(0.134, 0.100)89 Example 17295.557.58(0.133, 0.099)83 Example 18345.477.63(0.134, 0.101)83 Example 19375.487.85(0.133, 0.100)83 Example 20385.517.90(0.132, 0.102)85 Example 21445.677.80(0.132, 0.101)81 Example 22465.707.63(0.134, 0.100)81 Example 23525.357.79(0.133, 0.100)83 Example 24665.417.82(0.134, 0.100)82 Example 25675.457.88(0.134, 0.101)83 Example 26685.567.68(0.132, 0.101)85 Example 27735.387.90(0.135, 0.101)85 Example 28835.357.83(0.130, 0.100)84 Example 29875.457.80(0.132, 0.101)82 Example 30895.487.85(0.133, 0.100)83 Example 31985.637.83(0.134, 0.101)84 Example 321145.377.93(0.134, 0.100)84 Example 33 1155.45 7.84 (0.134, 0.101)84 Example 34 1175.50 7.80 (0.133, 0.101)84 Example 35 1225.44 7.85 (0.133, 0.101)85 Example 36 1265.65 7.77 (0.132, 0.101)81 Example 37 1325.72 7.53 (0.134, 0.100)81 Example 38 1375.47 7.78 (0.133, 0.100)83 Example 39 1505.38 7.58 (0.135, 0.101)82 Example 401515.427.70(0.134, 0.101)82 Example 411525.667.54(0.134, 0.100)80 Example 421705.457.71(0.132, 0.101)82 Example 432055.407.80(0.133, 0.101)97 Example 442095.387.82(0.133, 0.100)97 Example 452165.677.78(0.132, 0.101)85 Example 462175.757.60(0.134, 0.101)81 Example 472185.737.70(0.133, 0.099)82 Example 482255.637.72(0.134, 0.100)82 Example 492275.507.75(0.134, 0.100)81 Example 502355.447.60(0.132, 0.101)80 Example 512385.487.60(0.134, 0.101)81 Example 522435.527.62(0.134, 0.100)81 Example 532485.557.65(0.134, 0.100)93 Example 542545.587.68(0.134, 0.101)83Example 552825.537.68(0.134, 0.101)84Example 563215.447.73(0.132, 0.102)83Example 573525.357.78(0.134, 0.100)83Example 583595.457.70(0.133, 0.100)82Comparative Example 1E16.236.42(0.134, 0.100)50Comparative Example 2Comparative Compound A6.766.35(0.134, 0.101)48Comparative Example 3Comparative Compound B6.586.38(0.132, 0.101)55Comparative Example 4Comparative Compound C6.936.34(0.133, 0.100)49Comparative Example 5 Comparative Compound D6.896.21(0.133, 0.100)47Comparative Example 6 Comparative Compound E6.856.20(0.134, 0.100)47Comparative Example 7 Comparative Compound F7.026.33(0.134, 0.100)49Comparative Example 8 Comparative Compound G7.086.30(0.134, 0.098)49Comparative Example 9 Comparative Compound H6.956.44(0.134, 0.101)50Comparative Example 10 Comparative Compound I7.136.13(0.134, 0.100)52Comparative Example 11 Comparative Compound J7.206.22(0.132, 0.098)32Comparative Example 12Comparative Compound K7.006.12(0.134, 0.100)35Comparative Example 13Comparative Compound L7.156.10(0.134, 0.103)36.

[0491]

[0492] [Comparative Compound]

[0493]

[0494]

[0495] From the results in Table 10 above, Examples 1 to 58, which are organic light-emitting devices using the heterocyclic compound represented by the chemical formula 1 as the electron transport layer material of the blue organic light-emitting device of the present invention, showed lower driving voltage and significantly improved luminous efficiency and lifespan than Comparative Examples 1 to 13.

[0496] The heterocyclic compound represented by the above chemical formula 1 of the present invention is judged to have a core structure with an appropriate electron transport ability, and the compound becomes more stable due to stable bonding with metals used in the cathode from the P=O functional group (chemical formula 3) or the phenanthroline functional group (chemical formula 2), so that the compound can efficiently transport electrons without decomposition or destruction. Therefore, the heterocyclic compound represented by the above chemical formula 1 of the present invention can improve electron transport characteristics and stability, and as a result, the organic light-emitting device can obtain results with low driving voltage, excellent luminous efficiency, and excellent lifespan.

[0497] Comparative compounds A, B, D and E of Comparative Examples 2, 3, 5 and 6 have a core structure containing carbazole having a hole transport ability, and Comparative compound I of Comparative Example 10 has a core structure of dimethylfluorene, which is different from the heterocyclic compound represented by the above-described chemical formula 1 of the present invention. Comparative compounds F, G, J, K and L of Comparative Examples 7, 8, 11 to 13 have the same core structure as the heterocyclic compound represented by the above-described chemical formula 1 of the present invention. However, Comparative compounds F and G of Comparative Examples 7 and 8 have an arylamine group having a low electron transport ability as a substituent, Comparative compound J of Comparative Example 11 contains two phosphine oxides which are metal-acceptors, and Comparative compounds K and L of Comparative Examples 12 and 13 have a triazine group having a high electron transport ability as a substituent. Comparative compounds C and H of Comparative Examples 4 and 9 contain sulfur as a heteroatom, which has a lower electron transport ability than oxygen.

[0498] For this reason, differences in electron transport capacity occur, and an inappropriate electron movement rate leads to a charge imbalance in the light-emitting layer. As a result, the comparative example showed a higher driving voltage and lower luminous efficiency and lifespan characteristics than the examples.

[0499]

[0500] Experimental example 2.

[0501] Experimental Example 2-1. Fabrication of an Organic Light-Emitting Device

[0502] A glass substrate coated with a 1500Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), and plasma treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0503] An organic material was formed in a 2-stack WOLED (White Organic Light Device) structure on the above ITO transparent electrode (anode). For the first stack, TAPC was first thermally vacuum-deposited to a thickness of 300 Å to form a hole transport layer. After forming the hole transport layer, an emission layer was thermally vacuum-deposited thereon as follows. The emission layer was deposited to a thickness of 300 Å by doping 8% of FIrpic as a blue phosphorescent dopant into the host TCz1. The electron transport layer was formed to a thickness of 400 Å using TmPyPB, and then the charge generation layer was formed to a thickness of 100 Å by doping 20% ​​of Cs2CO3 into the compounds listed in Table 11 below.

[0504] The second stack was first formed by thermally vacuum depositing MoO3 to a thickness of 50Å to form a hole injection layer. The common layer, the hole transport layer, was formed by doping TAPC with 20% MoO3 to a thickness of 100Å, and then depositing TAPC to a thickness of 300Å. On top of that, the emission layer was formed by doping TCz1, the host, with 8% Ir(ppy)3, a green phosphorescent dopant, and depositing it to a thickness of 300Å, and then using TmPyPB as the electron transport layer to form a thickness of 600Å. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron transport layer to form an electron injection layer, and then aluminum (Al) was deposited to a thickness of 1,200Å on the electron injection layer to form a cathode, thereby manufacturing an organic electroluminescent device.

[0505] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0506]

[0507]

[0508] Experimental Example 2-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0509] The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured using M7000 from Max Science, and the standard luminance was determined to be 3,500 cd / m using the lifespan measurement equipment (M6000) manufactured by Max Science based on the measurement results. 2 The lifespan T is the time it takes for the initial luminance to reach 95% of its original brightness. 95 was measured.

[0510] The driving voltage, luminous efficiency and lifespan (T) of the white organic light-emitting device manufactured according to the above manufacturing method 95 ) are measured as shown in Table 11.

[0511]

[0512] Compound number, driving voltage (V), luminous efficacy (cd / A), CIE (x, y), lifetime (T) 95) Example 5916.9372.88(0.212, 0.430)90 Example 6027.0073.54(0.211, 0.428)91 Example 6147.1271.34(0.210, 0.430)84 Example 6267.0371.13(0.212, 0.430)90 Example 6377.1072.45(0.210, 0.430)88 Example 6487.1570.83(0.213, 0.428)84 Example 65107.0572.01(0.210, 0.425)88 Example 66117.1072.32(0.214, 0.427)85 Example 67136.9570.35(0.208, 0.424)83 Example 68147.1471.80(0.210, 0.430)85 Example 69157.2469.13(0.213, 0.426)83 Example 70187.1571.30(0.212, 0.425)84 Example 71197.0069.83(0.210, 0.425)83 Example 72237.0472.03(0.210, 0.425)95 Example 73267.1372.75(0.211, 0.428)88 Example 74277.1672.53(0.210, 0.430)87 Example 75297.2072.00(0.212, 0.428)84 Example 76347.2072.23(0.211, 0.429)85 Example 77377.0572.80(0.210, 0.430)89 Example 78387.0673.01(0.214, 0.430)89 Example 79447.2169.52(0.215, 0.425)82 Example 80467.3170.25(0.215, 0.435)82 Example 81527.1171.20(0.213, 0.430)83 Example 82667.0871.34(0.214, 0.425)83 Example 83677.0872.00(0.212, 0.430)88 Example 84687.2871.23(0.213, 0.428)90 Example 85737.0872.52(0.210, 0.428)90 Example 86836.9370.13(0.219, 0.425)88 Example 87877.1071.00(0.210, 0.428)85 Example 88897.1072.55(0.210, 0.430)87 Example 89986.9571.13(0.210, 0.425)85 Example 901146.9070.01(0.212, 0.430)83 Example 911157.0370.88(0.212, 0.428)85 Example 921177.1071.00(0.213, 0.430)85 Example 931227.0072.73(0.210, 0.430)86 Example 941267.1870.00(0.210, 0.428)85 Example 951327.2369.74(0.210, 0.428)87 Example 961376.9871.10(0.208, 0.424)86 Example 971506.9070.95(0.214, 0.427)87 Example 981517.0571.85(0.210, 0.428)88 Example 991527.1370.03(0.210, 0.425)85 Example 1001707.1072.00(0.212, 0.430)86 Example 1012057.1872.83(0.211, 0.429)96 Example 1022097.0771.88(0.212, 0.428)97 Example 1032167.1570.88(0.212, 0.430)85 Example 1042177.2070.59(0.210, 0.428)86 Example 1052187.1471.23(0.214, 0.427)85 Example 1062257.1271.00(0.210, 0.430)85 Example 1072277.0871.15(0.210, 0.425)84 Example 1082357.0971.47(0.210, 0.425)85 Example 1092387.1171.76(0.210, 0.430)85 Example 1102437.0572.05(0.212, 0.430)85 Example 1112487.0572.05(0.210, 0.428)96 Example 1122547.1571.83(0.210, 0.428)86 Example 1132827.1771.58(0.212, 0.430)86 Example 1143217.0772.32(0.211, 0.429)86 Example 1153527.1072.13(0.210, 0.428)85 Example 1163597.1171.23(0.212, 0.428)85 Comparative Example 14TmPyPB8.3558.80(0.210, 0.430)60Comparative Example 15Comparative Compound A8.7052.23(0.212, 0.428)58Comparative Example 16Comparative Compound B8.8852.55(0.210, 0.430)57Comparative Example 17Comparative Compound C8.4754.62(0.211, 0.428)59Comparative Example 18Comparative Compound D8.7553.31(0.210, 0.430)54Comparative Example 19Comparative Compound E8.7753.88(0.210, 0.430)53Comparative Example 20Comparative Compound F8.9553.33(0.210, 0.428)59Comparative Example 21Comparative Compound G9.0351.20(0.208, 0.428)60Comparative Example 22Comparative Compound H8.5553.44(0.210, 0.430)56Comparative Example 23Comparative Compound I8.7552.73(0.211, 0.430)58Comparative Example 24Comparative Compound J8.1053.35(0.212, 0.428)36Comparative Example 25Comparative Compound K8.5053.67(0.212, 0.430)38Comparative Example 26Comparative Compound L8.6553.42(0.210, 0.430)38.

[0513]

[0514] [Comparative Compound]

[0515]

[0516]

[0517] From the results in Table 11 above, Examples 59 to 116, which are organic light-emitting devices using the heterocyclic compound represented by the chemical formula 1 as a charge generation layer material of the 2-stack white organic electroluminescent device of the present invention, showed lower driving voltage and significantly improved lifespan and luminous efficiency compared to Comparative Examples 14 to 26.

[0518] The heterocyclic compound represented by the above chemical formula 1 of the present invention is judged to have a core structure having an appropriate electron transport capability, and has a P=O functional group (chemical formula 3) or a phenanthroline functional group (chemical formula 2) that can bind to metals such as lithium (Li) and ytterbium (Yb) used in forming an N-type charge generation layer. Due to this structural feature, when the compound used as an N-type charge generation layer is doped with a metal, a gap state is stably formed within the N-type charge generation layer, and electrons generated from the P-type charge generation layer can easily be injected into the electron transport layer through the gap state generated within the N-type charge generation layer.

[0519] Therefore, an organic light-emitting device with low operating voltage, excellent luminous efficiency, and excellent lifespan was obtained by improving the ability to inject electrons from the P-type charge generation layer to the N-type charge generation layer and subsequently transfer electrons to the electron transport layer.

[0520] The description of the comparative compound is the same as that described in Experimental Example 1 above. Therefore, the comparative compound shows a difference in the binding ability with metal and the electron transport ability from the heterocyclic compound represented by the chemical formula 1 of the present invention. That is, since the comparative compound has a different core structure or substituent from the heterocyclic compound represented by the chemical formula 1 of the present invention, it has a slow electron transport ability or a fast electron transport ability, or it shows a higher driving voltage, lower luminous efficiency, and lower lifespan characteristics than the examples due to an imbalance of charge caused by excessive binding ability with metals.

[0521]

[0522] [Explanation of symbols]

[0523] 100: Substrate

[0524] 200: Bipolar

[0525] 300: Organic layer

[0526] 301: Hole injection layer

[0527] 302: Hole transport layer

[0528] 303: Emissive layer

[0529] 304: Hole blocking layer

[0530] 305: Electron transport layer

[0531] 306: Electron injection layer

[0532] 400: Cathode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, wherein R1 to R10 are the same as or different from each other, and are each independently hydrogen; deuterium; 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; -SiR101R102R103; -NR101R102; selected from the group consisting of the following Chemical Formula 2; and the following Chemical Formula 3, or a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring in which two or more adjacent groups bind each other; or forms a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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, Any one of the above R1 to R10 is the following chemical formula 2; or the following chemical formula 3, [Chemical formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, wherein R11 to R14 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; 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; -SiR101R102R103; and -NR101R102, or are selected from the group consisting of a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring in which two or more adjacent groups bind each other; or forms a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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, The above a is an integer from 0 to 6, and when a is 2 or greater, R12 are equal to or different from each other, The above L1 and L2 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, The above b is an integer from 0 to 5, and when b is 2 or greater, L1 is equal to or different from each other, The above c is an integer from 0 to 5, and when c is 2 or greater, L2 are equal to or different from each other.

2. In paragraph 1, The heterocyclic compound represented by the above chemical formula 1 is a heterocyclic compound represented by any one of the following chemical formulas 1-1 to 1-3: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] In the above chemical formulas 1-1 to 1-3, wherein R21 and R22 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; 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; -SiR101R102R103; and -NR101R102, or two or more adjacent groups bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or forms a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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, The above d1 is an integer from 0 to 2, and when the above d1 is 2 or greater, R21 is equal to or different from each other, The above d2 is an integer from 0 to 1, The above e1 is an integer from 0 to 4, and when the above e1 is 2 or greater, R22 are equal to or different from each other, The above e2 is an integer from 0 to 3, and when the above e2 is 2 or greater, R22 are equal to or different from each other, The above Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, The above R1 to R4 are the same as the definitions of the above chemical formula 1, The above L1, R11, R12, a and b are the same as defined in the above chemical formula 2.

3. In paragraph 1, The heterocyclic compound represented by the above chemical formula 1 is a heterocyclic compound represented by any one of the following chemical formulas 1-4 to 1-6: [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-4 to 1-6, wherein R31 and R32 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; 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; -SiR101R102R103; and -NR101R102, or are selected from the group consisting of a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring in which two or more adjacent groups bind each other; or forms a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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, The above f1 is an integer from 0 to 2, and when the above f1 is 2 or greater, R31 are equal to or different from each other, The above f2 is an integer from 0 to 1, The above g1 is an integer from 0 to 4, and when the above g1 is 2 or greater, R32 are equal to or different from each other, The above g2 is an integer from 0 to 3, and when the above g2 is 2 or greater, R32 are equal to or different from each other, The above Ar2 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, The above R1 to R4 are the same as the definitions of the above chemical formula 1, The above L2, R13, R14 and c are the same as defined in the above chemical formula 3.

4. In paragraph 2, The heterocyclic compound represented by the above chemical formula 1-1 is represented by the following chemical formula 1-1a or 1-1b, The heterocyclic compound represented by the above chemical formula 1-2 is represented by the following chemical formula 1-2a: The heterocyclic compound represented by the above chemical formula 1-3 is a heterocyclic compound represented by the following chemical formula 1-3a: [Chemical Formula 1-1a] [Chemical Formula 1-1b] [Chemical Formula 1-2a] [Chemical Formula 1-3a] In the above chemical formulas 1-1a, 1-1b, 1-2a and 1-3a, The above R1 to R4 are the same as the definitions of the above chemical formula 1, The above L1, R11, R12, a and b are the same as the definitions of the above chemical formula 2, The above R21, R22, Ar1, d1, e1 and e2 are the same as the definitions of the above chemical formulas 1-1 to 1-3.

5. In paragraph 3, The heterocyclic compound represented by the above chemical formula 1-4 is represented by the following chemical formula 1-4a or 1-4b, The heterocyclic compound represented by the above chemical formula 1-5 is represented by the following chemical formula 1-5a, The heterocyclic compound represented by the above chemical formula 1-6 is a heterocyclic compound represented by the following chemical formula 1-6a: [Chemical Formula 1-4a] [Chemical Formula 1-4b] [Chemical Formula 1-5a] [Chemical Formula 1-6a] In the above chemical formulas 1-4a, 1-4b, 1-5a and 1-6a, The above R1 to R4 are the same as the definitions of the above chemical formula 1, The above L2, R13, R14 and c are the same as the definitions of the above chemical formula 3, The above R31, R32, Ar2, f1, g1 and g2 are the same as the definitions of the above chemical formulas 1-4 to 1-6.

6. In paragraph 1, A heterocyclic compound wherein R11 is hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

7. In paragraph 1, A heterocyclic compound wherein R13 and R14 are the same as or different from each other, 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.

8. In paragraph 1, The heterocyclic compound represented by the above chemical formula 1 is a heterocyclic compound which does not contain deuterium as a substituent or has a deuterium content of 1% to 100% with respect to the total number of hydrogen atoms and deuterium atoms.

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

10. First electrode; A second electrode provided opposite to the first electrode; and An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode, An organic light-emitting device, wherein at least one of the organic layers comprises a heterocyclic compound according to any one of claims 1 to 9.

11. In paragraph 10, The above organic layer includes an electron transport layer, An organic light-emitting device, wherein the electron transport layer comprises the heterocyclic compound.

12. In paragraph 10, An organic light-emitting device, wherein the organic light-emitting device further comprises one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole auxiliary layer, and a hole blocking layer.

13. In paragraph 10, The above organic light emitting device, 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 An organic light-emitting device comprising a second electrode provided on the second stack.

14. In paragraph 13, An organic light-emitting device, wherein the charge generating layer comprises the heterocyclic compound.

15. In paragraph 13, The above charge generation layer is an N-type charge generation layer, An organic light-emitting device, wherein the N-type charge generation layer comprises the heterocyclic compound.

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