Composition for organic material layer of organic light-emitting device, organic light-emitting device comprising same, and method for manufacturing same

Abstract

The present specification relates to a composition for an organic material layer of an organic light-emitting device, an organic light-emitting device comprising same, and a method for manufacturing same.

Description

Composition for organic layer of organic light-emitting device, organic light-emitting device including same, and method for manufacturing same

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

[0002] This application claims the benefit of Korean Patent Application No. 10-2023-0109910, filed with the Korean Intellectual Property Office on August 22, 2023, the entire contents of which are incorporated herein by reference.

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

[0004] Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting device of this structure, electrons and holes injected from the two electrodes combine in the organic thin film, forming pairs and then disappearing, emitting light. The organic thin film may be composed of a single layer or multiple layers, as needed.

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

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

[0007] <Prior Art Literature>

[0008] (Patent Document 1) U.S. Patent No. 4,356,429

[0009] The present specification provides a composition for an organic layer of an organic light-emitting device, an organic light-emitting device including the same, and a method for manufacturing the same.

[0010] One embodiment of the present specification provides a composition for an organic layer of an organic light-emitting device, comprising a compound of the following chemical formula 1; a compound of the following chemical formula 2; and a compound of the following chemical formula 3.

[0011] [Chemical Formula 1]

[0012]

[0013] In the above chemical formula 1,

[0014] X is O; or S,

[0015] R1 and R2, R2 and R3, or R3 and R4 combine to form a substituted or unsubstituted benzene ring,

[0016] When R3 and R4 combine to form a substituted or unsubstituted benzene ring, R1 is hydrogen; or deuterium,

[0017] The remainder of R1 to R4 and one of R5 to R8 is -(L1)l1-N(Ar1)(Ar2), and the other is -(L2)l2-Ar3,

[0018] The remainder of R1 to R8 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl 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; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0019] L1 and L2 are each independently a direct bond; or a substituted or unsubstituted C6 to C60 arylene group,

[0020] l1 and l2 are each integers from 1 to 3, and if each is 2 or greater, the substituents in each parenthesis are the same or different,

[0021] Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0022] Ar3 is a substituted or unsubstituted C6 to C60 aryl group,

[0023] [Chemical Formula 2]

[0024]

[0025] In the above chemical formula 2,

[0026] L11 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0027] l11 is an integer from 1 to 3, and if it is 2 or greater, L11 is equal or different,

[0028] R11 is a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl 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; or a substituted or unsubstituted silyl group,

[0029] Any one of R12 to R19 is a substituted or unsubstituted carbazole group, or two adjacent groups of R12 to R19 are combined to form a substituted or unsubstituted C2 to C30 heterocycle,

[0030] The remainder of R12 to R19 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl 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; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0031] [Chemical Formula 3]

[0032]

[0033] In the above chemical formula 3,

[0034] Y is O; or S,

[0035] Any one of R21 to R28 is -(L21)l21-(N-Het),

[0036] L21 is a direct bond; or a substituted or unsubstituted C6 to C60 arylene group,

[0037] l21 is an integer from 1 to 3, and if it is 2 or greater, L21 is equal or different,

[0038] N-Het is a substituted or unsubstituted heteroaryl group containing a C=N bond,

[0039] The remainder of R21 to R28 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted phosphine oxide group.

[0040] 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 a composition for an organic layer of the organic light-emitting device.

[0041] Another embodiment of the present specification provides a method for manufacturing an organic light-emitting device, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, wherein the step of forming the organic layer includes the step of forming one or more organic layers using the composition for an organic layer of the organic light-emitting device described above.

[0042] The composition for an organic layer of an organic light-emitting device described in this specification includes all three compounds represented by chemical formulas 1 to 3, and thus, when used as a material for an organic light-emitting device, the luminous efficiency and lifespan characteristics of the device can be improved.

[0043] Specifically, the compound of the above chemical formula 1 is characterized by a relatively long lifespan, the compound of the above chemical formula 2 provides high efficiency, and the compound of the above chemical formula 3 is a unipolar N-host with fast electron mobility. When these three compounds are mixed in an appropriate ratio and used as a material for a device, it can be confirmed that the efficiency and lifespan of the device are improved.

[0044] Figures 1 to 3 are diagrams each exemplifying a laminated structure of an organic light-emitting device according to one embodiment of the present specification.

[0045] <Explanation of symbols>

[0046] 100: Substrate

[0047] 200: Bipolar

[0048] 300: Organic layer

[0049] 301: Hole injection layer

[0050] 302: Hole transport layer

[0051] 303: Emissive layer

[0052] 304: Hole blocking layer

[0053] 305: Electron transport layer

[0054] 306: Electron injection layer

[0055] 400: Cathode

[0056] Hereinafter, the present specification will be described in more detail.

[0057] In this specification, when a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components, unless specifically stated otherwise.

[0058] In this specification, “N to N'” means N or more and N' or less.

[0059] In this specification, the chemical formula means the position where it is combined.

[0060] The term "substitution" above means that a hydrogen atom bonded to a carbon atom or nitrogen 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.

[0061] In this specification, "substituted or unsubstituted" means deuterium; halogen group; cyano group; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C1 to C60 haloalkyl group; C1 to C60 alkoxy group; C6 to C60 aryloxy group; C1 to C60 alkylthioxy group; C6 to C60 arylthioxy group; C1 to C60 alkylsulfoxy group; C6 to C60 arylsulfoxy group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; C2 to C60 heteroaryl group; silyl group; phosphine oxide group; And it means that it is substituted with one or more substituents selected from the group consisting of amine groups, or two or more substituents selected from the above substituents are connected to a substituent, or is unsubstituted.

[0062] In this specification, "when no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0063] In one embodiment of the present application, "when no substituent is indicated in the chemical formula or compound structure" may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, in which case the deuterium content may be 0% to 100%, and the deuterium content may also be expressed as a deuterium substitution ratio.

[0064] In one embodiment of the present application, in the case where “no substituent is indicated in the chemical formula or compound structure,” if deuterium is not explicitly excluded, such as “the deuterium content is 0%, the hydrogen content is 100%,” or “all substituents are hydrogen,” hydrogen and deuterium may be used in combination in the compound.

[0065] In one embodiment of the present application, deuterium is an element having a deuteron, which is one of the isotopes of hydrogen and is composed of one proton and one neutron, as its nucleus, and can be expressed as hydrogen-2, and its element symbol is D or 2 It can also be written as H.

[0066] In one embodiment of the present application, an isotope means an atom having the same atomic number (Z) but a different mass number (A). An isotope can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0067] In one embodiment of the present application, the meaning of the substitution rate T% of a specific substituent can be defined as T2 / T1Х100 = T%, where the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2.

[0068] That is, in one example, In the phenyl group represented by , a deuterium substitution rate of 20% means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and if the number of deuteriums among them is 1 (T2 in the formula), it can be expressed as 20%. In other words, a deuterium substitution rate of 20% in the phenyl group can be expressed by the structural formula below.

[0069]

[0070] Additionally, in one embodiment of the present application, the term "phenyl group having a deuterium substitution rate of 0%" may mean a phenyl group that does not contain a deuterium atom as a substituent, i.e., has 5 hydrogen atoms.

[0071] In this specification, halogen may be fluorine, chlorine, bromine or iodine.

[0072] In the present specification, an alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 40 carbon atoms, and more specifically 1 to 20 carbon atoms. Specific examples include 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, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, Examples include, but are not limited to, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0073] 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.

[0074] In the present specification, an alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0075] In this specification, a haloalkyl group means an alkyl group substituted with a halogen group, and specific examples include, but are not limited to, -CF3, -CF2CF3, etc.

[0076] In this specification, an alkoxy group is represented as -O(R101), and examples of the alkyl group described above can be applied to R101.

[0077] In this specification, the aryloxy group is represented as -O(R102), and R102 can be applied to the examples of the aryl group described above.

[0078] In this specification, the alkylthioxy group is represented as -S(R103), and examples of the alkyl group described above can be applied to R103.

[0079] In this specification, the arylthioxy group is represented as -S(R104), and R104 can be applied to the examples of the aryl group described above.

[0080] In this specification, an alkylsulfoxy group is represented as -S(=0)2(R105), and examples of the alkyl group described above can be applied to R105.

[0081] In this specification, an arylsulfoxy group is represented as -S(=0)2(R106), and examples of the aryl group described above can be applied to R106.

[0082] In the present specification, a cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, 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.

[0083] In the present specification, a heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, 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.

[0084] In the present specification, an aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, 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.

[0085] In this specification, the terphenyl group may be selected from the following structures.

[0086]

[0087] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0088] When the above fluorenyl group is substituted, the structures below can be formed, but are not limited thereto.

[0089]

[0090] In the present specification, a heteroaryl group includes S, O, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic ring means a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, 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 pyridine group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, a triazole group, a furazan group, an oxadiazole group, a thiadiazole group, a dithiazole group, a tetrazolyl group, a pyran group, a thiopyran group, a diazine group, an oxazine group, a thiazine group, a dioxin group, a triazine group, a tetrazine group, a quinoline group, an isoquinoline group, a quinazoline group, an isoquinazoline group, a quinozoline group, a naphthyridine group, an acridine group, a phenanthridine group, an imidazopyridine group, a diazanaphthalene group, a triazaindene group, an indole group, an indolizine group, a benzothiazole group, Benzoxazole group, benzimidazole group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazole group, benzocarbazole group, dibenzocarbazole group, phenazine group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazine group, phenoxazine group, phenanthridine group, thienyl group, indolo[2,3-a]carbazole group, indolo[2,3-b]carbazole group, indoline group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridine group, phenanthrazine group, phenothiathiazine group, phthalazine group, phenanthroline group, naphthobenzofuran group, naphthobenzothiophene group, benzo[c][1,2,5]thiadiazole group, Examples thereof include, but are not limited to, 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5,10-dihydrodibenzo[b,e][1,4]azacillin group, pyrazolo[1,5-c]quinazoline group, pyrido[1,2-b]indazole group, pyrido[1,2-a]imidazo[1,2-e]indolin group, and 5,11-dihydroindeno[1,2-b]carbazole group.

[0091] In the present specification, when the substituent is a carbazole group, a benzocarbazole group, or a dibenzocarbazole group, it means that it is bonded to the nitrogen or carbon of the carbazole group, the benzocarbazole group, or the dibenzocarbazole group.

[0092] In the present specification, when a carbazole group, a benzocarbazole group, or a dibenzocarbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole group, the benzocarbazole group, or the dibenzocarbazole group.

[0093] 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(R107)(R108)(R109), and R107 to R109 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.

[0094] In the present specification, a phosphine oxide group is represented by -P(=O)(R110)(R111), and R110 and R111 are the same as or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. Specifically, it can be substituted with an alkyl group or an aryl group, and the above-described examples can be applied to the alkyl group and the aryl group. For example, the phosphine oxide group includes, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, and dinaphthylphosphine oxide.

[0095] In the present specification, an amine group is represented by -N(R112)(R113), and R112 and R113 are the same as or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. The amine group can be selected from the group consisting of -NH2; a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group.

[0096] In this specification, the description of the aryl group described above may be applied, except that the arylene group is divalent.

[0097] In this specification, the description of the heteroaryl group described above may be applied, except that the heteroarylene group is divalent.

[0098] One embodiment of the present specification provides a composition for an organic layer of an organic light-emitting device, comprising a compound of the above chemical formula 1; a compound of the above chemical formula 2; and a compound of the above chemical formula 3.

[0099] In one embodiment of the present specification, X in the chemical formula 1 is O; or S.

[0100] In one embodiment of the present specification, X may be O.

[0101] In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 1-A.

[0102] [Chemical Formula 1-A]

[0103]

[0104] In the above chemical formula 1-A,

[0105] The definition of each substituent is the same as that in the chemical formula 1 above.

[0106] In one embodiment of the present specification, R1 and R2, R2 and R3, or R3 and R4 of the chemical formula 1 are combined to form a substituted or unsubstituted benzene ring, and when R3 and R4 are combined to form a substituted or unsubstituted benzene ring, R1 is hydrogen; or deuterium.

[0107] That is, the above chemical formula 1 includes a four-membered heterocycle containing O or S. In other words, the above chemical formula 1 includes a naphthobenzofuran ring or a naphthobenzothiophene ring.

[0108] In addition, when R3 and R4 of the above chemical formula 1 are combined, the 6th carbon of naphthobenzofuran or naphthobenzothiophene does not have a substituent other than hydrogen or deuterium.

[0109] In one embodiment of the present specification, R1 and R2 may combine to form a substituted or unsubstituted benzene ring.

[0110] In one embodiment of the present specification, R2 and R3 may combine to form a substituted or unsubstituted benzene ring.

[0111] In one embodiment of the present specification, R3 and R4 combine to form a substituted or unsubstituted benzene ring, and R1 may be hydrogen or deuterium.

[0112] In one embodiment of the present specification, the benzene ring may be substituted or unsubstituted with deuterium.

[0113] In one embodiment of the present specification, one of the remaining ones of R1 to R4 and one of R5 to R8 is -(L1)l1-N(Ar1)(Ar2), and the other one is -(L2)l2-Ar3.

[0114] The remainder of R1 to R4 refers to a substituent that does not form a benzene ring among R1 to R4.

[0115] When the above R3 and R4 are combined, the remainder of the above R1 to R4 may be R2.

[0116] That is, the above chemical formula 1 includes a naphthobenzofuran ring or a naphthobenzothiophene ring, and the naphthobenzofuran ring or the naphthobenzothiophene ring includes -(L1)l1-N(Ar1)(Ar2) and -(L2)l2-Ar3 as substituents.

[0117] In one embodiment of the present specification, the remainder of R1 to R8 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl 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; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0118] The remainder of R1 to R8 refers to the remaining substituents excluding i) two substituents forming a benzene ring (two of R1 to R4), ii) -(L1)l1-N(Ar1)(Ar2), and iii) -(L2)l2-Ar3 in R1 to R8.

[0119] When the above R3 and R4 are combined, R1 can be further excluded.

[0120] In one embodiment of the present specification, the remainder of R1 to R8 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; or a substituted or unsubstituted C2 to C60 heterocycloalkyl group.

[0121] In one embodiment of the present specification, the remainder of R1 to R8 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; or a substituted or unsubstituted C2 to C30 heterocycloalkyl group.

[0122] In one embodiment of the present specification, the remainder of R1 to R8 may each independently be hydrogen or deuterium.

[0123] 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 1-3.

[0124] [Chemical Formula 1-1]

[0125]

[0126] [Chemical Formula 1-2]

[0127]

[0128] [Chemical Formula 1-3]

[0129]

[0130] In the above chemical formulas 1-1 to 1-3,

[0131] One of S1 and S2 is -(L1)l1-N(Ar1)(Ar2), and the other is -(L2)l2-Ar3,

[0132] H1 to H3 are each independently hydrogen; or deuterium,

[0133] m is an integer from 1 to 3, n is an integer from 1 to 5, o is 1 or 2, p is an integer from 1 to 4, q is an integer from 1 to 6, and when o is 2 or m, n, p and q are each 2 or greater, the substituents in each parenthesis are the same or different,

[0134] The definitions of X, L1, L2, l1, l2, and Ar1 to Ar3 are the same as those in the above chemical formula 1.

[0135] In one embodiment of the present specification, L1 and L2 of the chemical formula 1 are each independently a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

[0136] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; or a substituted or unsubstituted C6 to C30 arylene group.

[0137] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; or a substituted or unsubstituted C6 to C15 arylene group.

[0138] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0139] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; or an arylene group having C6 to C60 substituted or unsubstituted with deuterium.

[0140] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; or a C6 to C30 arylene group substituted or unsubstituted with deuterium.

[0141] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; or a C6 to C15 arylene group substituted or unsubstituted with deuterium.

[0142] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; or a naphthylene group substituted or unsubstituted with deuterium.

[0143] In one embodiment of the present specification, when l1 is 2, it can be expressed as -L1-L1'-, and the definition of L1' is the same as the definition of L1.

[0144] In one embodiment of the present specification, when l2 is 2, it can be expressed as -L2-L2'-, and the definition of L2' is the same as the definition of L2.

[0145] In one embodiment of the present specification, Ar1 and Ar2 of the chemical formula 1 are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0146] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group containing O or S.

[0147] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group containing O or S.

[0148] In one embodiment of the present specification, Ar1 and Ar2 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 phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0149] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a C6 to C60 aryl group unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group, and an aryl group unsubstituted or substituted with deuterium; a spirobifluorenyl group; or a C2 to C60 heteroaryl group unsubstituted or substituted with deuterium and containing O or S.

[0150] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a C6 to C30 aryl group unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group, and an aryl group unsubstituted or substituted with deuterium; a spirobifluorenyl group; or a C2 to C30 heteroaryl group unsubstituted or substituted with deuterium and containing O or S.

[0151] In one embodiment of the present specification, Ar3 of the chemical formula 1 is a substituted or unsubstituted C6 to C60 aryl group.

[0152] In one embodiment of the present specification, Ar3 may be a substituted or unsubstituted C6 to C30 aryl group.

[0153] In one embodiment of the present specification, Ar3 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted phenanthrenyl group.

[0154] In one embodiment of the present specification, Ar3 may be an aryl group having C6 to C60 substituted or unsubstituted with deuterium.

[0155] In one embodiment of the present specification, Ar3 may be a C6 to C30 aryl group substituted or unsubstituted with deuterium.

[0156] In one embodiment of the present specification, Ar3 may be a C6 to C20 aryl group substituted or unsubstituted with deuterium.

[0157] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following compounds.

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165] In one embodiment of the present specification, L11 of the chemical formula 2 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0166] In one embodiment of the present specification, L11 may be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0167] In one embodiment of the present specification, L11 may be a direct bond; a substituted or unsubstituted C6 to C15 arylene group; or a substituted or unsubstituted C2 to C15 heteroarylene group.

[0168] In one embodiment of the present specification, L11 may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted divalent dibenzofuran group.

[0169] In one embodiment of the present specification, L11 may be a direct bond; a C6 to C30 arylene group substituted or unsubstituted with deuterium; or a C2 to C30 heteroarylene group substituted or unsubstituted with deuterium.

[0170] In one embodiment of the present specification, L11 may be a direct bond; a C6 to C15 arylene group substituted or unsubstituted with deuterium; or a C2 to C15 heteroarylene group substituted or unsubstituted with deuterium.

[0171] In one embodiment of the present specification, L11 may be a direct bond; a C6 to C15 arylene group substituted or unsubstituted with deuterium; or a C2 to C15 heteroarylene group substituted or unsubstituted with deuterium and containing O.

[0172] In one embodiment of the present specification, L11 may be a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

[0173] In one embodiment of the present specification, L11 may be a direct bond; or a substituted or unsubstituted C6 to C30 arylene group.

[0174] In one embodiment of the present specification, L11 may be a direct bond; or a substituted or unsubstituted C6 to C15 arylene group.

[0175] In one embodiment of the present specification, L11 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0176] In one embodiment of the present specification, L11 may be a direct bond; or a C6 to C15 arylene group substituted or unsubstituted with deuterium.

[0177] In one embodiment of the present specification, L11 may be a direct bond; a phenylene group substituted or unsubstituted with deuterium; or a biphenylene group substituted or unsubstituted with deuterium.

[0178] In one embodiment of the present specification, when l11 is 2, it can be represented as -L11-L11'-, and the definition of L11' is the same as the definition of L11.

[0179] In one embodiment of the present specification, R11 of the chemical formula 2 is a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl 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; or a substituted or unsubstituted silyl group.

[0180] In one embodiment of the present specification, R11 may be a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a substituted or unsubstituted silyl group.

[0181] In one embodiment of the present specification, R11 may be a cyano group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a substituted or unsubstituted silyl group.

[0182] In one embodiment of the present specification, R11 may be a cyano group; 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 fluorenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dibenzofuran group; or a silyl group substituted or unsubstituted with an aryl group.

[0183] In one embodiment of the present specification, R11 may be a cyano group; a C6 to C30 aryl group unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group, and an aryl group; a C2 to C30 heteroaryl group unsubstituted or substituted with one or more substituents selected from deuterium and an aryl group unsubstituted or substituted with deuterium; or a silyl group substituted with an aryl group.

[0184] In one embodiment of the present specification, any one of R12 to R19 of the chemical formula 2 is a substituted or unsubstituted carbazole group, or two adjacent groups of R12 to R19 combine to form a substituted or unsubstituted C2 to C30 heterocycle.

[0185] In one embodiment of the present specification, any one of R12 to R19 may be a substituted or unsubstituted carbazole group.

[0186] In one embodiment of the present specification, any one of R12 to R19 may be a carbazole group substituted or unsubstituted with one or more substituents among deuterium and an aryl group substituted or unsubstituted with deuterium.

[0187] In one embodiment of the present specification, two adjacent groups among R12 to R19 may combine to form a substituted or unsubstituted C2 to C30 heterocycle.

[0188] In one embodiment of the present specification, two adjacent groups among R12 to R19 may combine to form a substituted or unsubstituted C2 to C30 N-containing heterocycle.

[0189] In one embodiment of the present specification, two adjacent groups among R12 to R19 may combine to form a substituted or unsubstituted indole ring.

[0190] In one embodiment of the present specification, the remainder of R12 to R19 of the above chemical formula 2 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl 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; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0191] The remainder of the above R12 to R19 refers to a substituent that is not a substituted or unsubstituted carbazole group in R12 to R19, or does not form a substituted or unsubstituted C2 to C30 heterocycle when combined.

[0192] In one embodiment of the present specification, the remainder of R12 to R19 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; or a substituted or unsubstituted C2 to C60 heterocycloalkyl group.

[0193] In one embodiment of the present specification, the remainder of R12 to R19 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; or a substituted or unsubstituted C2 to C30 heterocycloalkyl group.

[0194] In one embodiment of the present specification, the remainder of R12 to R19 may each independently be hydrogen or deuterium.

[0195] In one embodiment of the present specification, the chemical formula 2 may be represented by the following chemical formula 2-1 or 2-2.

[0196] [Chemical Formula 2-1]

[0197]

[0198] [Chemical Formula 2-2]

[0199]

[0200] In the above chemical formulas 2-1 and 2-2,

[0201] The definitions of L11, l11 and R11 are the same as those in the above chemical formula 2,

[0202] Q1 and Q2 are each independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group,

[0203] H11 and H12 are hydrogen or deuterium, respectively;

[0204] e and f are integers from 1 to 7, respectively, g is an integer from 1 to 6, h is an integer from 1 to 4,

[0205] When e, f, g, and h are each 2 or more, the substituents in each parenthesis are the same or different.

[0206] In one embodiment of the present specification, Q1 and Q2 may each independently be a substituted or unsubstituted C6 to C30 aryl group.

[0207] In one embodiment of the present specification, Q1 and Q2 may each independently 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.

[0208] In one embodiment of the present specification, Q1 and Q2 may each independently be a C6 to C30 aryl group substituted or unsubstituted with deuterium.

[0209] In one embodiment of the present specification, Q1 and Q2 may each independently 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.

[0210] In one embodiment of the present specification, the chemical formula 2 may be represented by any one of the following compounds.

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217] In one embodiment of the present specification, Y in the chemical formula 3 is O; or S.

[0218] In one embodiment of the present specification, Y may be O.

[0219] In one embodiment of the present specification, any one of R21 to R28 of the chemical formula 3 is -(L21)l21-(N-Het), L21 is a direct bond; or a substituted or unsubstituted C6 to C60 arylene group, l21 is an integer of 1 to 3, and when it is 2 or more, L21 is the same or different, and N-Het is a substituted or unsubstituted heteroaryl group including a C=N bond.

[0220] In one embodiment of the present specification, the remainder of R21 to R28 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted phosphine oxide group.

[0221] In one embodiment of the present specification, any one of the remaining R21 to R28 is -(L22)l22-Ar11, L22 is a direct bond; or a substituted or unsubstituted C6 to C60 arylene group, l22 is an integer of 1 to 3, and when it is 2 or more, L22 is the same or different, and Ar11 may be a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted phosphine oxide group.

[0222] In one embodiment of the present specification, the remainder of R21 to R28, excluding -(L21)l21-(N-Het) and -(L22)l22-Ar11, may be hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; or a substituted or unsubstituted C2 to C60 heterocycloalkyl group.

[0223] In one embodiment of the present specification, the remainder of R21 to R28, excluding -(L21)l21-(N-Het) and -(L22)l22-Ar11, may be hydrogen or deuterium.

[0224] In one embodiment of the present specification, the chemical formula 3 may be represented by the following chemical formula 3-1.

[0225] [Chemical Formula 3-1]

[0226]

[0227] In the above chemical formula 3-1,

[0228] L21 and L22 are each independently a direct bond; or a substituted or unsubstituted C6 to C60 arylene group,

[0229] l21 and l22 are each an integer from 1 to 3, and if it is 2 or more, the substituents in each parenthesis are the same or different,

[0230] N-Het is a substituted or unsubstituted heteroaryl group containing a C=N bond,

[0231] Ar11 is a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted phosphine oxide group,

[0232] H13 and H14 are each independently hydrogen; or deuterium,

[0233] i and j are each integers from 1 to 4, the sum of i and j is an integer from 2 to 6, and when i and j are each 2 or greater, the substituents in each parenthesis are the same or different.

[0234] In one embodiment of the present specification, L21 may be a direct bond; or a substituted or unsubstituted C6 to C30 arylene group.

[0235] In one embodiment of the present specification, L21 may be a direct bond; or a substituted or unsubstituted C6 to C15 arylene group.

[0236] In one embodiment of the present specification, L21 may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0237] In one embodiment of the present specification, L21 may be a direct bond; or a C6 to C30 arylene group substituted or unsubstituted with deuterium.

[0238] In one embodiment of the present specification, L21 may be a direct bond; or a C6 to C15 arylene group substituted or unsubstituted with deuterium.

[0239] In one embodiment of the present specification, the N-Het may be a substituted or unsubstituted pyridine group; a substituted or unsubstituted pyrimidine group; or a substituted or unsubstituted triazine group.

[0240] In one embodiment of the present specification, the N-Het may be a substituted or unsubstituted triazine group.

[0241] In one embodiment of the present specification, the N-Het may be a triazine group substituted with one or more substituents among an aryl group substituted or unsubstituted with one or more substituents selected from among deuterium, a halogen group, a cyano group, and an alkyl group, and a heteroaryl group substituted or unsubstituted with deuterium, or two or more linking groups.

[0242] In one embodiment of the present specification, the N-Het may be a triazine group substituted with one or more substituents or two or more linking groups among a phenyl group substituted or unsubstituted with deuterium, a halogen group, or a cyano group, 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 phenanthrenyl group substituted or unsubstituted with deuterium, a fluorenyl group substituted or unsubstituted with an alkyl group, a chrysenyl group substituted or unsubstituted with deuterium, a carbazole group substituted or unsubstituted with deuterium, a dibenzofuran group substituted or unsubstituted with deuterium, and a dibenzothiophene group substituted or unsubstituted with deuterium.

[0243] In one embodiment of the present specification, L22 may be a direct bond; or a substituted or unsubstituted C6 to C30 arylene group.

[0244] In one embodiment of the present specification, L22 may be a direct bond; or a substituted or unsubstituted C6 to C15 arylene group.

[0245] In one embodiment of the present specification, L22 may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0246] In one embodiment of the present specification, L22 may be a direct bond; or a C6 to C30 arylene group substituted or unsubstituted with deuterium.

[0247] In one embodiment of the present specification, L22 may be a direct bond; or a C6 to C15 arylene group substituted or unsubstituted with deuterium.

[0248] In one embodiment of the present specification, Ar11 may be a cyano group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted phosphine oxide group.

[0249] In one embodiment of the present specification, Ar11 may be a cyano group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group containing O or S; a substituted or unsubstituted carbazole group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted phosphine oxide group.

[0250] In one embodiment of the present specification, Ar11 may be a cyano group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; a silyl group substituted with an alkyl group or an aryl group; or a phosphine oxide group substituted with an aryl group.

[0251] In one embodiment of the present specification, Ar11 may be a cyano group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a silyl group substituted with an alkyl group or an aryl group; or a phosphine oxide group substituted with an aryl group.

[0252] In one embodiment of the present specification, the chemical formula 3 may be represented by any one of the following compounds.

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261] In one embodiment of the present specification, the weight ratio of the compound of Chemical Formula 1 and the compound of Chemical Formula 3 and the weight ratio of the compound of Chemical Formula 2 and the compound of Chemical Formula 3 may be 1:1 to 1:10, respectively.

[0262] That is, the compound of the above chemical formula 1 and the compound of the above chemical formula 2 do not exceed the content of the compound of the above chemical formula 3, respectively. When the compound of the above chemical formula 1 or the compound of the above chemical formula 2 is included in a higher content than the compound of the above chemical formula 3, there is a problem that, due to charge imbalance, maximum efficiency is not achieved when used as a material for an organic light-emitting device, and the stability of the device is lowered, shortening the lifespan.

[0263] In one embodiment of the present specification, the weight ratio of the compound of Chemical Formula 1 and the compound of Chemical Formula 3 and the weight ratio of the compound of Chemical Formula 2 and the compound of Chemical Formula 3 may be 1:1 to 1:5, respectively.

[0264] In one embodiment of the present specification, the weight ratio of the compound of Chemical Formula 1 and the compound of Chemical Formula 3 and the weight ratio of the compound of Chemical Formula 2 and the compound of Chemical Formula 3 may be 1:1 to 1:3, respectively.

[0265] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 0% to 100%.

[0266] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 0%.

[0267] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 10% to 100%.

[0268] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 2 may be 0% to 100%.

[0269] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 2 may be 0%.

[0270] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 2 may be 10% to 100%.

[0271] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 3 may be 0% to 100%.

[0272] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 3 may be 0%.

[0273] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 3 may be greater than 0% and less than or equal to 100%.

[0274] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 3 may be 3% to 100%.

[0275] In one embodiment of the present specification, the deuterium substitution rate of each of the compounds of Chemical Formulas 1 to 3 is 0% or more than 0% and less than or equal to 100%.

[0276] In this specification, the deuterium substitution rate of the chemical formulae 1 to 3 refers to the substitution rate of deuterium with respect to the total number of hydrogens and deuteriums contained in the chemical formulae 1 to 3, respectively. For example, if the number of hydrogens and the number of deuteriums contained in chemical formula 1 are 20, the deuterium substitution rate of chemical formula 1 is 50%, which is the substitution rate of 20 deuteriums with respect to the total number of 40 hydrogens and deuteriums.

[0277] In one embodiment of the present specification, when the deuterium substitution rate of the chemical formulae 1 to 3 exceeds 0%, the photochemical characteristics of the compound not containing deuterium and the compound containing deuterium are almost similar, but when deposited in a thin film, the material containing deuterium tends to be packed with a narrower intermolecular distance.

[0278] Accordingly, by fabricating an EOD (Electron Only Device) and a HOD (Hole Only Device) and checking the current density according to voltage, it can be confirmed that the compound containing deuterium among the compounds of the present invention exhibits much more balanced charge transport characteristics than the compound not containing deuterium.

[0279] Additionally, when looking at the surface of the thin film with an atomic force microscope (AFM), it can be confirmed that the thin film made of a compound containing deuterium is deposited with a more uniform surface without any aggregated areas.

[0280] Additionally, since the single bond dissociation energy of carbon and deuterium is higher than the single bond dissociation energy of carbon and hydrogen, in the case of compounds having a deuterium substitution rate exceeding 0% among chemical formulas 1 to 3 of the present invention, the stability of the entire molecule increases, thereby improving the device lifespan.

[0281] In addition, by introducing various substituents into the structures of the above chemical formulas 1 to 3, compounds having unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, 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.

[0282] In addition, by introducing various substituents into the structures of the above chemical formulas 1 to 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.

[0283] In another embodiment of the present specification, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the composition for an organic layer of the organic light-emitting device described above.

[0284] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include a composition for an organic layer of the organic light-emitting device.

[0285] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, and the host may include a composition for an organic layer of the organic light-emitting device.

[0286] In one embodiment of the present specification, the compound of chemical formula 1 may be P-host.

[0287] In one embodiment of the present specification, the compound of chemical formula 2 may be P-host.

[0288] In one embodiment of the present specification, the compound of chemical formula 3 may be N-host.

[0289] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a green host, and the green host may include a composition for an organic layer of the organic light-emitting device.

[0290] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a red host, and the red host may include a composition for an organic layer of the organic light-emitting device.

[0291] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a blue host, and the blue host may include a composition for an organic layer of the organic light-emitting device.

[0292] The organic layer of the organic light-emitting device of the present invention may be formed as a single-layer structure, but may also be formed as a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0293] In one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0294] In another embodiment of the present specification, the first electrode may be a cathode and the second electrode may be an anode.

[0295] An organic light-emitting device according to one embodiment of the present specification can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the composition for an organic layer of the organic light-emitting device described above.

[0296] The compounds of the above chemical formulas 1 to 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.

[0297] In one embodiment of the present specification, the organic light-emitting device may be a blue organic light-emitting device, and the composition for an organic layer of the organic light-emitting device may be used as a material for the blue organic light-emitting device. For example, the composition for an organic layer of the organic light-emitting device may be included in a light-emitting layer of a blue organic light-emitting device.

[0298] In another embodiment of the present specification, the organic light-emitting device may be a green organic light-emitting device, and the composition for an organic layer of the organic light-emitting device may be used as a material for the green organic light-emitting device. For example, the composition for an organic layer of the organic light-emitting device may be included in a light-emitting layer of a green organic light-emitting device.

[0299] In another embodiment of the present specification, the organic light-emitting device may be a red organic light-emitting device, and the composition for an organic layer of the organic light-emitting device may be used as a material for the red organic light-emitting device. For example, the composition for an organic layer of the organic light-emitting device may be included in a light-emitting layer of a red organic light-emitting device.

[0300] The organic light-emitting device of the present invention may further include one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0301] 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 3. However, the scope of the present application is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present application.

[0302] 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.

[0303] Fig. 3 illustrates a case where the organic layer is multilayered. The organic light-emitting device according to Fig. 3 includes a hole injection layer (301), a hole transport layer (302), a light-emitting layer (303), a hole blocking layer (304), an electron transport layer (305), and an electron injection layer (306). However, the scope of the present application is not limited by such a laminated structure, and, if necessary, the remaining layers except for the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0304] The organic layer including the composition for the organic layer of the organic light-emitting device of the present invention may additionally include other materials as needed.

[0305] In the organic light-emitting device according to one embodiment of the present specification, materials other than the compounds of the chemical formulae 1 to 3 are exemplified below, but these are only for illustrative purposes and are not intended to limit the scope of the present application, and may be replaced with materials known in the art.

[0306] 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.

[0307] 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.

[0308] 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.

[0309] Pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport materials, and low molecular weight or high molecular weight materials can also be used.

[0310] 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.

[0311] For example, LiF is a representative material used in the art, but the present application is not limited thereto.

[0312] Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. At this time, two or more light-emitting materials may be deposited and used as individual sources, or may be premixed and deposited and used as a single source. In addition, a fluorescent material may be used as the light-emitting material, but it may also be used as a phosphorescent material. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used as the light-emitting material, but materials in which both the host material and the dopant material participate in light emission may also be used.

[0313] 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.

[0314] 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.

[0315] The composition for an organic layer of an organic light-emitting device according to one embodiment of the present specification can operate in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., using a principle similar to that applied to organic light-emitting devices.

[0316] In addition, by introducing various substituents into the structures of the above chemical formulas 1 to 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.

[0317] Another embodiment of the present specification provides a method for manufacturing an organic light-emitting device, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, wherein the step of forming the organic layer includes the step of forming one or more organic layers using a composition for an organic layer of the organic light-emitting device.

[0318] In one embodiment of the present specification, the step of forming the organic layer may include a step of premixing a composition for the organic layer of the organic light-emitting device and depositing it using one source.

[0319] 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.

[0320] [Manufacturing Example 1] Preparation of compound A26 and compounds in Table 1

[0321]

[0322] 1) Preparation of intermediate A26-1

[0323] In a 1 L two-neck flask, 30.0 g (90.5 mmol) of 5-bromo-9-chloronaphtho[1,2-b]benzofuran (A), 12.1 g (99.6 mmol) of phenylboronic acid (B), 5.2 g (4.5 mmol) of Pd(pph3)4(Tetrakis(triphenylphosphine)palladium(0)), and 25.0 g (181.0 mmol) of K2CO3 were dissolved in 1,4-dioxane / H2O (300 ml / 60 ml) and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 24.8 g (yield 83.3%) of intermediate A26-1 was obtained.

[0324] 2) Preparation of compound A26

[0325] In a 500 ml two-neck flask, 10.0 g (30.4 mmol) of intermediate A26-1, 11.3 g (30.4 mmol) of di([1,1'-biphenyl]-4-yl)amine(C), 1.4 g (1.5 mmol) of Pd2dba3(Tris(dibenzylideneacetone)dipalladium(0)), 1.4 g (3.0 mmol) of Xphos(2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl), and 5.8 g (60.8 mmol) of NaOtBu(Sodium tert-butoxide) were added, dissolved in toluene (150 ml), and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 17.6 g (yield 87.2%) of the target compound A26 was obtained.

[0326] The following compound was synthesized in the same manner as in the preparation of compound A26, except that (A), (B) and (C) of Table 1 were used instead of (A), (B) and (C) in the above Preparation Example 1.

[0327] [Table 1]

[0328]

[0329]

[0330] [Manufacturing Example 2] Preparation of compound A20 and compounds in Table 2

[0331]

[0332] 1) Preparation of intermediate A20-1

[0333] In a 1 L two-neck flask, 30.0 g (90.5 mmol) of 5-bromo-7-chloronaphtho[1,2-b]benzofuran (A), 12.1 g (99.6 mmol) of phenylboronic acid (B), 45.2 g (4.5 mmol) of Pd(pph3), and 25.0 g (181.0 mmol) of K2CO3 were dissolved in 1,4-dioxane / H2O (300 ml / 60 ml) and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 24.8 g (yield 83.3%) of intermediate A20-1 was obtained.

[0334] 2) Preparation of compound A20

[0335] In a 250 ml two-neck flask, 10.0 g (30.4 mmol) of intermediate A20-1, 11.1 g (30.4 mmol) of (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid(C), 11.4 g (1.5 mmol) of Pd2dba, 1.4 g (3.0 mmol) of Xphos, and 8.4 g (60.8 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O (100 ml / 20 ml) and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 15.1 g (yield 80.9%) of the target compound A20 was obtained.

[0336] The following compound was synthesized in the same manner as in the preparation of compound A20, except that (A), (B) and (C) of Table 2 were used instead of (A), (B) and (C) in the above Preparation Example 2.

[0337] [Table 2]

[0338]

[0339]

[0340] [Manufacturing Example 3] Preparation of compound A88 and compounds in Table 3

[0341]

[0342] 1) Preparation of intermediate A88-1

[0343] In a 500 ml two-neck flask, 10.0 g (30.31 mmol) of compounds 5-bromo-9-chloronaphtho[2,1-b]benzofuran(A), 11.3 g (30.31 mmol) of N-(4-(naphthalen-2-yl)phenyl)-[1,1'-biphenyl]-4-amine(B), 30.34 g (1.5 mmol) of Pd2dba, 1.4 g (60.62 mmol) of Xphos, and 5.8 g (60.62 mmol) of NaOtBu were added, dissolved in toluene (150 ml), and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 16.57 g (yield 88%) of intermediate A88-1 was obtained.

[0344] 2) Preparation of compound A88

[0345] In a 1 L two-neck flask, 16.57 g (26.67 mmol) of A88-1, 4.88 g (40.01 mmol) of phenylboronic acid (C), 41.54 g (1.33 mmol) of Pd (pph3), and 11.06 g (80.02 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O (300 ml / 60 ml) and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 15.22 g (yield 86%) of the target compound A88 was obtained.

[0346] The following compound was synthesized in the same manner as the preparation of compound A88, except that (A), (B) and (C) of Table 3 were used instead of (A), (B) and (C) in the above Preparation Example 3.

[0347] [Table 3]

[0348]

[0349] Compounds were prepared in the same manner as the above manufacturing examples, and the results of their synthesis are shown in Tables 4 and 5 below. Table 4 is 1The values ​​are measured by H NMR (CDCl3, 400 MHz), and Table 5 is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0350] Compound number 1H NMR(CDCl3, 400MHz)A1δ = 8.55 (1H, s), 8.18 (1H, d), 7.79 (2H, d), 7.71 (1H, d), 7.65 (1H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (6H, d), 7.41 (4H, dd), 6.69 (4H, d), 6.39 (1H, d)A3δ = 8.93 (1H, s), 8.68 (1H, d), 8.55 (1H, d), 8.18 (1H, d), 8.12 (1H, d), 7.88 (1H, d), 7.82 (1H, d), 7.79 (2H, d), 7.71 (3H, d), 7.65 (1H, dd), 7.55 (2H, d), 7.54 (2H, d), 7.52 (2H, dd), 7.51 (4H, dd), 7.41 (3H, s), 7.32 (1H, t), 7.08 (1H, t), 6.69 (2H, dd), 6.39 (1H, dd)A4δ = 8.55 (1H, s), 8.18 (1H, d), 7.81 (1H, d), 7.79 (2H, d), 7.72 (1H, d), 7.71 (2H, d), 7.55 (2H, d), 7.54 (6H, d), 7.52 (4H, d), 7.51 (6H, dd), 7.41 (3H, d), 6.69 (6H, d)A7δ = 8.55 (1H, s), 8.18 (1H, d), 7.89 (1H, d), 7.81 (1H, d), 7.79 (2H, d), 7.72 (1H, d), 7.71 (2H, d), 7.66 (1H, d), 7.64 (1H, d), 7.55 (2H, dd), 7.54 (4H, d), 7.52 (2H, d), 7.51 (4H, dd), 7.43 (1H, dd), 7.41 (2H, s), 7.38 (1H, t), 7.32 (1H, t), 6.69 (4H, dd), 6.33 (1H, dd)A11δ =8.55 (1H, s), 8.18 (1H, d), 7.88 (1H, d), 7.84 (1H, d), 7.79 (2H, d), 7.77 (1H, d), 7.74 (1H, d), 7.71 (1H, d), 7.55 (2H, d), 7.54 (2H, dd), 7.52 (2H, d), 7.51 (4H, d), 7.5 (1H, dd), 7.49 (1H, dd), 7.41 (2H, s), 7.36 (1H, t), 7.25 (1H, t), 7.07 (1H, dd), 6.69 (2H, dd), 6.39 (1H, t)A12δ =8.55 (1H, s), 8.18 (1H, d), 7.85 (1H, d), 7.81 (1H, d), 7.79 (2H, d), 7.71 (1H, d), 7.55 (2H, d), 7.54 (5H, d), 7.52 (2H, d), 7.51 (6H, dd), 7.41 (3H, d), 7.38 (1H, d), 7.16 (1H, dd), 7.08 (2H, dd), 6.87 (1H, s), 6.69 (5H, t)A13δ = 8.55 (1H, s), 8.18 (1H, d), 8 (2H, d), 7.95 (1H, d), 7.92 (1H, d), 7.75 (1H, d), 7.73 (1H, d), 7.71 (1H, d), 7.64 (1H, d), 7.59 (2H, dd), 7.58 (1H, d), 7.55 (2H, d), 7.54 (5H, dd), 7.52 (2H, dd), 7.51 (4H, s), 7.41 (2H, t), 7.16 (1H, t), 7.08 (2H, dd), 6.87 (1H, dd), 6.69 (5H, t)A16δ = 8.55 (1H, s), 8.18 (1H, d), 7.88 (1H, d), 7.84 (1H, d), 7.79 (2H, d), 7.77 (1H, d), 7.74 (1H, d), 7.71 (1H, d), 7.55 (2H, d), 7.54 (2H, dd), 7.52 (2H, d), 7.51 (4H, d), 7.5 (1H, dd), 7.49 (1H, dd), 7.41 (2H, s), 7.36 (1H, t), 7.25 (4H, t), 7.13 (1H, dd), 7.02 (1H, dd), 6.69 (2H, t), 6.33 (1H, d)A17δ = 8.55 (1H, s), 8.18 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.71 (1H, d), 7.62 (1H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (6H, dd), 7.44 (2H, d), 7.41 (3H, d), 7.25 (4H, dd), 6.89 (1H, dd), 6.88 (1H, s), 6.69 (4H, t), 6.59 (1H, t)A20δ = 8.55 (1H, s), 8.18 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.71 (1H, d), 7.62 (1H, d), 7.55 (2H, d), 7.54 (6H, d), 7.52 (4H, d), 7.51 (6H, dd), 7.44 (1H, d), 7.41 (3H, d), 6.69 (6H, dd)A21δ = 8.93 (2H, s), 8.55 (1H, d), 8.18 (1H, d), 8.12 (2H, d), 7.93 (1H, d), 7.88 (2H, d), 7.82 (2H, d), 7.79 (2H, d), 7.71 (1H, d), 7.55 (2H, dd), 7.54 (4H, d), 7.52 (2H, d), 7.51 (4H, dd), 7.41 (2H, dd), 7.13 (1H, s), 7.02 (1H, t), 6.69 (4H, t), 6.33 (1H, dd)A22δ = 8.55 (1H, s), 8.18 (1H, d), 7.87 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.71 (1H, d), 7.62 (2H, d), 7.55 (3H, d), 7.54 (4H, d), 7.52 (2H, dd), 7.51 (4H, d), 7.44 (1H, d), 7.41 (2H, dd), 7.38 (1H, dd), 7.28 (1H, s), 6.75 (1H, t), 6.69 (4H, t), 6.58 (1H, dd), 1.72 (2H, dd)A24δ = 8.55 (1H, s), 8.18 (1H, d), 7.89 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.71 (1H, d), 7.66 (1H, d), 7.64 (1H, d), 7.62 (1H, d), 7.55 (2H, dd), 7.54 (4H, d), 7.52 (2H, d), 7.51 (4H, dd), 7.44 (1H, dd), 7.43 (1H, s), 7.41 (2H, t), 7.38 (1H, t), 7.32 (1H, dd), 6.69 (4H, dd), 6.33 (1H, t)A25δ = 8.55 (1H, s), 8.18 (1H, d), 7.95 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.71 (1H, d), 7.64 (1H, d), 7.55 (2H, d), 7.54 (6H, d), 7.52 (4H, dd), 7.51 (6H, d), 7.41 (3H, d), 6.69 (6H, dd)A26δ = 8.55 (1H, s), 8.18 (1H, d), 7.79 (2H, d), 7.71 (1H, d), 7.64 (1H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (6H, d), 7.43 (1H, dd), 7.41 (3H, d), 6.69 (4H, d), 6.33 (1H, dd)A29δ = 8.93 (2H, s), 8.55 (1H, d), 8.18 (1H, d), 8.12 (2H, d), 7.93 (1H, d), 7.88 (2H, d), 7.82 (2H, d), 7.79 (2H, d), 7.71 (1H, d), 7.64 (1H, dd), 7.55 (2H, d), 7.54 (2H, d), 7.51 (2H, dd), 7.43 (1H, dd), 7.41 (1H, s), 7.2 (2H, t), 6.81 (1H, t), 6.69 (2H, dd), 6.63 (2H, dd), 6.33 (1H, t)A31δ = 8.55 (1H, s), 8.<h2 style=";text-align:left;direction:ltr">18 (1H, d), 7.87 (1H, d), 7.79 (2H, d), 7.71 (1H, d), 7.64 (1H, d), 7.62 (1H, d), 7.55 (3H, d), 7.54 (2H, d), 7.52 (2H, dd), 7.51 (4H, d), 7.43 (1H, d), 7.41 (2H, dd), 7.38 (1H, dd), 7.28 (1H, s), 6.75 (1H, t), 6.69 (2H, t), 6.58 (1H, dd), 6.33 (1H, dd), 1.72 (2H, t)A37δ = 7.52 (2H, s), 7.51 (2H, d), 7.41 (1H, d)A41δ = 8.55 (2H, s), 7.79 (2H, d), 7.64 (2H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (6H, d), 7.43 (1H, d), 7.41 (3H, d), 6.69 (4H, dd), 6.33 (1H, d)A58δ = 8.55 (2H, s), 7.95 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.64 (2H, d), 7.55 (2H, d), 7.54 (2H, d), 7.52 (2H, d), 7.51 (4H, d), 7.44 (1H, dd), 7.41 (2H, d), 7.2 (2H, d), 6.89 (1H, dd), 6.88 (1H, dd), 6.81 (1H, s), 6.69 (2H, t), 6.63 (2H, t), 6.59 (1H, dd)A62δ = 8.55 (4H, s), 8 (4H, d), 7.92 (2H, d), 7.73 (2H, d), 7.64 (4H, d), 7.59 (4H, d), 7.58 (2H, d), 7.55 (4H, d), 7.54 (4H, d), 7.52 (4H, dd), 7.51 (4H, d), 7.43 (2H, d), 7.41 (2H, dd), 7.2 (4H, dd), 6.81 (2H, s), 6.69 (4H, t), 6.63 (4H, t), 6.33 (2H, dd)A63δ = 8.55 (2H, d), 7.64 (2H, d), 7.55 (2H, d), 7.54 (3H, d), 7.52 (4H, d), 7.51 (6H, d), 7.43 (1H, d), 7.41 (3H, d), 7.25 (4H, d), 7.41 (3H, d), 7.25 (4H, d), 7.08 (7.1H), d (2H, d), 6.87 (1H, d), 6.69 (3H, dd), 6.33 (1H, dd)A64δ = 8.55 (4H, s), 7.64 (2H, d), 7.55 (4H, d), 7.54 (6H, d), 7.52 (1H, d), 17.52 (1H, d), 7.43 (1H, d), 7.41 (6H, d), 7.25 (7H, d), 6.69 (6H, dd), 6.33 (1H, d)A66δ = 8.55 (2H, s), 7.79 (2H, d), 7.64 (1H, d), 7.5 (2H, d). 7.52 (2H, d), 7.51 (4H, d), 7.41 (2H, d), 7.25 (5H, d), 7.2 (2H, dd), 7.07 (1H, d), 6.81 (1H, d), 6.69 (2H, dd), 6.63 (2H, dd), (16H, dd), 6.63 (2H, dd). =8.55 (2H, s), 7.88 (1H, d), 7.84 (1H, d), 7.79 (2H, d), 7.77 (1H, d), 7.74 (1H, d), 7.65 (1H, d), 7.64 (1H, d), 7.55 (2H, d), 7.54 (2H, d), 7.55 (2H, d). (2H, d), 7.51 (4H, d), 7.5 (1H, dd), 7.49 (1H, dd), 7.41 (3H, s), 7.36 (1H, t), 6.69 (2H, t), 6.39 (1H, dd)A74δ = 8.55 (2H, s), (2.7H, dd), (2.7H, dd). (1H, d), 7.55 (2H, d), 7.54 (2H, d), 7.52 (2H, d), 7.51 (4H, d), 7.41 (2H, d), 7.25 (4H, d), 7.2 (2H, dd), 7.13 (1H, d), 7.02 (1H, d), 6.81 (1H, dd), 6.69 (2H, dd), 6.63 (2H, s), 6.33 (1H, t)A78δ = 8.55 (2H, s), 7.81 (1H, d), 7.79 (2H, d), 7.72 (1H, d), 7.71 (1H, d), 7.64 (1H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (2H, d), 7.51 (4H, dd), 7.41 (2H, d), 7.2 (2H, d), 6.81 (1H, dd), 6.69 (4H, dd), 6.63 (2H, s)A84δ = 8.93 (2H, s), 8.55 (1H, d), 8.12 (2H, d), 8.08 (1H, d), 7.93 (1H, d), 7.88 (2H, d), 7.85 (1H, d), 7.82 (2H, d), 7.81 (1H, d), 7.55 (2H, dd), 7.54 (2H, d), 7.52 (2H, d), 7.51 (2H, dd), 7.46 (1H, dd), 7.41 (1H, s), 7.38 (1H, t), 7.2 (2H, t), 6.81 (1H, dd), 6.69 (2H, dd), 6.63 (2H, t)A88δ = 8.55 (1H, s), 8.08 (1H, d), 8 (2H, d), 7.95 (1H, d), 7.92 (1H, d), 7.75 (1H, d), 7.73 (1H, d), 7.64 (1H, d), 7.59 (2H, d), 7.58 (1H, dd), 7.55 (2H, d), 7.54 (4H, d), 7.52 (4H, dd), 7.51 (4H, dd), 7.46 (1H, s), 7.41 (2H, t), 6.69 (4H, t)A91δ = 8.93 (2H, s), 8.55 (1H, d), 8.12 (2H, d), 8.08 (1H, d), 7.93 (1H, d), 7.88 (2H, d), 7.82 (2H, d), 7.81 (1H, d), 7.72 (1H, d), 7.71 (1H, dd), 7.55 (2H, d), 7.54 (2H, d), 7.<h2 style=";text-align:left;direction:ltr">A93δ = 8.55 (1H, s), 8.08 (1H, d), 7.89 (1H, d), 7.75 (1H, d), 7.66 (1H, d), 7.64 (1H, d), 7.62 (1H, d), 7.55 (2H, d), 7.54 (2H, d), 7.52 (4H, dd), 7.51 (4H, d), 7.46 (1H, d), 7.44 (1H, dd), 7.43 (1H, dd), 7.41 (2H, s), 7.38 (1H, t), 7.32 (1H, t), 7.25 (4H, dd), 6.69 (2H, dd), 6.33 (1H, t)A98δ = 7.95 (1H, s), 7.79 (2H, d), 7.64 (1H, d), 7.51 (2H, d), 7.5 (1H, d), 7.41 (2H, d), 6.8 (1H, d)A101δ = 8.16 (2H, s), 7.79 (2H, d), 7.67 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (7H, d), 7.49 (1H, d), 7.42 (1H, d), 7.41 (3H, d), 7.39 (1H, dd), 6.69 (4H, d)A106δ = 8.16 (2H, s), 7.79 (2H, d), 7.67 (2H, d), 7.6 (1H, d), 7.57 (1H, d), 7.54 (4H, d), 7.52 (2H, d), 7.51 (4H, d), 7.49 (1H, d), 7.42 (1H, dd), 7.41 (2H, d), 7.2 (2H, d), 6.81 (1H, dd), 6.69 (4H, dd), 6.63 (2H, s)A110δ = 8.16 (2H, s), 8 (2H, d), 7.92 (1H, d), 7.73 (1H, d), 7.67 (2H, d), 7.59 (2H, d), 7.58 (1H, d), 7.54 (4H, d), 7.<h2 style=";text-align:left;direction:ltr">52 (4H, d), 7.51 (5H, dd), 7.49 (1H, d), 7.42 (1H, d), 7.41 (2H, dd), 7.39 (1H, dd), 6.69 (4H, s)A116δ = 8.16 (2H, s), 8 (2H, d), 7.92 (1H, d), 7.73 (1H, d), 7.67 (2H, d), 7.59 (2H, d), 7.58 (1H, d), 7.54 (2H, d), 7.52 (2H, d), 7.51 (3H, dd), 7.49 (1H, d), 7.42 (1H, d), 7.41 (1H, dd), 7.39 (1H, dd), 7.25 (4H, s), 7.2 (2H, t), 6.81 (1H, t), 6.69 (2H, dd), 6.63 (2H, dd)A118δ = 8.16 (2H, s), 7.67 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (6H, d), 7.49 (2H, d), 7.46 (1H, d), 7.42 (1H, d), 7.41 (3H, d), 7.08 (2H, dd), 6.69 (4H, d)A119δ = 8.16 (2H, s), 7.67 (2H, d), 7.6 (1H, d), 7.54 (2H, d), 7.52 (4H, d), 7.51 (4H, d), 7.49 (1H, d), 7.42 (1H, d), 7.41 (2H, d), 7.25 (4H, dd), 7.2 (2H, d), 6.81 (1H, d), 6.69 (2H, dd), 6.63 (2H, dd), 6.39 (1H, s)A136δ = 8.16 (2H, s), 8 (2H, d), 7.92 (1H, d), 7.79 (2H, d), 7.73 (1H, d), 7.67 (2H, d), 7.59 (2H, d), 7.58 (1H, d), 7.54 (4H, d), 7.52 (2H, dd), 7.51 (5H, d), 7.49 (1H, d), 7.42 (1H, dd), 7.41 (2H, dd), 7.39 (1H, s), 6.69 (4H, t).<h2 style=";text-align:left;direction:ltr">

[0351] 화합물 번호FD-MS화합물 번호FD-MSA1m / z= 613.24 (C 46 H 31 NO, 613.74)A62m / z= 587.22 (C44H29NO, 587.71)A3m / z= 637.24 (C 48 H 31 NO, 637.77)A63m / z= 689.27 (C52H35NO, 689.84)A4m / z= 689.27 (C 52 H 35 NO, 689.84)A64m / z= 689.27 (C52H35NO, 689.84)A7m / z= 703.25 (C 52 H 33 NO2, 703.82)A66m / z= 613.24 (C 46 H 31 NO, 613.74)A11m / z= 587.22 (C 44 H 29 NO, 587.71)A69m / z= 587.22 (C 44 H 29 NO, 587.71)A12m / z= 689.27 (C 52 H 35 NO, 689.84)A74m / z= 613.24 (C 46 H 31 NO, 613.74)A13m / z= 739.29 (C 56 H 37 NO, 739.90)A78m / z= 613.24 (C 46 H 31 NO, 613.74)A16m / z= 663.26 (C 50 H 33 NO, 663.80)A84m / z= 637.24 (C48H31NO, 637.77)A17m / z= 765.30 (C 58 H 39 NO, 765.94)A88m / z= 663.26 (C 50 H 33 NO, 663.80)A20m / z= 689.27 (C 52 H 35NO, 689.84)A91m / z= 637.24 (C 48 H 31 NO, 637.77)A21m / z= 713.27 (C 54 H 35 NO, 713.86)A93m / z= 703.25 (C 52 H 33 NO2, 703.82)A22m / z= 729.30 (C55H39NO, 729.90)A98m / z= 634.37 (C 46 H 10 D 21 NO, 634.87)A24m / z= 703.25 (C 52 H 33 NO2, 703.82)A101m / z= 613.24 (C 46 H 31 NO, 613.74)A25m / z= 689.27 (C 52 H 35 NO, 689.84)A106m / z= 613.24 (C 46 H 31 NO, 613.74)A26m / z= 613.24 (C 46 H 31 NO, 613.74)A110m / z= 663.26 (C50H33NO, 663.80)A29m / z= 637.24 (C 48 H 31 NO, 637.77)A116m / z= 663.26 (C50H33NO, 663.80)A31m / z= 653.27 (C49H35NO, 653.81)A118m / z= 613.24 (C 46 H 31 NO, 613.74)A37m / z= 639.40 (C 46 H5D 26 NO, 639.90)A119m / z= 613.24 (C 46 H 31 NO, 613.74)A41m / z= 613.24 (C 46 H 31 NO, 613.74)A136m / z= 663.26 (C50H33NO, 663.80)A58m / z= 613.24 (C 46H 31 NO, 613.74)

[0352] <Manufacturing Example 4> Preparation of compound B1 and compounds in Table 6

[0353]

[0354] 1) Preparation of intermediate B1-1

[0355] 10 g (49.59 mmol) of 3-bromo-9H-carbazole, 24.2 g (148.77 mmol) of 2-bromobenzene-1-ylium(a), 32.27 g (2.48 mmol) of Pd2(dba), 2.42 mL (9.92 mmol) of P(t-Bu)3(Tri-tert-butylphosphine), and 9.53 g (99.18 mmol) of NatOBu were added to a reaction flask, 100 mL of toluene was added, and the mixture was heated at 135°C for 15 hours. After the reaction was completed, the mixture was extracted with MC (methylene chloride) and water, and then purified by column chromatography to obtain 14 g (yield 98%) of intermediate B1-1.

[0356] 2) Preparation of compound B1

[0357] 14 g (43.4 mmol) of intermediate B1-1, 14.9 g (52 mmol) of (9-phenyl-9H-carbazol-3-yl)boronic acid(b), 42.5 g (2.17 mmol) of Pd(PPh3), and 17.9 g (130 mmol) of K2CO3 were added to a reaction flask, 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. Afterwards, 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 B1.

[0358] The following compound was synthesized in the same manner as the preparation of Compound B1, except that (a) and (b) of Table 6 were used instead of (a) and (b) in Manufacturing Example 4.

[0359] [Table 6]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368] <Manufacturing Example 5> Preparation of compound B41 and compounds in Table 7

[0369]

[0370] 1) Preparation of intermediate B41-1

[0371] 10 g (39.0 mmol) of 5,8-dihydroindolo[2,3-c]carbazole(a), 6.12 g (39.0 mmol) of 1-bromobenzene(b), 31.79 g (1.95 mmol) of Pd2(dba), 30.92 mL (3.9 mmol) of P(t-Bu), and 7.50 g (78.0 mmol) of NatOBu were added to a reaction flask, 100 mL of toluene was added, and the mixture was heated at 135°C for 15 hours. After the reaction was completed, the mixture was extracted with MC and water, and then purified by column chromatography to obtain 7.3 g (yield 56%) of intermediate B41-1.

[0372] 2) Preparation of compound B41

[0373] Intermediate B41-1 7.3 g (22.0 mmol), 1-bromobenzene(c) 3.8 g (24.2 mmol), Pd2(dba) 31.01 g (1.1 mmol), P(t-Bu) 30.52 mL (3.9 mmol), and NatOBu 4.23 g (44.0 mmol) were added, then 70 mL of toluene was added and heated at 135°C for 15 hours. After the reaction was completed, the mixture was extracted with MC and water, and purified by column chromatography to obtain 8.3 g (yield 93%) of compound B41.

[0374] The following compound was synthesized in the same manner as the preparation of compound B41, except that (a), (b) and (c) of Table 7 were used instead of (a), (b) and (c) in Manufacturing Example 5.

[0375] [Table 7]

[0376]

[0377]

[0378] Compounds were prepared in the same manner as the above manufacturing examples, and the results of their synthesis are shown in Tables 8 and 9 below. Table 8 is 1 The values ​​are measured by H NMR (CDCl3, 400 MHz), and Table 9 is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0379] Compound number 1H NMR(CDCl3, 400MHz)B1δ =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)B2δ =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)B3δ =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)B4δ =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)B5δ =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)B6δ =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)B7δ =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)B11δ =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)B16δ =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)B19δ =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)B20δ =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)B21δ =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)B22δ =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)B23δ =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)B26δ =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)B27δ =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)B28δ =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)B29δ =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)B30δ =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)B32δ =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)B33δ =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)B34δ =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)B38δ =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)B40δ =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)B41δ = 8.55(2H,f d), 7.94(2H, d), 7.62-7.35(14H, m), 7.16(2H, d)B44δ = 8.55(2H, d), 7.94-7.91(10H, m), 7.75(4H, d), 7.49-7.35(10H, m), 7.16(2H, t)B45δ = 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)B61δ = 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)B62δ = 8.55 (2H, s), 8.12 (1H, d), 8.09 (1H, d), 7.94 (2H, d), 7.79 (2H, d), 7.68 (2H, d), 7.57 (1H, d), 7.52 (5H, d), 7.51 (5H, d), 7.46 (1H, dd), 7.41 (2H, d), 7.33 (2H, d), 7.25 (2H, dd)B64δ = 8.55 (2H, s), 8.12 (1H, d), 7.94 (2H, d), 7.89 (2H, d), 7.73 (1H, d), 7.66 (1H, d), 7.58 (2H, d), 7.57 (1H, d), 7.5 (2H, d), 7.45 (1H, dd), 7.44 (1H, d), 7.38 (1H, d), 7.33 (2H, dd), 7.32 (2H, dd), 7.25 (4H, s)B81δ = 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)B82δ = 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)B83δ = 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)B84δ = 8.55 (1H, s), 8.18 (1H, d), 8.12 (1H, d), 8 (1H, d), 7.94 (1H, d), 7.87 (1H, d), 7.77 (2H, d), 7.69 (1H, d), 7.63 (1H, d), 7.5 (1H, dd), 7.33 (1H, d), 7.29 (1H, d), 7.25 (1H, dd)B85δ = 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)B86δ = 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)B88δ = 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)B89δ = 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)B90δ = 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)B91δ = 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)B92δ = 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)B95δ = 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)B97δ = 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)B100δ = 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)B101δ = 8.55(2H, d), 7.94(2H, d), 7.42-7.35(4H, m), 7.16(2H, t)B119δ = -.

[0380] 화합물 번호FD-MS화합물 번호FD-MSB1m / z= 484.59(C 36 H 24 N2=484.19)B40m / z= 686.84(C 52 H 34 N2=686.27)B2m / z= 560.69(C 42 H 28 N2=560.23)B41m / z= 408.16(C 30 H 20 N2=408.50)B3m / z= 560.69(C 42 H 28 N2=560.23)B44m / z= 560.23(C 42 H 28 N2=560.70)B4m / z= 560.69(C 42 H 28 N2=560.23)B45m / z= 560.23(C 42 H 28 N2=560.70)B5m / z= 636.78(C 48 H 32 N2=636.26)B61m / z= 560.23(C 42 H 28 N2=560.70)B6m / z= 636.78(C 48 H 32N2=636.26)B62m / z= 560.23 (C42H28N2, 560.69)B7m / z= 636.78(C 48 H 32 N2=636.26)B64m / z= 498.17 (C36H22N2O, 498.57)B11m / z= 600.75(C 45 H 35 N2=600.26)B81m / z= 494.65(C 36 H 14 D 10 N2=494.26)B16m / z= 634.77(C 48 H 30 N2=634.24)B82m / z= 654.89(C 48 H 14 D 18 N2=654.37)B19m / z= 636.78(C 48 H 32 N2=636.26)B83m / z= 574.77(C 41 H 14 D 14 N2=574.31)B20m / z= 636.78(C 48 H 32 N2=636.26)B84m / z= 654.37 (C48H14D18N2, 654.89)B21m / z= 636.78(C 48 H 32 N2=636.26)B85m / z= 654.89(C 48 H 14 D 18 N2=654.37)B22m / z= 712.88(C 54 H 36 N2=712.29)B86m / z= 654.89(C 48 H 14 D 18 N2=654.37)B23m / z= 712.88(C 54 H 36 N2=712.29)B88m / z= 654.89(C 48 H 14 D 18 N2=654.37)B26m / z= 712.88(C 54 H 36N2=712.29)B89m / z= 654.89(C 48 H 14 D 18 N2=654.37)B27m / z= 712.88(C 54 H 36 N2=712.29)B90m / z= 734.43(C 54 H 14 D 22 N2=735.03)B28m / z= 712.88(C 54 H 36 N2=712.29)B91m / z= 735.01(C 54 H 14 D 22 N2=734.43)B30m / z= 712.88(C 54 H 36 N2=712.29)B92m / z= 735.01(C 54 H 14 D 22 N2=734.43)B29m / z= 712.88(C 54 H 36 N2=712.29)B95m / z= 735.01(C 54 H 14 D 22 N2=734.43)B32m / z= 636.78(C 48 H 32 N2=636.26)B97m / z= 815.13(C 60 H 14 D 26 N2=814.48)B33m / z= 712.88(C 54 H 36 N2=712.29)B100m / z= 666.86(C 48 H 14 D 16 N2O=666.34)B34m / z= 712.88(C 54 H 36 N2=712.29)B101m / z= 578.34(C 42 H 10 D 18 N2=578.81)B38m / z= 788.97(C 60 H 40N2=788.32)B119m / z= 508.34 (C36D24N2=508.74)

[0381] [Manufacturing Example 6] Preparation of compound C24 and compounds of Table 10

[0382]

[0383] 1) Preparation of intermediate C24-1

[0384] 2-(7-chlorodibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(A)(8 g, 24.35 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine(B)(8.62 g, 23.86 mmol), Pd(PPh3)4(1.41 g, 1.22 mmol), K2CO3(7.74 g, 73.04 mmol) were added to 1.4-Dioxane / H2O (80 mL / 16 mL) and stirred at 110 ℃ for 2 h. After cooling to room temperature, the resulting solid was filtered to obtain intermediate C24-1 (11 g, 86.23%).

[0385] 2) Preparation of compound C24

[0386] Intermediate C24-1 (11.0 g, 20.9 mmol), (4-(naphthalen-2-yl)phenyl)boronic acid(C)(6.25 g, 25.19 mmol), pd2dba3(0.6 g, 1.15 mmol), Xphos (1.0 g, 2.1 mmol), NaOH (2.52 g, 62.98 mmol) were added to 1.4-Dioxane / H2O (110 mL / 22 mL) and stirred at 120 °C for 2 h. After cooling to room temperature, the resulting solid was filtered. The target compound C24 (12 g, 83%) was obtained by silica purification.

[0387] The following compound was synthesized in the same manner as the preparation of compound C24, except that (A), (B) and (C) of Table 10 were used instead of (A), (B) and (C) in the above Preparation Example 6.

[0388] [Table 10]

[0389]

[0390]

[0391]

[0392] [Manufacturing Example 7] Preparation of compound C131 and compounds of Table 11

[0393]

[0394] 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(A)(8 g, 27.20 mmol), 2-([1,1':4',1''-terphenyl]-4-yl)-4-chloro-6-(naphthalen-2-yl)-1,3,5-triazine(B)(12.50 g, 65.65 mmol), Pd(PPh3)4(1.57 g, 1.36 mmol), K2CO3(11.28 g, 81.59 mmol) were added to 1.4-Dioxane / H2O (80 mL / 16 mL) and stirred at 110 °C for 2 h. After cooling to room temperature, the produced solid was filtered to obtain the target compound C131 (14.59 g, 89.23%).

[0395] The following compound was synthesized in the same manner as the preparation of compound C131, except that (A) and (B) of Table 11 were used instead of (A) and (B) in Manufacturing Example 7.

[0396] [Table 11]

[0397]

[0398] Compounds were prepared in the same manner as the above manufacturing examples, and the results of their synthesis are shown in Tables 12 and 13 below. Table 12 1 The values ​​are measured by H NMR (CDCl3, 400 MHz), and Table 13 is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0399] Compound number 1<h2 style=";text-align:left;direction:ltr">H NMR (CDCl3, 400MHz) C1δ = 8.28 (4H, s), 7.89 (1H, d), 7.83 (2H, d), 7.79 (2H, d), 7.77 (4H, d), 7.66 (1H, d), 7.6 (1H, d), 7.57 (1H, d), 7.51 (4H, d), 7.45 (6H, dd), 7.41 (2H, d), 7.38 (1H, d), 7.32 (1H, dd) C7δ = 8.28 (4H, s), 7.89 (1H, d), 7.66 (1H, d), 7.6 (1H, d), 7.57 (1H, d), 7.52 (2H, d), 7.51 (6H, d), 7.41 (3H, d), 7.38 (1H, d), 7.32 (1H, dd), 7.25 (8H, d)C9δ = 8.28 (4H, s), 8 (2H, d), 7.92 (1H, d), 7.89 (1H, d), 7.73 (1H, d), 7.66 (1H, d), 7.6 (1H, d), 7.59 (2H, d), 7.58 (1H, d), 7.57 (1H, dd), 7.51 (4H, d), 7.41 (2H, d), 7.38 (1H, dd), 7.32 (1H, dd), 7.25 (4H, s)C11δ = 8.28 (4H, s), 7.92 (2H, d), 7.89 (1H, d), 7.73 (2H, d), 7.66 (1H, d), 7.6 (1H, d), 7.58 (2H, d), 7.57 (1H, d), 7.52 (2H, d), 7.51 (6H, dd), 7.41 (3H, d), 7.38 (1H, d), 7.32 (1H, dd)C14δ = 8.28 (4H, s), 7.89 (2H, d), 7.81 (1H, d), 7.72 (1H, d), 7.71 (1H, d), 7.66 (2H, d), 7.6 (1H, d), 7.57 (1H, d), 7.51 (4H, d), 7.41 (2H, dd), 7.38 (2H, d), 7.32 (2H, d)C15δ = 8.45 (1H, s), 8.28 (4H, d), 8.11 (1H, d), 8.08 (1H, d), 8.05 (1H, d), 7.98 (1H, d), 7.89 (1H, d), 7.66 (1H, d), 7.6 (1H, d), 7.57 (1H, dd), 7.52 (1H, d), 7.51 (4H, d), 7.5 (1H, dd), 7.41 (2H, dd), 7.38 (1H, s), 7.32 (1H, t)C17δ = 9.09 (1H, s), 8.49 (1H, d), 8.28 (2H, d), 8 (2H, d), 7.92 (1H, d), 7.89 (1H, d), 7.84 (2H, d), 7.82 (2H, d), 7.66 (1H, d), 7.6 (1H, dd), 7.59 (2H, d), 7.57 (1H, d), 7.51 (2H, dd), 7.41 (1H, dd), 7.38 (1H, s), 7.32 (1H, t)C20δ = 8.28 (2H, s), 8 (2H, d), 7.92 (1H, d), 7.89 (1H, d), 7.85 (2H, d), 7.73 (1H, d), 7.66 (1H, d), 7.6 (1H, d), 7.59 (2H, d), 7.58 (1H, dd), 7.57 (1H, d), 7.52 (2H, d), 7.51 (4H, dd), 7.41 (2H, dd), 7.38 (1H, s), 7.32 (1H, t), 7.25 (2H, t)C24δ = 8.28 (2H, s), 8 (2H, d), 7.92 (1H, d), 7.89 (2H, d), 7.75 (1H, d), 7.73 (1H, d), 7.66 (2H, d), 7.62 (1H, d), 7.6 (1H, d), 7.59 (2H, dd), 7.58 (1H, d), 7.57 (1H, d), 7.51 (2H, dd), 7.44 (1H, dd), 7.41 (1H, s), 7.38 (2H, t), 7.32 (2H, t), 7.25 (4H, dd)C27δ = 8.28 (2H, s), 8 (2H, d), 7.92 (1H, d), 7.89 (2H, d), 7.75 (1H, d), 7.73 (1H, d), 7.66 (2H, d), 7.62 (1H, d), 7.6 (1H, d), 7.59 (2H, dd), 7.58 (1H, d), 7.57 (1H, d), 7.51 (2H, dd), 7.44 (1H, dd), 7.41 (1H, s), 7.38 (2H, t), 7.32 (2H, t)C37δ = 8.55 (1H, s), 8.28 (2H, d), 8.12 (1H, d), 7.94 (1H, d), 7.89 (1H, d), 7.66 (1H, d), 7.63 (1H, d), 7.6 (1H, d), 7.57 (1H, d), 7.52 (2H, dd), 7.51 (4H, d), 7.5 (1H, d), 7.41 (2H, dd), 7.38 (1H, dd), 7.33 (1H, s), 7.32 (1H, t), 7.29 (1H, t), 7.25 (5H, dd)C42δ = 8 (2H, s), 7.92 (1H, d), 7.89 (1H, d), 7.77 (4H, d), 7.73 (1H, d), 7.66 (1H, d), 7.6 (1H, d), 7.59 (2H, d), 7.58 (1H, d), 7.57 (1H, dd), 7.38 (1H, d), 7.32 (1H, d), 7.3 (4H, dd)C51δ = 8.28 (2H, s), 8 (2H, d), 7.92 (1H, d), 7.89 (1H, d), 7.85 (2H, d), 7.79 (2H, d), 7.73 (1H, d), 7.66 (1H, d), 7.6 (1H, d), 7.59 (2H, dd), 7.58 (1H, d), 7.57 (1H, d), 7.51 (4H, dd), 7.41 (2H, dd), 7.38 (1H, s), 7.32 (1H, t), 7.25 (2H, t)C52δ = 8.55 (1H, s), 8.42 (1H, d), 8.28 (4H, d), 8.08 (1H, d), 8.04 (1H, d), 7.89 (1H, d), 7.87 (1H, d), 7.68 (1H, d), 7.66 (1H, d), 7.61 (1H, dd), 7.55 (2H, d), 7.51 (4H, d), 7.41 (2H, dd), 7.38 (1H, dd), 7.32 (1H, s), 7.25 (4H, t)C54δ = 8.28 (4H, s), 8 (2H, d), 7.92 (1H, d), 7.89 (1H, d), 7.87 (1H, d), 7.81 (1H, d), 7.73 (1H, d), 7.66 (1H, d), 7.59 (2H, d), 7.58 (1H, dd), 7.51 (4H, d), 7.41 (2H, d), 7.38 (1H, dd), 7.32 (1H, dd), 7.25 (4H, s)C55δ = 9.09 (1H, s), 8.49 (1H, d), 8.28 (2H, d), 7.92 (2H, d), 7.89 (1H, d), 7.87 (1H, d), 7.81 (1H, d), 7.79 (2H, d), 7.73 (1H, d), 7.66 (1H, dd), 7.58 (1H, d), 7.52 (2H, d), 7.51 (6H, dd), 7.41 (3H, dd), 7.38 (1H, s), 7.32 (1H, t)C67δ = 8.28 (4H, s), 8 (2H, d), 7.95 (1H, d), 7.92 (1H, d), 7.75 (2H, d), 7.73 (1H, d), 7.64 (1H, d), 7.62 (1H, d), 7.59 (2H, d), 7.58 (1H, dd), 7.51 (4H, d), 7.44 (1H, d), 7.41 (2H, dd), 7.25 (4H, dd)C69δ = 8.49 (1H, s), 8.28 (4H, d), 8.12 (1H, d), 8.1 (1H, d), 7.95 (1H, d), 7.75 (2H, d), 7.64 (1H, d), 7.63 (1H, d), 7.62 (2H, d), 7.58 (2H, dd), 7.51 (4H, d), 7.5 (3H, d), 7.45 (1H, dd), 7.44 (1H, dd), 7.41 (2H, s), 7.29 (1H, t)C71δ = 8.99 (1H, s), 8.93 (1H, d), 8.34 (1H, d), 8.28 (4H, d), 8.12 (1H, d), 8.1 (1H, d), 7.95 (1H, d), 7.88 (1H, d), 7.82 (1H, d), 7.75 (2H, dd), 7.71 (2H, d), 7.64 (1H, d), 7.62 (1H, dd), 7.51 (4H, dd), 7.44 (1H, s), 7.41 (2H, t)C72δ = 9.15 (1H, s), 8.93 (2H, d), 8.28 (4H, d), 8.18 (1H, d), 8.12 (2H, d), 8.04 (1H, d), 7.95 (1H, d), 7.88 (2H, d), 7.82 (2H, d), 7.75 (2H, dd), 7.64 (1H, d), 7.62 (1H, d), 7.51 (4H, dd), 7.44 (1H, dd), 7.41 (2H, s)C89δ = 9.09 (1H, s), 8.49 (1H, d), 8 (4H, d), 7.95 (1H, d), 7.92 (2H, d), 7.89 (1H, d), 7.75 (3H, d), 7.73 (1H, d), 7.66 (1H, d), 7.64 (1H, dd), 7.62 (2H, d), 7.59 (4H, d), 7.58 (1H, dd), 7.44 (2H, dd), 7.38 (1H, s), 7.32 (1H, t)C92δ = 9.09 (1H, s), 8.49 (1H, d), 8.28 (2H, d), 8 (2H, d), 7.95 (1H, d), 7.92 (1H, d), 7.75 (2H, d), 7.64 (1H, d), 7.62 (1H, d), 7.59 (2H, dd), 7.52 (2H, d), 7.51 (4H, d), 7.44 (1H, dd), 7.41 (2H, dd), 7.25 (4H, s)C99δ = 8.28 (2H, s), 8 (2H, d), 7.92 (1H, d), 7.89 (1H, d), 7.85 (2H, d), 7.79 (2H, d), 7.77 (1H, d), 7.73 (1H, d), 7.7 (1H, d), 7.66 (1H, dd), 7.59 (2H, d), 7.58 (1H, d), 7.51 (4H, dd), 7.41 (2H, dd), 7.38 (1H, s), 7.32 (1H, t), 7.25 (2H, t)C100δ = 9.09 (2H, s), 8.49 (2H, d), 8 (4H, d), 7.92 (2H, d), 7.91 (1H, d), 7.89 (1H, d), 7.81 (1H, d), 7.66 (1H, d), 7.59 (4H, d), 7.52 (2H, dd), 7.51 (2H, d), 7.41 (1H, d), 7.38 (1H, dd), 7.32 (1H, dd), 7.25 (4H, s)C107δ = 8.28 (4H, s), 8 (2H, d), 7.95 (1H, d), 7.92 (1H, d), 7.75 (2H, d), 7.73 (1H, d), 7.64 (1H, d), 7.62 (1H, d), 7.59 (2H, d), 7.58 (1H, dd), 7.51 (4H, d), 7.44 (1H, d), 7.41 (2H, dd), 7.25 (4H, dd)C119δ = 8.28 (2H, s), 8 (2H, d), 7.95 (1H, d), 7.92 (1H, d), 7.85 (2H, d), 7.81 (1H, d), 7.75 (1H, d), 7.73 (1H, d), 7.72 (1H, d), 7.71 (1H, dd), 7.64 (1H, d), 7.59 (2H, d), 7.58 (1H, dd), 7.52 (2H, dd), 7.51 (4H, s), 7.41 (2H, t), 7.25 (2H, t)C122δ = 8.28 (4H, s), 7.92 (2H, d), 7.85 (1H, d), 7.81 (1H, d), 7.75 (1H, d), 7.73 (2H, d), 7.62 (1H, d), 7.58 (2H, d), 7.52 (2H, d), 7.51 (6H, dd), 7.44 (1H, d), 7.41 (3H, d), 7.38 (1H, dd)C131δ = 9.09 (1H, s), 8.49 (1H, d), 8 (2H, d), 7.92 (1H, d), 7.89 (1H, d), 7.85 (2H, d), 7.75 (1H, d), 7.66 (1H, d), 7.62 (1H, d), 7.59 (2H, dd), 7.52 (2H, d), 7.51 (2H, d), 7.44 (1H, dd), 7.41 (1H, dd), 7.38 (1H, s), 7.32 (1H, t), 7.25 (6H, t)C132δ = 7.89 (1H, s), 7.85 (4H, d), 7.75 (1H, d), 7.66 (1H, d), 7.62 (1H, d), 7.52 (4H, d), 7.51 (4H, d), 7.44 (1H, d), 7.41 (2H, d), 7.38 (1H, dd), 7.32 (1H, d), 7.25 (8H, d)C134δ = 8 (2H, s), 7.95 (1H, d), 7.92 (1H, d), 7.89 (2H, d), 7.85 (2H, d), 7.75 (2H, d), 7.73 (1H, d), 7.66 (2H, d), 7.64 (1H, d), 7.62 (1H, dd), 7.59 (2H, d), 7.58 (1H, d), 7.44 (1H, dd), 7.38 (2H, dd), 7.32 (2H, s), 7.25 (2H, t)C143δ = 7.89 (1H, s), 7.75 (1H, d), 7.66 (1H, d), 7.62 (1H, d), 7.44 (1H, d), 7.38 (1H, d), 7.32 (1H, d)C145δ = 8 (2H, s), 7.92 (1H, d), 7.89 (1H, d), 7.73 (1H, d), 7.66 (1H, d), 7.6 (1H, d), 7.59 (2H, d), 7.58 (1H, d), 7.57 (1H, d), 7.38 (1H, dd), 7.32 (1H, d), 7.25 (4H, d).

[0400] 화합물번호FD-MS화합물번호FD-MSC1m / z= 675.21 (C45H30N3O2P, 675.71)C67m / z = 601.22 (C 43 H 27<h2 style=";text-align:left;direction:ltr">N3O, 601.69)C7m / z = 627.23 (C<h2 style=";text-align:left;direction:ltr"> 45 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O, 627.73)C69m / z= 640.23 (C45H28N4O, 640.73)C9m / z = 601.22 (C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> N3O, 601.69)C71m / z = 575.20 (C41H25N3O, 575.66)C11m / z = 601.22 (C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> N3O, 601.69)C72m / z= 625.22 (C45H27N3O, 625.72)C14m / z= 565.18 (C39H23N3O2, 565.62)C89m / z= 665.21 (C47H27N3O2, 665.74)C15m / z= 581.16 (C39H23N3OS, 581.68)C92m / z = 601.22 (C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> N3O, 601.69)C17m / z = 550.18 (C38H22N4O, 550.61)C99m / z = 601.22 (C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> N3O, 601.69)C20m / z = 601.22 (C)<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> N3O, 601.69)C100m / z = 651.23 (C)<h2 style=";text-align:left;direction:ltr"> 47 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O, 651.75)C24m / z = 691.23 (C)<h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2, 691.77)C107m / z = 601.22 (C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> N3O, 601.69)C27m / z = 615.19 (C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> N3O2, 615.68)C119m / z = 601.22 (C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> N3O, 601.69)C37m / z= 640.23 (C45H28N4O, 640.73)C122m / z = 601.22 (C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27N3O, 601.69)C42m / z= 561.17 (C37H21F2N3O, 561.58)C131m / z = 601.22 (C 43 H 27 N3O, 601.69)C51m / z = 601.22 (C 43 H 27 N3O, 601.69)C132m / z = 627.23 (C 45 H 29 N3O, 627.73)C52m / z = 601.22 (C 43 H 27 N3O, 601.69)C134m / z = 615.19 (C 43 H 25 N3O2, 615.68)C54m / z = 601.22 (C 43 H 27 N3O, 601.69)C143m / z = 633.31 (C 43 H7D 18 N3O2, 633.79)C55m / z = 601.22 (C 43 H 27 N3O, 601.69)C145m / z = 611.28 (C 43 H 17 D 10 N3O, 611.76)

[0401] [Experimental Example]

[0402] [Experimental Example 1]

[0403] 1) Manufacturing of organic light-emitting devices

[0404] A glass substrate coated with a 1,500 Å thick indium tin oxide (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 using UV (Ultraviolet) in a UV (Ultraviolet) cleaner. After that, the substrate was transferred to a plasma cleaner (PT), and plasma treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic vapor deposition.

[0405] 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′-Di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine), were formed on the ITO transparent electrode (anode).

[0406] On top of that, a light-emitting layer was thermally vacuum-deposited as follows. Specifically, as a red host for the light-emitting layer, the compounds described in Table 14 below were used alone, or two compounds described in Table 15 below, or three compounds described in Table 16 below were used together, and a red phosphorescent dopant, (piq)2(Ir)(acac), was doped in an amount of 3 wt% into the red host to deposit a light-emitting layer having a thickness of 500 Å. Thereafter, 60 Å of bathocuproine (hereinafter, BCP) was deposited as a hole-blocking layer, and 200 Å of Alq3 was deposited thereon as an electron-transporting layer.

[0407] Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode, thereby manufacturing an organic light-emitting device.

[0408] 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.

[0409] The structures of the compounds used as comparative examples in Tables 14 and 16 below are as follows.

[0410] [Comparative example compound]

[0411]

[0412] 2) Driving voltage and luminous efficiency of organic light-emitting devices

[0413] The electroluminescence (EL) characteristics of the organic light-emitting devices of Examples and Comparative Examples of Tables 14 to 16 manufactured as described above were measured using M7000 of Max Science, and the standard luminance was determined to be 6,000 cd / m using the measurement results using M6000 (life measurement equipment) manufactured by Max Science. 2 When, T 90 was measured. The above T 90 refers to the lifespan (unit: h, hours), which is the time it takes for the initial brightness to drop to 90%.

[0414] The measured characteristics of the organic light-emitting device were as shown in Tables 14 to 16 below.

[0415] Compound threshold voltage (V) on )driving voltage (V) op )Efficiency (cd / A)Color coordinates (x, y)Lifespan (T 90) Comparative Example 1A12.646.2717.65(0.684, 0.316)4 Comparative Example 2A32.676.6017.34(0.685, 0.314)5 Comparative Example 3A42.755.3418.58(0.684, 0.315)4 Comparative Example 4A72.536.0018.27(0.684, 0.316)4 Comparative Example 5A112.736.7016.72(0.684, 0.316)5 Comparative Example 6A122.786.6717.03(0.684, 0.316)5 Comparative Example 7A132.816.6716.73(0.684, 0.316)5Comparative example 8A162.907.4019.51(0.684, 0.315)4Comparative example 9A173.047.6720.75(0.683, 0.317)3Comparative example 10A203.067.6020.44(0.684, 0.316)3Comparative example 11A212.877.4719.82(0.683, 0.318)3Comparative example 12A243.017.5420.13(0.685, 0.314)3Comparative example 13A252.755.7419.20(0.684, 0.315)4Comparative example 14A292.566.3417.96(0.685, 0.315)4Comparative example 15A372.735.6018.89(0.683, 0.318)4Comparative example 16A412.666.7013.38(0.684, 0.315)12Comparative example 17A582.645.3415.39(0.683, 0.318)9Comparative example 18A662.555.6015.73(0.680, 0.319)9Comparative example 19A692.726.2714.39(0.684, 0.316)11Comparative example 20A742.735.7416.06(0.685, 0.315)8Comparative example 21A782.786.3414.72(0.683, 0.317)10Comparative example 22A882.556.6014.05(0.684, 0.315)11Comparative example 23A912.676.0015.06(0.684, 0.316)10Comparative example 24A932.797.4016.40(0.683, 0.318)8Comparative example 25A982.636.6713.72(0.685, 0.314)12Comparative example 26A1012.567.6012.38(0.684, 0.315)6Comparative example 27A1062.567.6712.05(0.685, 0.315)6Comparative example 28A1 182.65 7.54 12.71 (0.683, 0.318)7Comparative example 29A1 192.67 7.47 13.05 (0.684, 0.316)7Comparative example 30C7 2.23.44 1.25 (0.684, 0.316)60Comparative example 31C9 2.21 3.32 42.90 (0.685, 0.314)64Comparative example 32C1 12.23.25 43.73 (0.684, 0.315)65Comparative example 33C20 2.22 3.48 39.19 (0.684, 0.316)51Comparative example 34C242.173.345.38(0.684, 0.316)65Comparative example 35C272.193.2344.55(0.684, 0.316)61Comparative example 36C512.183.4141.04(0.684, 0.316)57Comparative example 37C522.243.5138.98(0.684, 0.315)50Comparative example 38C542.23.3542.08(0.683, 0.317)62Comparative example 39C552.23.4439.39(0.684, 0.316)51Comparative example 40C672.383.837.74(0.683, 0.318)46Comparative example 41C922.43.8237.54(0.685, 0.314)45Comparative example 42C992.253.538.78(0.684, 0.315)49Comparative example 43C1002.233.5238.57(0.685, 0.315)48Comparative example 44C1072.4437.13(0.683, 0.318)44Comparative example 45C1192.414.136.92(0.684, 0.315)44Comparative example 46C1222.393.8837.33(0.683, 0.318)45Comparative example 47C1312.313.5838.16(0.680, 0.319)47Comparative example 48C1322.293.637.95(0.684, 0.316)47Comparative example 49C1342.33.5838.36(0.685, 0.315)48Comparative example 50C1432.23.344.55(0.683, 0.317)81Comparative example 51C1452.193.3543.73(0.684, 0.316)72Comparative example 52N2.926.7533.92(0.684, 0.315)7Comparative example 53O2.163.2935.06(0.684, 0.315)39Comparative example 54P2.183.2235.27(0.683, 0.317)39Comparative example 55Q2.193.2434.86(0.684, 0.315)39Comparative example 56R2.203.3134.65(0.684, 0.315)39Comparative example 57S2.193.3434.24(0.684, 0.316)39Comparative example 58T2.163.2834.44(0.684, 0.316)41Comparative example 59U2.183.2134.65(0.684, 0.315)40Comparative example 60V2.163.2834.24(0.684, 0.315)41Comparative example 61W2.183.2133.83(0.683, 0.317)41Comparative example 62X2.193.2333.91(0.684, 0.315)42Comparative example 63Y2.203.3033.62(0.684, 0.315)42Comparative example 64Z2.193.3333.41(0.684, 0.316)42.

[0416] 1st host (P) 2nd host (N) ratio (P:N) driving voltage (V) op )Efficiency (cd / A)Color coordinates (x, y)Lifespan (T 90) Comparative example 65A17C241:13.9154.80(0.684, 0.316)81 Comparative example 66A17C111:13.8552.81(0.684, 0.315)82 Comparative example 67A17C1321:14.2745.83(0.684, 0.316)59 Comparative example 68A17C671:14.5145.58(0.684, 0.316)58 Comparative example 69A17C921:14.5345.33(0.684, 0.316)57 Comparative example 70A21C241:13.8854.08(0.685, 0.315)83Comparative example 71A21C111:13.8352.11(0.684, 0.316)84Comparative example 72A21C1321:14.2445.23(0.683, 0.318)60Comparative example 73A21C671:14.4744.98(0.685, 0.314)59Comparative example 74A21C921:14.5044.74(0.684, 0.315)59Comparative example 75A25C241:13.6453.60(0.685, 0.315)85Comparative example 76A25C111:13.5851.65(0.683, 0.318)85Comparative example 77A25C1321:13.9744.83(0.683, 0.317)61Comparative example 78A25C671:14.1944.59(0.684, 0.316)60Comparative example 79A25C921:14.2144.35(0.683, 0.317)59Comparative example 80A106C241:13.9148.08(0.684, 0.316)93Comparative example 81A106C111:13.8546.33(0.683, 0.317)94Comparative example 82A106C1321:14.2740.21(0.684, 0.316)67Comparative example 83A106C671:14.5139.99(0.683, 0.317)66Comparative example 84A106C921:14.5339.77(0.684, 0.316)65Comparative example 85A98C241:13.7749.37(0.683, 0.318)120Comparative example 86A98C111:13.7147.57(0.683, 0.317)121Comparative example 87A98C1321:14.1141.29(0.684, 0.316)86Comparative example 88A98C671:14.3441.07(0.683, 0.317)85Comparative example 89A98C921:14.3740.84(0.684, 0.316)84Comparative example 90A41C241:13.7849.11(0.683, 0.317)122Comparative example 91A41C111:13.7247.33(0.684, 0.316)123Comparative example 92A41C1321:14.1241.08(0.683, 0.317)88Comparative example 93A41C671:14.3540.85(0.684, 0.316)87Comparative example 94A41C921:14.3740.63(0.683, 0.318)86.

[0417] 1st host (P1) 2nd host (P2) 3rd host (N) ratio (P1:P2:N) driving voltage (V) op )Efficiency (cd / A)Color coordinates (x, y)Lifespan (T 90) Example 1 A17B29C24 1:1:14.76 7.19 (0.684, 0.316) 181 Example 2 A17B29C4 1:1:14.86 9.91 (0.684, 0.316) 179 Example 3 A25B29C 111:1:14.33 73.93 (0.684, 0.315) 192 Example 4 A25B86C 111:1:14.23 72.87 (0.684, 0.316) 220 Example 5 A106B4C9 1:1:14.76 1.65 (0.684, 0.316) 213 Example 6A106B76C91:1:14.661.40(0.684, 0.315)192 Example 7A41B4C71:1:14.5362.64(0.684, 0.316)303 Example 8A41B4C11:1:14.861.40(0.684, 0.316)240 Example 9A62B4C71:1:14.5663.55(0.684, 0.316)240 Example 10A17B41C541:1:14.5983.35(0.684, 0.316)198 Example 11A84B41C541:1:14.675.84(0.684, 0.316)179 Example 12A25B44C71:1:14.1885.51(0.685, 0.315)207 Example 13A25B44C541:1:14.2373.54(0.685, 0.315)180 Example 14A106B45C241:1:14.5475.70(0.684, 0.316)246 Example 15A106B45C371:1:14.370.72(0.685, 0.315)220 Example 16A116B45C241:1:14.5871.27(0.685, 0.315)209 Example 17A106B45C141:1:14.4372.93(0.684, 0.316)239 Example 18A106B45C151:1:14.3973.95(0.684, 0.316)203 Example 19A41B61C111:1:14.2576.20(0.683, 0.318)341 Example 20A41B61C711:1:14.4573.87(0.684, 0.316)275 Example 21A41B61C721:1:14.5271.29(0.683, 0.318)192Example 22A20B41C1341:1:14.6780.68(0.685, 0.314)182 Example 23A22B41C1341:1:14.5281.80(0.684, 0.316)172 Example 24A37B44C1311:1:14.2383.21(0.684, 0.315)194 Example 25A101B45C1221:1:14.7671.39(0.685, 0.315)229 Example 26A110B45C1221:1:14.7861.53(0.683, 0.318)194 Example 27A136B45C1221:1:14.762.44(0.685, 0.315)189 Example 28A98B61C1311:1:14.3873.37(0.683, 0.318)312 Example 29A17B41C1221:1:14.8180.53(0.683, 0.317)176 Example 30A17B45C1221:1:14.778.53(0.683, 0.318)180 Example 31A25B44C1071:1:14.4383.05(0.684, 0.316)188 Example 32A31B44C1071:1:14.3183.19(0.683, 0.317)179 Example 33A106B45C921:1:14.7571.03(0.683, 0.317)222 Example 34A106B45C171:1:14.671.60(0.683, 0.317)180 Example 35A106B45C421:1:14.5872.73(0.684, 0.316)189 Example 36A41B61C671:1:14.4872.63(0.684, 0.316)317 Example 37A63B61C671:1:14.5370.58(0.683, 0.317)260 Example 38A17B44C241:1:14.5590.26(0.684, 0.316)202 Example 39A17B64C241:1:14.4588.66(0.683, 0.317)210 Example 40A20B44C111:1:14.5288.82(0.684, 0.316)205 Example 41A24B45C271:1:14.4887.14(0.684, 0.316)209 Example 42A21B101C1431:1:14.5885.19(0.684, 0.316)237 Example 43A41B101C1451:1:14.4475.23(0.684, 0.316)351 Example 44A64B101C1451:1:14.3472.31(0.683, 0.317)315 Example 45A98B119C241:1:14.3576.45(0.684, 0.316)336 Example 46A98B119C691:1:14.2573.24(0.684, 0.316)280 Example 47A41B44C241:1:14.3579.41(0.684, 0.316)334 Example 48A41B44C891:1:14.2974.91(0.683, 0.317)276 Example 49A98B101C1451:1:14.4375.70(0.684, 0.316)344 Example 50A17B44C242:1:14.5588.46(0.684, 0.316)206 Example 51A17B44C241:2:14.5589.36(0.684, 0.316)200 Example 52A17B44C241:1:24.5592.97(0.684, 0.316)203 Example 53A17B44C241:1:34.5590.09(0.684, 0.316)200 Example 54A17B44C241:2:24.5590.09(0.684, 0.316)194 Example 55A20B44C111:1:24.5291.48(0.684, 0.316)206 Example 56A41B101C1452:1:14.4473.72(0.684, 0.316)358 Example 57A41B101C1451:2:14.4474.47(0.684, 0.316)348 Example 58A41B101C1451:1:24.4477.47(0.684, 0.316)353 Example 59A98B101C1451:1:24.4377.98(0.684, 0.316)345Comparative Example 95OB4C241:1:14.4347.13(0.684, 0.316)113Comparative Example 96PB4C541:1:14.4345.81(0.684, 0.315)111Comparative Example 97NB4C921:1:14.6246.32(0.684, 0.316)103Comparative Example 98QB29C1341:1:14.6044.94(0.684, 0.316)102Comparative Example 99RB29C671:1:14.7244.59(0.684, 0.316)101Comparative example 100OB29C1451:1:14.5347.31(0.684, 0.316)121Comparative example 101NB29C541:1:14.6247.21(0.685, 0.315)118Comparative example 102PB41C271:1:14.2553.52(0.685, 0.315)125Comparative example 103QB44C541:1:14.2955.8(0.684, 0.316)127Comparative example 104RB45C1311:1:14.4052.83(0.683, 0.318)120Comparative example 105OB61C921:1:14.4452.39(0.685, 0.314)118Comparative example 106PB101C1431:1:14.3354.75(0.684, 0.315)146Comparative example 107SB4C111:1:14.4346.08(0.685, 0.315)114Comparative example 108TB29C541:1:14.5246.34(0.683, 0.318)115Comparative example 109UB4C1321:1:14.5343.81(0.683, 0.317)100Comparative example 110VB4C1221:1:14.6743.36(0.684, 0.316)99Comparative example 111SB29C1451:1:14.5546.96(0.683, 0.317)121Comparative example 112TB119C91:1:14.3153.52(0.684, 0.316)136Comparative example 113UB41C541:1:14.3052.22(0.684, 0.316)127Comparative example 114VB44C1341:1:14.2956.59(0.684, 0.316)142Comparative example 115SB45C1071:1:14.5952.22(0.684, 0.316)118Comparative example 116NB44C1341:1:14.6456.77(0.684, 0.316)139Comparative example 117TB61C1431:1:14.2255.11(0.684, 0.316)147Comparative example 118WB29C241:1:14.4747.48(0.684, 0.316)117Comparative example 119XB29C541:1:14.5046.11(0.684, 0.316)116Comparative example 120YB29C1311:1:14.6344.33(0.684, 0.316)104Comparative example 121ZB4C921:1:14.6743.1(0.684, 0.316)101Comparative example 122WB4C1451:1:14.4245.9(0.684, 0.316)120Comparative example 123XB119C271:1:14.2554(0.684, 0.316)134Comparative example 124YB101C541:1:14.3953(0.684, 0.315)134Comparative example 125ZB61C1321:1:14.3651.86(0.685, 0.315)121Comparative example 126WB45C671:1:14.4552.3(0.683, 0.318)121Comparative example 127XB44C1451:1:14.2956.1(0.683, 0.317)136Comparative example 128VB44C1342:1:14.2955.45(0.684, 0.316)145Comparative example 129VB44C1341:2:14.2956.03(0.683, 0.317)141Comparative example 130VB44C1341:1:24.2958.29(0.684, 0.316)143Comparative example 131VB44C1341:1:34.2956.47(0.684, 0.316)141.

[0418] As can be seen from the results in Tables 14 to 16 above, when the organic layer of an organic light-emitting device is deposited by mixing three types of compounds according to the present application, it was confirmed that the efficiency and / or lifespan of the organic light-emitting device is improved.

[0419] Specifically, among the compounds of the above chemical formulas 1 to 3, the compound of chemical formula 1 is characterized by a relatively long lifespan, the compound of chemical formula 2 provides high efficiency, and the compound of chemical formula 3 is a unipolar N-host with fast electron mobility. When these three compounds are mixed in an appropriate ratio and used as a material for a device, it can be confirmed that the efficiency and lifespan of the device are improved.

[0420] The core structure of Comparative Example Compound N is formed by combining R3 and R4 in Chemical Formula 1 of the present invention to form a benzene ring, and unlike the present invention, it has a substituent at R1. In the case of Comparative Example 52, which used this as a material for a device, it was confirmed that not only was the operating voltage very high, but the lifespan was also significantly reduced.

[0421] In addition, when a compound containing an azine group and an amine group, such as comparative compounds O to Z, is used in combination with the compound of chemical formula 3 of the present invention, the charge balance is broken, resulting in a decrease in efficiency or lifespan.

Claims

1. A compound of the following chemical formula 1; A compound of the following chemical formula 2; and A composition for an organic layer of an organic light-emitting device comprising a compound of the following chemical formula 3: [Chemical Formula 1] In the above chemical formula 1, X is O; or S, R1 and R2, R2 and R3, or R3 and R4 combine to form a substituted or unsubstituted benzene ring, When R3 and R4 combine to form a substituted or unsubstituted benzene ring, R1 is hydrogen; or deuterium, The remainder of R1 to R4 and one of R5 to R8 is -(L1)l1-N(Ar1)(Ar2), and the other is -(L2)l2-Ar3, The remainder of R1 to R8 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl 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; or a substituted or unsubstituted C2 to C60 heteroaryl group, L1 and L2 are each independently a direct bond; or a substituted or unsubstituted C6 to C60 arylene group, l1 and l2 are each integers from 1 to 3, and if each is 2 or greater, the substituents in each parenthesis are the same or different, Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, Ar3 is a substituted or unsubstituted C6 to C60 aryl group, [Chemical Formula 2] In the above chemical formula 2, L11 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, l11 is an integer from 1 to 3, and if it is 2 or greater, L11 is equal or different, R11 is a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl 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; or a substituted or unsubstituted silyl group, Any one of R12 to R19 is a substituted or unsubstituted carbazole group, or two adjacent groups of R12 to R19 are combined to form a substituted or unsubstituted C2 to C30 heterocycle, The remainder of R12 to R19 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl 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; or a substituted or unsubstituted C2 to C60 heteroaryl group, [Chemical Formula 3] In the above chemical formula 3, Y is O; or S, Any one of R21 to R28 is -(L21)l21-(N-Het), L21 is a direct bond; or a substituted or unsubstituted C6 to C60 arylene group, l21 is an integer from 1 to 3, and if it is 2 or greater, L21 is equal or different, N-Het is a substituted or unsubstituted heteroaryl group containing a C=N bond, The remainder of R21 to R28 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted phosphine oxide group.

2. In claim 1, the chemical formula 1 is a composition for an organic layer of an organic light-emitting device represented by any one of the following chemical formulas 1-1 to 1-3: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] In chemical formulas 1-1 to 1-3, One of S1 and S2 is -(L1)l1-N(Ar1)(Ar2), and the other is -(L2)l2-Ar3, H1 to H3 are each independently hydrogen; or deuterium, m is an integer from 1 to 3, n is an integer from 1 to 5, o is 1 or 2, p is an integer from 1 to 4, q is an integer from 1 to 6, and when o is 2 or m, n, p and q are each 2 or greater, the substituents in each parenthesis are the same or different, The definitions of X, L1, L2, l1, l2, and Ar1 to Ar3 are the same as those in the above chemical formula 1.

3. A composition for an organic layer of an organic light-emitting device, wherein in claim 1, Ar3 is an aryl group having C6 to C20 substituted or unsubstituted with deuterium.

4. A composition for an organic layer of an organic light-emitting device, wherein the weight ratio of the compound of the chemical formula 1 and the compound of the chemical formula 3 and the weight ratio of the compound of the chemical formula 2 and the compound of the chemical formula 3 are each 1:1 to 1:5 in claim 1.

5. A composition for an organic layer of an organic light-emitting device, wherein the deuterium substitution rate of each of the compounds of Chemical Formulas 1 to 3 in claim 1 is 0% or more than 0% and less than or equal to 100%.

6. In claim 1, a composition for an organic layer of an organic light-emitting device, wherein the chemical formula 1 is represented by any one of the following compounds: .

7. In claim 1, a composition for an organic layer of an organic light-emitting device, wherein the chemical formula 2 is represented by any one of the following compounds: .

8. In claim 1, a composition for an organic layer of an organic light-emitting device, wherein the chemical formula 3 is represented by any one of the following compounds: .

9. 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 composition for an organic layer of an organic light-emitting device according to any one of claims 1 to 8.

10. An organic light-emitting device according to claim 9, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes a composition for an organic layer of the organic light-emitting device.

11. Step for preparing the substrate; A step of forming a first electrode on the substrate; A step of forming one or more organic layers on the first electrode; and A method for manufacturing an organic light-emitting device, comprising the step of forming a second electrode on the organic layer, A method for manufacturing an organic light-emitting device, wherein the step of forming the organic layer includes a step of forming one or more organic layers using the composition for an organic layer of an organic light-emitting device according to claim 1.

12. In claim 11, A method for manufacturing an organic light-emitting device, wherein the step of forming the organic layer includes the step of premixing a composition for the organic layer of the organic light-emitting device and depositing it using one source.

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