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. 10-2023-0163820, filed November 22, 2023, and Korean Patent Application No. 10-2024-0143678, filed October 21, 2024, 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] The above X is O; or S,

[0022] wherein R1 to R6 are the same as or different from each other, and each independently represent hydrogen; deuterium; 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; the following chemical formula 2; the following chemical formula 3; the following chemical formula 4; And selected from the group consisting of the following chemical formula 5, or two or more adjacent groups are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and are each independently 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,

[0023] Any one of the above R1, R4 and R6 is any one of the following chemical formulas 2 to 5,

[0024] The above a is an integer from 0 to 3, and when a is 2 or greater, R2 are equal to or different from each other,

[0025] The above b is an integer from 0 to 3, and when b is 2 or greater, R5 are equal to or different from each other,

[0026] [Chemical Formula 2]

[0027]

[0028] [Chemical Formula 3]

[0029]

[0030] [Chemical Formula 4]

[0031]

[0032] [Chemical Formula 5]

[0033]

[0034] In the above chemical formulas 2 to 5,

[0035] The above R11 to R20 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; 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; -SiR201R202R203; And -NR201R202, or two or more adjacent groups are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202 and R203 are the same or different from each other and are each independently 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,

[0036] The above d is an integer from 0 to 6, and when d is 2 or more, R12 are equal to or different from each other,

[0037] The above h is an integer from 0 to 4, and when h is 2 or greater, R15 are equal to or different from each other,

[0038] The above i is an integer from 0 to 2, and when i is 2 or greater, R16 are equal to or different from each other,

[0039] The above j is an integer from 0 to 4, and if i is greater than or equal to j, R17 are equal to or different from each other,

[0040] The above l is an integer from 0 to 3, and when l is 2 or greater, R18 are equal to or different from each other,

[0041] The above m is an integer from 0 to 2, and when m is 2 or greater, R19 are equal to or different from each other,

[0042] The above n is an integer from 0 to 4, and when n is 2 or greater, R20 are equal to or different from each other,

[0043] The above Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0044] The above L1 to L4 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,

[0045] The above c is an integer from 0 to 5, and when c is 2 or greater, L1 are equal to or different from each other,

[0046] The above e is an integer from 0 to 5, and when e is 2 or greater, L2 are equal to or different from each other,

[0047] The above k is an integer from 0 to 5, and when k is 2 or greater, L3 are equal to or different from each other,

[0048] The above o is an integer from 0 to 5, and when o is 2 or greater, L4 are equal to or different from each other.

[0049]

[0050] In addition, the present invention

[0051] First electrode;

[0052] A second electrode provided opposite to the first electrode; and

[0053] An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode,

[0054] 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.

[0055]

[0056] 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.

[0057]

[0058] 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.

[0059]

[0060] Hereinafter, the present invention will be described in more detail.

[0061]

[0062] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the 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.

[0063] 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 substituted or unsubstituted 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 substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned substituents are linked, wherein R, R' and R" 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.

[0064] In this specification, halogen may be fluorine; chlorine; bromine; or iodine.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0075] When the above fluorenyl group is substituted, It can be, but is not limited to, the following.

[0076] 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.

[0077]

[0078] 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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%.

[0084] 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.”

[0085] 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.

[0086] 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.

[0087] 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.

[0088] That is, in one 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.

[0089]

[0090]

[0091] 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.

[0092] 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.

[0093]

[0094] The present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0095] [Chemical Formula 1]

[0096]

[0097] In the above chemical formula 1,

[0098] The above X is O; or S,

[0099] wherein R1 to R6 are the same as or different from each other, and each independently represent hydrogen; deuterium; 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; the following chemical formula 2; the following chemical formula 3; the following chemical formula 4; And selected from the group consisting of the following chemical formula 5, or two or more adjacent groups are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and are each independently 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,

[0100] Any one of the above R1, R4 and R6 is any one of the following chemical formulas 2 to 5,

[0101] The above a is an integer from 0 to 3, and when a is 2 or greater, R2 are equal to or different from each other,

[0102] The above b is an integer from 0 to 3, and when b is 2 or greater, R5 are equal to or different from each other,

[0103] [Chemical Formula 2]

[0104]

[0105] [Chemical Formula 3]

[0106]

[0107] [Chemical Formula 4]

[0108]

[0109] [Chemical Formula 5]

[0110]

[0111] In the above chemical formulas 2 to 5,

[0112] The above R11 to R20 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; 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; -SiR201R202R203; And -NR201R202, or two or more adjacent groups are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202 and R203 are the same or different from each other and are each independently 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,

[0113] The above d is an integer from 0 to 6, and when d is 2 or more, R12 are equal to or different from each other,

[0114] The above h is an integer from 0 to 4, and when h is 2 or greater, R15 are equal to or different from each other,

[0115] The above i is an integer from 0 to 2, and when i is 2 or greater, R16 are equal to or different from each other,

[0116] The above j is an integer from 0 to 4, and if i is greater than or equal to j, R17 are equal to or different from each other,

[0117] The above l is an integer from 0 to 3, and when l is 2 or greater, R18 are equal to or different from each other,

[0118] The above m is an integer from 0 to 2, and when m is 2 or greater, R19 are equal to or different from each other,

[0119] The above n is an integer from 0 to 4, and when n is 2 or greater, R20 are equal to or different from each other,

[0120] The above Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0121] The above L1 to L4 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,

[0122] The above c is an integer from 0 to 5, and when c is 2 or greater, L1 are equal to or different from each other,

[0123] The above e is an integer from 0 to 5, and when e is 2 or greater, L2 are equal to or different from each other,

[0124] The above k is an integer from 0 to 5, and when k is 2 or greater, L3 are equal to or different from each other,

[0125] The above o is an integer from 0 to 5, and when o is 2 or greater, L4 are equal to or different from each other.

[0126]

[0127] In one embodiment of the present invention, R1 to R6 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; the above chemical formula 2; the above chemical formula 3; the above chemical formula 4; Or, the above chemical formula 5, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle, and R101, R102 and R103 are the same as or different from each other, and can each independently 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.

[0128] In another embodiment of the present invention, R1 to R6 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; the above chemical formula 3; the above chemical formula 4; Or, the above chemical formula 5, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle, and R101, R102 and R103 are the same as or different from each other, and can each independently 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.

[0129] In another embodiment of the present invention, R1 to R6 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; the above chemical formula 3; the above chemical formula 4; Or, the above chemical formula 5, wherein R101, R102 and R103 are the same as or different from each other, and may each independently 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.

[0130] In another embodiment of the present invention, R1, R4 and R6 are the same as or different from each other, and each independently represent hydrogen; deuterium; the above formula 2; the above formula 3; the above formula 4; or the above formula 5, and any one of R1, R4 and R6 is any one of the above formulas 2 to 5, and the others are the same as or different from each other, and each independently represent hydrogen; or deuterium.

[0131] In another embodiment of the present invention, R1 is any one of the chemical formulas 2 to 5, and R4 and R6 are the same as or different from each other and may each independently be hydrogen or deuterium.

[0132] In another embodiment of the present invention, R4 is any one of the chemical formulas 2 to 5, and R1 and R6 are the same as or different from each other and may each independently be hydrogen or deuterium.

[0133] In another embodiment of the present invention, R6 is any one of the chemical formulas 2 to 5, and R1 and R4 are the same as or different from each other and may each independently be hydrogen or deuterium.

[0134] In another embodiment of the present invention, R2, R3 and R5 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0135]

[0136] In one embodiment of the present invention, R11 to R20 are the same as or different from each other, are each independently the same as or different from each other, and are 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; -SiR201R202R203; Or -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R201, R202 and R203 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.

[0137] In another embodiment of the present invention, R11 to R20 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; -SiR201R202R203; or -NR201R202, 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 R201, R202 and R203 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.

[0138] In another embodiment of the present invention, R11 to R20 are the same as or different from each other, and each independently represent 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; -SiR201R202R203; Or -NR201R202, wherein R201, R202, and R203 may be the same as or different from each other, and may each independently 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.

[0139] In another embodiment of the present invention, R11 to R20 may be the same as or different from each other, and may each independently be hydrogen; deuterium; halogen; cyano group; 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.

[0140] In another embodiment of the present invention, R11 to R20 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.

[0141] In another embodiment of the present invention, R11 to R12 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0142] In another embodiment of the present invention, R11 to R12 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0143] In another embodiment of the present invention, R11 to R12 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] 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.

[0148] In another embodiment of the present invention, R12 may be hydrogen or deuterium.

[0149] 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 C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0150] 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 C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0151] 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 C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0152] 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 ethyl group; a substituted or unsubstituted isopropyl group; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted pyridinyl group.

[0153] In another embodiment of the present invention, R15 to R20 may be the same as or different from each other, and may each independently be hydrogen or deuterium.

[0154]

[0155] 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.

[0156] 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.

[0157] In another embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6 to C60 aryl group.

[0158] In another embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6 to C30 aryl group.

[0159] In another embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6 to C20 aryl group.

[0160] In another embodiment of the present invention, Ar1 may be a substituted or unsubstituted phenyl group.

[0161]

[0162] In one embodiment of the present invention, L1 to L4 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.

[0163] In another embodiment of the present invention, L1 to L4 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.

[0164] 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 phenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted pyridinylene group; a substituted or unsubstituted quinolinylene group; or a substituted or unsubstituted isoquinolinylene group.

[0165] In another embodiment of the present invention, L3 and L4 may be the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

[0166] In another embodiment of the present invention, L3 and L4 may be the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted C6 to C30 arylene group.

[0167] In another embodiment of the present invention, L3 and L4 may be the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0168] In another embodiment of the present invention, L3 and L4 are the same as or different from each other, and each independently may be a direct bond; or a substituted or unsubstituted phenylene group.

[0169]

[0170] 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 1-12.

[0171] [Chemical Formula 1-1]

[0172]

[0173] [Chemical Formula 1-2]

[0174]

[0175] [Chemical Formula 1-3]

[0176]

[0177] [Chemical Formula 1-4]

[0178]

[0179] [Chemical Formula 1-5]

[0180]

[0181] [Chemical Formula 1-6]

[0182]

[0183] [Chemical Formula 1-7]

[0184]

[0185] [Chemical Formula 1-8]

[0186]

[0187] [Chemical Formula 1-9]

[0188]

[0189] [Chemical Formula 1-10]

[0190]

[0191] [Chemical Formula 1-11]

[0192]

[0193] [Chemical Formula 1-12]

[0194]

[0195] In the above chemical formulas 1-1 to 1-12,

[0196] The above X, R1 to R6, a and b are the same as the definitions in the above chemical formula 1,

[0197] The above L1, R11, R12, c and d are the same as the definitions in the above chemical formula 2,

[0198] The above L2, R13, R14 and e are the same as the definitions in the above chemical formula 3,

[0199] The above L3, R15 to R17 and h to k are the same as the definitions in the above chemical formula 4,

[0200] The above L4, R18 to R20 and l to o are the same as defined in the above chemical formula 5.

[0201]

[0202] In one embodiment of the present invention, R1 to R6, R11 to R20, Ar1 and L1 to L4 may all include non-deuterated hydrogen (H).

[0203] In another embodiment of the present invention, at least one of the R1 to R6, R11 to R20, Ar1 and L1 to L4 may contain deuterium (D), and at least one of the R1 to R6, R11 to R20, Ar1 and L1 to L4 may contain non-deuterated hydrogen.

[0204] In another embodiment of the present invention, all of R1 to R6, R11 to R20, Ar1 and L1 to L4 may contain deuterium.

[0205]

[0206] 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.

[0207] 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%.

[0208] 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%.

[0209] 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%.

[0210] 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%.

[0211]

[0212] 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.

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250] In addition, by introducing various substituents into the structure of the above chemical formula 1, compounds having unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents 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, a material satisfying the conditions required for each organic layer can be synthesized.

[0251] In addition, by introducing various substituents into the structure of 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.

[0252] Meanwhile, the heterocyclic compound exhibits excellent thermal stability due to its high glass transition temperature (Tg). This increased thermal stability is an important factor in providing operating stability to the device.

[0253] The heterocyclic compound according to one embodiment of the present invention can be prepared through a multi-step chemical reaction. Some intermediate compounds are prepared first, and then the heterocyclic compound represented by Chemical Formula 1 can be prepared from these intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present invention can be prepared based on the preparation example described below.

[0254]

[0255] 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”.

[0256]

[0257] In addition, the present invention

[0258] First electrode;

[0259] A second electrode provided opposite to the first electrode; and

[0260] An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode,

[0261] 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.

[0262]

[0263] In one embodiment of the present invention, the first electrode may be an anode, and the second electrode may be a cathode.

[0264] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0265]

[0266] 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.

[0267] 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.

[0268] 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.

[0269] The specific details of the heterocyclic compound represented by the above chemical formula 1 are the same as described above.

[0270]

[0271] 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.

[0272] The above heterocyclic compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0273] 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.

[0274] In the organic light-emitting device of the present invention, the organic layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound.

[0275] In the organic light-emitting device of the present invention, the organic layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound.

[0276] 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 the heterocyclic compound.

[0277] 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 the heterocyclic compound.

[0278] 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 the heterocyclic compound.

[0279] 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.

[0280]

[0281] 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.

[0282] 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.

[0283] 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.

[0284]

[0285] In addition, in one embodiment of the present invention, the organic light-emitting element,

[0286] anode;

[0287] cathode; and

[0288] comprising two or more stacks provided between the positive and negative electrodes;

[0289] The above two or more stacks each independently include a light-emitting layer,

[0290] A charge generation layer is included between the two or more stacks,

[0291] The charge generation layer includes a heterocyclic compound represented by the chemical formula 1.

[0292]

[0293] In addition, in one embodiment of the present invention, the organic light-emitting element,

[0294] First electrode;

[0295] A first stack provided on the first electrode and including a first light-emitting layer;

[0296] A charge generation layer provided on the first stack;

[0297] A second stack provided on the charge generation layer and including a second light-emitting layer; and

[0298] It includes a second electrode provided on the second stack.

[0299] 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.

[0300] 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.

[0301]

[0302] 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.

[0303]

[0304] 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.

[0305] The organic layer including the heterocyclic compound represented by the above chemical formula 1 may additionally include other substances as needed.

[0306] 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.

[0307]

[0308] 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.

[0309] The specific details of the heterocyclic compound represented by the above chemical formula 1 are the same as described above.

[0310] 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.

[0311]

[0312] 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.

[0313] 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.

[0314] The above M can be iridium, platinum, osmium, etc.

[0315] 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.

[0316]

[0317] 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.

[0318]

[0319] 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.

[0320]

[0321] 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.

[0322]

[0323] The present invention,

[0324] Steps to prepare the substrate;

[0325] A step of forming a first electrode on the substrate;

[0326] A step of forming one or more organic layers on the first electrode; and

[0327] 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.

[0328]

[0329] 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.

[0330] The organic layer including the heterocyclic compound represented by the above chemical formula 1 may additionally include other substances as needed.

[0331]

[0332] 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.

[0333]

[0334] 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.

[0335]

[0336] 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.

[0337]

[0338] 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.

[0339]

[0340] 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.

[0341]

[0342] 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.

[0343]

[0344] For example, LiF is typically used as an electron injection layer material in the art, but the present application is not limited thereto.

[0345]

[0346] 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.

[0347]

[0348] 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.

[0349]

[0350] 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.

[0351]

[0352] 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.

[0353]

[0354] 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.

[0355]

[0356] <Manufacturing Example>

[0357] Manufacturing Example 1. Manufacturing of Compound 001

[0358]

[0359]

[0360] Manufacturing Example 1-1. Manufacturing of Compound 1-1

[0361] 7-Chlorobenzo[b]thiophene (81.21 g, 0.481 mol, 1 eq) and tetrahydrofuran (THF) (1,200 mL) were stirred in an ice bath below 0°C under a nitrogen atmosphere. n-Butyllithium solution (37.02 g, 0.578 mol, 1.2 eq) was added dropwise, stirred for 3 minutes, and then trimethylborate (75.06 g, 0.722 mol, 1.5 eq) was added dropwise using a syringe. The mixture was stirred at room temperature for 1 hour, and saturated NH4Cl solution was added and stirred for 1 hour.

[0362] After this, the organic layer was extracted and concentrated to obtain 82.87 g (yield 81%) of compound 1-1.

[0363]

[0364] Manufacturing Example 1-2. Preparation of Compound 1-2

[0365] Compound 1-1 (82.87 g, 0.39 mol, 1 eq), 2-bromobenzaldehyde (60 g, 0.324 mol, 1 eq), Pd(OAc)2 (3.6 g, 0.016 mol, 0.05 eq), Na2CO3 (102.07 g, 0.963 mol, 3 eq), 1200 mL of acetone, and 1200 mL of distilled water (H2O) were added and stirred at room temperature for 4 hours.

[0366] Afterwards, water and methylene chloride were added to separate the layers, and the organic layer was concentrated. Afterwards, a silica pass was performed to obtain 39 g (45% yield) of compound 1-2.

[0367]

[0368] Manufacturing Example 1-3. Preparation of Compound 1-3

[0369] Dry ice was added to acetone to create conditions below 0℃, and then 600mL of tetrahydrofuran (THF) and (methoxymethyl)tri-phenylphosphonium chloride were added to dissolve. Potassium tert-butoxide was slowly added under conditions of a temperature below 0℃, the inlet was blocked, and the mixture was stirred at room temperature for 30 minutes to prepare a mixed solution.

[0370] A solution of compound 1-2 dissolved in 400 mL of tetrahydrofuran was placed in a dropping funnel. The mixed solution was stirred again in a bath below 0°C, and the compound 1-2 solution was added dropwise. The mixture was stirred at room temperature for 3 hours to obtain 24.7 g (yield 66%) of compound 1-3.

[0371]

[0372] Manufacturing Example 1-4. Preparation of Compound 1-4

[0373] Compound 1-3 (24.7 g, 0.092 mol, 1 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (22.69 g, 0.089 mol, 1.5 eq), KOAc (14.92 g, 0.152 mol, 2.5 eq), Pd2(dba)3 (2.7 g, 0.003 mol, 0.05 eq) and P(Cy)3 (1.69 g, 0.006 mol, 0.1 eq) was stirred at 120°C for 3 hours. At this temperature, the substance dissolved transparently, and the temperature was lowered to room temperature.

[0374] After filtration with Celite, it was concentrated, dissolved in methylene chloride, and passed through a silica pass using methylene chloride:hexane (1:1 volume ratio) as a developing solvent.

[0375] After that, it was concentrated, re-dissolved in methylene chloride, slowly added to 2 L of methanol to precipitate a solid, and filtered to obtain 30.1 g (yield 82%) of compound 1-4.

[0376]

[0377] Manufacturing Example 1-5. Preparation of Compound 1

[0378] Compound 1-4 (10 g, 0.028 mol, 1 eq), 2-bromo-9-phenyl-1,10-phenanthroline (7.58 g, 0.029 mol, 1.05 eq), Pd(pph3)4 (1.6 g, 0.001 mol, 0.05 eq), and K3PO4 (11.51 g, 0.083 mol, 3 eq) were dissolved in 120 mL of 1,4-dioxane and 30 mL of water, and stirred at 120°C for 4 hours.

[0379] After the reaction was completed, the solid was filtered and washed with 1,4-dioxane to remove the base. The solid was then concentrated, dissolved in methylene chloride, and passed through a silica pass using methylene chloride:hexane (5:1 volume ratio) as a developing solvent.

[0380] After reconcentration, the product was purified with methylene chloride and acetone to obtain 8.34 g (48% yield) of compound 1.

[0381]

[0382] The target compound of Table 1 was synthesized in the same manner as in Manufacturing Example 1, except that Compound A of Table 1 was used instead of 7-chlorobenzo[b]thiophene in Manufacturing Example 1, Compound B of Table 1 was used instead of 2-bromobenzaldehyde, and Compound C of Table 1 was used instead of 2-bromo-9-phenyl-1,10-phenanthroline.

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395] Manufacturing Example 2. Preparation of Compound 9

[0396]

[0397]

[0398] Benzo(B)naphtho(2,1-D)thiophene (25 g, 0.093 mol, 1 eq), N-bromosuccinimide (NBS) (18.21 g, 0.102 mol, 1.1 eq), and dimethylformamide (DMF) (375 mL) were added and stirred at 60°C for 4 hours.

[0399] When the reaction is complete, a solid precipitates. Water is added to the reaction flask, stirred, and filtered while washing with water. The solid is washed with methanol and dried to obtain compound 9-1.

[0400] Afterwards, the same procedure as in Manufacturing Examples 1-4 and 1-5 was performed to obtain compound 9 (yield 55%).

[0401]

[0402] The target compound of Table 2 was synthesized in the same manner as in Manufacturing Example 1, except that Compound D of Table 2 was used instead of benzo(B)naphtho(2,1-D)thiophene in Manufacturing Example 2, and Compound E of Table 2 was used instead of 2-bromo-9-phenyl-1,10-phenanthroline.

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410] Manufacturing Example 3. Preparation of Compound 566

[0411]

[0412]

[0413] Compound 005 (5 g, 12.12 mmol) was added to 650 mL of C6D and purged with nitrogen for 2 hours. 623.9 g of trifluoromethanesulfonic acid (84.84 mmol, 7 eq) was added dropwise using a syringe, and the reaction mixture was refluxed and heated for 2 hours.

[0414] After cooling to room temperature, 50 mL of heavy water (D2O) was added to extract, and the organic layer was dried over anhydrous MgSO4 and concentrated using a rotary evaporator.

[0415] Afterwards, 4.4 g (yield 85%) of compound 566 was obtained through ethyl acetate (EA) slurry.

[0416]

[0417] Except that the reaction temperature, reaction time, and equivalent amount of trifluoromethanesulfonic acid of Manufacturing Example 3 were performed under the conditions of Table 3 below, the target compound of Table 3 was synthesized using the same method as Manufacturing Example 3 above.

[0418]

[0419]

[0420]

[0421]

[0422]

[0423] The results of the synthesis of the compounds described in Manufacturing Examples 1 to 3 and Tables 1 to 3, and the results of the synthesis of the heterocyclic compound represented by Chemical Formula 1 are shown in Tables 4 and 5 below.

[0424] Table 4 below 1 The values ​​are measured by H NMR (DMSO, 200 MHz), and Table 5 below is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0425]

[0426] Compound number 1<h2 style=";text-align:left;direction:ltr">H NMR(CDCl3, 200MHz)0018.80(1H, d), 8.71(1H, d), 8.55(1H, d), 8.45(1H, d), 8.31(1H, d), 8.20~8.16(2H, d), 8.05~8.01(2H, d), 7.90~7.83 (2H, d), 7.70~7.56(4H, t), 7.29(1H, d)0048.71(2H, d), 8.59(1H, s), 8.33~8.16(6H, d), 8.05~8.01(2H, d), 7.90~7.83(2H, d), 7.64~7.49(5H, t), 7.29(2H, d)0058.80(1H, d), 8.71(1H, d), 8.51~8.45(2H, m), 8.31(1H, d), 8.20~8.16(2H, d), 8.05~7.83(5H, d), 7.64~7.56(3H, t), 7.29(1H, d)0088.71(2H, d), 8.33(3H, d), 8.20~8.16(2H, d), 8.05~8.01(3H, d), 7.90~7.83(2H, d), 7.64~7.49(6H, t), 7.29(2H, d)0098.97(1H, d), 8.80(1H, d), 8.71(1H, d), 8.51~8.45(3H, m), 8.20~8.12 (2H, d), 7.93~7.90(2H, d), 7.59~7.49(5H, t), 7.29(1H, d)0118.97(1H, d), 8.80(1H, d), 8.71(1H, d), 8.45(2H, d), 8.35(1H, d), 8.20~8.12(2H, d), 7.96~7.90(3H, d), 7.67~7.49(8H, m), 7.29(1H, d)0138.97(1H, d), 8.80(1H, d), 8.71~8.69(3H, d), 8.45(2H, d), 8.20~8.12(2H, d), 7.93~7.90(2H, d), 7.67~7.49(6H, m), 7.29~7.25(3H, d)0158.97(1H, d), 8.71(2H, d), 8.45(1H, d), 8.33(4H, m), 8.20~8.12(2H, d), 7.93~7.90(2H, d), 7.<h2 style=";text-align:left;direction:ltr">73~7.49(10H, m), 7.29(2H, d)0168.97(1H, d), 8.71~8.69(4H, d), 8.45(1H, d), 8.33(2H, d), 8.20~8.12(2H, d), 7.93~7.90(2H, d), 7.67~7.49(8H, m), 7.29~7.25(4H, d)0188.71(2H, d), 8.49~8.45(2H, d), 8.33(2H, d), 8.22~8.20(2H, d), 8.05~7.90(4H, m), 7.60~7.49(6H, m), 7.29(2H, d)0218.71(2H, d), 8.50~8.45(2H, d), 8.33(4H, m), 8.20(1H, d), 8.06~8.05(2H, d), 7.93~7.90(2H, d), 7.77~7.73(2H, t), 7.61~7.49(7H, m), 7.29(2H, d)0238.85~8.80(2H, d), 8.71(1H, d), 8.45~8.37(3H, d), 8.20~8.17(2H, d), 8.05(1H, d), 7.93~7.83(3H, d), 7.56~7.49(3H, t), 7.29(1H, d)0248.85(1H, s), 8.71(2H, d), 8.45~8.33(4H, d), 8.20~8.17(2H, d), 8.05(1H, d), 7.93~7.83(3H, d), 7.56~7.49(5H, t), 7.29(2H, d)0288.80(1H, d), 8.71(1H, d), 8.45(2H, d), 8.33~8.32(3H, m), 8.20(1H, d), 8.05~7.83(5H, d), 7.73(1H, t), 7.61~7.49(4H, m), 7.38(1H, d), 7.29(1H, d)0328.71~8.69(4H, d), 8.45(1H, d), 8.33~8.32(3H, m), 8.20(1H, d), 8.05~7.83(7H, d), 7.56~7.49(5H, t), 7.38(1H, d), 7.29(2H, d)0358.80(1H, d), 8.71(1H, d), 8.50~8.45(3H, d), 8.35(1H, d), 8.<h2 style=";text-align:left;direction:ltr">20(1H, d), 8.09~7.83(7H, m), 7.60~7.49(5H, t), 7.29(1H, d)0428.95(1H, d), 8.71(2H, d), 8.55~8.47(2H, d), 8.33~8.32(3H, d), 8.21~8.16(3H, d), 8.05~7.83(5H, d), 7.70~7.49(8H, t), 7.29(1H, d)0458.97~8.93(2H, m), 8.80(1H, d), 8.55(1H, d), 8.45~8.32(4H, d), 8.16~8.00(5H, d), 7.89~7.83(2H, d), 7.70~7.56(4H, t)0468.71(1H, d), 8.55(1H, d), 8.41~8.32(5H, d), 8.16~8.01(7H, m), 7.89~7.83(3H, m), 7.71~7.49(7H, t), 7.29(1H, d)0699.29(1H, s), 8.80(1H, d), 8.65(1H, d), 8.45(1H, d), 8.33(1H, d), 8.20~8.14(3H, d), 8.05~8.01(4H, d), 7.89~7.83(2H, d), 7.68~7.56(5H, m) 0729.02~8.95(2H, d), 8.71(2H, d), 8.45(1H, d), 8.33(2H, d), 8.20~8.16(2H, d), 8.05~7.84(7H, d), 7.68~7.46(8H, t), 7.29(2H, d) 0779.29(1H, s), 8.97(1H, d), 8.80(1H, d), 8.65(1H, d), 8.51~8.45(3H, m), 8.20~8.12(3H, d), 8.01~7.89(3H, d), 7.63~7.49(6H, m), 8.09.2~8.95(3H, d), 8.71(2H, d), 8.45(2H, d), 8.33(2H, d), 8.20~8.12(2H, d), 7.93~7.84(3H, d), 7.67~7.46(10H, m), 7.29(2H, d), 8.97~8.93(2H, m), 8.71(1H, d), 8.45~8.33(5H, d), 8.17~8.14(2H, d), 8.05~7.83(5H, d), 7.72~7.69(2H, m), 7.56~7.49(5H, t), 7.29(1H, d)0938.80(1H, d), 8.50~8.37(6H, m), 8.14(1H, d), 8.05~7.83(6H, d), 7.72(1H, d), 7.56~7.49(3H, t), 7.28(1H, t)1059.02~8.95(2H, d), 8.80(1H, d), 8.71(1H, d), 8.50~8.45(4H, d), 8.20(1H, d), 8.09~8.05(2H, d), 7.93~7.77(5H, m), 7.56~7.46(5H, t), 7.29(1H, d)1379.18(1H, d), 9.02~8.95(2H, d), 8.71(1H, d), 8.55(1H, d), 8.45~8.37(3H, d), 8.16~7.64(13H, m), 7.52~7.46(2H, t), 7.29~7.23(2H, d)1598.85~8.71(4H, m), 8.45~8.37(5H, d), 8.17~7.83(9H, d), 7.61~7.49(4H, t), 7.37~7.29(2H, m), 6.88(1H, d)1778.80(1H, d), 8.71(1H, d), 8.45(1H, d), 8.20~8.08(5H, d), 7.90~7.84(2H, d), 7.69~7.67(2H, t), 7.56~7.48(3H, m), 7.29(1H, d)1808.71(2H, d), 8.33(2H, d), 8.21~8.03(6H, m), 7.90~7.80(2H, d), 7.69~7.67(2H, t), 7.55~7.48(4H, m), 7.29(2H, d)1858.97(1H, d), 8.80(1H, d), 8.71(1H, d), 8.45(1H, d), 8.22~8.18(3H, m), 7.98~7.90(2H, d), 7.64~7.54(4H, m), 7.39~7.29(3H, m)1878.97(1H, d), 8.80(1H, d), 8.71(1H, d), 8.45(1H, d), 8.35(1H, d), 8.20~8.18(2H, d), 7.98~7.90(3H, d), 7.64~7.54(6H, m), 7.39~7.29(4H, m)1888.97(1H, d), 8.80(1H, d), 8.71(1H, d), 8.45(1H, d), 8.33(2H, m), 8.20~8.18(2H, d), 7.98~7.90(2H, d), 7.73~7.54(6H, m), 7.39~7.29(4H, m)1918.97(1H, d), 8.71(2H, d), 8.33(4H, m), 8.20~8.18(2h, d), 7.98(1H, d), 7.90(1H, d), 7.73~7.29(13H, m)1928.97(1H, d), 8.71~8.69(4H, d), 8.33(2H, d), 8.20~8.18(2h, d), 7.98~7.90(2H, d), 7.64~7.29(13H, m)1948.71(1H, d), 8.49(1H, d), 8.33~8.20(4H, d), 8.00~7.84(4H, m), 7.55~7.29(9H, m)1998.71(2H, d), 8.50(1H, d), 8.33(4H, m), 8.20(1H, d), 8.12(1H, d), 7.98(1H, d), 7.90~7.73(4H, m), 7.61~7.29(10H, m)2018.85~8.71(3H, d), 8.45~8.37(2H, d), 8.20~8.17(2H, d), 7.98~7.84(3H, d), 7.56~7.29(6H, m)2108.71~8.69(4H, d), 8.33~8.32(3H, m), 8.20(1H, d), 7.99~7.84(6H, d),7.55~7.29(10H, m)2138.80(1H, d), 8.71(1H, d), 8.50~8.45(2H, d), 8.35(1H, d), 8.20(1H, d), 8.09(1H, d), 7.98~7.77(5H, m), 7.60~7.29(8H, m)2208.95(1H, d), 8.71(2H, d), 8.47(1H, d), 8.33(2H, d), 8.21~7.84(9H, d), 7.69~7.48(9H, m), 7.29(2H, d)2238.97~8.93(2H, m), 8.80(1H, d), 8.45~8.37(3H, d), 8.16~8.00(6H, d),7.89~7.84(2H, d), 7.69~7.67(2H, t), 7.56~7.48(3H, m)2479.29(1H, s), 8.80(1H, d), 8.65(1H, d), 8.45(1H, d), 8.21~8.11(5H, m), 8.01(1H, d), 7.89~7.84(2H, d), 7.69~7.48(7H, m)2559.29(1H, s), 8.97(1H, d), 8.80(1H, d), 8.65(1H, d), 8.45(1H, d), 8.22~8.14(4H, m), 8.01~7.98(2H, d), 7.89(1H, d), 7.64~7.54(5H, m), 7.39~7.31(2H, t)2589.02~8.95(3H, d), 8.71(2H, d), 8.45(1H, d), 8.33(2H, d), 8.20~8.18(2H, d), 7.98~7.84(3H, d), 7.64~7.29(13H, m)2639.29(1H, s), 8.80(1H, d), 8.65(1H, d), 8.49~8.45(2H, d), 8.28~8.14(3H, d), 8.01~7.89(5H, m), 7.63~7.31(6H, m)2999.63(1H, s), 9.29(1H, s), 8.81(1H, d), 8.70~8.65(3H, d), 8.21~8.01(8H, m), 7.89~7.84(2H, d), 7.69~7.48(6H, m)3558.55(1H, d), 8.32(1H, d), 8.16(1H, d), 8.05~7.95(4H, d), 7.83~7.61(10H, m), 7.51(6H, t)3598.24~8.13(5H, m), 8.05~8.01(2H, d), 7.87~7.74(8H, m), 7.64(2H, t), 7.51(6H, t)3638.16~7.96(10H, d), 7.83~7.77(5H, d), 7.64(2H, t), 7.51(6H, t)3678.45(1H, d), 8.31(1H, s), 8.12(2H, d), 7.93(1H, d), 7.77(4H, d), 7.59~7.49(10H, t)3828.45(1H, d), 8.32(1H, s), 8.05~7.93(7H, d), 7.83~7.77(5H, d), 7.56~7.49(8H, t), 7.38(1H, d)3838.45~8.40(2H, d), 8.05~8.01(2H, d), 7.93~7.77(7H, m), 7.56~7.49(8H, t)4409.12(1H, s), 8.97~8.95(2H, d), 8.75(1H, d); 8.62(2H, d), 8.45(1H, d), 8.28~8.12(4H, d), 7.97~7.91(4H, d), 7.59~7.39(8H, m)4488.50~8.45(2H, d), 8.17(1H, d), 8.05~7.93(3H, d), 7.83(1H, d), 7.72~7.69(2H, d), 7.56~7.49(3H, t), 2.06(6H, s)4718.18~8.12(2H, d), 8.02~7.98(2H, d), 7.77(4H, d), 7.64~7.51(9H, m), 7.39~7.31(2H, t)5449.12(1H, d), 8.97~8.95(2H, d), 8.75(1H, d), 8.62(2H, d), 8.28~8.18(4H, d), 7.98~7.91(4H, d), 7.64~7.52(5H, m), 7.39~7.31(4H, m)5469.12~9.09(2H, s), 8.97(1H, d), 8.75(1H, d), 8.60(1H, d), 8.28~8.18(3H, m), 8.02~7.86(5H, m), 7.66~7.54(5H, m), 7.39~7.31(2H, t)566All D substituents576All D substituents593All D substituents599All D substituents602All D substituents612All D substituents618All D substituents619All D substituents6219.18~9.14(4H, d), 8.97(1H, d), 8.55(2H, d), 8.18(1H, d), 7.98(1H, d), 7.83(1H, d), 7.74~7.54(5H, m), 7.39~7.23(4H, t)6249.18~9.14(4H, m), 8.97(1H, d), 8.55(2H, d), 8.45(1H, d), 8.12(1H, d), 7.93(1H, d), 7.74~7.67(3H, m), 7.59~7.49(4H, t), 7.25~7.23(6H, t)6269.18~9.14(4H, m), 8.55(2H, d),8.32(1H, s), 7.99~7.98(2H, d), 7.84(1H, d), 7.74(2H, t), 7.54~7.48(2H, d), 7.39~7.23(9H, m)6389.18~9.14(4H, m), 8.55(2H, d),8.16~7.99(6H, m), 7.83(1H, d), 7.74(2H, t), 7.64(2H, t), 7.25~7.23(6H, m)6429.18~9.14(4H, m), 8.97(1H, d), 8.55(2H, d), 8.45(1H, d), 8.12(1H, d), 7.94~7.93(2H, m), 7.74~7.49(10H, m), 7.23(2H, t)6479.18~9.14(4H, m), 8.55(2H, d),8.16~8.11(2H, d), 7.94(1H, s), 7.84~7.48(12H, m), 7.23(2H, t)6539.18~9.14(4H, m), 8.55(2H, d), 8.45(1H, d),8.23(1H, d), 8.05 (1H, d), 7.94~7.93(2H, m),7.83~7.73(4H, m),7.61~7.49(5H, m), 7.38(1H, d), 7.23(2H, t)6599.18~9.14(3H, m), 8.97(1H, d), 8.78(1H, d), 8.55(1H, d), 8.22~8.18(2H, m), 7.98(1H, d), 7.75~7.23(13H, m), 6.88(1H, d)6629.18~9.14(3H, m), 8.85~8.78(2H, m), 8.55(1H, d), 8.37(1H, d), 7.98~7.93(2H, d), 7.84~7.74(4H, m), 7.54~7.23(9H, m), 6.88(1H, d)6759.18~9.14(3H, m), 8.78(1H, d), 8.59~8.55(2H, m), 8.33(1H, d), 8.24~8.16(2H, d), 8.05~8.01(2H, d), 7.83~7.64(6H, m), 7.49~7.37(4H, t), 7.23(1H, t), 6.88(1H, d)6779.18~9.14(3H, m), 8.97~8.93(3H, m), 8.55(1H, d), 8.18(1H, d), 8.00~7.98(2H, d), 7.83~7.23(13H, m)6819.18~9.14(3H, m), 8.97~8.93(2H, m), 8.55(1H, d), 8.17(1H, d), 8.00~7.98(2H, d), 7.84~7.69(6H, m), 7.54~7.23(8H, m)6929.18~9.14(3H, m), 8.97~8.93(2H, m), 8.55(1H, d),8.16~7.99(7H, m), 7.83~7.64(6H, m), 7.49~7.41(3H, t), 7.23(1H, t)703All D substituents704All D substituents709All D substituents713All D substituents.

[0427]

[0428] Compound number FD-MS Compound FD-MS001 m / z = 412.10 (C 28 H 16 N2S =412.51)004m / z= 488.13(C 34 H 20 N2S =488.61)005m / z= 412.10(C 28 H 16 N2S =412.51)008m / z= 488.13(C 34 H 20 N2S =488.61)009m / z= 412.10(C 28 H 16 N2S =412.51)011m / z= 488.13(C 34 H 20 N2S =488.61)013m / z= 488.13(C 34 H 20 N2S =488.61)015m / z= 564.17(C 40 H24 N2S =564.71)016m / z= 564.17(C 40 H 24 N2S =564.71)018m / z= 488.13(C 34 H 20 N2S =488.61)021m / z= 564.17(C 40 H 24 N2S =564.71)023m / z= 412.10(C 28 H 16 N2S =412.51)024m / z= 488.13(C 34 H 20 N2S =488.61)028m / z= 488.13(C 34 H 20 N2S =488.61)032m / z= 564.17(C 40 H 24 N2S =564.71)035m / z= 488.13(C 34 H 20 N2S =488.61)042m / z= 614.18(C 44 H 26 N2S =614.77)045m / z= 489.13(C 33 H 19 N3S =489.60)046m / z= 615.18(C 43 H 25 N3S =615.75)069m / z= 489.13(C 33 H 19 N3S =489.60)072m / z= 614.18(C 44 H 26 N2S =614.77)077m / z= 489.13(C 33 H 19 N3S =489.60)080m / z= 614.18(C 44 H 26 N2S =614.77)092m / z= 565.16(C 39 H 23 N3S =565.69)093m / z= 489.13(C 33 H 19 N3S =489.60)105m / z= 538.15(C 38 H 22N2S =538.67)137m / z= 615.18(C 43 H 25 N3S =615.75)159m / z= 615.18(C 43 H 25 N3S =615.75)177m / z= 396.13(C 28 H 16 N2O =396.45)180m / z= 472.16(C 34 H 20 N2O =472.55)185m / z= 396.13(C 28 H 16 N2O =396.45)187m / z= 472.16(C 34 H 20 N2O =472.55)188m / z= 472.16(C 34 H 20 N2O =472.55)191m / z= 548.19(C 40 H 24 N2O =548.65)192m / z= 548.19(C 40 H 24 N2O =548.65)194m / z= 472.16(C 34 H 20 N2O =472.55)199m / z= 548.19(C 40 H 24 N2O =548.65)201m / z= 396.13(C 28 H 16 N2O =396.45)210m / z= 548.19(C 40 H 24 N2O =548.65)213m / z= 472.16(C 34 H 20 N2O =472.55)220m / z= 598.20(C 44 H 26 N2O =598.70)223m / z= 473.15(C 33 H 19 N3O =473.54)247m / z= 522.17(C 38 H 22 N2O =522.61)255m / z= 473.15(C 33 H 19N3O =473.54)258m / z= 598.20(C 44 H 26 N2O =598.70)263m / z= 473.15(C 33 H 19 N3O =473.54)299m / z= 550.18(C 38 H 22 N4O =550.62)355m / z= 510.12(C 34 H 23 OPS =510.59)359m / z= 510.12(C 34 H 23 OPS =510.59)363m / z= 510.12(C 34 H 23 OPS =510.59)367m / z= 434.09(C 28 H 19 OPS =434.49)382m / z= 510.12(C 34 H 23 OPS =510.59)383m / z= 434.09(C 28 H 19 OPS =434.49)440m / z= 562.13(C 36 H 23 N2OPS =562.63)448m / z= 387.08(C 23 H 18 NOPS =387.44)471m / z= 418.11(C 28 H 19 O2P =418.43)544m / z= 546.15(C 36 H 23 N2O2P =546.57)546m / z= 497.13(C 31 H 20 N3O2P =497.49)557m / z= 427.17(C 27 H 26 NO2P =427.48)566m / z= 428.20(C 28 D 16 N2S = 428.61)576m / z= 508.26(C 34 D 20 N2S = 508.73)593m / z= 492.28(C 34 D 20N2O = 492.67)599m / z= 676.40(C 48 D 28 N2O =676.94)602m / z= 533.27(C 34 D 23 OPS = 533.73)612m / z= 585.29(C 38 D 25 OPS = 585.80)618m / z= 517.29(C 34 D 23 O2P = 517.67)619m / z= 437.23(C 28 D 19 O2P = 437.55)621m / z= 449.15(C 31 H 19 N3O =449.51)624m / z= 541.16(C 37 H 23 N3S =541.67)626m / z= 525.18(C 37 H 23 N3O =525.61)638m / z= 541.16(C 37 H 23 N3S =541.67)642m / z= 541.16(C 37 H 23 N3S =541.67)647m / z= 525.18(C 37 H 23 N3O =525.61)653m / z= 541.16(C 37 H 23 N3S =541.67)659m / z= 525.18(C 37 H 23 N3O =525.61)662m / z= 525.18(C 37 H 23 N3O =525.61)675m / z= 541.16(C 37 H 23 N3S =541.67)677m / z= 525.18(C 37 H 23 N3O =525.61)681m / z= 525.18(C 37 H 23 N3O =525.61)692m / z= 541.16(C 37 H 23N3S =541.67)703m / z= 548.33(C 37 D 23 N3O = 548.75)704m / z= 564.31(C 37 D 23 N3S = 564.81)709m / z= 548.33 (C 37 D 23 N3O = 548.75)713m / z= 564.31(C 37 D 23 N3S = 564.81)

[0429]

[0430] <Experimental Example>

[0431] Experimental Example 1.

[0432] Experimental Example 1-1. Fabrication of an Organic Light-Emitting Device

[0433] 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.

[0434]

[0435] Then the vacuum level inside the chamber is 10 -6After 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.

[0436]

[0437] 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.

[0438]

[0439] Next, a compound of the following structural formula E1 was deposited as an electron transport layer with a thickness of 300 Å.

[0440]

[0441] 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.

[0442] 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.

[0443] 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 compounds shown in Table 6 below were used instead of E1.

[0444]

[0445] Experimental Example 1-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0446] 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.

[0447] 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 6.

[0448]

[0449] Compound Driving Voltage (V) Luminous Efficiency (cd / A) CIE (x, y) Lifetime (T 95) Example 1 14.86 6.82 (0.133, 0.101) 88 Example 2 44.85 6.79 (0.134, 0.101) 85 Example 3 54.84 6.79 (0.133, 0.100) 86 Example 4 84.79 6.82 (0.133, 0.100) 88 Example 5 94.86 6.74 (0.134, 0.102) 85 Example 6 114.90 6.86 (0.135, 0.100) 83 Example 7 134.89 6.77 (0.133, 0.101) 84 Example 8 154.90 6.76 (0.132, 0.099)87 Example 9164.886.75(0.134, 0.100)86 Example 10184.846.89(0.134, 0.099)87 Example 11214.896.73(0.133, 0.101)84 Example 12234.886.86(0.133, 0.102)86 Example 13244.846.80(0.133, 0.100)85 Example 14284.906.77(0.134, 0.099)83 Example 15324.856.81(0.135, 0.100)87 Example 16354.916.73(0.133, 0.099)82 Example 17424.896.84(0.134, 0.100)83 Example 18454.836.86(0.134, 0.099)85 Example 19464.836.85(0.132, 0.102)85 Example 20694.866.81(0.133, 0.100)81 Example 21724.876.88(0.136, 0.101)83 Example 22774.826.87(0.134, 0.102)88 Example 23804.856.89(0.134, 0.101)82 Example 24924.906.85(0.132, 0.100)84 Example 25934.876.86(0.133, 0.100)85 Example 261054.856.79(0.134, 0.098)83 Example 271374.846.80(0.135, 0.102)86 Example 281594.906.83(0.132, 0.100)84 Example 291804.876.84(0.135, 0.101)85 Example 301884.906.81(0.132, 0.100)82 Example 311914.896.79(0.135, 0.102)82 Example 321924.866.83(0.135, 0.099)84Example 332014.906.73(0.134, 0.102)81Example 342474.896.75(0.135, 0.101)83Example 352554.876.91(0.133, 0.102)85Example 362634.896.82(0.133, 0.101)84Example 372994.866.78(0.134, 0.100)82Example 383674.836.89(0.134, 0.100)84Example 394714.826.93(0.132, 0.102)86 Example 405444.836.94(0.134, 0.101)95 Example 415574.816.90(0.132, 0.100)87 Example 425664.816.91(0.133, 0.099)93 Example 435764.796.87(0.135, 0.099)90 Example 445934.866.85(0.134, 0.100)91 Example 456184.836.83(0.135, 0.101)92 Example 466194.856.88(0.133, 0.100)93 Example 476214.896.85(0.133, 0.099)87 Example 486244.826.89(0.135, 0.100)84 Example 496264.846.86(0.132, 0.101)86 Example 506384.886.83(0.134, 0.099)86 Example 516424.826.90(0.134, 0.099)89 Example 526474.836.83(0.134, 0.100)87 Example 536534.866.88(0.135, 0.101)83 Example 546594.866.85(0.132, 0.102)85 Example 556624.836.79(0.133, 0.103)88 Example 566754.846.82(0.132, 0.103)88 Example 576774.876.83(0.132, 0.101)89 Example 586814.886.84(0.134, 0.101)87 Example 596924.866.81(0.135, 0.102)85 Example 607034.806.90(0.134, 0.101)94 Example 617044.816.89(0.133, 0.101)93 Example 627094.856.92(0.134, 0.100)90Example 637134.886.93(0.134, 0.101)90Comparative Example 1E15.506.21(0.134, 0.102)39Comparative Example 2Comparative Compound A5.296.40(0.134, 0.102)48Comparative Example 3Comparative Compound B5.306.39(0.133, 0.101)55Comparative Example 4Comparative Compound C5.346.35(0.135, 0.102)49Comparative Example 5Comparative Compound D5.276.34(0.134,(0.102)51Comparative Example 6Comparative Compound E5.386.40(0.135, 0.099)53Comparative Example 7Comparative Compound F5.316.39(0.132, 0.102)50Comparative Example 8Comparative Compound G5.356.41(0.131, 0.100)54Comparative Example 9Comparative Compound H5.326.38(0.133, 0.101)56.

[0450]

[0451] [Comparative Compound]

[0452]

[0453] From the results in Table 6 above, Examples 1 to 63, 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 compared to Comparative Examples 1 to 9.

[0454] The heterocyclic compound represented by the above chemical formula 1 of the present invention has a core structure with an appropriate electron transport ability, and at the same time, has a functional group of the chemical formula 2 (phenanthroline), chemical formula 3 (phosphine oxide), chemical formula 4 (terpyridine), or chemical formula 5 (terpyridine), thereby having a fast electron transport ability. The above functional group also acts as a metal-acceptor, forming a stable bond with metals used in the cathode. For this reason, electrons can be efficiently transferred in a state where decomposition or destruction of the compound occurs relatively less. Therefore, it is believed that the heterocyclic compound represented by the above chemical formula 1 of the present invention has an appropriate electron transport ability to induce light emission, and can improve stability when laminating an electron transport layer, resulting in a low driving voltage and excellent light emission efficiency and lifespan.

[0455]

[0456] Experimental example 2.

[0457] Experimental Example 2-1. Fabrication of an Organic Light-Emitting Device

[0458] 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.

[0459] 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 7 below.

[0460] 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. The emission layer on top of that 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 on the electron transport layer to a thickness of 10Å to form an electron injection layer, and then aluminum (Al) was deposited on the electron injection layer to a thickness of 1,200Å to form a cathode, thereby manufacturing an organic electroluminescent device.

[0461] 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.

[0462]

[0463]

[0464] Experimental Example 2-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0465] 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.

[0466] 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 7.

[0467]

[0468] Compound Driving Voltage (V) Luminous Efficiency (cd / A) CIE (x, y) Lifetime (T 95) Example 6417.0470.18(0.213,0.419)86 Example 6547.1968.07(0.214,0.418)84 Example 6657.4369.78(0.215,0.419)85 Example 6787.3369.33(0.212,0.420)86 Example 6897.3768.13(0.213,0.421)86 Example 69137.0869.54(0.214,0.418)85 Example 70157.1268.83(0.215,0.419)82 Example 71167.3168.79(0.213,0.420)83 Example 72247.2269.44(0.215,0.421)83 Example 73287.2868.18(0.212,0.421)84 Example 74467.3869.98(0.214,0.420)85 Example 75697.3068.74(0.213,0.420)81 Example 76727.2968.35(0.212,0.423)83 Example 77777.4168.92(0.214,0.419)87 Example 78807.3566.52(0.212,0.418)86 Example 79927.4170.01(0.215,0,421)84 Example 80937.3967.86(0.216,0.422)83 Example 811057.2467.97(0.215,0.419)82 Example 821377.4067.88(0.213,0.424)85 Example 831597.2769.08(0.212,0.419)81 Example 841777.2369.23(0.214,0.424)82 Example 851807.2669.04(0.218,0.423)81 Example 861857.2867.53(0.215,0.418)83 Example 871877.4068.64(0.212,0.421)86 Example 881887.3969.07(0.213,0.419)81 Example 891917.3167.99(0.213,0.421)84 Example 901927.2868.50(0.214,0.422)83 Example 911947.3369.48(0.210,0.422)80 Example 921997.3768.03(0.211,0.425)82 Example 932017.3268.24(0.211,0.429)81 Example 942107.3769.87(0.214,0.428)83 Example 952137.4169.99(0.215,0.426)82 Example 962477.2968.68(0.216,0.424)81 Example 972637.3068.11(0.213,0.425)80 Example 982997.4267.90(0.213,0.426)83 Example 993597.3770.03(0.217,0.425)84 Example 1003637.3370.41(0.215,0.416)85 Example 1013677.3570.12(0.214,0.419)84 Example 1023827.3669.35(0.213,0.418)83 Example 1033837.4469.74(0.213,0.418)85 Example 1044407.2969.84(0.216,0.420)88 Example 1054487.2868.84(0.218,0.424)86 Example 1065937.3069.19(0.212,0.423)91 Example 1075997.2970.12(0.214,0.422)93 Example 1086027.2969.90(0.215,0.418)94 Example 1096127.2870.08(0.215,0.415)92 Example 1106217.3169.97(0.216,0.414)84 Example 1116247.2768.85(0.213,0.415)81 Example 1126267.4369.73(0.217,0.419)86 Example 1136387.2969.88(0.215,0.417)88 Example 1146427.3570.03(0.216,0.413)90 Example 1156477.3469.69(0.218,0.415)85 Example 1166537.3868.37(0.213,0.416)85 Example 1176597.4069.24(0.213,0.412)86 Example 1186627.3069.50(0.215,0.419)82 Example 1196757.3170.11(0.214,0.416)87 Example 1206777.2968.19(0.216,0.420)82 Example 1216817.3369.40(0.212,0.420)83 Example 1226927.3769.85(0.214,0.423)88 Example 1237037.2870.00(0.211,0.427)94 Example 1247047.3068.43(0.212,0.426)93Example 1257097.2871.33(0.211,0.427)95Example 1267137.3368.78(0.211,0.427)95Comparative Example 10TmPyPB8.2255.70(0.211,0.427)49Comparative Example 11Comparative Compound A8.0359.27(0.211,0.428)53Comparative Example 12Comparative Compound B8.1159.41(0.214,0.427)52Comparative Example 13Comparative Compound C7.9358.44(0.210,0.430)53Comparative Example 14 Comparative compound D8.0458.10(0.214,0.423)52 Comparative example 15 Comparative compound E8.0558.63(0.211,0.423)51 Comparative example 16 Comparative compound F8.0158.38(0.212,0.428)50 Comparative example 17 Comparative compound G8.0857.71(0.213,0.424)51 Comparative example 18 Comparative compound H7.9053.47(0.210,0.428)45.

[0469]

[0470] [Comparative Compound]

[0471]

[0472] From the results in Table 7 above, Examples 64 to 126, 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 10 to 18.

[0473] The core structure of the heterocyclic compound represented by the above chemical formula 1 of the present invention has an appropriate electron transport ability. At the same time, since it has a functional group of the chemical formula 2 (phenanthroline), chemical formula 3 (phosphine oxide), chemical formula 4 (terpyridine), or chemical formula 5 (terpyridine), it has an appropriate LUMO level. In addition, the functional groups have the characteristic of being able to bind to metals such as Li and Yb used in the N-type charge generation layer. Due to this structural characteristic, electrons formed in the N-type charge generation layer can easily be injected into the electron transport layer.

[0474] Therefore, it is expected that the heterocyclic compound represented by the chemical formula 1 of the present invention is doped with an alkali metal or an alkaline earth metal to form a gap state in the N-type charge generation layer, and that electrons generated from the P-type charge generation layer are easily injected into the electron transport layer through the gap state generated in the N-type charge generation layer. For this reason, it is believed that the driving voltage of the organic light-emitting device is lowered and the efficiency and lifespan are improved. Therefore, it can be seen that the heterocyclic compound represented by the chemical formula 1 of the present invention can lower the driving voltage and improve the luminous efficiency and lifespan by improving the electron transport characteristics and the bonding stability with the metal in the N-type charge generation layer for the reasons presented above.

[0475]

[0476] [Explanation of symbols]

[0477] 100: Substrate

[0478] 200: Bipolar

[0479] 300: Organic layer

[0480] 301: Hole injection layer

[0481] 302: Hole transport layer

[0482] 303: Emissive layer

[0483] 304: Hole blocking layer

[0484] 305: Electron transport layer

[0485] 306: Electron injection layer

[0486] 400: Cathode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, The above X is O; or S, wherein R1 to R6 are the same as or different from each other, and are each independently hydrogen; deuterium; 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; the following chemical formula 2; the following chemical formula 3; the following chemical formula 4; And is selected from the group consisting of the following chemical formula 5, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and are each independently 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, R4 and R6 is any one of the following chemical formulas 2 to 5, The above a is an integer from 0 to 3, and when a is 2 or greater, R2 are equal to or different from each other, The above b is an integer from 0 to 3, and when b is 2 or greater, R5 are equal to or different from each other, [Chemical formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] In the above chemical formulas 2 to 5, The above R11 to R20 are the same as or different from each other, and are each independently hydrogen; deuterium; halogen; 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; -SiR201R202R203; And -NR201R202, or two or more adjacent groups are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202 and R203 are the same as or different from each other and are each independently 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 d is an integer from 0 to 6, and when d is 2 or greater, R12 are equal to or different from each other, The above h is an integer from 0 to 4, and when h is 2 or greater, R15 are equal to or different from each other, The above i is an integer from 0 to 2, and when i is 2 or greater, R16 are equal to or different from each other, The above j is an integer from 0 to 4, and if i is greater than or equal to j, R17 are equal to or different from each other, The above l is an integer from 0 to 3, and when l is 2 or greater, R18 are equal to or different from each other, The above m is an integer from 0 to 2, and when m is 2 or greater, R19 are equal to or different from each other, The above n is an integer from 0 to 4, and when n is 2 or greater, R20 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 L1 to L4 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 c is an integer from 0 to 5, and when c is 2 or greater, L1 is equal to or different from each other, The above e is an integer from 0 to 5, and when e is 2 or greater, L2 are equal to or different from each other, The above k is an integer from 0 to 5, and when k is 2 or greater, L3 are equal to or different from each other, The above o is an integer from 0 to 5, and when o is 2 or greater, L4 are equal to or different from each other.

2. In paragraph 1, The above R1, R4 and R6 are the same as or different from each other, and are each independently hydrogen; deuterium; the above chemical formula 2; the above chemical formula 3; the above chemical formula 4; or the above chemical formula 5, A heterocyclic compound, wherein any one of the above R1, R4 and R6 is any one of the above chemical formulas 2 to 5, and the rest are the same or different from each other and are each independently hydrogen; or deuterium.

3. In paragraph 1, A heterocyclic compound wherein the above R2, R3 and R5 are the same or different and each independently hydrogen or deuterium.

4. In paragraph 1, A heterocyclic compound wherein R13 and R14 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.

5. 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 1-12: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] In the chemical formulas 1-1 to 1-12 above, The above X, R1 to R6, a and b are the same as the definitions of the above chemical formula 1, The above L1, R11, R12, c and d are the same as the definitions in the above chemical formula 2, The above L2, R13, R14 and e are the same as the definitions of the above chemical formula 3, The above L3, R15 to R17 and h to k are the same as the definitions in the above chemical formula 4, The above L4, R18 to R20 and l to o are the same as defined in the above chemical formula 5.

6. 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.

7. 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: .

8. 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 7.

9. In paragraph 8, The above organic layer includes an electron transport layer, An organic light-emitting device, wherein the electron transport layer comprises the heterocyclic compound.

10. In paragraph 8, 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.

11. In paragraph 8, 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.

12. In paragraph 11, An organic light-emitting device, wherein the charge generating layer comprises the heterocyclic compound.

13. In paragraph 11, 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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