Heterocyclic compound and organic light-emitting element including same

Abstract

The present specification pertains to: a heterocyclic compound of chemical formula 1; and an organic light-emitting element including same.

Description

Heterocyclic compound and organic light-emitting device containing the same

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

[0002] This application claims the benefit of Korean Patent Application No. 10-2023-0086448 filed with the Korean Intellectual Property Office on July 4, 2023, the entire contents of which are incorporated herein by reference.

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

[0004] Organic light-emitting devices 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.

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

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

[0007] [Prior Art Document] (Patent Document 1) U.S. Patent No. 4,356,429

[0008] The present specification provides a heterocyclic compound and an organic light-emitting device including the same.

[0009] In one embodiment of the present specification, a heterocyclic compound of the following chemical formula 1 is provided.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] X is CRaRb,

[0014] R1 to R4 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R"; and two or more adjacent groups selected from the group consisting of substituted or unsubstituted amine groups, or 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,

[0015] L1 and L2 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0016] Ar1 and Ar2 are the same as or different from each other, and are each independently selected from a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R"; and the group consisting of the following chemical formula 1-1,

[0017] m and p are integers from 0 to 4,

[0018] n and q are integers from 1 to 5,

[0019] a and c are integers from 0 to 4,

[0020] b is an integer of 0 or 1,

[0021] If a, c, m, n, p and q are 2 or more, the substituents in parentheses are the same or different,

[0022] R, R' and R" are the same or different 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,

[0023] Ra and Rb are the same or different and each independently a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group,

[0024] At least one of the above Ar1 and Ar2 is represented by the following chemical formula 1-1,

[0025] [Chemical Formula 1-1]

[0026]

[0027] In the above chemical formula 1-1,

[0028] means a position connected to the above chemical formula 1,

[0029] L3 and L4 are the same or different, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0030] r and s are integers from 0 to 4,

[0031] If r and s are 2 or more, the substituents in parentheses are the same or different,

[0032] Ar3 and Ar4 are the same or different, 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.

[0033] In another embodiment of the present specification, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes at least one type of the heterocyclic compound.

[0034] The heterocyclic compound described herein, when used in an organic light-emitting device, can lower the driving voltage of the device, improve the luminous efficiency, and improve the lifespan characteristics of the device. Specifically, the heterocyclic compound of the present invention is characterized in that it includes a core structure in which X has CRaRb as in Chemical Formula 1, and necessarily includes -(L1)m-(Ar1)n at a specific position in the core structure and simultaneously includes a substituent of -(L2)p-(Ar2)q, and at least one of Ar1 and Ar2 is substituted with Chemical Formula 1-1.

[0035] As described above, since the heterocyclic compound according to the present application has a characteristic structure, the band gap and T1 (energy level of triplet state) value can be adjusted through the excellent hole transport properties of the amine functional group, thereby controlling the hole transport ability and electron blocking ability, thereby lowering the driving voltage of the device and improving the light efficiency. In addition, by bonding one of the two substituents (-(L1)m-(Ar1)n) to a specific position, the hole properties are strengthened while the planarity and glass transition temperature of the amine derivative are increased, thereby improving the thermal stability of the compound, thereby having the effect of improving the lifespan characteristics of the device.

[0036] As in the examples above, heterocyclic compounds can be used as organic layer materials of organic light-emitting devices. The compounds can serve as hole injection materials, hole transport materials, luminescent materials, etc. in organic light-emitting devices, and the compounds of the above chemical formula can be used as materials with excellent hole transport capabilities. In particular, heterocyclic compounds in which X is CRaRb have higher electron mobility than heterocyclic compounds in which X is O or S, and can be used as materials with better hole transport capabilities.

[0037] Figures 1 to 4 are diagrams each exemplifying a laminated structure of an organic light-emitting device according to one embodiment of the present specification.

[0038] Description of the symbol

[0039] 100: Substrate

[0040] 200: Bipolar

[0041] 300: Organic layer

[0042] 301: Hole injection layer

[0043] 302: Hole transport layer

[0044] 303: Electronic barrier layer

[0045] 304: Emissive layer

[0046] 305: Electron transport layer

[0047] 306: Electron injection layer

[0048] 400: Cathode

[0049] Hereinafter, the present specification will be described in more detail.

[0050] In this specification, when a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components, unless specifically stated otherwise.

[0051] In this specification, the chemical formula means the position where it is combined.

[0052] The term "substitution" above 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.

[0053] In this specification, "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a C1 to C60 alkyl group; a C2 to C60 alkenyl group; a C2 to C60 alkynyl group; a C3 to C60 cycloalkyl group; a C2 to C60 heterocycloalkyl group; a C6 to C60 aryl group; a C2 to C60 heteroaryl group; a silyl group; a phosphine oxide group; and an amine group, or a substituent in which two or more substituents selected from the above-mentioned substituents are linked.

[0054] In this specification, "when no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0055] In one embodiment of the present application, "when no substituent is indicated in the chemical formula or compound structure" may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the deuterium content may be 0% to 100%.

[0056] In one embodiment of the present application, in the case where "no substituent is indicated in the chemical formula or compound structure", if the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents are hydrogen, etc., and deuterium is not explicitly excluded, hydrogen and deuterium may be used in combination in the compound.

[0057] In one embodiment of the present application, deuterium is an element having a deuteron, which is one of the isotopes of hydrogen and is composed of one proton and one neutron, as its nucleus, and can be expressed as hydrogen-2, and its element symbol is D or 2 It can also be written as H.

[0058] In one embodiment of the present application, an isotope means an atom having the same atomic number (Z) but a different mass number (A). An isotope can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0059] In one embodiment of the present application, the meaning of the content T% of a specific substituent can be defined as T2 / T1×100 = T% when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2.

[0060] That is, in one example, In the phenyl group represented by , the content of deuterium of 20% means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and if the number of deuterium among them is 1 (T2 in the formula), it can be expressed as 20%. In other words, the content of deuterium of 20% in the phenyl group can be expressed by the structural formula below.

[0061]

[0062] Additionally, in one embodiment of the present application, the term “phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, i.e., has 5 hydrogen atoms.

[0063] In the present specification, the halogen may be fluorine, chlorine, bromine or iodine.

[0064] In the present specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 40 carbon atoms, and more specifically 1 to 20 carbon atoms. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, Examples include, but are not limited to, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0065] In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0066] In the present specification, the 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.

[0067] In the present specification, the alkoxy group may be straight chain, branched chain, or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.

[0068] In the present specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The cycloalkyl group may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. Specifically, there are, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc.

[0069] In the present specification, the heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

[0070] In the present specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. The aryl group includes a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the above aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof.

[0071] In this specification, the terphenyl group may be selected from the following structures.

[0072]

[0073] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0074] When the above fluorenyl group is substituted, , , , , , It can be, but is not limited to, the following.

[0075] In the present specification, the heteroaryl group includes S, O, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic ring means a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.Specific examples of the above heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene 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 deoxynyl 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, Triazindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiathiazinyl 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 2,3-dihydrobenzo[b]thiophene, a 2,3-dihydrobenzofuran, a 5,10-dihydrodibenzo[b,e][1,4]azasilinyl 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.

[0076] In the present specification, a silyl group is a substituent that includes Si and is directly connected to the Si atom as a radical, and is represented by -Si(R101)(R102)(R103), and R101 to R103 are the same as or different from each other, and may be a substituent independently composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. Specific examples of the silyl group include (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), but is not limited thereto.

[0077] In the present specification, the phosphine oxide group is represented by -P(=O)(R104)(R105), and R104 and R105 are the same as or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. Specifically, it can be substituted with an alkyl group or an aryl group, and the above-described examples can be applied to the alkyl group and the aryl group. For example, the phosphine oxide group includes, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, and dinaphthylphosphine oxide.

[0078] In the present specification, the amine group is represented by -N(R106)(R107), and R106 and R107 are the same as or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. The amine group can be selected from the group consisting of -NH2; a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group.

[0079] In the present specification, the arylene group may be applied to the examples of the aryl group described above, except that it is a divalent group.

[0080] In the present specification, the heteroarylene group may be applied to the examples of the heteroaryl group described above, except that it is a divalent group.

[0081] One embodiment of the present specification provides a heterocyclic compound of the above chemical formula 1.

[0082] In one embodiment of the present application, the chemical formula 1 provides a heterocyclic compound represented by any one of the following chemical formulas 2 to 5.

[0083] [Chemical Formula 2]

[0084]

[0085] [Chemical Formula 3]

[0086]

[0087] [Chemical Formula 4]

[0088]

[0089] [Chemical Formula 5]

[0090]

[0091] In the above chemical formulas 2 to 5,

[0092] The definition of each substituent is the same as that in the chemical formula 1 above.

[0093] In one embodiment of the present application, the chemical formula 1 may be represented by any one of the following chemical formulas 6 to 11.

[0094] [Chemical Formula 6]

[0095]

[0096] [Chemical Formula 7]

[0097]

[0098] [Chemical Formula 8]

[0099]

[0100] [Chemical Formula 9]

[0101]

[0102] [Chemical Formula 10]

[0103]

[0104] [Chemical Formula 11]

[0105]

[0106] In the above chemical formulas 6 to 11,

[0107] The definition of each substituent is the same as that in the chemical formula 1 above.

[0108] In one embodiment of the present application, the chemical formula 1-1 may be represented by the following chemical formula 1-1-1 or 1-1-2.

[0109] [Chemical Formula 1-1-1]

[0110]

[0111] [Chemical Formula 1-1-2]

[0112]

[0113] In the above chemical formulas 1-1-1 and 1-1-2,

[0114] , the definitions of L3, L4, r and s are the same as those in the above chemical formula 1-1,

[0115] X1 is O; or S,

[0116] Ar13 and Ar14 are the same or different and are each independently a substituted or unsubstituted C6 to C60 aryl group,

[0117] R11 and R12 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0118] a1 is an integer from 0 to 4,

[0119] a2 is an integer from 0 to 3,

[0120] If a1 and a2 are 2 or more, the substituents within the parentheses are the same or different.

[0121] In one embodiment of the present application, Ar1 is represented by the chemical formula 1-1, and Ar2 is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; or -SiRR'R".

[0122] In one embodiment of the present application, Ar2 is represented by the chemical formula 1-1, and Ar1 is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; or -SiRR'R".

[0123] In one embodiment of the present application, Ar1 and Ar2 are represented by the chemical formula 1-1.

[0124] In one embodiment of the present application, X is CRaRb.

[0125] In one embodiment of the present application, Ra and Rb are the same as or different from each other and each independently a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group.

[0126] In another embodiment, Ra and Rb are the same as or different from each other and each independently a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 aryl group.

[0127] In another embodiment, Ra and Rb are the same as or different from each other and each independently a substituted or unsubstituted C1 to C20 alkyl group; or a substituted or unsubstituted C6 to C20 aryl group.

[0128] In another embodiment, Ra and Rb are the same or different and are each independently a substituted or unsubstituted C1 to C20 alkyl group.

[0129] In another embodiment, Ra and Rb are the same or different and are each independently a C1 to C20 alkyl group substituted or unsubstituted with deuterium.

[0130] In another embodiment, Ra and Rb are the same or different and are each independently a straight-chain C1 to C20 alkyl group substituted or unsubstituted with deuterium.

[0131] In another embodiment, Ra and Rb are the same or different and are each independently a straight-chain C1 to C10 alkyl group substituted or unsubstituted with deuterium.

[0132] In another embodiment, Ra and Rb are the same or different and are each independently a methyl group substituted or unsubstituted with deuterium.

[0133] In one embodiment of the present application, R1 to R4 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R"; and two or more adjacent groups selected from the group consisting of substituted or unsubstituted amine groups may combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle.

[0134] In another embodiment, R1 to R4 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle.

[0135] In another embodiment, R1 to R4 are the same as or different from each other, and can each independently be selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.

[0136] In another embodiment, R1 to R4 are the same as or different from each other, and can each independently be selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; and a substituted or unsubstituted C2 to C40 heteroaryl group.

[0137] In another embodiment, R1 to R4 are the same as or different from each other, and can each independently be selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group.

[0138] In another embodiment, R1 to R4 are the same as or different from each other, and can each independently be selected from the group consisting of hydrogen; deuterium; halogen; -CN; a C1 to C20 alkyl group; a C6 to C20 aryl group; and a C2 to C20 heteroaryl group.

[0139] In another embodiment, R1 to R4 are the same or different from each other and can each independently be hydrogen or deuterium.

[0140] In one embodiment of the present application, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0141] In another embodiment, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0142] In another embodiment, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0143] In another embodiment, L1 and L2 are the same as or different from each other, and each independently may be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0144] In another embodiment, L1 and L2 are the same as or different from each other, and each independently may be a direct bond; or an arylene group having C6 to C20 substituted or unsubstituted with deuterium.

[0145] In another embodiment, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0146] In another embodiment, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a phenylene group substituted or unsubstituted with deuterium; or a biphenylene group substituted or unsubstituted with deuterium.

[0147] In another embodiment, L1 may be a direct bond.

[0148] In another embodiment, L2 may be a direct bond; a phenylene group substituted or unsubstituted with deuterium; or a biphenylene group substituted or unsubstituted with deuterium.

[0149] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the group consisting of a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R"; and chemical formula 1-1, wherein at least one of Ar1 and Ar2 is chemical formula 1-1.

[0150] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the group consisting of a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and chemical formula 1-1, wherein at least one of Ar1 and Ar2 is chemical formula 1-1.

[0151] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the group consisting of a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; and chemical formula 1-1, wherein at least one of Ar1 and Ar2 is chemical formula 1-1.

[0152] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the group consisting of a C6 to C20 aryl group substituted or unsubstituted with deuterium; and chemical formula 1-1, wherein at least one of Ar1 and Ar2 is chemical formula 1-1.

[0153] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; or chemical formula 1-1, and at least one of Ar1 and Ar2 is chemical formula 1-1.

[0154] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the group consisting of a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R"; and chemical formula 1-1, wherein one of Ar1 and Ar2 is chemical formula 1-1.

[0155] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the group consisting of a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and chemical formula 1-1, wherein one of Ar1 and Ar2 is chemical formula 1-1.

[0156] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the group consisting of a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; and chemical formula 1-1, wherein one of Ar1 and Ar2 is chemical formula 1-1.

[0157] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the group consisting of a C6 to C20 aryl group substituted or unsubstituted with deuterium; and chemical formula 1-1, wherein one of Ar1 and Ar2 is chemical formula 1-1.

[0158] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; or chemical formula 1-1, and one of Ar1 and Ar2 is chemical formula 1-1.

[0159] In one embodiment of the present application, Ar1 is selected from the group consisting of a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", and Ar2 is chemical formula 1-1.

[0160] In one embodiment of the present application, Ar1 is selected from the group consisting of a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; and a substituted or unsubstituted C2 to C40 heteroaryl group; and Ar2 is chemical formula 1-1.

[0161] In one embodiment of the present application, Ar1 is selected from the group consisting of a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group, and Ar2 is represented by Chemical Formula 1-1.

[0162] In one embodiment of the present application, Ar1 is a C6 to C20 aryl group substituted or unsubstituted with deuterium, and Ar2 is chemical formula 1-1.

[0163] In one embodiment of the present application, Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted phenanthrenyl group, and Ar2 is chemical formula 1-1.

[0164] In one embodiment of the present application, L3 and 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 C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0165] In another embodiment, L3 and 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 C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0166] In another embodiment, L3 and 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.

[0167] In another embodiment, 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 C6 to C20 arylene group.

[0168] In another embodiment, L3 and L4 may be the same as or different from each other, and may each independently be a direct bond; or an arylene group having C6 to C20 substituted or unsubstituted with deuterium.

[0169] In another embodiment, L3 and L4 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0170] In another embodiment, L3 and L4 may be the same as or different from each other, and may each independently be a direct bond; a phenylene group substituted or unsubstituted with deuterium; or a biphenylene group substituted or unsubstituted with deuterium.

[0171] In one embodiment of the present application, Ar3 and Ar4 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.

[0172] In another embodiment, Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0173] In another embodiment, Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0174] In another embodiment, Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0175] In another embodiment, Ar3 and Ar4 are the same as or different from each other, and each independently represents a C6 to C20 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C1 to C20 alkyl groups; or a C2 to C20 heteroaryl group unsubstituted or substituted with deuterium.

[0176] In another embodiment, Ar3 and Ar4 may be the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted diphenylfluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted dimethylfluorenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0177] In one embodiment of the present application, Ar13 and Ar14 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group.

[0178] In another embodiment, Ar13 and Ar14 may be the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted diphenylfluorenyl group; a substituted or unsubstituted spirobifluorenyl group; or a substituted or unsubstituted dimethylfluorenyl group.

[0179] In one embodiment of the present application, R11 and R12 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0180] In another embodiment, R11 and R12 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0181] In another embodiment, R11 and R12 are the same as or different from each other, and each independently represents hydrogen; deuterium; a C1 to C40 alkyl group; a C6 to C40 aryl group; or a C2 to C40 heteroaryl group.

[0182] In another embodiment, R11 and R12 are the same or different and are each independently hydrogen or deuterium.

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

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

[0185] In one embodiment of the present specification, the deuterium content of the chemical formula 1 may be 10% to 100%.

[0186] In one embodiment of the present specification, the deuterium content of the chemical formula 1 may be 15% to 100%.

[0187] In one embodiment of the present specification, the deuterium content of the chemical formula 1 may be 25% to 100%.

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

[0189] In one embodiment of the present specification, the deuterium content of the heterocyclic compound of the chemical formula 1 satisfies the above range, and the photochemical characteristics of the compound not containing deuterium and the compound containing deuterium are almost similar, but when deposited in a thin film, the material containing deuterium tends to be packed with a narrower intermolecular distance.

[0190] Accordingly, by fabricating an EOD (Electron Only Device) and a HOD (Hole Only Device) and checking the current density according to the voltage, it can be confirmed that among the heterocyclic compounds of chemical formula 1 of the present invention, the compound containing deuterium exhibits much more balanced charge transport characteristics than the compound not containing deuterium.

[0191] Additionally, when looking at the surface of the thin film with an atomic force microscope (AFM), it can be confirmed that the thin film made of a compound containing deuterium is deposited with a more uniform surface without any aggregated areas.

[0192] Additionally, since the single bond dissociation energy of carbon and deuterium is higher than the single bond dissociation energy of carbon and hydrogen, in the case of a heterocyclic compound of chemical formula 1 of the present invention in which the deuterium content satisfies the above range, the stability of the entire molecule increases, thereby improving the lifespan of the device.

[0193] In one embodiment of the present specification, the deuterium content of the chemical formula 1 may be 0% or 10% to 100%.

[0194] In one embodiment of the present specification, the deuterium content of the chemical formula 1 may be 0% or 15% to 100%.

[0195] In one embodiment of the present specification, the deuterium content of the chemical formula 1 may be 0% or 20% to 100%.

[0196] In one embodiment of the present specification, the deuterium content of the chemical formula 1 may be 0% or 25% to 100%.

[0197] In one embodiment of the present specification, the deuterium content of the chemical formula 1 may be 0% or 100%.

[0198] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following compounds.

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[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] In addition, by introducing various substituents into the structure of the above chemical formula 1, compounds having the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport 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.

[0240] 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.

[0241] In another embodiment of the present specification, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one layer of the organic layer comprises at least one heterocyclic compound of the chemical formula 1.

[0242] In one embodiment of the present specification, the organic layer includes a hole transport layer, and the hole transport layer may include one or more types of the heterocyclic compound.

[0243] In one embodiment of the present specification, the organic layer includes an electron blocking layer, and the electron blocking layer may include one or more types of the heterocyclic compound.

[0244] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include one or more types of the heterocyclic compound.

[0245] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include one type of the heterocyclic compound.

[0246] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, and the host may include one or more of the heterocyclic compounds.

[0247] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, and the host may include one type of the heterocyclic compound.

[0248] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a green host, and the green host may include one or more of the heterocyclic compounds.

[0249] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a red host, and the red host may include one or more of the heterocyclic compounds.

[0250] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a blue host, and the blue host may include one or more of the heterocyclic compounds.

[0251] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the heterocyclic compound as a P-type host.

[0252] The organic layer of the organic light-emitting device of the present invention may be formed as a single-layer structure, but may also be formed as a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

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

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

[0255] An organic light-emitting device according to one embodiment of the present specification 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 of the above-described chemical formula 1.

[0256] The heterocyclic compound of the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0257] In one embodiment of the present specification, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound of the chemical formula 1 may be used as a material of the blue organic light-emitting device. For example, the heterocyclic compound of the chemical formula 1 may be included in a hole transport layer, an electron blocking layer, or a light-emitting layer of the blue organic light-emitting device.

[0258] In another embodiment of the present specification, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound of the chemical formula 1 may be used as a material of the green organic light-emitting device. For example, the heterocyclic compound of the chemical formula 1 may be included in a hole transport layer, an electron blocking layer, or a light-emitting layer of the green organic light-emitting device.

[0259] In another embodiment of the present specification, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound of the chemical formula 1 may be used as a material of the red organic light-emitting device. For example, the heterocyclic compound of the chemical formula 1 may be included in a hole transport layer, an electron blocking layer, or a light-emitting layer of the red organic light-emitting device.

[0260] The organic light-emitting device of the present invention may further include one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0261] The stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present disclosure is exemplified in Figures 1 to 4. However, the scope of the present application is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present application.

[0262] 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.

[0263] FIG. 3 and FIG. 4 illustrate 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 (304), an electron transport layer (305), and an electron injection layer (306), and the organic light-emitting device according to FIG. 4 includes a hole injection layer (301), a hole transport layer (302), an electron blocking layer (303), a light-emitting 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, layers other than the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0264] The organic layer containing the heterocyclic compound of the above chemical formula 1 may additionally contain other substances as needed.

[0265] In an organic light-emitting device according to one embodiment of the present specification, materials other than the heterocyclic compound of 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.

[0266] 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.

[0267] 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.

[0268] As the hole injection material, a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a starburst amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), a soluble conductive polymer such as polyaniline / dodecylbenzenesulfonic acid, or Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate) can be used.

[0269] Pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport materials, and low molecular weight or high molecular weight materials can also be used.

[0270] As the electron transport material, metal complexes of oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, etc. can be used, and not only low molecular weight substances but also high molecular weight substances can be used.

[0271] For example, LiF is a representative material used in the art, but the present application is not limited thereto.

[0272] Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. At this time, two or more light-emitting materials may be deposited and used as individual sources, or may be premixed and deposited and used as a single source. In addition, a fluorescent material may be used as the light-emitting material, but it may also be used as a phosphorescent material. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used as the light-emitting material, but materials in which both the host material and the dopant material participate in light emission may also be used.

[0273] When using a mixture of hosts for light-emitting materials, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more types of materials, either N-type host materials or P-type host materials, may be selected and used as the host materials for the light-emitting layer.

[0274] An organic light-emitting device according to one embodiment of the present specification may be a front-emitting, back-emitting, or double-sided emitting device depending on the material used.

[0275] The heterocyclic compound according to one embodiment of the present specification can function in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., by a similar principle to that applied to organic light-emitting devices.

[0276] 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.

[0277] In one embodiment of the present specification, a composition for forming an organic layer including the heterocyclic compound is provided.

[0278] In one embodiment of the present specification, a method for manufacturing an organic light-emitting device is provided, comprising: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, wherein the forming of the organic layer comprises forming one or more organic layers using an organic layer forming composition including the heterocyclic compound.

[0279] In one embodiment of the present specification, a method for manufacturing an organic light-emitting device is provided, wherein the step of forming the organic layer comprises pre-mixing a heterocyclic compound represented by the chemical formula 1 and forming the organic layer using a thermal vacuum deposition method.

[0280] The above pre-mixed means that the heterocyclic compound represented by the above chemical formula 1 and the additional compound are first mixed in one container before being deposited on the organic layer.

[0281] The premixed material may be referred to as a composition for forming an organic layer according to one embodiment of the present specification.

[0282] Hereinafter, the present specification will be described in more detail through examples, but these are only intended to illustrate the present application and are not intended to limit the scope of the present application.

[0283] <Manufacturing Example>

[0284] <Manufacturing Example 1> Preparation of compound 001

[0285]

[0286] 1) Preparation of compound 001-P7

[0287] Compound 2-bromonaphthalen-1-ol (50 g, 0.22 mol, 1 eq), (4-bromo-2-chloro-6-fluorophenyl)boronic acid (A) (70.9 g, 0.28 mol, 1.3 eq), Pd(PPh3)4 (12.7 g, 0.011 mol, 0.05 eq), K2CO3 (60.8 g, 0.44 mol, 2 eq), 1,4-dioxane (500 ml), and water (100 ml) were added and stirred at 100°C for 12 h. After quenching the reaction by adding water, extraction was performed using EA and water. Subsequently, moisture was removed with MgSO4. Compound 001-P7 (38.6 g) was obtained in a yield of 50% by separation using a silica gel column.

[0288] 2) Preparation of compound 001-P6

[0289] Compound 001-P7 (38.6 g, 0.11 mol, 1 eq), Cs2CO3 (71.6 g, 0.22 mol, 2 eq), and DMA (400 ml) were added and stirred at 130°C for 5 h. After quenching the reaction by adding water, extraction was performed using EA and water. Afterwards, moisture was removed with MgSO4. Compound 001-P6 (33.2 g) was obtained in a yield of 90% by separation using a silica gel column.

[0290] 3) Preparation of compound 001-P5

[0291] Compound 001-P6 (33.2 g, 0.1 mol, 1 eq), 2-boronobenzoic acid (18.3 g, 0.11 mol, 1.1 eq), Pd(PPh3)4 (5.7 g, 0.005 mol, 0.05 eq), K2CO3 (27.6 g, 0.2 mol, 2 eq), 1,4-dioxane (330 ml), and water (7 ml) were added and stirred at 100°C for 6 h. After quenching the reaction by adding water, extraction was performed using EA and water. Afterwards, moisture was removed with MgSO4. Compound 001-P5 (33.5 g) was obtained in a yield of 90% by separation using a silica gel column.

[0292] 4) Preparation of compound 001-P4

[0293] Compound 001-P5 (33.5 g, 0.09 mol, 1 eq), CH3MgBr(1M) (225 mL, 0.225 mol, 2.5 eq), and THF (400 ml) were added and stirred at 70°C for 3 h. After quenching the reaction by adding water, extraction was performed using MC and water. Afterwards, moisture was removed with CaCl2. Compound 001-P4 (27.8 g) was obtained in 80% yield by separation using a silica gel column.

[0294] 5) Preparation of compound 001-P3

[0295] Compound 001-P4 (27.8 g, 0.072 mol, 1 eq), BF3diethyl etherate (9.4 mL, 0.076 mol, 1.05 eq), and DCM (200 ml) were added and stirred at room temperature for 1 h. After quenching the reaction by adding water, extraction was performed using MC and water. Afterwards, moisture was removed with CaCl2. Compound 001-P3 (13.3 g) was obtained in a yield of 50% by separation using a silica gel column.

[0296] 6) Preparation of compound 001-P2

[0297] Compound 001-P3 (13.3 g, 0.036 mol, 1 eq), NBS (15.8 g, 0.089 mol, 1.05 eq), and DMF (200 ml) were added and stirred at 80°C for 5 h. After adding water to terminate the reaction, the mixture was filtered to obtain 15.8 g of compound 001-P2 in a yield of 98%.

[0298] 7) Preparation of compound 001-P1

[0299] Compound 001-P2 (10 g, 0.022 mol, 1 eq), phenylboronic acid (B) (2.9 g, 0.024 mol, 1.1 eq), Pd(PPh3)4 (1.32 g, 0.0011 mol, 0.05 eq), K2CO3 (6.08 g, 0.044 mol, 2 eq), 1,4-dioxane (100 ml), and water (20 ml) were added and stirred at 100°C for 4 h. After quenching the reaction by adding water, extraction was performed using EA and water. Afterwards, moisture was removed with MgSO4. Compound 001-P18.32 g was obtained in a yield of 85% by separation using a silica gel column.

[0300] 8) Preparation of compound 001

[0301] Compound 001-P1 (8.32 g, 0.019 mol, 1 eq), di([1,1'-biphenyl]-4-yl)amine (C) (6.1 g, 0.019 mol, 1 eq), Pd2(dba)3 (0.9 g, 0.001 mol, 0.05 eq), XPhos (0.9 g, 0.002 mol, 0.1 eq), NaOt-Bu (3.84 g, 0.04 mol, 2 eq), and toluene (80 mL) were added and stirred at 100°C for 4 h. After quenching the reaction by adding water, extraction was performed using EA and water. Afterwards, moisture was removed with MgSO4. Compound 001, 10.2 g, was obtained in a yield of 74% by separation using a silica gel column.

[0302] In the above Preparation Example 1, the compound was synthesized in the same manner using intermediate A in Table 1 below instead of (4-bromo-2-chloro-6-fluorophenyl)boronic acid (A), intermediate B instead of phenylboronic acid (B), and intermediate C instead of di([1,1'-biphenyl]-4-yl)amine (C).

[0303]

[0304]

[0305] [Manufacturing Example 2] Preparation of Compound 169

[0306]

[0307] The above manufacturing example 2 was synthesized using the same method as the above manufacturing example 1.

[0308] In the above Preparation Example 2, the compound was synthesized using the same method as in the preceding Preparation Example 2, using intermediate A in Table 2 below instead of (3-bromo-6-chloro-2-fluorophenyl)boronic acid (A), intermediate B instead of naphthalen-2-ylboronic acid (B), and intermediate C instead of bis(9,9-diphenyl-9H-fluoren-2-yl)amine (C).

[0309]

[0310]

[0311] [Manufacturing Example 3] Preparation of Compound 338

[0312]

[0313] In Manufacturing Example 3, the synthesis was carried out in the same manner as in Manufacturing Examples 1 and 2, except for the synthesis of compound 338.

[0314] 1) Preparation of compound 338

[0315] Compound 338-P1 (11 g, 0.02 mol, 1 eq), N-(4-(phenanthren-9-yl)phenyl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (C) (12.8 g, 0.2 mol, 1 eq), Pd2(dba)3 (0.9 g, 0.001 mol, 0.05 eq), XPhos (0.9 g, 0.002 mol, 0.1 eq), K2CO3 (5.5 g, 0.04 mol, 2 eq), 1,4-dioxane (100 ml), and water (320 ml) were added and stirred at 100°C for 6 h. The organic layer was extracted using EA and water, and then moisture was removed with MgSO4. The resultant was separated using a silica gel column to obtain 13 g of compound 338 with a yield of 71.6%.

[0316] In the above Preparation Example 3, the compound was synthesized in the same manner using intermediate A in Table 3 below instead of (3-bromo-2-chloro-6-fluorophenyl)boronic acid (A), intermediate B instead of phenanthren-9-ylboronic acid (B), and intermediate C instead of N-(4-(phenanthren-9-yl)phenyl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (C).

[0317]

[0318]

[0319] [Manufacturing Example 4] Preparation of Compound 424

[0320]

[0321] Manufacturing Example 4 was synthesized using the same method as Manufacturing Example 1.

[0322] In the above Preparation Example 4, the compound was synthesized using the same method as in Table 4, using intermediate A instead of (4-bromo-3-chloro-2-fluorophenyl)boronic acid (A), using intermediate B instead of naphthalen-2-ylboronic acid (B), and using intermediate C instead of bis(9,9-dimethyl-9H-fluoren-2-yl)amine (C).

[0323]

[0324]

[0325] [Manufacturing Example 5] Preparation of Compound 507

[0326]

[0327] Manufacturing Example 5 was synthesized using the same method as Manufacturing Example 1.

[0328] In the above Preparation Example 5, the compound was synthesized using the same method as in the following Table 5, using intermediate A instead of (2-bromo-4-chloro-6-fluorophenyl)boronic acid (A), intermediate B instead of phenylboronic acid (B), and intermediate C instead of N-([1,1'-biphenyl]-3-yl)dibenzo[b,d]thiophen-4-amine (C).

[0329]

[0330]

[0331] [Manufacturing Example 6] Preparation of Compound 672

[0332]

[0333] Manufacturing Example 6 was synthesized using the same method as Manufacturing Example 3.

[0334] In the above Preparation Example 6, the compound was synthesized in the same manner using intermediate A of Table 6 below instead of (5-bromo-4-chloro-2-fluorophenyl)boronic acid (A), intermediate B instead of naphthalen-2-ylboronic acid (B), and intermediate C instead of N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (C).

[0335]

[0336]

[0337] [Manufacturing Example 7] Preparation of Compound 721

[0338]

[0339] Compound 043 (5 g, 6 mmol) was added to 650 mL of C6D and purged with nitrogen for 2 hours. 3.8 mL of trifluoromethanesulfonic acid (42 mmol, 7 eq) was added dropwise via a syringe, and the reaction mixture was heated under reflux for 2 hours. After cooling to room temperature, 50 mL of deuterated water was added for extraction, and the organic layer was dried over anhydrous MgSO4 and concentrated using a rotary evaporator. Compound 721 (4.5 g, 90%) was obtained through an ethylene acetate (EA) slurry.

[0340] Except for the reaction temperature and time and the equivalent amount of trifluoromethanesulfonic acid described in Manufacturing Example 7 above, the compound in Table 7 below was synthesized using the same method as Manufacturing Example 7 above.

[0341] Compound number Reaction temperature Reaction time Trifluoromethane Equivalent yield 733 RT 1 HR 5 eq 88% 747 Reflux 2 HR 7 eq 85% 784 Reflux 2 HR 3 eq 79%

[0342] [Manufacturing Example 8] Preparation of Compound 727

[0343]

[0344] Compound 089 (5 g, 5 mmol) was added to 650 mL of C6D and purged with nitrogen for 2 hours. 3.1 mL of trifluoromethanesulfonic acid (35 mmol, 7 eq) was added dropwise via a syringe, and the reaction mixture was refluxed and heated for 2 hours. After cooling to room temperature, 50 mL of deuterated water was added for extraction, and the organic layer was dried over anhydrous MgSO4 and concentrated using a rotary evaporator. Compound 727 (4.3 g, 88%) was obtained through an ethylene acetate (EA) slurry.

[0345] Except for the reaction temperature and time and the equivalent amount of trifluoromethanesulfonic acid described in Manufacturing Example 8, the compound in Table 8 below was synthesized using the same method as Manufacturing Example 8.

[0346] Compound number Reaction temperature Reaction time Trifluoromethane Equivalent yield 736 RT 1 HR 5 eq 85% 773 Reflux 2 HR 7 eq 88%

[0347] [Manufacturing Example 9] Preparation of Compound 728

[0348]

[0349] Compound 043 (5 g, 6 mmol) was added to 650 mL of C6D and purged with nitrogen for 2 hours. 3.8 mL of trifluoromethanesulfonic acid (42 mmol, 7 eq) was added dropwise via a syringe, and the reaction mixture was heated under reflux for 2 hours. After cooling to room temperature, 50 mL of deuterated water was added for extraction, and the organic layer was dried over anhydrous MgSO4 and concentrated using a rotary evaporator. Compound 728 (4.5 g, 88%) was obtained through an ethylene acetate (EA) slurry.

[0350] Except for the reaction temperature and time and the equivalent amount of trifluoromethanesulfonic acid described in Manufacturing Example 9, the compound in Table 9 below was synthesized using the same method as Manufacturing Example 9.

[0351] Compound number Reaction temperature Reaction time Trifluoromethane Equivalent yield 731 RT 1 HR 5 eq 88% 753 Reflux 2 HR 7 eq 85% 776 Reflux 2 HR 3 eq 79% 790 RT 12 HR 5 eq 88%

[0352] Compounds were prepared in the same manner as the above manufacturing examples, and the results of their synthesis are shown in Tables 10 and 11 below. Table 10 below shows the measured values ​​of 1H NMR (DMSO, 500 MHz), and Table 11 below shows the measured values ​​of FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0353] compound 1H NMR(DMSO, 500MHz)0028.94(1H, dd), 8.45(1H, dd), 8.10(1H, dd), 7.93(1H, d), 7.79(1H, d), 7.64(1H, t), 7.55(1H, d), 7.49~7.37(9H, m), 7.14(4H, t), 7.11~7.00(8H, m), 6.89~6.83(2H, d), 1.69(12H, s)0138.97(1H, dd), 8.18(1H, d), 7.98(1H, dd), 7.90~7.79(7H, dd), 7.64~7.46(16H, m), 7.34~7.28(14H, m), 7.18(1H, tt), 1.69(6H, s)0278.97(1H, dd), 8.45(1H, d), 8.11(3H, s), 7.98(2H, d), 7.75~7.72(4H, dd), 7.64~7.39(18H, m), 7.17(2H, d), 1.69(6H, s)0368.97(1H, dd), 8.45(1H, dd), 8.18(1H, dd) 7.93~7.85(6H, m), 7.75(2H dd), 7.55~7.41(20H, ,m), 7.38(3H, tt), 7.28(3H, tt), 7.27(1H, s), 7.06(1H, dd), 1.69(6H, s)0468.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.09(2H, t), 7.95(1H, s), 7.93(1H, dd), 7.63~7.45(25H, m), 7.38(1H, s), 1.69(6H, s)0508.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.07~8.03(2H, d), 7.95(1H, s), 7.93 (1H, d), 7.90(4H, d), 7.64~7.49(10H, m), 7.38~7.28(8H, m), 7.16(1H, d), 6.97(1H, s), 1.82(6H, s), 1.69(6H, s)0658.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 7.90~7.86(4H, d), 7.75(1H, d), 7.55~7.25(24H, m), 7.16~7.08(4H, m), 6.97(1H, s), 1.69(6H, s)0698.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 7.90~7.85(3H, d), 7.72(1H, s), 7.64~7.24(24H, m), 7.16~7.11(11H, m), 6.97(1H, s), 1.69(6H, s)0888.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.09~8.07(2H, d), 7.78~7.71(7H, m), 7.60~7.37(21H, m), 7.29~7.25(5H, m), 7.11~7.10(2H, dd), 6.97(1H, s), 1.69(6H, s)0958.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.09~8.07(2H, d), 7.90~7.81(8H, m), 7.72(1H, s), 7.63~7.25(19H, m), 7.16~7.09(3H, m), 6.97(1H, s), 1.68(12H, s)1048.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 7.82~7.75(4H, m), 7.55~7.31(20H, m), 7.20~7.11(4H, m), 6.97(1H, s), 1.82(12H, s), 1.69(6H, s)1148.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 7.87~7.69(8H, m), 7.56~7.28(18H, m), 7.20~7.11(9H, m), 7.09(4H, dd), 6.97(1H, s), 1.69(6H, s)1248.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 7.93~7.64(5H, m), 7.59~7.28(18H, m), 7.16(2H, d), 6.94(1H, s), 1.69(12H, s), 1.64(6H, s)1278.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.11(1H, d), 7.98~7.93(2H, dd), 7.74~7.64(6H, m), 7.58~7.31(18H, m), 7.16(1H, s), 1.69(6H, s)1468.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.11(1H, d), 7.90~7.86(4H, m), 7.80~7.69(23H, m), 7.11(1H, s), 1.69(6H, s)1558.97(1H, dd), 8.22(1H, s), 8.18(1H, d), 8.11(2H, d), 7.98~7.93(6H, m), 7.64~7.46(9H, m), 7.33(1H, s) 7.32~7.28(12H, m), 1.69(12H, s)1708.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.11(1H, d), 7.90~7.83(4H, dd), 7.66~7.36(21H, m), 7.28(1H, s), 6.97(1H, d), 1.69(12H, s)1748.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.11(1H, d), 7.85~7.81(6H, dd), 7.75(2H, dd), 7.64~7.48(24H, m), 7.28(4H, m), 7.06(1H, d), 1.69(6H, s)1818.97(1H, dd), 8.22(1H, s), 8.18(1H, d), 8.11(2H, d), 7.75(4H, d), 7.64~7.49(19H, m), 7.38(1H, s), 7.32~7.28(4H, m), 1.69(6H, s)1938.97(1H, dd), 8.22(1H, s), 8.18(1H, d), 8.09(2H, d), 7.90(2H, d), 7.75(2H, dd), 7.69~7.47(18H, m), 7.41~7.38(12H, m) 7.26(4H, dd), 1.69(6H, s)2039.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.18(1H, d), 8.09~7.98(4H, m), 7.74(1H, s) 7.70~7.41(20H, m), 7.37(4H, d), 7.29(4H, d), 7.21(1H, t), 1.69(6H, s)2089.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.45(1H, d), 8.27(1H, d), 8.05(1H, s), 7.98~7.90(2H, dd), 7.74~7.41(32H, m), 7.38(1H, s), 1.69(6H, s)2259.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.50(1H, d), 8.18~7.96(6H, m), 7.74(1H, s) 7.77~7.41(15H, m), 7.37~7.29(8H, m), 7.29(4H, dd), 1.69(6H, s)2369.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.45(1H, d), 8.18(1H, d), 7.93~7.85(4H, dd), 7.64~7.59(12H, dd), 7.50(1H, s), 7.47~7.28(19H, m), 7.06(1H, dd), 1.69(6H, s)2418.97(1H, d), 8.18(2H, d), 7.98(1H, d), 7.79~7.75(4H, dd), 7.64~7.38(24H, m), 7.08(1H, s), 1.69(6H, s)2599.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.27(1H, dd) 8.18(1H, d), 8.05(1H, d), 7.98(1H, dd), 7.94(1H, dd), 7.93~7.85(4H, dd), 7.64~7.59(12H, m), 7.47~7.28(16H, m), 1.69(6H, s)2628.97(1H, dd), 8.45(1H, dd), 8.27(1H, dd) 8.18(1H, dd), 7.99~7.86(6H, m), 7.56~7.28(20H, m), 6.80(1H, s), 1.68(12H, s)2758.97(1H, dd), 8.45(1H, dd), 7.98~7.79(12H, m), 7.64~7.28(18H, m), 6.80(1H, s), 1.68(12H, s)2838.97(1H, dd), 8.45(1H, dd), 7.98~7.94(4H, dd), 7.76(4H, dd), 7.68~7.48(18H, m) 7.37~7.28(8H, m), 6.80(1H, s), 1.69(6H, s)2918.97(1H, dd), 8.45(1H, dd), 8.18(1H, dd), 8.11(1H, dd), 7.98~7.94(6H, dd), 7.84 ~7.68(18H, m), 7.64~7.38(8H, m), 7.08(2H, dd), 6.80(1H, s), 1.69(6H, s)3048.97(1H, dd), 8.45(1H, dd), 8.18(1H, dd), 8.11(1H, dd), 7.98~7.94(8H, dd), 7.84 ~7.68(10H, m), 7.64~7.38(8H, m), 7.08(1H, s), 1.69(12H, s), 1.64(6H, s)3208.97(1H, dd), 8.45(1H, dd), 8.18(1H, dd), 8.11~7.94(8H, m), 7.79 ~7.59(19H, m), 7.39~7.24(8H, m), 7.08(1H, s), 1.69(12H, s)3258.97(1H, dd), 8.45(1H, dd), 7.98~7.94(4H, dd), 7.76(4H, dd), 7.68~7.48(20H, m) 7.37~7.28(8H, m), 6.80(1H, s), 1.69(6H, s)3369.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.27(1H, dd) 8.18(1H, d), 8.05(1H, d), 7.98(1H, dd), 7.94(4H, dd), 7.93~7.85(8H, m), 7.79~7.59(12H, m), 7.52~7.28(11H, m), 1.69(6H, s)3469.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.27(1H, dd) 8.18(1H, d), 8.05(1H, d), 7.98(1H, dd), 7.94(2H, dd), 7.93~7.85(12H, m), 7.79~7.59(12H, m), 7.08(1H, s), 1.69(6H, s)3529.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.27(1H, dd) 8.18(1H, d), 8.05(1H, d), 7.98(4H, dd), 7.94(4H, dd), 7.93~7.86(14H, m), 7.80~7.59(12H, m), 7.08(1H, s), 1.69(6H, s)3658.94(1H, dd), 8.45(1H, dd), 8.10(1H, dd), 7.93(1H, d), 7.79(1H, d), 7.64(1H, t), 7.55(1H, d), 7.49~7.37(14H, m), 7.14(4H, t), 7.11~7.00(8H, m), 6.89~6.83(2H, d), 1.69(6H, s)3778.97(1H, dd), 8.18(1H, d), 7.98(1H, dd), 7.90~7.79(7H, dd), 7.64~7.46(16H, m), 7.34~7.28(14H, m), 7.18(1H, tt), 1.69(6H, s)3868.97(1H, dd), 8.45(1H, d), 8.11(4H, dd), 7.98(2H, d), 7.75~7.72(4H, dd), 7.64~7.39(20H, m), 7.17(1H, s), 1.69(6H, s)3948.97(1H, dd), 8.45(1H, dd), 8.18(1H, dd) 7.93~7.85(6H, m), 7.75(2H dd), 7.55~7.41(20H, m), 7.38~7.28(6H, m), 7.27(1H, s), 1.69(6H, s)4078.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.09(2H, t), 7.95(1H, s), 7.93(1H, dd), 7.63~7.45(25H, m), 7.38(1H, s), 1.69(6H, s)4118.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.07~8.03(1H, d), 7.95(1H, s), 7.93 (1H, d), 7.90(4H, d), 7.64~7.49(16H, m), 7.38~7.28(12H, m), 7.16(1H, d), 6.97(1H, s), 1.69(6H, s)4288.97(1H, dd), 8.45(2H, dd), 8.18(2H, d), 7.90~7.86(4H, d), 7.75(1H, d), 7.55~7.25(24H, m), 7.16~7.08(4H, m), 6.97(1H, s), 1.69(6H, s)4358.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 7.90~7.85(4H, d), 7.72(1H, s), 7.64~7.24(12H, m), 7.16~7.11(14H, m), 6.97(1H, s), 1.68(12H, s)4498.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.09~8.07(2H, d), 7.78~7.71(11H, m), 7.60~7.37(21H, m), 7.29~7.25(5H, m), 7.11~7.10(2H, dd), 6.97(1H, s), 1.69(6H, s)4548.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.09~8.07(2H, d), 7.90~7.81(8H, m), 7.72(1H, s), 7.63~7.25(22H, m), 7.16~7.09(6H, m), 6.97(1H, s), 1.69(6H, s)4708.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 7.82~7.75(11H, m), 7.55~7.31(20H, m), 7.20~7.11(4H, m), 6.97(1H, s), 1.69(6H, s)4738.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 7.87~7.69(8H, m), 7.56~7.28(18H, m), 7.20~7.11(11H, m), 7.09(4H, dd), 6.97(1H, s), 1.69(6H, s)4898.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 7.93~7.64(13H, m), 7.59~7.28(18H, m), 7.16(6H, dd), 6.94(1H, s), 1.69(6H, s)4968.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.11(1H, d), 7.98~7.93(2H, dd), 7.74~7.64(14H, m), 7.58~7.31(18H, m), 7.16(1H, s), 1.69(6H, s)5018.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.11(1H, d), 7.90~7.86(4H, m), 7.80~7.69(24H, m), 7.11(1H, s), 1.69(6H, s)5118.97(1H, dd), 8.22(1H, s), 8.18(1H, d), 8.11(2H, d), 7.98~7.93(6H, m), 7.64~7.46(13H, m), 7.33(1H, s) 7.32~7.28(12H, m), 1.69(6H, s)5228.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.11(1H, d), 7.90~7.83(14H, m), 7.66~7.36(21H, m), 7.28(1H, s), 6.97(1H, d), 1.69(6H, s)5328.97(1H, dd), 8.45(1H, dd), 8.18(1H, d), 8.11(1H, d), 7.85~7.81(6H, dd), 7.75(2H, dd), 7.64~7.48(24H, m), 7.28(4H, m), 7.06(1H, d), 1.69(6H, s)5438.97(1H, dd), 8.22(1H, s), 8.18(1H, d), 8.11(2H, d), 7.75(4H, d), 7.64~7.49(19H, m), 7.38(1H, s), 7.32~7.28(8H, m), 1.69(6H, s)5588.97(1H, dd), 8.22(1H, s), 8.18(1H, d), 8.09(2H, d), 7.90(2H, d), 7.75(2H, dd), 7.69~7.47(16H, m), 7.41~7.38(12H, m) 7.26(4H, dd), 1.69(6H, s)5649.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.18(1H, d), 8.09~7.98(6H, m), 7.74(1H, s) 7.70~7.41(20H, m), 7.37(4H, d), 7.29(4H, d), 7.21(1H, t), 1.69(6H, s)5779.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.45(2H, d), 8.27(1H, d), 8.05(1H, s), 7.98~7.90(14H, m), 7.74~7.41(26H, m), 7.38(1H, s), 1.69(6H, s)5869.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.50(1H, d), 8.18~7.96(6H, m), 7.74(1H, s) 7.77~7.41(11H, m), 7.37~7.29(8H, m), 7.29(4H, dd), 1.69(6H, s)5999.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.45(1H, d), 8.18(1H, d), 7.93~7.85(4H, dd), 7.64~7.59(12H, dd), 7.50(1H, s), 7.47~7.28(21H, m), 7.06(1H, dd), 1.69(6H, s)6018.97(1H, d), 8.18(2H, d), 7.98(1H, d), 7.79~7.75(4H, dd), 7.64~7.38(24H, m), 7.08(1H, s), 1.69(6H, s)6209.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.27(1H, dd) 8.18(1H, d), 8.05(1H, d), 7.98(1H, dd), 7.94(1H, dd), 7.93~7.85(4H, dd), 7.64~7.59(12H, m), 7.47~7.28(12H, m), 1.68(12H, s)6298.97(1H, dd), 8.45(1H, dd), 8.27(1H, dd) 8.18(1H, dd), 7.99~7.86(16H, m), 7.56~7.28(20H, m), 6.80(1H, s), 1.69(6H, s)6328.97(1H, dd), 8.45(1H, dd), 7.98~7.79(18H, m), 7.64~7.28(18H, m), 6.80(1H, s), 1.69(6H, s)6448.97(1H, dd), 8.45(1H, dd), 7.98~7.94(4H, dd), 7.76(4H, dd), 7.68~7.48(12H, m) 7.37~7.28(8H, m), 6.80(1H, s), 1.69(12H, s), 1.64(6H, s)6578.97(1H, dd), 8.45(1H, dd), 8.18(1H, dd), 8.11(1H, dd), 7.98~7.94(6H, dd), 7.84 ~7.68(18H, m), 7.64~7.38(16H, m), 7.08(2H, dd), 6.80(1H, s), 1.69(6H, s)6628.97(1H, dd), 8.45(1H, dd), 8.18(2H, dd), 8.11(1H, dd), 7.98~7.94(8H, dd), 7.84 ~7.68(10H, m), 7.64~7.38(8H, m), 7.08(1H, s), 1.69(12H, s)6798.97(1H, dd), 8.45(1H, dd), 8.18(1H, dd), 8.11~7.94(8H, m), 7.79 ~7.59(19H, m), 7.39~7.24(12H, m), 7.08(1H, s), 1.69(6H, s)6908.97(1H, dd), 8.45(1H, dd), 7.98~7.94(4H, dd), 7.76(4H, dd), 7.68~7.48(14H, m) 7.37~7.28(8H, m), 6.80(1H, s), 1.68(12H, s)6919.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.27(1H, dd) 8.18(1H, d), 8.05(1H, d), 7.98(1H, dd), 7.94(4H, dd), 7.93~7.85(8H, m), 7.79~7.59(12H, m), 7.52~7.28(9H, m), 1.69(6H, s)7039.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.27(1H, dd) 8.18(1H, d), 8.05(1H, d), 7.98(1H, dd), 7.94(2H, dd), 7.93~7.85(16H, m), 7.79~7.59(12H, m), 7.08(1H, s), 1.69(6H, s)7189.08(1H, d), 8.97(1H, dd), 8.84(2H, dd), 8.27(1H, dd) 8.18(1H, d), 8.05(2H, d), 7.98(4H, dd), 7.94(4H, dd), 7.93~7.86(14H, m), 7.80~7.59(12H, m), 7.08(1H, s), 1.69(6H, s)7318.18(1H, d), 8.12(1H, d), 7.74(1H, d), 7.73(2H, d), 7.71(2H, d), 7.65(2H, d), 7.52(2H, d), 7.45(1H, t)7338.29(1H, s), 8.12(1H, d), 8.09(1H, d), 8.06(1H, d), 7.99(1H, d), 7.75(4H, d), 7.63(2H, d), 7.55(4H, d), 7.50(1H, s), 7.49(2H, d), 7.41(1H, t), 7.38(1H, d), 7.37(4H, d), 7.33(1H, d)7368.97(1H, d), 8.45(1H, d), 8.18(1H, d), 7.93(1H, d), 7.79(3H, d), 7.64(4H, t), 7.46(4H, d), 7.44(1H, s), 7.38(1H, s), 7.35(2H, d), 1.69(6H, s)7478.45(1H, d), 8.11(1H, d), 7.93(1H, d), 7.75(4H, d), 7.71(4H, d), 7.65(4H, d), 7.49(4H, d), 7.41(1H, t), 7.40(1H, t), 7.27(2H, d), 7.17(1H, s)7538.12(1H, d), 8.05(1H, d), 7.71(2H, d), 7.65(2H, d), 7.46(1H, d), 7.43(1H, s), 7.33(1H, s)7738.97(1H, d), 8.45(1H, d), 8.18(1H, d), 7.93(1H, d), 7.79~7.72(5H, m), 7.64(4H, dd), 7.46(4H, d), 7.44(1H, s), 7.38(1H, s), 7.35(4H, d), 1.69(6H, s)7768.18(1H, d), 8.10(1H, d),7.73(1H, s), 7.66(2H, t), 7.64(2H, d), 7.52(1H, d), 7.43(1H, d)7848.97(1H, d), 8.45(1H, d), 8.18(1H, d), 7.93(1H, d), 7.78~7.69(8H, m), 7.64(3H, dd), 7.46(2H, d), 7.44(1H, s), 7.11(1H, s), 1.69(6H, s)7907.73(2H, d), 7.43(1H, s), 7.36(1H, s), 7.16(1H, d), 7.06(1H, d).

[0354] 화합물FD-MS화합물FD-MS002m / z = 769.33(C58H43NO = 769.99)013m / z = 893.37(C68H47NO = 894.13)027m / z = 759.26(C55H37NOS = 759.97)036m / z = 891.35(C68H45NO = 892.11)046m / z = 753.30(C57H39NO = 753.94)050m / z = 833.33(C62H43NO2 = 834.03)065m / z = 829.33(C63H43NO = 830.04)069m / z = 943.38(C72H49NO = 944.19)088m / z = 929.37(C71H47NO = 930.16)095m / z = 959.38(C72H49NO2 = 960.19)104m / z = 925.37(C69H51NS = 926.23)114m / z = 991.38(C76H49NO = 992.23)124m / z = 809.37(C61H47NO = 810.05)127m / z = 759.26(C55H37NOS = 759.97)146m / z = 703.29(C53H37NO = 703.88)155m / z = 843.31(C63H41NO2 = 844.03)170m / z = 833.33(C62H43NO2 = 834.03)174m / z = 941.37(C72H47NO = 942.17)181m / z = 779.32(C59H41NO = 779.98)193m / z = 943.38(C72H49NO = 944.19)203m / z = 879.35(C67H45NO = 880.10)208m / z = 929.37(C71H47NO = 930.16)225m / z = 879.35(C67H45NO = 880.10)236m / z = 991.38(C76H49NO = 992.23)241m / z = 729.30(C55H39NO = 729.92)259m / z = 905.37(C69H47NO = 906.14)262m / z = 769.33(C58H43NO = 769.99)275m / z = 859.35(C64H45NO2 = 860.07)283m / z = 829.33(C63H43NO = 830.04)291m / z = 855.35(C65H45NO = 856.08)304m / z = 859.38(C65H49NO = 860.11)320m / z = 985.39(C74H51NO2 = 986.23)325m / z = 879.35(C67H45NO = 880.10)336m / z = 991.38(C76H49NO = 992.23)346m / z = 803.32(C61H41NO = 804.00)352m / z = 995.38(C75H49NO2 = 996.22)365m / z = 779.32(C59H41NO = 779.98)377m / z = 969.40(C74H51NO = 970.23)386m / z = 703.29(C53H37NO = 703.88)394m / z = 891.35(C68H45NO = 892.11)407m / z = 809.28(C59H39NOS = 810.03)411m / z = 855.35(C65H45NO = 856.08)428m / z = 879.35(C67H45NO = 880.10)435m / z = 909.36(C68H47NO2 = 910.13)449m / z = 993.40(C76H51NO = 994.25)454m / z = 991.38(C76H49NO = 992.23)470m / z = 883.35(C66H45NO2 = 884.09)473m / z = 993.40(C76H51NO = 994.25)489m / z = 893.37(C68H47NO = 894.13)496m / z = 891.35(C68H45NO = 892.11)501m / z = 729.30(C55H39NO = 729.92)511m / z = 805.33(C61H43NO = 806.02)522m / z = 819.35(C62H45NO = 820.05)532m / z = 945.36(C71H47NO2 = 946.16)543m / z = 829.33(C63H43NO = 830.04)558m / z = 905.37(C69H47NO = 906.14)564m / z = 909.40(C69H51NO = 910.17)577m / z = 1069.43(C82H55NO = 1070.35)586m / z = 803.32(C61H41NO = 804.00)599m / z = 1005.40(C77H51NO = 1006.26)601m / z = 729.30(C55H39NO = 729.92)620m / z = 935.38(C70H49NO2 = 936.17)629m / z = 893.37(C68H47NO = 894.13)632m / z = 895.35(C67H45NO2 = 896.10)644m / z = 859.38(C65H49NO = 860.11)657m / z = 1019.41(C78H53NO = 1020.29)662m / z = 819.35(C62H45NO = 820.05)679m / z = 955.38(C73H49NO = 956.20)690m / z = 883.35(C66H45NO2 = 884.09)691m / z = 905.37(C69H47NO = 906.14)703m / z = 879.35(C67H45NO = 880.10)718m / z = 955.38(C73H49NO = 956.20)731m / z = 992.61(C73H12D37NO = 993.43)733m / z = 850.47(C63H22D21NO = 851.17)736m / z = 797.40(C58H25D15NO2 = 798.05)747m / z = 876.40(C63H24D17NOS = 877.19)753m / z = 890.49(C63H10D31NOS = 891.28)773m / z = 975.51(C73H29D20NO = 976.32)776m / z = 862.54(C63H10D33NO = 863.24)784m / z = 799.41(C58H25D16NO2 = 800.07)790m / z = 934.62(C68H6D41NO = 935.38).

[0355] <실험예 1>

[0356] 1) 유기 발광 소자의 제작

[0357] A transparent electrode ITO thin film obtained from OLED glass (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.

[0358]

[0359] Then the vacuum level inside the chamber is 10 -6 After evacuating to reach 10 torr, a current was applied to the cell to evaporate 2-TNATA and deposit a 600 Å thick hole injection layer on an ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was added to another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it and deposit a 300 Å thick hole transport layer on the hole injection layer.

[0360]

[0361] 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.

[0362]

[0363] Next, a compound of the following structural formula E1 was deposited as an electron transport layer with a thickness of 300 Å.

[0364]

[0365] An OLED device was fabricated by depositing lithium fluoride (LiF) as an electron injection layer with a thickness of 10 Å and using an Al cathode with a thickness of 1,000 Å. Meanwhile, all organic compounds required for fabricating an OLED device were each 10 Å thick. -6 ~10 -8 torr, and used for OLED fabrication. An organic electroluminescent device was fabricated in the same manner as in Experimental Example 1, except that the compounds shown in Table 12 were used instead of NPB used in forming the hole transport layer in Experimental Example 1. The electroluminescence (EL) characteristics of the organic light-emitting device fabricated as described above were measured using M7000 from MacScience, and the reference luminance was measured to be 700 cd / m using the lifespan measuring equipment (M6000) manufactured by MacScience with the measurement results. 2 When, T 95 The driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the blue organic light-emitting device manufactured according to the present invention were measured. The results are shown in Table 12 below.

[0366] nO. Compound (hole transport) Driving voltage (V) Luminous efficacy (cd / A) CIE (x, y) Lifetime (T 95) Example 10024.466.89(0.133, 0.100)89 Example 20274.436.85(0.134, 0.102)90 Example 30504.466.80(0.133, 0.100)90 Example 41814.456.84(0.133, 0.100)86 Example 51934.436.85(0.133, 0.101)87 Example 62034.416.80(0.133, 0.101)88 Example 72364.446.88(0.133, 0.102)86 Example 82594.476.82(0.133, 0.100)84 Example 93524.496.88(0.133, 0.100)83 Example 103654.446.83(0.133, 0.100)90 Example 113774.416.82(0.133, 0.100)86 Example 123864.406.84(0.134, 0.101)91 Example 133944.416.81(0.133, 0.100)88 Example 144074.406.88(0.133, 0.100)80 Example 155434.466.91(0.133, 0.100)86 Example 165584.436.79(0.133, 0.101)89 Example 175774.456.86(0.134, 0.100)81 Example 185864.466.81(0.134, 0.100)81 Example 195994.476.79(0.133, 0.100)83 Example 206014.416.90(0.133, 0.100)88 Example 216204.486.85(0.134, 0.100)89 Example 226324.406.86(0.133, 0.100)86 Example 236444.466.81(0.134, 0.101)83 Example 246574.466.88(0.133, 0.101)81 Example 256624.446.89(0.133, 0.100)87 Example 266794.426.84(0.134, 0.101)90 Example 276904.426.86(0.133, 0.100)86 Example 286914.466.90(0.133, 0.100)81 Example 297314.416.92(0.134, 0.100)95 Example 307534.406.84(0.133, 0.101)96 Example 317904.466.94(0.133, 0.101)94Comparative Example 1NPB5.446.05(0.134, 0.100)61Comparative Example 2Comparative Compound A5.126.21(0.133, 0.100)63Comparative Example 3Comparative Compound B5.216.29(0.133, 0.101)61Comparative Example 4Comparative Compound C5.585.58(0.134, 0.100)59Comparative Example 5Comparative Compound D5.096.55(0.133, 0.100)76Comparative Example 6Comparative Compound E5.566.30(0.134, 0.101)73.

[0367]

[0368] As can be seen from the results in Table 12 above, the organic light-emitting device using the hole transport layer material of the blue organic light-emitting device of the present invention has a lower driving voltage and significantly improved luminous efficiency and lifespan compared to Comparative Examples 1 to 6. The reason for these results is that, unlike Comparative Examples 2 and 3, the present invention uses heterocyclic compounds having different substituent types and positions, so that hole mobility is implemented at a speed suitable for the device, forming a more stable compound, and thus, decomposition or destruction of the compound does not occur, so that holes can be efficiently transported. In addition, Comparative Example 2 has an arylamine di-substituted structure, and unlike the present invention, has a higher HOMO energy level and a slower hole transport ability. The carbazole skeleton included in Comparative Example 4 has a high T1 value, requiring a high driving voltage, and also, when forming a pyrimidine substituent structure included in the carbazole skeleton as in Comparative Example 4, it has an energy level more suitable for an electron transport device than a hole transport device. The present invention, unlike Comparative Example 4, has the advantage of being easy to express appropriate physical properties as a hole transport layer, and it is judged that the compound of the present invention has brought about excellence in all aspects of improved operation, efficiency, and lifespan. Comparative Example 6 has a similar type and position of substituents, but the core itself has a core with a smaller number of pi orbital stacks, which reduces the transport ability and shows a higher operation voltage and lower efficiency.

[0369] Experimental Example 2

[0370] Fabrication of organic light-emitting devices

[0371] A transparent electrode ITO thin film obtained from OLED glass (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.

[0372]

[0373] Then the vacuum level inside the chamber is 10 -6 After evacuating to 10 torr, a current was applied to the cell to evaporate 2-TNATA, thereby depositing 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, thereby depositing a 300 Å thick hole transport layer on the hole injection layer.

[0374]

[0375] 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.

[0376]

[0377] Next, a compound of the following structural formula E1 was deposited as an electron transport layer with a thickness of 300 Å.

[0378]

[0379] An OLED device was fabricated by depositing lithium fluoride (LiF) as an electron injection layer with a thickness of 10 Å and using an Al cathode with a thickness of 1,000 Å. Meanwhile, all organic compounds required for fabricating an OLED device were each 10 Å thick. -6 ~10 -8 torr, vacuum sublimation purification was performed and used in OLED fabrication. In Experimental Example 2, the hole transport layer NPB was formed with a thickness of 250 Å, and then an electron blocking layer with a thickness of 50 Å of the compound shown in Table 13 below was formed on top of the hole transport layer, and the same procedure as Experimental Example 2 was performed to fabricate an organic electroluminescent device. The results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the blue organic light-emitting device fabricated according to the present invention were as shown in Table 13 below.

[0380] No. Compound (electron blocking) Driving voltage (V) Luminous efficacy (cd / A) CIE (x, y) Lifespan (T 95) Example 320364.866.83(0.134, 0.101)86 Example 330424.826.84(0.134, 0.102)91 Example 340464.836.81(0.133, 0.102)84 Example 350884.846.90(0.134, 0.100)86 Example 360954.866.84(0.133, 0.100)91 Example 371044.796.80(0.133, 0.100)88 Example 381144.806.88(0.133, 0.101)87 Example 391244.866.70(0.133, 0.100)86 Example 401274.726.81(0.133, 0.100)85 Example 411464.816.86(0.134, 0.101)84 Example 421554.846.90(0.133, 0.100)88 Example 431704.796.84(0.133, 0.101)85 Example 441744.816.91(0.134, 0.100)90 Example 452754.886.84(0.133, 0.100)90 Example 462834.896.81(0.133, 0.100)84 Example 472914.846.82(0.134, 0.100)86 Example 483044.766.88(0.134, 0.101)83 Example 493204.816.86(0.134, 0.100)88 Example 503254.846.81(0.133, 0.100)90 Example 514734.716.80(0.133, 0.101)81 Example 524894.866.90(0.133, 0.100)85 Example 534964.796.91(0.133, 0.101)86 Example 545014.816.90(0.134, 0.101)85 Example 555114.886.81(0.134, 0.100)83 Example 565224.816.88(0.133, 0.100)86 Example 575324.796.85(0.133, 0.100)88 Example 587034.846.86(0.134, 0.100)87 Example 597184.856.88(0.133, 0.101)90 Example 607334.796.96(0.134, 0.100)97 Example 617764.776.94(0.134, 0.100)97 Example 627844.866.97(0.133, 0.100)96 Comparative Example 5NPB5.556.07(0.134, 0.100)53 Comparative Example 7 Comparative Compound F5.116.55(0.133, 0.101)81 Comparative Example 8 Comparative Compound G5.096.48(0.133, 0.100)87.

[0381]

[0382] As can be seen from the results in Table 13 above, the organic light-emitting device using the hole-blocking layer material of the blue organic light-emitting device of the present invention has a lower driving voltage and significantly improved luminous efficiency and lifespan compared to Comparative Examples 7 to 8. The reason for these results is that, unlike Comparative Examples 7 and 8, the heterocyclic compound having an arylamine group and an aryl group di-substituted form can implement a lower T1 level as an electron-blocking layer, and has the advantage of being able to control the LUMO level to a more suitable level as an electron-blocking layer by the arylamine group and aryl group substituents used. In addition, unlike Comparative Examples 7 and 8, when the compound of the present invention, in which a dimethylfluorene ring is additionally connected to a heterocyclic compound containing O, is used as an electron-blocking layer, the probability that electrons trying to pass through the light-emitting layer to the anode will form excitons in the light-emitting layer increases. In addition, compared to Comparative Examples 7 to 8, the absence of an aryl group substituent reduces intermolecular space, resulting in a higher driving voltage due to a decrease in electron-blocking ability. As a result, it is judged that the compound of the present invention has superiority in all aspects of operation, efficiency, and lifespan.

Claims

1. A heterocyclic compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is CRaRb, R1 to R4 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R"; and two or more adjacent groups selected from the group consisting of substituted or unsubstituted amine groups, or 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, L1 and L2 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, Ar1 and Ar2 are the same as or different from each other, and are each independently selected from a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R"; and the group consisting of the following chemical formula 1-1, m and p are integers from 0 to 4, n and q are integers from 1 to 5, a and c are integers from 0 to 4, b is an integer of 0 or 1, If a, c, m, n, p and q are 2 or more, the substituents in parentheses are the same or different, R, R' and R" are the same or different 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, Ra and Rb are the same or different and each independently a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, At least one of the above Ar1 and Ar2 is represented by the following chemical formula 1-1, [Chemical Formula 1-1] In the above chemical formula 1-1, means a position connected to the above chemical formula 1, L3 and L4 are the same or different, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, r and s are integers from 0 to 4, If r and s are 2 or more, the substituents in parentheses are the same or different, Ar3 and Ar4 are the same or different, 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.

2. In claim 1, the chemical formula 1 is a heterocyclic compound represented by any one of the following chemical formulas 2 to 5: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] In the above chemical formulas 2 to 5, The definition of each substituent is the same as that in the chemical formula 1 above.

3. In claim 1, the chemical formula 1 is a heterocyclic compound represented by any one of the following chemical formulas 6 to 11: [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] In the above chemical formulas 6 to 11, The definition of each substituent is the same as that in the chemical formula 1 above.

4. In claim 1 The above chemical formula 1-1 is a heterocyclic compound represented by the following chemical formula 1-1-1 or 1-1-2: [Chemical Formula 1-1-1] [Chemical Formula 1-1-2] In the above chemical formulas 1-1-1 and 1-1-2, , the definitions of L3, L4, r and s are the same as those in the above chemical formula 1-1, X1 is O; or S, Ar13 and Ar14 are the same or different and are each independently a substituted or unsubstituted C6 to C60 aryl group, R11 and R12 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, a1 is an integer from 0 to 4, a2 is an integer from 0 to 3, If a1 and a2 are 2 or more, the substituents within the parentheses are the same or different.

5. In claim 1, Ar2 is represented by the chemical formula 1-1, and Ar1 is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; or -SiRR'R", A heterocyclic compound in which the definitions of R, R' and R" are the same as those in the above chemical formula 1.

6. A heterocyclic compound according to claim 1, wherein the deuterium content of the chemical formula 1 is 0% or 10% to 100%.

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

8. An organic light-emitting device comprising a first electrode; a second electrode; and 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 at least one heterocyclic compound according to any one of claims 1 to 7.

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

10. An organic light-emitting device according to claim 8, wherein the organic layer includes an electron blocking layer, and the electron blocking layer includes at least one heterocyclic compound.

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

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