Compound, organic light-emitting device, and composition for organic material layer of organic light-emitting device

Abstract

The present specification provides a compound represented by chemical formula 1, an organic light-emitting device comprising same, and a composition for an organic material layer. The compound set forth in the present specification, when used in an organic light-emitting device, can reduce the driving voltage of the device, improve the luminous efficiency, and improve the lifespan characteristics of the device.

Description

Compound, organic light-emitting device and composition for organic layer of organic light-emitting device

[0001] The present specification relates to a compound, an organic light-emitting device, and a composition for an organic layer of an organic light-emitting device.

[0002] This application claims the benefit of Korean Patent Application No. 10-2023-0156214, filed with the Korean Intellectual Property Office on November 13, 2023, the entire contents of which are incorporated herein by reference.

[0003] Light-emitting 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 disclosure provides a compound, an organic light-emitting device, and a composition for an organic layer of an organic light-emitting device.

[0009] One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] X1 is CRa or N, X2 is CRb or N, X3 is CRc or N, but at least one of X1 to X3 is N,

[0014] Ar1 to Ar4 are the same 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,

[0015] L1 to L4 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0016] R1 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C3 to C60 cycloalkyl group,

[0017] R2 is 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,

[0018] Ra, Rb and Rc are the same 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 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; -P(=O)R R'; and -SiR R'R",

[0019] The above R, R' and R" are the same 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,

[0020] a is an integer from 0 to 3,

[0021] b is an integer from 0 to 7,

[0022] m, n, o and p are the same or different and are each independently an integer from 0 to 4,

[0023] If each of a, b, m, n, o, and p is an integer greater than or equal to 2, the substituents within the parentheses are the same or different.

[0024] Another embodiment of the present specification provides an organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the compound.

[0025] Another embodiment of the present specification provides a composition for forming an organic layer of an organic light-emitting device, comprising the compound and a heterocyclic compound represented by the following chemical formula 2 or 3.

[0026] [Chemical Formula 2]

[0027]

[0028] [Chemical Formula 3]

[0029]

[0030] In the above chemical formulas 2 and 3,

[0031] R11, R12, R22 and R23 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR',

[0032] L11, L12, L22 and L23 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,

[0033] Ar11, Ar12, Ar22 and Ar23 are the same or different from each other, and each independently represents a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R",

[0034] The above R, R' and R" are the same 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,

[0035] a11 and a12 are integers from 0 to 7, respectively,

[0036] a22 is an integer from 0 to 6,

[0037] a23 is an integer from 0 to 4,

[0038] p11, p12, p22 and p23 are integers from 0 to 4, respectively.

[0039] q11, q12, q22 and q23 are integers from 1 to 4, respectively,

[0040] When each of a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 is 2 or more, the substituents in the parentheses are the same or different from each other.

[0041] The compound of chemical formula 1 described herein may have low driving voltage, high luminous efficiency, and / or long life characteristics when used in an organic light-emitting device.

[0042] Specifically, the first substituent (C-carbazole) acts as a strong donor and HOMO within the molecule, and the heteroaryl group composed of the second substituents X1 to X3 acts as a LUMO within the molecule, and as a strong electron acceptor, it can effectively pull electrons from the strong donor of the C-carbazole and the bonded sub-donor of the benzene core to stabilize electrons within the molecule and thereby improve the lifetime. In particular, when the strong donor of the first substituent and the strong acceptor of the second substituent are directly bonded within the molecule, a decrease in lifetime may occur due to the overlap of HOMO-LUMO, but by introducing a benzene core between them, the overlap of HOMO-LUMO can be offset, and electrons can be effectively stabilized through the expansion of LUMO.

[0043] Additionally, with respect to the benzene core, the first substituent (C-carbazole) and the third substituent Ar1 are fixed in the ortho position, and the 4th position of the first substituent (C-carbazole) is fixed, so that the molecule has a distorted shape due to strong steric hindrance, which can cancel out the HOMO-LUMO overlap. In addition, this strong steric hindrance can reduce the crystallinity of the molecule, thereby forming an amorphous morphology during device fabrication.

[0044] Figures 1 to 4 are drawings each exemplifying a laminated structure of an organic light-emitting device according to one embodiment of the present specification.

[0045] 100: Substrate

[0046] 200: Bipolar

[0047] 300: Organic layer

[0048] 301: Hole injection layer

[0049] 302: Hole transport layer

[0050] 303: Emissive layer

[0051] 304: Hole-locking layer

[0052] 305: Electron transport layer

[0053] 306: Electron injection layer

[0054] 400: Cathode

[0055] Hereinafter, the present specification will be described in more detail.

[0056] In this specification, when a part is said to "include" a component, this means that it may include other components, but not to the exclusion of other components, unless specifically stated otherwise.

[0057] In this specification, the chemical formula means the position where it is combined.

[0058] 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.

[0059] 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.

[0060] 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) or tritium is an isotope of hydrogen, so it can be interpreted as a concept included in hydrogen unless it is explicitly excluded.

[0061] That is, in the present application, deuterium is, in accordance with Chem. Commun., 2014, 50, 14870, compared to hydrogen, equivalent effects in driving voltage, luminous efficiency, and lifespan, or improved effects in some evaluation criteria, and falls within a range that a person skilled in the art can predict to have equivalent effects even without specific experiments. Therefore, deuterium, an isotope of hydrogen, is interpreted as a concept included in hydrogen unless explicitly excluded.

[0062] According to one embodiment of the present specification, “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%.

[0063] According to one embodiment of the present specification, 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.

[0064] According to one embodiment of the present specification, 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.

[0065] According to one embodiment of the present specification, an isotope is 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.

[0066] According to one embodiment of the present specification, the meaning of the content T% of a specific substituent can be defined as T2 / T1×100 = T%, where the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2.

[0067] in other words, For example, in the case of a phenyl group represented by , a content of 20% of deuterium here 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, a content of 20% of deuterium in the phenyl group can be expressed by the structural formula below.

[0068]

[0069] In addition, according to one embodiment of the present specification, “a phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain a deuterium atom, i.e., has 5 hydrogen atoms.

[0070] In this specification, the halogen may be fluorine, chlorine, bromine or iodine.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] In this specification, the terphenyl group may be selected from the following structures.

[0079]

[0080] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0081] When the above fluorenyl group is substituted, it may be selected from the following structures, but is not limited thereto.

[0082]

[0083] 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) group, 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 group, a 2,3-dihydrobenzofuran group, 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.

[0084] In the present specification, when the substituent is a carbazole group, it means that it is bonded to the nitrogen or carbon of the carbazole.

[0085] In the present specification, when a carbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole.

[0086] In the present specification, the benzocarbazole group may have any of the following structures.

[0087]

[0088] In the present specification, the dibenzocarbazole group may have any of the following structures.

[0089]

[0090] In the present specification, the naphthobenzofuran group may have any of the following structures.

[0091]

[0092] In the present specification, the naphthobenzothiophene group may have any of the following structures.

[0093]

[0094] In the present specification, a silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -Si(R101)(R102)(R103), and R101 to R103 are the same as or different from each other, and may each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group.

[0095] A specific example of a cylinder is (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), but is not limited thereto.

[0096] In the present specification, the phosphine oxide group is represented by -P(=O)(R104)(R105), and R104 and R105 are the same 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, a dinaphthylphosphine oxide group, and the like.

[0097] In the present specification, the amine group is represented by -N(R106)(R107), and R106 and R107 are the same 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.

[0098] In this specification, the arylene group may be applied to the examples of the aryl group described above, except that it is a divalent group.

[0099] In this specification, the heteroarylene group may be applied to the examples of the heteroaryl group described above, except that it is a divalent group.

[0100] As used herein, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

[0101] Hydrocarbon rings and heterocycles that adjacent groups can form include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles, and structures exemplified by the aforementioned cycloalkyl groups, aryl groups, heterocycloalkyl groups, and heteroaryl groups can be applied to the rings, except that they are not monovalent groups.

[0102] One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[0103] [Chemical Formula 1]

[0104]

[0105] In the above chemical formula 1, the description of each substituent is as described above.

[0106] The compound according to the above embodiment may have low driving voltage, high luminous efficiency, and / or long life characteristics when used in an organic light-emitting device.

[0107] Specifically, the first substituent, C-carbazole, acts as a strong donor and HOMO within the molecule, thereby enabling high hole mobility and smooth charge transfer within the molecule, resulting in high efficiency. In addition, the second substituent, the heteroaryl group composed of X1 to X3, acts as a LUMO within the molecule and, as a strong electron acceptor, effectively pulls electrons from the strong donor of the C-carbazole and the combined sub-donor of the benzene core, thereby stabilizing electrons within the molecule and thereby improving the lifespan.

[0108] However, when the strong donor of the first substituent and the strong acceptor of the second substituent are directly combined within the molecule, a decrease in lifetime may occur due to the overlap of HOMO-LUMO. However, by introducing a benzene core between them, the overlap of HOMO-LUMO can be offset, and the electrons can be effectively stabilized through the expansion of LUMO.

[0109] Additionally, with respect to the benzene core, the first substituent (C-carbazole) and the third substituent Ar1 are fixed in the ortho position, and the 4th position of the first substituent (C-carbazole) is fixed, so that the molecule has a distorted shape due to strong steric hindrance, which can cancel out the HOMO-LUMO overlap. In addition, this strong steric hindrance can reduce the crystallinity of the molecule, thereby forming an amorphous morphology during device fabrication.

[0110] In the case of a material with high crystallinity, aggregation is caused, and an uneven morphology is formed during future device deposition, thereby reducing the device lifespan. On the other hand, the compound according to the present specification can increase the device lifespan by reducing the crystallinity and forming an even morphology by introducing the 4th position of the first substituent (C-carbazole).

[0111] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-4.

[0112] [Chemical Formula 1-1]

[0113]

[0114] [Chemical Formula 1-2]

[0115]

[0116] [Chemical Formula 1-3]

[0117]

[0118]

[0119] [Chemical Formula 1-4]

[0120]

[0121] In the above chemical formulas 1-1 to 1-4,

[0122] X1 to X3, L1 to L4, Ar1 to Ar4, R1, R2, a, b, m, n, o and p are as defined in the above chemical formula 1.

[0123] In one embodiment of the present specification, X1 may be N, X2 may be CRb, and X3 may be CRc.

[0124] In one embodiment of the present specification, X2 may be N, X1 may be CRa, and X3 may be CRc.

[0125] In one embodiment of the present specification, X3 may be N, X1 may be CRa, and X2 may be CRb.

[0126] In one embodiment of the present specification, X1 and X2 may be N, and X3 may be CRc.

[0127] In one embodiment of the present specification, X2 and X3 may be N, and X1 may be CRa.

[0128] In one embodiment of the present specification, X1 and X3 may be N, and X2 may be CRb.

[0129] In one embodiment of the present specification, X1 to X3 may all be N.

[0130] In one embodiment of the present specification, Ar1 to Ar4 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0131] In one embodiment of the present specification, Ar1 to Ar4 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0132] In one embodiment of the present specification, Ar1 may be a C6 to C30 aryl group substituted or unsubstituted with deuterium; or a C2 to C30 heteroaryl group substituted or unsubstituted with deuterium or an aryl group.

[0133] In one embodiment of the present specification, Ar1 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted indolocarbazole group; a substituted or unsubstituted benzothienocarbazole; or a substituted or unsubstituted benzofuranocarbazole.

[0134] In one embodiment of the present specification, Ar1 may be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium or a phenyl group; a dibenzothiophene group substituted or unsubstituted with deuterium or a phenyl group; a carbazole group substituted or unsubstituted with deuterium or a phenyl group; an indolocarbazole group substituted or unsubstituted with deuterium or a phenyl group; a benzothienocarbazole substituted or unsubstituted with deuterium or a phenyl group; or a benzofuranocarbazole substituted or unsubstituted with deuterium or a phenyl group.

[0135] In one embodiment of the present specification, Ar2 may be a C6 to C30 aryl group substituted or unsubstituted with deuterium; or a C2 to C30 heteroaryl group substituted or unsubstituted with deuterium or an aryl group.

[0136] In one embodiment of the present specification, Ar2 may be a substituted or unsubstituted C6 to C20 aryl group.

[0137] In one embodiment of the present specification, Ar2 may be a C6 to C20 aryl group substituted or unsubstituted with deuterium.

[0138] In one embodiment of the present specification, Ar2 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group.

[0139] In one embodiment of the present specification, Ar2 may be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium.

[0140] In one embodiment of the present specification, Ar2 may be a substituted or unsubstituted phenyl group.

[0141] In one embodiment of the present specification, Ar2 may be a phenyl group substituted or unsubstituted with deuterium.

[0142] In one embodiment of the present specification, Ar3 and Ar4 may be the same as or different from each other, and may each independently be a C6 to C20 aryl group substituted or unsubstituted with deuterium; or a C2 to C20 heteroaryl group substituted or unsubstituted with deuterium or an aryl group.

[0143] In one embodiment of the present specification, 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 terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group.

[0144] In one embodiment of the present specification, Ar3 and Ar4 may be the same as or different from each other, and each independently be a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; a terphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; a dibenzofuran group unsubstituted or substituted with deuterium or a phenyl group; a dibenzothiophene group unsubstituted or substituted with deuterium or a phenyl group; or a carbazole group unsubstituted or substituted with deuterium or a phenyl group.

[0145] In one embodiment of the present specification, L1 to L4 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0146] In one embodiment of the present specification, L1 to L4 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0147] In one embodiment of the present specification, L1 to L4 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted dibenzofuranylene group; or a substituted or unsubstituted dibenzothiophenylene group.

[0148] In one embodiment of the present specification, R1 may be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C3 to C40 cycloalkyl group.

[0149] In one embodiment of the present specification, R1 may be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C20 alkyl group; or a substituted or unsubstituted C3 to C20 cycloalkyl group.

[0150] In one embodiment of the present specification, R1 may be hydrogen; or deuterium.

[0151] In one embodiment of the present specification, R2 may be 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.

[0152] In one embodiment of the present specification, R2 may be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0153] In one embodiment of the present specification, R2 may be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0154] In one embodiment of the present specification, R2 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group.

[0155] In one embodiment of the present specification, R2 may be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a dibenzothiophene group substituted or unsubstituted with deuterium; or a carbazole group substituted or unsubstituted with deuterium.

[0156] In one embodiment of the present specification, Ra, Rb and Rc are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; -P(=O)RR'; and -SiRR'R".

[0157] In one embodiment of the present specification, Ra, Rb and Rc are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; -P(=O)RR'; and -SiRR'R".

[0158] In one embodiment of the present specification, R, R' and R" are the same as or different from each other, and each independently may be 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.

[0159] In one embodiment of the present specification, R, R' and R" are the same as or different from each other, and each independently may be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0160] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 1% to 100%.

[0161] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 10% to 100%.

[0162] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 20% to 100%.

[0163] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 30% to 100%.

[0164] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 60% to 100%.

[0165] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 80% to 100%.

[0166] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 90% to 100%.

[0167] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following.

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175] In addition, by introducing various substituents into the structure of the above chemical formula 1, a compound having the unique characteristics of the introduced substituent can be synthesized. For example, by introducing a substituent mainly used in hole injection layer material, hole transport layer material, hole transport auxiliary layer material, light emitting layer material, electron transport layer material, electron transport auxiliary layer material, and charge generation layer material used in the manufacture of organic light emitting devices into the above core structure, a material satisfying the conditions required for each organic layer can be synthesized.

[0176] 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 changing the use of the material in various ways.

[0177] Another embodiment of the present specification provides an organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the compound (represented by Chemical Formula 1).

[0178] In another embodiment of the present specification, the organic layer including the compound may additionally include a heterocyclic compound represented by the following chemical formula 2 or 3.

[0179] [Chemical Formula 2]

[0180]

[0181] [Chemical Formula 3]

[0182]

[0183] In the above chemical formulas 2 and 3,

[0184] R11, R12, R22 and R23 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR',

[0185] L11, L12, L22 and L23 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,

[0186] Ar11, Ar12, Ar22 and Ar23 are the same or different from each other, and each independently represents a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R",

[0187] The above R, R' and R" are the same 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,

[0188] a11 and a12 are integers from 0 to 7, respectively,

[0189] a22 is an integer from 0 to 6,

[0190] a23 is an integer from 0 to 4,

[0191] p11, p12, p22 and p23 are integers from 0 to 4, respectively.

[0192] q11, q12, q22 and q23 are integers from 1 to 4, respectively,

[0193] When each of a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 is 2 or more, the substituents in the parentheses are the same or different from each other.

[0194] In one embodiment of the present specification, R11, R12, R22 and R23 are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0195] In one embodiment of the present specification, R11, R12, R22 and R23 are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0196] In one embodiment of the present specification, R11, R12, R22 and R23 are the same as or different from each other, and can each independently be selected from the group consisting of hydrogen; deuterium; halogen; cyano group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0197] In one embodiment of the present specification, R11, R12, R22 and R23 are the same or different from each other, and may each independently be hydrogen or deuterium.

[0198] In one embodiment of the present specification, L11, L12, L22 and L23 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.

[0199] In one embodiment of the present specification, L11, L12, L22 and L23 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.

[0200] In one embodiment of the present specification, L11, L12, L22 and L23 may be the same as or different from each other, and may each independently be a direct bond; a C6 to C20 arylene group substituted or unsubstituted with deuterium; or a C2 to C20 heteroarylene group substituted or unsubstituted with deuterium.

[0201] In one embodiment of the present specification, L11, L12, L22 and L23 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; a biphenylene group substituted or unsubstituted with deuterium; a dibenzofuranylene group substituted or unsubstituted with deuterium; or a dibenzothiophenylene group substituted or unsubstituted with deuterium.

[0202] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 may be the same as or different from each other, and may each independently be a cyano group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or SiRR'R".

[0203] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 may be the same as or different from each other, and may each independently be a cyano group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or SiRR'R".

[0204] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 may be the same as or different from each other, and may each independently be a cyano group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C6 to C30 heteroaryl group; or SiRR'R".

[0205] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 may be the same as or different from each other, and may each independently be a cyano group; a C6 to C30 aryl group substituted or unsubstituted with deuterium; a C2 to C30 heteroaryl group substituted or unsubstituted with deuterium; or SiRR'R".

[0206] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 may be the same as or different from each other, and each independently be a phenyl group unsubstituted or substituted with deuterium or a cyano group; a biphenyl group unsubstituted or substituted with deuterium; a terphenyl group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; a triphenylenyl group unsubstituted or substituted with deuterium; a fluorenyl group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a spirobifluorenyl group unsubstituted or substituted with deuterium; a dibenzofuranyl group unsubstituted or substituted with deuterium or a phenyl group; a dibenzothiophenyl group unsubstituted or substituted with deuterium or a phenyl group; or a triphenylsilyl group unsubstituted or substituted with deuterium.

[0207] In one embodiment of the present specification, R, R' and R" defined in the chemical formula 2 or 3 may be applied as is to R, R' and R" of the chemical formula 1 described above.

[0208] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0%, or 1% to 100%.

[0209] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0% or 10% to 100%.

[0210] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0% or 20% to 100%.

[0211] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0% or 30% to 100%.

[0212] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0% or 60% to 100%.

[0213] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0% or 80% to 100%.

[0214] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0% or 90% to 100%.

[0215] In one embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 2 or 3 may be represented by any one of the following.

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] In addition, by introducing various substituents into the structure of the above chemical formula 2 or 3, a heterocyclic compound having the unique characteristics of the introduced substituent can be synthesized. For example, by introducing a substituent mainly used in hole injection layer materials, hole transport layer materials, hole transport auxiliary layer materials, light emitting layer materials, electron transport layer materials, electron transport auxiliary 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.

[0229] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound (represented by Chemical Formula 1).

[0230] In one embodiment of the present specification, the light-emitting layer including the compound (represented by Chemical Formula 1) may additionally include a heterocyclic compound represented by Chemical Formula 2 or 3.

[0231] In one embodiment of the present specification, the organic layer includes at least one layer selected from a hole transport layer, a hole transport auxiliary layer, and an electron blocking layer, and at least one layer selected from the hole transport layer, the hole transport auxiliary layer, and the electron blocking layer may include the compound (represented by Chemical Formula 1).

[0232] In one embodiment of the present specification, at least one layer selected from the hole transport layer, hole transport auxiliary layer, and electron blocking layer including the compound may additionally include a heterocyclic compound represented by the chemical formula 2 or 3.

[0233] In one embodiment of the present specification, the organic light-emitting device may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0234] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, an electron transport layer, an electron transport auxiliary 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.

[0235] In one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0236] In another embodiment of the present specification, the first electrode may be a cathode and the second electrode may be an anode.

[0237] 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 a compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3).

[0238] The compound represented by the above chemical formula 1 (in addition, the heterocyclic compound represented by the above chemical formula 2 or 3) 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.

[0239] In another embodiment of the present specification, the organic light-emitting device may be a red organic light-emitting device, and the compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3) may be used as a material of the red organic light-emitting device. For example, the compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3) may be included in a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, or a light-emitting layer of the red organic light-emitting device.

[0240] In another embodiment of the present specification, the organic light-emitting device may be a green organic light-emitting device, and the compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3) may be used as a material of the green organic light-emitting device. For example, the compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3) may be included in a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, or a light-emitting layer of the green organic light-emitting device.

[0241] In one embodiment of the present specification, the organic light-emitting device may be a blue organic light-emitting device, and the compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3) may be used as a material of the blue organic light-emitting device. For example, the compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3) may be included in a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, or a light-emitting layer of the blue organic light-emitting device.

[0242] 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 disclosure 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 disclosure.

[0243] 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.

[0244] 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 (303), 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), a light-emitting layer (303), a hole blocking layer (304), an electron transport layer (305), and an electron injection layer (306). However, the scope of the present specification is not limited by such a laminated structure, and layers other than the light-emitting layer may be omitted as needed, and other necessary functional layers may be further added.

[0245] For example, the organic layer may further include a hole transport auxiliary layer, and the hole transport auxiliary layer may be included between the hole transport layer (302) and the electron blocking layer (303) based on the laminated structure.

[0246] The organic layer including the compound of the above chemical formula 1 and / or the heterocyclic compound of the above chemical formula 2 or 3 may additionally include other substances as needed.

[0247] In an organic light-emitting device according to one embodiment of the present specification, materials other than the compound of the chemical formula 1 and / or the heterocyclic compound of the chemical formula 2 or 3 are exemplified below, but these are only for exemplification and are not intended to limit the scope of the present specification, and may be replaced with materials known in the art.

[0248] 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.

[0249] 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.

[0250] 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.

[0251] In addition to the compound represented by the above chemical formula 1 and / or the heterocyclic compound represented by the above chemical formula 2 or 3, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used as a hole transport material, and a low-molecular-weight or high-molecular-weight material may also be used.

[0252] 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.

[0253] LiF is a representative example used in the art as an electron injection material, but is not limited thereto.

[0254] As a light-emitting material, in addition to the compound of the above chemical formula 1 and / or the heterocyclic compound of the above chemical formula 2 or 3, a red, green or blue light-emitting material may be used, 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 a host material and a dopant material participate in light emission may also be used.

[0255] 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.

[0256] 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.

[0257] The compound of the above chemical formula 1 and / or the heterocyclic compound of the above chemical formula 2 or 3 according to an 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.

[0258] In addition, by introducing various substituents into the structure of the compound of the above chemical formula 1 and / or the heterocyclic compound of the above chemical formula 2 or 3, 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.

[0259] Another embodiment of the present specification provides a composition for forming an organic layer of an organic light-emitting device, comprising a compound represented by the above chemical formula 1 and a heterocyclic compound represented by the following chemical formula 2 or 3.

[0260] [Chemical Formula 2]

[0261]

[0262] [Chemical Formula 3]

[0263]

[0264] In the above chemical formulas 2 and 3,

[0265] R11, R12, R22 and R23 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR',

[0266] L11, L12, L22 and L23 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,

[0267] Ar11, Ar12, Ar22 and Ar23 are the same or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R",

[0268] The above R, R' and R" are the same 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,

[0269] a11 and a12 are integers from 0 to 7, respectively,

[0270] a22 is an integer from 0 to 6,

[0271] a23 is an integer from 0 to 4,

[0272] p11, p12, p22 and p23 are integers from 0 to 4, respectively.

[0273] q11, q12, q22 and q23 are integers from 1 to 4, respectively,

[0274] When each of a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 is 2 or more, the substituents in the parentheses are the same or different from each other.

[0275] In one embodiment of the present specification, the definition of the substituent of the chemical formula 2 or 3 can be applied as described in the organic light-emitting device.

[0276] In one embodiment of the present specification, the weight ratio of the compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 2 or 3 may be 1:10 to 10:1.

[0277] In one embodiment of the present specification, the weight ratio of the compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 2 or 3 may be 1:5 to 5:1.

[0278] In one embodiment of the present specification, the weight ratio of the compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 2 or 3 may be 1:3 to 3:1.

[0279] 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 a composition for forming an organic layer of an organic light-emitting device, the composition including a compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 2 or 3.

[0280] 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 compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 2 or 3 and forming the organic layer using a thermal vacuum deposition method.

[0281] The above pre-mixing means that the compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 2 or 3 (optionally, other additional compounds) are mixed in one container before being deposited on the organic layer.

[0282] The above pre-mixed material may be referred to as a composition for forming an organic layer according to one embodiment of the present specification.

[0283] 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.

[0284] Manufacturing example

[0285] <Manufacturing Example 1> Manufacturing of target compound 1-1

[0286]

[0287] 1) Preparation of compound 1-1-3

[0288] 10 g (31.51 mmol) of the above compound 1-1-4, 12.8 g (34.66 mmol) of (A) 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, 1.82 g (1.58 mmol) of Pd(PPh3), and 8.71 g (63.02 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM (dichloromethane) were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex(hexane)=1:3) and 13.1 g (96.07%) of compound 1-1-3 was obtained with methanol.

[0289] 2) Preparation of compound 1-1-2

[0290] 13.1 g (30.27 mmol) of the compound 1-1-3, 4.14 g (33.3 mmol) of (B) phenyl boronic acid, 41.75 g (1.51 mmol) of Pd(PPh3), and 8.37 g (60.54 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) and 10.8 g (92.98%) of the compound 1-1-2 was obtained with methanol.

[0291] 3) Preparation of compound 1-1-1

[0292] 10.8 g (30.47 mmol) of the above compound 1-1-2, 11.61 g (45.7 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 31.4 g (1.52 mmol) of Pd2(dba), 1.45 g (3.05 mmol) of Xphos, and 5.98 g (60.94 mmol) of KOAc were dissolved in 150 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 10.5 g (77.09%) of compound 1-1-1.

[0293] 4) Preparation of target compound 1-1

[0294] 10.5 g (19.61 mmol) of the above compound 1-1-1, 5 g (18.68 mmol) of (C) 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.03 g (0.89 mmol) of Pd(PPh3), and 5.16 g (37.35 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, methanol was added to precipitate a solid and filtered. The solid was purified by column chromatography (DCM:Hex=1:1) and 10.5 g (89.7%) of the target compound 1-1 was obtained with methanol.

[0295] <Manufacturing Example 2> Manufacture of target compounds 1-5, 1-29, 1-53, 1-77, 1-93, 1-117, 1-145, 1-179, 1-187, 1-217, 1-241, 1-265, and 1-287

[0296] In the above Manufacturing Example 1, (A) Intermediate A of Table 1 below was used instead of 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, (B) Intermediate B of Table 1 below was used instead of phenyl boronic acid, and (C) Intermediate C of Table 1 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and the target compounds of Table 1 below were synthesized in the same manner as Manufacturing Example 1, respectively.

[0297] For reference, in the case of target compound 1-287, 2-bromo-4-chloro-1-iodobenzene-5,6-d2 was used as the starting material corresponding to compound 1-287-4 instead of compound 1-1-4.

[0298] [Table 1]

[0299]

[0300]

[0301]

[0302] <Manufacturing Example 3> Manufacturing of target compound 1-3

[0303]

[0304] 1) Preparation of compound 1-3-3

[0305] 10 g (31.51 mmol) of the above compound 1-3-4, 12.8 g (34.66 mmol) of (A) 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, 1.82 g (1.58 mmol) of Pd(PPh3), and 8.71 g (63.02 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and compound 1-3-3 12.5 (91.67%) was obtained with methanol.

[0306] 2) Preparation of compound 1-3-2

[0307] 12.5 g (30.27 mmol) of the compound 1-3-3, 3.95 g (31.77 mmol) of (B) phenyl boronic acid, 41.67 g (1.44 mmol) of Pd(PPh3), and 7.98 g (57.77 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) and 10.4 g (83.74%) of the compound 1-3-2 was obtained with methanol.

[0308] 3) Preparation of compound 1-3-1

[0309] 10.4 g (24.19 mmol) of the above compound 1-3-2, 9.21 g (36.28 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 31.11 g (1.21 mmol) of Pd2(dba), 1.15 g (2.42 mmol) of Xphos, and 6.69 g (48.38 mmol) of KOAc were dissolved in 100 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 9.7 g (76.9%) of compound 1-3-1.

[0310] 4) Preparation of target compounds 1-3

[0311] The compound 1-3-1 9.7 g (18.68 mmol), (C) 2-chloro-4,6-diphenyl-1,3,5-triazine 5 g (18.68 mmol), Pd(PPh3) 41.08 g (0.93 mmol), and K2CO3 5.16 g (37.35 mmol) were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, methanol was added to precipitate a solid and filtered. The solid was purified by column chromatography (DCM:Hex=1:1), and 8 g (68.34%) of the target compound 1-3 was obtained with methanol.

[0312] <Manufacturing Example 4> Manufacture of target compounds 1-15, 1-23, 1-39, 1-47, 1-63, 1-71, 1-87, 1-103, 1-111, 1-127, 1-135, 1-203, 1-235, 1-251, 1-259, 1-280, 1-294, and 1-299

[0313] In the above Manufacturing Example 3, (A) Intermediate A of Table 2 below was used instead of 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, (B) Intermediate B of Table 2 below was used instead of phenyl boronic acid, and (C) Intermediate C of Table 2 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and the target compounds of Table 2 below were synthesized in the same manner as Manufacturing Example 3, respectively.

[0314] For reference, in the case of target compound 1-294, 1-bromo-4-chloro-2-iobenzene-3,5,6-d3 was used as the starting material corresponding to compound 1-294-4 instead of compound 1-3-4, and in the case of target compound 1-299, 1-bromo-4-chloro-2-iodobenzene-3,6-d2 was used as the starting material corresponding to compound 1-299-4 instead of compound 1-3-4.

[0315] [Table 2]

[0316]

[0317] <Manufacturing Example 5> Manufacturing of target compound 1-2

[0318]

[0319] 1) Preparation of compound 1-2-3

[0320] 10 g (31.51 mmol) of the above compound 1-2-4, 12.8 g (34.66 mmol) of (A) 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, 1.82 g (1.58 mmol) of Pd(PPh3), and 8.71 g (63.02 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and compound 1-2-3 10.8 (79.2%) was obtained with methanol.

[0321] 2) Preparation of compound 1-2-2

[0322] The compound 1-2-3 10.8 (24.96 mmol), (B) phenyl boronic acid 3.42 g (7.45 mmol), Pd(PPh3) 41.44 g (1.25 mmol), and K2CO3 6.9 g (49.91 mmol) were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) and 8.7 g (81.08%) of compound 1-2-2 was obtained with methanol.

[0323] 3) Preparation of compound 1-2-1

[0324] The compound 1-2-2 8.7 g (20.24 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 7.71 g (30.35 mmol), Pd2(dba) 30.93 g (1.01 mmol), Xphos 0.96 g (2.02 mmol), and KOAc 5.59 g (40.47 mmol) were dissolved in 100 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 7.7 g (72.97%) of compound 1-2-1.

[0325] 4) Preparation of target compound 1-2

[0326] The compound 1-2-1 7.7 g (14.77 mmol), (C) 2-chloro-4,6-diphenyl-1,3,5-triazine 4 g (14.94 mmol), Pd(PPh3) 40.86 g (0.75 mmol), and K2CO3 4.13 g (29.88 mmol) were dissolved in 1,4-Dioxane / H2O 80 mL / 24 mL and refluxed for 6 hours. After the reaction was completed, methanol was added to precipitate a solid and filtered. The solid was purified by column chromatography (DCM:Hex=1:1) and 6.4 g (68.34%) of the target compound 1-2 was obtained with methanol.

[0327] <Manufacturing Example 6> Manufacture of target compounds 1-10, 1-26, 1-34, 1-50, 1-58, 1-74, 1-90, 1-98, 1-114, 1-122, 1-138, 1-150, 1-184, 1-190, 1-198, 1-214, 1-222, 1-238, 1-246, 1-262, 1-270, and 1-286

[0328] In the above Manufacturing Example 5, (A) Intermediate A of Table 3 below was used instead of 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, (B) Intermediate B of Table 3 below was used instead of phenyl boronic acid, and (C) Intermediate C of Table 3 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and the target compounds of Table 3 below were synthesized in the same manner as Manufacturing Example 5, respectively.

[0329] [Table 3]

[0330]

[0331] <Manufacturing Example 7> Manufacturing of target compounds 1-4

[0332]

[0333] 1) Preparation of compound 1-4-3

[0334] 10 g (31.51 mmol) of the compound 1-4-4, 12.8 g (34.66 mmol) of (A) 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, 1.82 g (1.58 mmol) of Pd(PPh3), and 8.71 g (63.02 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 11.3 g (82.87%) of compound 1-4-3 was obtained with methanol.

[0335] 2) Preparation of compound 1-4-2

[0336] 11.3 g (26. mmol) of the above compound 1-4-3, 3.57 g (28.72 mmol) of (B) phenyl boronic acid, 41.51 g (1.31 mmol) of Pd(PPh3), and 7.22 g (52.23 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) and 9.5 g (84.62%) of compound 1-4-2 was obtained with methanol.

[0337] 3) Preparation of compound 1-4-1

[0338] The compound 1-4-2 9.5 g (22.1 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 8.42 g (33.14 mmol), Pd2(dba) 31.01 g (1.1 mmol), Xphos 1.05 g (2.21 mmol), and KOAc 6.11 g (44.19 mmol) were dissolved in 150 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 8.8 g (78.37%) of compound 1-4-1.

[0339] 4) Preparation of target compounds 1-4

[0340] The compound 1-4-1 8.8 g (16.88 mmol), (C) 2-chloro-4,6-diphenyl-1,3,5-triazine 4.5 g (18.68 mmol), Pd(PPh3) 40.97 g (0.84 mmol), and K2CO3 3.27 g (23.63 mmol) were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, methanol was added to precipitate a solid and filtered. The solid was purified by column chromatography (DCM:Hex=1:1), and 6.9 g (65.49%) of the target compound 1-4 was obtained with methanol.

[0341] <Manufacturing Example 8> Manufacture of target compounds 1-20, 1-44, 1-68, 1-108, 1-132, 1-160, 1-174, 1-208, 1-232, and 1-256

[0342] In the above Manufacturing Example 7, (A) Intermediate A of Table 4 below was used instead of 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, (B) Intermediate B of Table 4 below was used instead of phenyl boronic acid, and (C) Intermediate C of Table 4 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and the target compounds of Table 4 below were synthesized in the same manner as Manufacturing Example 7, respectively.

[0343] [Table 4]

[0344]

[0345]

[0346] <Manufacturing Example 9> Manufacturing of target compound 1-169

[0347]

[0348] 1) Preparation of compound 1-169-3

[0349] 10 g (31.51 mmol) of the compound 1-169-4, 12.8 g (34.66 mmol) of (A) 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, 1.82 g (1.58 mmol) of Pd(PPh3), and 8.71 g (63.02 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 13.1 g (96.07%) of compound 1-169-3 was obtained with methanol.

[0350] 2) Preparation of compound 1-169-2

[0351] 13.1 g (30.32 mmol) of the compound 1-169-3, 7.8 g (30.32 mmol) of (B) 5H-benzofuran[3,2-c]carbazole, 31.39 g (1.52 mmol) of Pd2(dba), 5.83 g (60.63 mmol) of NaOtBu, and 318.4 g (90.95 mmol) of P(t-Bu) were dissolved in 100 mL of toluene and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) and 15.7 g (85.02%) of the compound 1-169-2 was obtained with methanol.

[0352] 3) Preparation of compound 1-169-1

[0353] 15.7 g (25.78 mmol) of the above compound 1-169-2, 9.82 g (38.66 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 31.18 g (1.29 mmol) of Pd2(dba), 1.22 g (2.55 mmol) of Xphos, and 7.12 g (51.55 mmol) of KOAc were dissolved in 150 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 14 g (77.63%) of compound 1-169-1.

[0354] 4) Preparation of compound 1-169

[0355] 14g (20.01mmol) of the above compound 1-169-1, 5.36g (20.01mmol) of (C) 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.16g (1mmol) of Pd(PPh3), and 5.53g (40.2mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 150mL / 45mL and refluxed for 6 hours. After the reaction was completed, methanol was added to precipitate a solid and filtered. The solid was purified by column chromatography (DCM:Hex=1:1) and 11.7g (72.55%) of the target compound 1-169 was obtained with methanol.

[0356] <Manufacturing Example 10> Manufacturing of target compound 1-193

[0357] In the above Manufacturing Example 9, (A) Intermediate A of Table 5 below was used instead of 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, (B) Intermediate B of Table 5 below was used instead of 5H-benzofuran[3,2-c]carbazole, and (C) Intermediate C of Table 5 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and the target compound 1-193 was synthesized in the same manner as Manufacturing Example 9.

[0358] [Table 5]

[0359]

[0360] <Manufacturing Example 11> Manufacturing of target compound 1-155

[0361]

[0362] 1) Preparation of compound 1-155-3

[0363] 10 g (31.51 mmol) of the compound 1-155-4, 12.8 g (34.66 mmol) of (A) 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, 1.82 g (1.58 mmol) of Pd(PPh3), and 8.71 g (63.02 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 11.7 g (85.8%) of compound 1-155-3 was obtained with methanol.

[0364] 2) Preparation of compound 1-155-2

[0365] 13.1 g (30.32 mmol) of the compound 1-155-3, 7.39 g (27.04 mmol) of (B) 12H-benzo[4,5]thio[2,3a]carbazole, 31.24 g (1.35 mmol) of Pd2(dba), 5.2 g (54.07 mmol) of NaOtBu, and 316.41 g (81.11 mmol) of P(t-Bu) were dissolved in 100 mL of toluene and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the residue, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) and 12 g (70.09%) of compound 1-155-2 was obtained with methanol.

[0366] 3) Preparation of compound 1-155-1

[0367] 12 g (19.19 mmol) of the above compound 1-155-2, 7.31 g (28.79 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 30.88 g (0.96 mmol) of Pd2(dba), 0.91 g (1.9 mmol) of Xphos, and 5.31 g (38.39 mmol) of KOAc were dissolved in 150 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 10.9 g (79.23%) of compound 1-155-1.

[0368] 4) Preparation of compound 1-155

[0369] The compound 1-155-1 10.9g (15.21mmol), (C) 2-chloro-4,6-diphenyl-1,3,5-triazine 4.07g (15.21mmol), Pd(PPh3) 40.88g (0.76mmol), K2CO3 4.2g (30.42mmol) were dissolved in 1,4-Dioxane / H2O 100mL / 30mL and refluxed for 6 hours. After the reaction was completed, methanol was added to precipitate a solid and filtered. The solid was purified by column chromatography (DCM:Hex=1:1) and 8g (63.99%) of the target compound 1-155 was obtained with methanol.

[0370] <Manufacturing Example 12> Manufacturing of target compound 1-163

[0371] In the above Manufacturing Example 11, (A) Intermediate A of Table 6 below was used instead of 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole, (B) Intermediate B of Table 6 below was used instead of 12H-benzo[4,5]thio[2,3a] carbazole, and (C) Intermediate C of Table 6 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and the target compound 1-163 was synthesized in the same manner as Manufacturing Example 10.

[0372] [Table 6]

[0373]

[0374] Compounds were manufactured using the same method as the above manufacturing examples, and the results of their synthesis are shown in Tables 7 and 8 below, respectively. Table 7 shows the measured values ​​of FD-MS (Field desorption mass spectrometry), and Table 8 shows the measured values ​​of 1 This is the measured value of H NMR (CDCl3, 400 MHz).

[0375] Compound FD-MS Compound FD-MS1-1 m / z = 262.25 (C 45 H 30 N4=626.76)1-145m / z= 808.27 (C 57 H 36 N4S=809.00)1-2m / z= 262.25 (C 45 H 30 N4=626.76)1-150m / z= 808.27 (C 57 H 36 N4S=809.00)1-3m / z= 262.25 (C 45 H 30 N4=626.76)1-155m / z= 821.26 (C 57 H 35 N5S=822.00)1-4m / z= 262.25 (C 45 H 30 N4=626.76)1-160m / z= 805.28 (C 57 H 35N5O=805.94)1-5m / z= 262.25 (C 45 H 30 N4=626.76)1-163m / z= 805.28 (C 57 H 35 N5O=805.94)1-10m / z= 702.28 (C 51 H 34 N4=702.86)1-166m / z= 805.28 (C 57 H 35 N5O=805.94)1-15m / z= 702.28 (C 51 H 34 N4=702.86)1-174m / z=716.26 (C 51 H 36 N4O=716.84)1-20m / z= 702.28 (C 51 H 34 N4=702.86)1-179m / z= 732.23 (C51H32N4S=732.90)1-23m / z= 702.28 (C 51 H 34 N4=702.86)1-184m / z= 808.27 (C 57 H 36 N4S=809.00)1-26m / z= 702.28 (C 51 H 34 N4=702.86)1-187m / z= 791.30 (C 57 H 37 N5=791.96)1-29m / z= 702.28 (C 51 H 34 N4=702.86)1-190m / z= 791.30 (C 57 H 37 N5=791.96)1-34m / z= 778.31 (C 57 H 38 N4=778.96)1-193m / z= 791.30 (C 57 H 37 N5=791.96)1-39m / z= 778.31 (C 57 H 38 N4=778.96)1-198m / z= 702.28 (C 51 H 34N4=702.86)1-44m / z= 778.31 (C 57 H 38 N4=778.96)1-203m / z= 778.31 (C 57 H 38 N4=778.96)1-47m / z= 778.31 (C 57 H 38 N4=778.96)1-208m / z= 791.30 (C 57 H 37 N5=791.96)1-50m / z= 778.31 (C 57 H 38 N4=778.96)1-211m / z= 792.29 (C 57 H 36 N4O=792.94)1-53m / z= 778.31 (C 57 H 38 N4=778.96)1-214m / z= 792.29 (C 57 H 36 N4O=792.94)1-58m / z= 792.29 (C 57 H 36 N4O=792.94)1-217m / z= 792.29 (C 57 H 36 N4O=792.94)1-63m / z= 792.29 (C 57 H 36 N4O=792.94)1-222m / z= 808.27 (C 57 H 36 N4S=809.00)1-68m / z= 792.29 (C 57 H 36 N4O=792.94)1-227m / z= 808.27 (C 57 H 36 N4S=809.00)1-71m / z= 792.29 (C 57 H 36 N4O=792.94)1-232m / z= 808.27 (C 57 H 36 N4S=809.00)1-74m / z= 792.29 (C 57 H 36 N4O=792.94)1-235m / z=716.26 (C 51 H36 N4O=716.84)1-77m / z= 792.29 (C 57 H 36 N4O=792.94)1-238m / z= 792.29 (C 57 H 36 N4O=792.94)1-82m / z= 808.27 (C 57 H 36 N4S=809.00)1-241m / z= 792.29 (C 57 H 36 N4O=792.94)1-87m / z= 808.27 (C 57 H 36 N4S=809.00)1-246m / z= 792.29 (C 57 H 36 N4O=792.94)1-90m / z= 808.27 (C 57 H 36 N4S=809.00)1-251m / z= 792.29 (C 57 H 36 N4O=792.94)1-93m / z= 808.27 (C 57 H 36 N4S=809.00)1-256m / z= 732.23 (C51H32N4S=732.90)1-98m / z= 808.27 (C 57 H 36 N4S=809.00)1-259m / z= 808.27 (C 57 H 36 N4S=809.00)1-103m / z= 808.27 (C 57 H 36 N4S=809.00)1-262m / z= 808.27 (C 57 H 36 N4S=809.00)1-108m / z= 808.27 (C 57 H 36 N4S=809.00)1-265m / z= 808.27 (C 57 H 36 N4S=809.00)1-111m / z= 791.30 (C 57 H 37 N5=791.96)1-270m / z= 808.27 (C 57 H36 N4S=809.00)1-114m / z= 791.30 (C 57 H 37 N5=791.96)1-275m / z= 702.28 (C 51 H 34 N4=702.86)1-117m / z= 702.28 (C 51 H 34 N4=702.86)1-280m / z= 717.37 (C 51 H 19 D 15 N4=717.95)1-122m / z= 778.31 (C 57 H 38 N4=778.96)1-283m / z= 728.33 (C 51 H 20 D 12 N4O=728.92)1-127m / z= 778.31 (C 57 H 38 N4=778.96)1-286m / z=723.32 (C 51 H 25 D8N5=723.91)1-132m / z= 792.29 (C 57 H 36 N4O=792.94)1-289m / z= 816.46 (C 57 H 12 D 25 N5=817.11)1-135m / z= 792.29 (C 57 H 36 N4O=792.94)1-294m / z= 846.42 (C 51 H 10 D 25 N5S=847.15)1-138m / z= 792.29 (C 57 H 36 N4O=792.94)1-299m / z= 808.39 (C 57 H 20 D 16 N4O=809.04)

[0376] compound no 1<h2 style=";text-align:left;direction:ltr">H NMR (CDCl3, 400MHz)1-1δ= 8.55(1H, d), 8.36-8.29(5H, m), 8.15-8.13(2H, m), 8.06(2H, d), 7.94(1H, d), 7.79(2H, d), 7.62-7.35(16H, m), 7.16(1H, t)1-2δ= 8.55(1H, d), 8.46-8.29(5H, m), 8.06(3H, d), 7.9 (1H, d), 7.83-7.68(3H, d), 7.5-7.35(16H, m), 7.16(1H, t)1-3δ= 8.55(1H, d), 8.15-8.13(2H, m), 8.06(2H, d), 7.94(1H, d), 7.79(2H, d), 7.62-7.3(16H, m), 7.16(1H, t)1-4δ= 8.5 (1H, d), 8.36-8.29(5H, m), 8.06(3H, d), 7.94(1H, d), 7.62(1H, t), 7.5-7.35(18H, m), 7.16(1H, t)1-5δ= 8.65(1H, d), 8.42-8.36(6H, m), 8.13(2H, m), 8.06(1H, d), 7.79(2H, d), 7.6-7.41(16H, m), 7.19(4H, m)1-10δ= 8.62(1H, d), 8.36-8.22(6H, m), 8.06(3H, m) 7.8-7.74(6H, m), 7.62-7.5(18H, m)1-15δ= 8.36-8.29(6H, d), 8.15-8.06(5H, d), 7.89(1H, s), 7.79-7.75(4H, d). 7.62-7.41(18H, m)1-20δ= 8.36-8.29(5H, d), 8.22(1H, d), 8.06-8.04(4H, d), 7.89(3H, s), 7.79-7.75(3H, d). 7.62-7.41(21H, m)1-23δ= 8.55(1H, d), 8.41-8.36(5H, d), 8.10-8.06(3H, d), 7.94(1H, d), 7.79(4H, d), 7.5-7.41(18H, m)1-26δ= 8.55(1H,d), 8.36(4H,d), 8.06(2H,d), 7.99-7.94(2H, m), 7.83-7.75(5H, m), 7.5-7.35(18H, m)1-29δ= 8.55(1H,d), 8.36(4H, d), 8.13(5H, m), 7.94(1H, d), 7.79(3H, d), 7.5-7.35(18H, m), 7.16(1H, t)1-34δ= 8.62(1H,d), 8.36(4H, d), 8.22(1H, d), 8.06-7.99(3H, m), 7.99-7.75(9H, m), 7.5-7.41(20H, m)1-39δ= 8.41-8.3(6H, d), 8.13-8.06(5H, m), 7.89(1H, s), 7.79(6H, d), 7.62-7.41(20H, m)1-44δ= 8.36(4H, d), 8.22(2H, d), 8.1-8.04(4H, d), 7.79(5H, m), 7.62-7.41(23H, m)1-47δ= 7.55(1H, d), 8.42-8.36(5H, d), 8.18-8.06(5H, m), 7.79(4H, d), 7.5-7.41(19H, m)1-50δ= 8.49(1H, d), 8.36-8.23(6H, d), 8.06(3H, d), 7.83-7.79(5H, m), 7.65-7.4(23H, m)1-53δ= 8.55(1H, d), 8.36(4H, d), 8.13(2H, m), 8.06(1H, d), 7.94(2H, m), 7.79(4H, m), 7.62-7.35(23H, m), 7.16(1H, t)1-58δ= 8.55(1H, d), 8.36(4H, d), 8.13(1H, d), 8.08-7.94(6H, m), 7.79(3H, d), 7.5-7.31(19H, m), 7.16(1H, t)1-63δ= 8.36-8.29(6H, m), 8.15-7.98(7H, m), 7.89(1H, s), 7.82-7.76(4H, m), 7.54-7.31(18H, m)1-68δ= 8.65(1H, d), 8.6-8.29(6H, m), 8.06(3H, d), 7.98(1H, d), 7.83(4H, m), 7.54-7.31(21H, m)1-71δ= 8.36-8.29(5H, d), 8.15-8.13(2H, m), 8.06-7.98(4H, d), 7.88-7.79(5H, m), 7.54-7.31(19H, m)1-74δ= 8.55(1H, d), 8.41-8.36(5H, d), 8.1-8.06(3H, d), 7.98-7.79(8H, m), 7.5-7.31(18H, m), 7.16(1H, t)1-77δ= 8.36-8.29(6H, m), 8.13-8.07(5H, m), 7.98(1H, d), 7.82-7.79(3H, d), 7.69-7.31(20H, m)1-82δ= 8.65(1H, d), 8.55(1H, d), 8.45-8.29(8H, d), 8.06(3H, m), 7.93(1H, d), 7.83-7.79(3H, d), 7.5-7.41(19H, m)1-87δ= 8.55(2H, d), 8.45(1H, d), 8.36-8.32(5H, d), 8.13(2H, m), 7.99-7.94(3H, m), 7.5-7.35(21H, m), 7.16(1H, t)1-90δ= 8.62(1H, d), 8.45(1H, d), 8.36-8.2(9H, m), 8.06-8.02(3H, d), 7.93(1H, d), 7.83-7.74(4H, m), 7.56-7.41(17H, m)1-93δ= 8.55(1H, d), 8.45(1H, d), 8.36(4H, d), 8.24-8.0(8H, m), 7.94(2H, d), 7.79(2H, d), 7.62-7.41(17H, m), 7.16(1H, t)1-98δ= 8.45(1H, d), 8.36-8.29(6H, d), 8.13-7.79(12H, m), 7.56-7.41(17H, m)1-103δ= 8.65(1H, d), 8.45-8.36(7H, m), 8.13(2H, m), 7.93(2H, d), 7.79(2H, d), 7.5-7.41(19H, m)1-108δ= 8.55(1H, d), 8.45(1H, d), 8.36(4H, d), 8.06-7.93(7H, m), 7.8(2H, m), 7.56-7.35(20H, m), 7.16(1H, t)1-111δ= 8.55(1H, d), 8.36-8.29(5H, m), 8.15-8.06(6H, m), 7.94(1H, d), 7.79(3H, d), 7.4-7.35(19H, m), 7.2-7.16(2H, t)1-114δ= 8.55(2H, d), 8.36(4H, d), 8.19(1H, d), 8.06(2H, d), 7.94(2H, d), 7.83-7.77(4H, m), 7.58-7.35(18H, m), 7.2-7.16(3H, m)1-117δ= 8.55(1H, d), 8.36-8.29(5H, m), 8.13--7.94(4H, m), 7.75(3H, m), 7.62-7.35(18H, m), 7.16(1H, t)1-122δ= 8.55(1H, d), 8.36(4H, d), 8.06-7.94(7H, m), 7.83-7.79(4H, m), 7.62-7.35(17H, m), 7.16(1H, t)1-127δ= 8.55(1H, d), 8.36(4H, d), 8.15-8.06(4H, m), 7.94(1H, d), 7.75(2H, d), 7.5-7.35(16H, m), 7.25(8H, d), 7.16(1H, t)1-132δ= 8.55(1H, d), 8.36-8.29(5H, m), 8.06-7.94(6H, m), 7.76(4H, m), 7.62-7.35(18H, m), 7.16(1H, t)1-135δ= 8.55(1H, m), 8.36(4H, d), 8.15-8.06(4H, m), 7.94-7,73(7H, m), 7.61-7.35(18H, m), 7.16(1H, t)1-138δ= 8.55(1H, d), 8.46-8.29(5H, m), 8.06(3H, d), 7.9 (1H, d), 7.83(1H, t), 7.69-7.35(22H, m), 7.16(1H, t)1-145δ= 8.55(1H, d), 8.45(1H, d), 8.35-8.17(10H, m), 7.94(2H, d), 7.62-7.47(14H, m), 7.35(1H, d), 7.25(4H, d), 7.16(1H, d)1-150δ= 8.55(1H, d), 8.45(1H, d), 8.36(5H, d), 8.06-8.03(4H, m), 7.94(3H, m), 7.83(1H, t), 7.68-7.5(14H, m), 7.35-7.16(6H, m)1-155δ= 8.55(2H, d), 8.45(1H, d), 8.36-8.29(5H, m), 8.11-7.94(7H, m), 7.6-7.5(15H, m), 7.35(2H, m), 7.16(2H, t)1-163δ= 8.55(2H, d), 8.36-8.29(5H, m), 7.62-7.39(19H, m), 7.16(2H, m)1-166δ= 8.55(2H, d), 8.36(5H, m), 7.98-7.94(6H, m), 7.79(1H, t), 7.5-7.31(20H, m), 7.16(2H, t)1-169δ= 8.55(2H, d), 8.36-8.29(6H, m), 8.06(2H, d), 7.98-7.94(4H, m), 7.84(1H, d), 7.5-7.31(17H, m), 7.16-7.13(3H, m)1-174δ= 8.55(1H, d), 8.36(4H, m), 8.06(3H, m), 7.98-7.94(3H, m), 7.82(2H, m), 7.62-7.35(18H, m), 716(1H, t)1-179δ= 8.55(2H, d), 8.45(1H, d), 8.36(6H, m), 8.13(2H, m), 7.94(2H, d), 7.62-7.48(15H, m), 7.35(1H, t), 7.16(1H, t)1-184δ= 8.55(1H, d), 8.36-7.94(15H, m), 7.83-7.75(3H, m), 7.62-7.35(16H, m), 7.16(1H, t)1-187δ= 8.55(2H, d), 8.36-8.29)6H, m), 8.15-8.13(2H, m), 8.06(4H, d), 7.94(2H, d), 7.62-7.48(18H, m), 7.35(2H, t), 7.16(2H, t)1-190δ= 8.55(2H, d), 8.36(6H, m), 8.05(3H, d), 7.94-7.83(4H, m), 7.62-7.5(19H, m), 7,35(2H, t), 7.16(2H, t)1-193δ= 8.55(2H, d), 8.4-8.29(6H, m), 7.99-7.94(7H, m), 7.77-7.75(3H, m), 7.62-7.35(17H, m), 7.16(2H, d)1-198δ= 8.55(1H, d), 8.36-8.29(3H, m), 8.06(3h, m), 7.96(3H, m), 7.84-7.75(5H, m), 7.62-7.16(19H, m)1-203δ= 8.55(1H, m), 8.29(1H, d), 8.15-7.96(9H, m), 7.79-7.75(6H, m), 7.5-7.41(16H, m), 7.25(4H, m)1-208δ= 8.55(2H, d), 8.36-8.19(6H, m), 8.06(3H, d), 7.94(2H, d), 7.62(1H, t), 7.68-7.35(20H, m), 7.2-7.16(3H, m)1-211δ= 8.55(1H, d), 8.36-8.29(3H, m), 8.06-7.94(7H, m), 7.82--7.76(4H, m), 7.6-7.35(18H, m), 7.16(1H, t)1-214δ= 8.55(1H, d), 8.38-8.29(4H, m), 8.08-7.94(8H, m), 7.79-7.73(4H, m), 7.61-7.31(18H, m), 7.16(1H, t)1-217δ= 8.55(1H, d), 8.38-8.29(4H, m), 8.08-7.94(8H, m), 7.69-7.35(23H, m), 7.16(1H, t)1-222δ= 8.55(2H, d), 8.36-8.29(4H, m), 8.06(3H, d), 7.96-7.93(4H, m), 7.83-7.793H, m), 7.6-7.41(18H, m), 7.16(1H, t)1-227δ= 8.55(1H, d), 8.45-8.2(10H, m), 8.06(2H, d), 7.94(3H, m), 7.79-7.73(3H, m), 7.56-7.41(16H, m)7.16(1H, t)1-232δ= 8.55(1H, d), 8.45(1H, d), 8.36-8.29(3H, m), 8.12-7.93(10H, m), 7.83(1H, t), 7.62-7.41(17H, m), 7.25(2H, d), 7.16(1H, t)1-235δ= 8.55(1H, d), 8.36-8.29(3H, m), 8.15(2H, m), 8.06(2h, d), 7.98-7.79(7H, m), 7.54-7.35(16H, m), 7.16(1H, d)1-238δ= 8.55(1H, d), 8.36-8.29(3H, m), 8.08-8(6H, m), 7.94(1H, d), 7.83-7.79(5h, m), 7.62-7.35(19H, m), 7.16(1H, t)1-241δ= 8.55(1H, d), 8.36-8.29(3H, m), 8.13-8.03(6H, m), 7.94-7.75(8H, m), 7.62-7.35(17H, m), 7.16(1H, t)1-246δ= 8.55(1H, d), 8.36-8.29(3H, m), 8.06-8.03(4H, m), 7.94-7.75(11H, m), 7.62-7.35(17H, m), 7.16(1H, t)1-251δ= 8.55(1H, d), 8.36-8.29(3H, m), 8.15(2H, m), 8.06(2h, d), 7.98-7.79(9H, m), 7.69-7.35(18H, m), 7.16(1H, d)1-256δ= 8.55(1H, d), 8.45(1H, d), 8.36-8.29(3H, m), 8.06-8.03(3H, m), 7.93(2H, d), 7.82(1H, t), 7.68-7.35(18H, m), 7.16(1H, t)1-259δ= 8.55(1H, d), 8.36-8.29(3H, m), 8.13-7.94(8H, m), 7.79(2H, d), 7.51-7.35(19H, m), 7.16(1H, t)1-262δ= 8.55(1H, d), 8.36-8.17(8H, m), 8.06(3H, m), 7.94(2H, d), 7.83-7.75(5H, m), 7,62-7.35(16H, m), 7.16(1H t)1-265δ= 8.55(2H, d), 8.36-8.29(3H, m), 8.12-7.92(9H, m), 7.62-7.35(21H, m), 7.16(1H, t)1-270δ= 8.55(1H, d), 8.36-8.2(5H, m), 8.06-8.03(4H, m), 7.95(3H, d), 7.83-7.79(5H, m), 7.62-7.35(18H, m), 7.16(1H, t)1-275δ= 8.55(1H, d), 8.36-8.29(5H, m), 8.13(2H, m), 8.6(1H, d), 7.96-7.94(3H, m), 7.79(2H, d), 7.62-7.35(19H, m), 7.16(1H, t)1-280δ= 8.36(4H, d), 8.15(2H, m), 7.79(2H, d), (7.5-7.41(9H, m)1-283δ= 8.36(2H, d), 8.06-7.98(4H, m), 7.82(3H, m), 7.65-7.31(11H, m)1-286δ= 8.55(1H, d), 8.36(2H, d), 8.19(1H, d), 8.06(2H, d), 7.94(1H, d), 7.83-7.79(4H, m), 7.58-7.16(13H, m)1-289δ= 8.36(3H, d), 8.2(1H, s), 7.5(6H, m)1-294δ= 8.36(4H, d), 7.5(6H, m)1-299δ= 8.36(2H, d), 7.96(1H, d), 7.83-7.79(6H, m), 7.52-7.41(9H, m), 7.29(1H, t).

[0377] <제조예 13> 화합물 2-1의 제조

[0378] 1) 화합물 2-1-1의 제조

[0379] In a reaction flask, 10 g (49.59 mmol) of 3-bromo-9H-carbazole, 24.2 g (148.77 mmol) of 2-bromobenzene-1-ylium (a), 2.27 g (2.48 mmol) of Tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 2.42 mL (9.92 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 9.53 g (99.18 mmol) of sodium tert-butoxide (NatOBu) were added, and then 100 mL of toluene was added. It was heated at 135℃ for 15 hours. After the reaction was completed, it was extracted with methylene chloride (MC) and water, and purified by column chromatography to obtain 14 g (yield 98%) of compound 2-1-1.

[0380] 2) Preparation of target compound 2-1

[0381] In a reaction flask, 14 g (43.4 mmol) of the compound 2-1-1, 14.9 g (52 mmol) of (9-phenyl-9H-carbazol-3-yl)boronic acid (b), 2.5 g (2.17 mmol) of tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4, and 17.9 g (130 mmol) of potassium carbonate (K2CO3) were placed, and then 140 mL of 1,4-dioxane and 35 mL of distilled water were added, and the mixture was stirred at 120°C for 4 hours.

[0382] After that, the temperature was lowered to room temperature, and the resulting solid was washed with distilled water and methanol to obtain 17 g (80% yield) of the target compound 2-1.

[0383] <Manufacturing Example 14> Manufacture of target compounds 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-11, 2-16, 2-19, 2-20, 2-21, 2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-32, 2-33, 2-34, 2-38, 2-40, 2-41, 2-42, 2-43, 2-45, 2-46, 2-48, 2-49, 2-50, 2-51, 2-52, 2-55, 2-57 and 2-60

[0384] Except that compound a of Table 9 below was used instead of 2-bromobenzene-1-yllium (a) in Manufacturing Example 13 above, and compound b of Table 9 below was used instead of (9-phenyl-9H-carbozol-3-yl)boronic acid (b), the target compounds of Table 9 below were each synthesized in the same manner as Manufacturing Example 13 above.

[0385] [Table 9]

[0386]

[0387] <Manufacturing Example 15> Preparation of compound 2-61

[0388]

[0389] 1) Preparation of compound 2-61-4

[0390] 10 g (40.23 mmol) of 3-bromo-9H-carbazole, 1,000 mL of D6-benzene, and 170 g (1,075 mmol) of triflic acid (CF3SO3H) were added and stirred at 50°C.

[0391] After the reaction was completed, the mixture was neutralized with D2O, extracted with aqueous sodium carbonate (Na2CO3) solution and dichloromethane (DCM) at room temperature, and the organic layer was dried over anhydrous magnesium sulfate (MgSO4) and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (dichloromethane:hexane = 1:2) and recrystallized from methanol to obtain 10 g (yield 98%) of compound 2-61-4.

[0392] 2) Preparation of compound 2-61-3

[0393] 10 g (39.5 mmol) of the above compound 2-61-4, 12.4 g (79 mmol) of bromobenzene, 1.81 g (1.98 mmol) of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 1.93 mL (7.9 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 11.4 g (118.51 mmol) of sodium tert-butoxide (NatOBu) were added, and then 100 mL of toluene was added and heated at 135°C for 15 hours. After the reaction was completed, the mixture was extracted with methylene chloride (MC) and water, and purified by column chromatography to obtain 11 g (yield 84%) of compound 2-61-3.

[0394] 3) Preparation of compound 2-61-2

[0395] 10 g (47.3 mmol) of 9H-carbazol-3-ylboronic acid, 1,000 mL of D6-benzene, and 170 g (1,075 mmol) of triflic acid (CF3SO3H) were added and stirred at 50°C.

[0396] After the reaction was completed, the mixture was neutralized with D2O, extracted with aqueous sodium carbonate (Na2CO3) solution and dichloromethane (DCM) at room temperature, and the organic layer was dried over anhydrous magnesium sulfate (MgSO4) and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (dichloromethane:hexane = 1:2) and recrystallized from methanol to obtain 9 g of compound 2-61-2 (yield 87%).

[0397] 4) Preparation of compound 2-61-1

[0398] After adding 9 g (41.3 mmol) of the above compound 2-61-2, 12.9 g (82.5 mmol) of bromobenzene, 1.89 g (2.06 mmol) of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 2 mL (8.25 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 7.93 g (82.574 mmol) of sodium tert-butoxide (NatOBu), 100 mL of toluene was added and heated at 135°C for 10 hours. After the reaction was completed, the mixture was extracted with methylene chloride (MC) and water, and purified by column chromatography to obtain 10 g (yield 82%) of compound 2-61-1.

[0399] 5) Preparation of target compound 2-61

[0400] 10 g (30.37 mmol) of the above compound 2-61-3, 17.87 g (60.75 mmol) of the above compound 2-61-1, 1.39 g (1.52 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4), and 12.59 g (91.13 mmol) of potassium carbonate (K2CO3) were added, and then added to 140 mL of 1,4-dioxane and 35 mL of distilled water, and stirred at 120°C for 4 hours.

[0401] After that, the temperature was lowered to room temperature, and the resulting solid was washed with distilled water and methanol to obtain 13 g (yield 85%) of compound 2-61.

[0402] <Manufacturing Example 16> Manufacture of target compounds 2-62, 2-63, 2-64, 2-65, 2-66, 2-68, 2-69, 2-70, 2-74, 2-75, 2-81, 2-82, 2-83, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-92, 2-100, and 2-102

[0403] The target compounds were synthesized in the same manner as in Manufacturing Example 15, except that compound c of Table 10 below was used instead of bromobenzene (c) in Manufacturing Example 15, and compound d of Table 10 below was used instead of bromobenzene (d).

[0404] [Table 10]

[0405]

[0406] Compounds were prepared in the same manner as the above manufacturing examples, and the results of their synthesis are shown in Tables 11 and 12 below. Table 11 shows the measured values ​​of FD-MS, and Table 12 shows the measured values ​​of 1 This is the measured value of H NMR (CDCl3, 400 MHz).

[0407] 포리번호FD-MS화합물 번리FD-MS2-1m / z= 484.59(C 36 H 24 N2=484.19)2-2m / z= 560.69(C 42 H 28 N2=560.23)2-3m / z= 560.69(C 42 H 28 N2=560.23)2-4m / z= 560.69(C 42 H 28 N2=560.23)2-5m / z= 636.78(C 48 H 32 N2=636.26)2-6m / z= 636.78(C 48 H 32 N2=636.26)2-7m / z= 636.78(C 48 H 32 N2=636.26)2-8m / z= 543.65(C 40 H 26 N2=543.21)2-9m / z= 543.65(C 40 H 26 N2=543.21)2-10m / z= 600.75(C 45 H 35 N2=600.26)2-11m / z= 600.75(C 45 H 35 N2=600.26)2-12m / z= 724.89(C 55 H 36 N2=724.29)2-13m / z= 724.89(C 55 H 36 N2=724.29)2-14m / z= 724.89(C 55 H 36 N2=724.29)2-15m / z= 724.89(C 55 H 36 N2=724.29)2-16m / z= 634.77(C 48 H 30 N2=634.24)2-17m / z= 509.60(C 37 H 23 N3=509.19)2-18m / z= 742.98(C 54 H 38N2Si=742.28)2-19m / z= 636.78(C 48 H 32 N2=636.26)2-20m / z= 636.78(C 48 H 32 N2=636.26)2-21m / z= 636.78(C 48 H 32 N2=636.26)2-22m / z= 712.88(C 54 H 36 N2=712.29)2-23m / z= 712.88(C 54 H 36 N2=712.29)2-24m / z= 712.88(C 54 H 36 N2=712.29)2-25m / z= 710.86(C 54 H 34 N2=710.27)2-26m / z= 712.88(C 54 H 36 N2=712.29)2-27m / z= 712.88(C 54 H 36 N2=712.29)2-28m / z= 712.88(C 54 H 36 N2=712.29)2-29m / z= 712.88(C 54 H 36 N2=712.29)2-30m / z= 712.88(C 54 H 36 N2=712.29)2-31m / z= 710.86(C 54 H 34 N2=710.27)2-32m / z= 636.78(C 48 H 32 N2=636.26)2-33m / z= 712.88(C 54 H 36 N2=712.29)2-34m / z= 712.88(C 54 H 36 N2=712.29)2-35m / z= 788.97(C 60 H 40 N2=788.32)2-36m / z= 686.84(C 52 H 34 N2=686.27)2-37m / z= 788.97(C60 H 40 N2=788.32)2-38m / z= 788.97(C 60 H 40 N2=788.32)2-39m / z= 686.84(C 52 H 34 N2=686.27)2-40m / z= 686.84(C 52 H 34 N2=686.27)2-41m / z= 494.65(C 36 H 14 D 10 N2=494.26)2-42m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-43m / z= 574.77(C 41 H 14 D 14 N2=574.31)2-44m / z= 650.86(C 48 H 14 D 16 N2=650.34)2-45m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-46m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-47m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-48m / z=654.89(C 48 H 14 D 18 N2=654.37)2-49m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-50m / z: 734.43(C 54 H 14 D 22 N2=735.03)2-51m / z= 735.01(C 54 H 14 D 22 N2=734.43)2-52m / z= 735.01(C 54 H 14 D 22N2=734.43)2-53m / z= 730.98(C 54 H 14 D 20 N2=730.40)2-54m / z= 735.01(C 54 H 14 D 22 N2=734.43)2-55m / z=735.01(C 54 H 14 D 22 N2=734.43)2-56m / z= 815.13(C 60 H 14 D 26 N2=814.48)2-57m / z= 815.13(C 60 H 14 D 26 N2=814.48)2-58m / z= 815.13(C 60 H 14 D 26 N2=814.48)2-59m / z= 815.13(C 60 H 14 D 26 N2=814.48)2-60m / z= 666.86(C 48 H 14 D 16 N2O=666.34)2-61m / z= 498.68(C 36 H 10 D 14 N2=498.28)2-62m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-63m / z= 574.77(C 41 H 14 D 14 N2=574.31)2-64m / z= 648.85(C 48 H 16 D 14 N2=648.33)2-65m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-66m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-67m / z= 650.87(C 48 H18 D 14 N2=650.34)2-68m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-69m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-70m / z=726.38(C 54 H 22 D 14 N2=726.98)2-71m / z= 726.96(C 54 H 22 D 14 N2=726.38)2-72m / z= 726.96(C 54 H 22 D 14 N2=726.38)2-73m / z= 724.95(C 54 H 20 D 14 N2=724.36)2-74m / z= 726.96(C 54 H 22 D 14 N2=726.38)2-75m / z= 726.96(C 54 H 22 D 14 N2=726.38)2-76m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-77m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-78m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-79m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-80m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-81m / z= 508.74(C 36 D 24 N2=508.34)2-82m / z= 668.98(C 48D 32 N2=668.46)2-83m / z= 588.86(C 42 D 28 N2=588.40)2-84m / z= 664.95(C 48 D 30 N2=664.43)2-85m / z= 668.98(C 48 D 32 N2=668.46)2-86m / z= 668.98(C 48 D 32 N2=668.46)2-87m / z= 668.98(C 48 D 32 N2=668.46)2-88m / z= 668.98(C 48 D 32 N2=668.46)2-89m / z= 668.98(C 48 D 32 N2=668.46)2-90m / z= 748.518(C 54 D 36 N2=749.12)2-91m / z= 749.10(C 54 D 36 N2=748.51)2-92m / z= 749.10(C 54 D 36 N2=748.51)2-93m / z= 745.07(C 54 D 34 N2=744.49)2-94m / z= 749.10(C 54 D 36 N2=748.51)2-95m / z= 749.10(C 54 D 36 N2=748.51)2-96m / z= 829.22(C 60 D 40 N2=828.57)2-97m / z= 829.22(C 60 D 40 N2=828.57)2-98m / z= 829.22(C 60 D 40 N2=828.57)2-99m / z= 829.22(C 60 D 40 N2=828.57)2-100m / z= 680.95(C 48 D 30N2O=680.42)2-101m / z= 697.02(C 48 D 30 N2S=696.40)2-102m / z=829.22(C 60 D 40 N2=828.57)2-103m / z= 632.95(C 45 D 32 N2=632.46)2-104m / z= 713.07(C 51 D 36 N2=712.51)

[0408] Compound number 1H NMR(CDCl3, 400MHz)2-1δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.62-7.50(m, 12H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-2δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 6H), 7.80-7.77(m, 2H), 7.62-7.35(m, 10H), 7.20-7.16(m, 6H)2-3δ =8.55(d, 1H), 8.18-8.09(m, 3H), 8.00-7.87(m, 3H), 7.77(s, 2H), 7.58-7.25(m, 18H)2-4δ =8.55(d, 1H), 8.18-8.12(m, 2H), 8.00-7.84(m, 3H), 7.79-7.77(m, 4H), 7.68-7.25(m, 22H)2-5δ =8.55(d, 1H), 8.30(d, 1H), 8.21-8.13(m, 3H), 7.99-7.89(m, 4H), 7.77-7.35(m, 17H), 7.25-7.16(m, 6H)2-6δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.94-7.89(m, 8H), 7.77-7.75(m, 3H), 7.62-7.35(m, 11H), 7.25-7.16(m, 6H)2-7δ =8.55(d, 1H), 8.18-8.09(m, 4H), 8.00-7.94(m, 2H), 7.87(m, 1H), 7.77(m, 2H), 7.69-7.63(m, 2H), 7.52-7.25(m, 20H)2-11δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 5H), 7.77(d, 1H), 7.58-7.28(m, 16H), 1.69(s, 6H)2-16δ =9.05(s, 1H), 8.55(d, 1H), 8.33-8.13(m, 7H), 7.99-7.89(m, 5H), 7.77-7.50(m, 13H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-19δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 8H), 7.80-7.77(m, 3H), 7.58(d, 1H), 7.50-7.35(m, 6H), 7.20-7.16(m, 10H)2-20δ =8.55(d, 1H), 8.30(d, 1H), 8.21-8.13(m, 3H), 7.99-7.89(m, 6H), 7.80-7.35(m, 15H), 7.20-7.16(6H)2-21δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2h), 7.99-7.89(m, 10H), 7.80-7.75(m, 4H), 7.50-7.35(m, 8H), 7.20-7.16(m, 6H)2-22δ =8.55(d, 1H), 8.30(d, 1H), 8.21-8.13(m, 3H), 7.99-7.89(m, 6H), 7.80-7.35(m, 15H), 7.25-7.16(10H)2-23δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2h), 7.99-7.89(m, 10H), 7.80-7.75(m, 4H), 7.50-7.35(m, 8H), 7.25-7.16(m, 10H)2-26δ =8.55(m, 1H), 8.30(d, 1H), 8.21-8.13(m, 4h), 7.99-7.89(m, 4H), 7.77-7.35(m, 20H), 7.25-7.16(6H)2-27δ =8.55(m, 1H), 8.30(d, 1H), 8.21-8.13(m, 4h), 7.99-7.89(m, 4H), 7.77-7.35(m, 20H), 7.20-7.16(2H)2-28δ =8.55(m, 1H), 8.18-8.09(m, 3H), 8.00-8.79(m, 2H), 7.87(m, 1H), 7.79-7.77(m, 4H), 7.69-7.63(m, 4H), 7.52-7.25(m, 12H)2-29δ =8.55(m, 1H), 8.18-8.09(m, 3H), 8.00-7.94(m, 2H0, 7.87(m, 1H), 7.87(m, 1H), 7.79-7.77(m, 4H), 7.69-7.63(m, 4H), 7.52-7.25(m, 21H)2-30δ =8.55(m, 1H), 8.31-8.30(m, 3H), 8.21-8.13(m, 3h), 7.99-7.89(m, 3H), 7.75-7.35(m, 22H), 7.20-7.16(m, 2H)2-32δ =8.55(m, 1H), 8.18-8.12(m, 2H), 8.00-7.87(m, 3H), 7.79-7.77(m, 6H), 7.69-7.63(m, 6H), 7.52-7.25(m, 14H)2-33δ =8.55(m, 1H), 8.30(d, 1H), 8.21-8.13(m, 3H), 7.99-7.89(m, 8H), 7.77-7.35(m, 17H), 7.25-7.16(6H)2-34δ =8.55(m, 1H), 8.18-8.12(m, 2H), 8.00-7.87(m, 3H), 7.79-7.77(m, 6H), 7.67-7.63(m, 6H), 7.52-7.25(m, 18H)2-38δ =8.55(m, 1H), 8.18-8.12(m, 2H), 8.05-7.87(m, 6H), 7.79-7.77(m, 4H), 7.69-7.63(m, 4H), 7.52-7.25(m, 23H)2-40δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 8.03-7.75(m, 15H), 7.58-7.35(m, 9H), 7.25-7.16(m, 6H)2-41δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-42δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-43δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-45δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-46δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-48δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-49δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-50δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-51δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-52δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-55δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-57δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-60δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-61δ =7.62-7.50(m, 10H)2-62δ =7.79(m, 4H), 7.68(m. 4H), 7.52-7.41(m, 10H)2-63δ =8.21(s, 1H) 7.75-7.41(m, 13H)2-64δ =9.05(s, 1H), 8.33-8.25(m, 4H), 7.94(d, 1H), 7.70-7.50(m, 10H)2-65δ =7.79(m, 2H), 7.70-7.68(m, 3H), 7.58-7.41(m, 13H)2-66δ =7.92-7.91(m, 4H), 7.75(d, 2H), 7.62-7.41(m, 8H), 7.25(s, 4H)2-68δ =8.21(s, 2H), 7.75-7.60(m, 8H), 7.49-7.41(8H)2-69δ =8.21(s, 1H), 7.92-7.91(m, 4H), 7.75-7.60(m, 6H), 7.49-7.41(m, 7H)2-70δ =8.21(s, 1H), 7.94-7.91(m, 5H), 7.75-7.61(m, 9H), 7.49-7.41(m, 7H)2-74δ =7.94-7.91(m, 9H), 7.75-7.73(m, 5H), 7.61(d, 2H), 7.49-7.41(m, 6H)2-75δ =7.92-7.91(m, 8H), 7.75(d, 4H), 7.49-7.41(m, 6H), 7.25(s, 4H).

[0409] <Manufacturing Example 17> Manufacturing of target compound 3-1

[0410] 1) Preparation of compound 3-1-1

[0411] In a reaction flask, 10 g (39.0 mmol) of 5,8-dihydroindolo[2,3-c]carbazole (a), 6.12 g (39.0 mmol) of 1-bromobenzene (b), 1.79 g (1.95 mmol) of Tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.92 mL (3.9 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 7.50 g (78.0 mmol) of sodium tert-butoxide (NatOBu) were added, and then 100 mL of toluene was added. It was heated at 135℃ for 15 hours. After the reaction was completed, it was extracted with methylene chloride (MC) and water, and purified by column chromatography to obtain 7.3 g (yield 56%) of compound 3-1-1.

[0412] 2) Preparation of target compound 3-1

[0413] After adding 7.3 g (22.0 mmol) of the above compound 3-1-1, 3.8 g (24.2 mmol) of 1-bromobenzene (c), 1.01 g (1.1 mmol) of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.52 mL (3.9 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 4.23 g (44.0 mmol) of sodium tert-butoxide (NatOBu), 70 mL of toluene was added and heated at 135°C for 15 hours. After the reaction was completed, the mixture was extracted with methylene chloride (MC) and water, and purified by column chromatography to obtain 8.3 g (yield 93%) of target compound 3-1.

[0414] <Manufacturing Example 18> Manufacture of target compounds 3-4, 3-5, 3-22, 3-23, 3-32, 3-35, 3-41, 3-61, 3-69, and 3-77

[0415] The target compounds of Table 13 were synthesized in the same manner as in Manufacturing Example 17, except that compound a of Table 13 was used instead of (a), compound b of Table 13 was used instead of (b), and compound c of Table 13 was used instead of (c).

[0416] [Table 13]

[0417]

[0418] Compounds were prepared in the same manner as the above manufacturing examples, and the results of their synthesis are shown in Tables 14 and 15 below. Table 14 shows the measured values ​​of FD-mass spectrometry (FD-MS), and Table 15 shows the measured values ​​of 1 This is the measured value of H NMR (CDCl3, 400 MHz).

[0419] Compound number FD-MS Compound number FD-MS3-1 m / z = 408.16 (C 30 H 20 N2=408.50)3-4m / z= 560.23(C 42 H 28 N2=560.70)3-5m / z=m / z=560.23(C 42 H 28 N2=560.70)3-22m / z=m / z=560.23(C 42 H 28 N2=560.70)3-23m / z= m / z= 560.23(C 42 H 28 N2=560.70)3-32m / z=m / z=560.23(C 42 H 28 N2=560.70)3-35m / z=m / z=560.23(C 42 H 28 N2=560.70)3-41m / z=m / z=560.23(C 42 H 28 N2=560.70)3-61m / z= 578.34(C 42 H 10 D 18 N2=578.81)3-69m / z= 570.29(C 42 H 18 D 10 N2=570.76)3-77m / z= 588.40(C 42 D 28 N2=588.87)

[0420] Compound number 1H NMR(CDCl3, 400MHz)3-1δ = 8.55(2H, d), 7.94(2H, d), 7.62-7.35(14H, m), 7.16(2H, d)3-4δ = 8.55(2H, d), 7.94-7.91(10H, m), 7.75(4H, d), 7.49-7.35(10H, m), 7.16(2H, t)3-5δ = 8.55(2H, d), 8.21(1H, s), 7.94-7.91(6H, m), 7.75-7.35(16H, m), 7.26(1H, d), 7.16(2H, t)3-22δ = 8.55(1H, d), 8.19(1H, d), 7.94-7.91(9H, m), 7.75(4H, d), 7.58-7.35(11H, m), 7.20-7.16(2H, m)3-23δ = 8.55(1H, d), 8.21-8.19(2H, m), 7.94-7.91(5H, m), 7.75-7.35(18H, m), 7.20-7.16(2H, m)3-32δ = 8.55(1H, d), 8.19(1H, d), 7.94-7.91(9H, m), 7.75(4H, d), 7.58-7.35(11H, m), 7.20-7.16(2H, m)3-35δ = 8.55(1H, d), 8.21-8.19(2H, m), 7.94-7.91(5H, m), 7.68-7.35(18H, m), 7.20-7.16(2H, m)3-41δ = 8.55(2H, d), 7.94-7.91(10H, m), 7.84(2H, d), 7.75(4H, d), 7.49-7.35(8H, m), 7.16(2H, t)3-61δ = 8.55(2H, d), 7.94(2H, d), 7.42-7.35(4H, m), 7.16(2H, t)3-69δ = 7.92-7.91(8H, m), 7.75(4H, d), 7.49-7.41(6H, m)

[0421] <실험예 1>

[0422] 1) 유기 발광 소자의 제작

[0423] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (ultraviolet ozone) for 5 minutes in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), where it was plasma-treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic vapor deposition.

[0424] A common layer, a hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), were formed on the ITO transparent electrode (anode).

[0425] On top of that, a light-emitting layer was thermally vacuum deposited as follows. The light-emitting layer used the compound described in Table 16 as a host, and Ir(ppy)3(tris(2-phenylpyridine)iridium) as a green phosphorescent dopant, and the host was doped with 7% Ir(ppy)3 and deposited to a thickness of 400Å. Then, BCP(Bathocuproine) was deposited to a thickness of 60Å as a hole-blocking layer, and Alq3 was deposited to a thickness of 200Å as an electron-transport layer thereon. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron-transport layer to form an electron-injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1200Å on the electron-injection layer to form a cathode, thereby manufacturing an organic light-emitting device.

[0426] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0427] 2) Driving voltage and luminous efficiency of organic light-emitting devices

[0428] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using M7000 from MaxScience, and the standard luminance was determined to be 6,000 cd / m using the life measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 When, T 90 was measured.

[0429] The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention were as shown in Table 16 below.

[0430] [Table 16]

[0431]

[0432]

[0433]

[0434] The compounds used in each of Comparative Examples 1 to 11 are as follows.

[0435]

[0436] As can be seen from the results in Table 16 above, it was confirmed that Examples 1 to 67, which are organic light-emitting devices using the compound represented by Chemical Formula 1 of the present invention as a light-emitting layer material (particularly, a green phosphorescent host), had lower operating voltages and significantly improved luminous efficiency and lifespans compared to Comparative Examples 1 to 11, which are organic light-emitting devices not using the compound represented by Chemical Formula 1 of the present invention as a light-emitting layer material.

[0437] In the case of the present invention, the first substituent (C-carbazole) and the third substituent Ar1 are fixed in the ortho position based on the benzene core, and the 4th position of the first substituent (C-carbazole) is fixed, so it is judged that the operation is lowered and the lifespan is increased due to the distorted form caused by strong steric hindrance.

[0438] In addition, it is believed that the efficiency increased because the aryl group in the carbazole is positioned orthogonally, which allows for better charge transfer due to a closer spatial distance.

[0439] Structurally, the compounds according to the present specification are believed to have increased lifetimes due to cancellation of HOMO-LUMO overlap.

[0440] Experimental Example 2

[0441] 1) Fabrication of organic light-emitting devices

[0442] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT), where it was plasma-treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0443] A common layer, a hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-diphenyl-(1,1′-biphenyl)-4,4′-diamine), were formed on the ITO transparent electrode (anode).

[0444] On top of that, a light-emitting layer was thermally vacuum deposited as follows.

[0445] The light-emitting layer was deposited at 400Å in one space by pre-mixing one heterocyclic compound having the structure of chemical formula 1 as a host and one heterocyclic compound having the structure of chemical formula 2 or 3 according to Table 17 below, and the green phosphorescent dopant was deposited by doping Ir(ppy)3 at 7% of the thickness of the light-emitting layer deposition.

[0446] Afterwards, BCP was deposited to a thickness of 60Å as a hole blocking layer, and Alq3 was deposited to a thickness of 200Å as an electron transport layer on top of it. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200Å on the electron injection layer to form a cathode, thereby manufacturing an organic light-emitting device.

[0447] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0448] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using MacScience's M7000, and the standard luminance was determined to be 6,000 cd / m using the lifespan measuring equipment (M6000) manufactured by MacScience based on the measurement results. 2 When, T 90 was measured.

[0449] The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention were as shown in Table 17 below.

[0450] [Table 17]

[0451]

[0452]

[0453] The compounds used in Comparative Examples 12 to 32 are as described above.

[0454]

[0455] From the results in Table 17 above, when the compound of formula 1 and the heterocyclic compound of formula 2 were simultaneously included, or when the compound of formula 1 and the heterocyclic compound of formula 3 were simultaneously included, better efficiency and lifespan effects were observed. From the above results, it can be expected that an exciplex phenomenon will occur when both compounds are simultaneously included.

[0456] The above exciplex phenomenon is a phenomenon in which energy of the size of the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) is released due to electron exchange between two molecules. When the exciplex phenomenon between two molecules occurs, Reverse Intersystem Crossing (RISC) occurs, and this can increase the internal quantum efficiency of fluorescence up to 100%. When a donor (p-host) with a good hole transport ability and an acceptor (n-host) with a good electron transport ability are used as a host for the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host, so the driving voltage can be lowered, which can help improve the lifespan. In the present invention, it was confirmed that excellent device characteristics were exhibited when a compound of the above chemical formula 2 or 3 was used as the donor and a compound of the above chemical formula 1 was used as the acceptor as the light-emitting layer host.

[0457] In particular, it can be confirmed that the life and efficiency characteristics are excellent when an ortho-aryl group or heteroaryl group (Ar) is combined with carbazole. This is the result shown in Table 17.

[0458] On the other hand, when compounds not included in the scope of the present invention (Comparative Examples 12 to 32) are used in combination with the compound of Chemical Formula 2 or Chemical Formula 3, it can be seen that the performance in terms of driving voltage, luminous efficiency, and lifespan is inferior to that of the present invention.

[0459] That is, when the compound of chemical formula 1 of the present invention and the compound of chemical formula 2 or 3 are simultaneously used as a host for the light-emitting layer, it can be confirmed that the driving voltage, light-emitting efficiency, and lifespan are remarkably excellent.

[0460] The present invention is not limited to the above-described embodiments, but can be manufactured in a variety of different forms. Those skilled in the art will appreciate that the present invention can be implemented in other specific forms without altering the technical spirit or essential characteristics of the present invention. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X1 is CRa or N, X2 is CRb or N, X3 is CRc or N, and at least one of X1 to X3 is N, Ar1 to Ar4 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, L1 to L4 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, R1 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C3 to C60 cycloalkyl group, R2 is 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, Ra, Rb and Rc are the same 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 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; -P(=O)RR'; and -SiRR'R", The above R, R' and R" are the same 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, a is an integer from 0 to 3, b is an integer from 0 to 7, m, n, o and p are the same or different from each other and are each independently an integer from 0 to 4, If each of a, b, m, n, o, and p is an integer greater than or equal to 2, the substituents within the parentheses are the same or different.

2. In claim 1, The above chemical formula 1 is a compound represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, X1 to X3, L1 to L4, Ar1 to Ar4, R1, R2, a, b, m, n, o and p are as defined in the chemical formula 1.

3. In claim 1, A compound wherein Ar1 to Ar4 are the same or different and each independently represent a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

4. In claim 1, A compound wherein L1 to L4 are the same or different and each independently represent a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

5. In claim 1, A compound wherein R1 is hydrogen; or deuterium.

6. In claim 1, A compound wherein R2 is hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

7. In claim 1, A compound wherein X1 to X3 are all N.

8. In claim 1, A compound having the chemical formula 1 above and having a deuterium content of 0% or between 1% and 100%.

9. In claim 1, The above chemical formula 1 is a compound represented by one of the following: .

10. 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 a compound according to any one of claims 1 to 9.

11. In claim 10, An organic layer comprising the compound further comprises an organic light-emitting device comprising a heterocyclic compound represented by the following chemical formula 2 or 3: [Chemical formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, R11, R12, R22 and R23 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR', L11, L12, L22 and L23 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, Ar11, Ar12, Ar22 and Ar23 are the same or different from each other, and each independently represents a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R", The above R, R' and R" are the same 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, a11 and a12 are integers from 0 to 7, respectively. a22 is an integer from 0 to 6, a23 is an integer from 0 to 4, p11, p12, p22 and p23 are integers from 0 to 4, respectively. q11, q12, q22 and q23 are integers from 1 to 4, respectively, When each of a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 is 2 or more, the substituents in the parentheses are the same or different.

12. In claim 11, An organic light-emitting device wherein the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 is 0% or 1% to 100%.

13. In claim 11, An organic light-emitting device in which the heterocyclic compound represented by the chemical formula 2 or 3 is represented by one of the following: .

14. In claim 10, An organic light-emitting device, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

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

16. A composition for forming an organic layer of an organic light-emitting device, comprising a compound according to any one of claims 1 to 9 and a heterocyclic compound represented by the following chemical formula 2 or 3: [Chemical formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, R11, R12, R22 and R23 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR', L11, L12, L22 and L23 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, Ar11, Ar12, Ar22 and Ar23 are the same or different from each other, and each independently represents a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R", The above R, R' and R" are the same 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, a11 and a12 are integers from 0 to 7, respectively. a22 is an integer from 0 to 6, a23 is an integer from 0 to 4, p11, p12, p22 and p23 are integers from 0 to 4, respectively. q11, q12, q22 and q23 are integers from 1 to 4, respectively, When each of a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 is 2 or more, the substituents in the parentheses are the same or different.

17. In claim 16, A composition for forming an organic layer of an organic light-emitting device, wherein the weight ratio of the compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 2 or 3 is 1:10 to 10:1.

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