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

Abstract

Provided in the preset specification are a compound represented by chemical formula 1, and an organic light-emitting element and a composition for an organic material layer of an organic light-emitting element each comprising the compound. The compound described in the present specification, when used in an organic light-emitting element, can lower the driving voltage of the device, improve the luminescence efficiency, and enhance the lifespan characteristics of the device.

Description

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

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

[0002] This application claims the benefit of Korean Patent Application No. 10-2023-0162376 filed with the Korean Intellectual Property Office on November 21, 2023, the entire contents of which are incorporated herein by reference.

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

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

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

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

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

[0008] The present specification provides a compound, an organic light-emitting device, and a composition for an organic layer of an organic light-emitting device.

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

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] X1 to X3 are the same or different from each other, and are each independently N or CRa, but at least one of X1 to X3 is N,

[0014] Ra is selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; -P(=O)R R'; and -SiR R'R",

[0015] Ar1 to Ar3 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group containing at least one heteroatom selected from O and S; or a combination thereof,

[0016] L1 and L2 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0017] R1 and R4 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR',

[0018] R2 and R3 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR', or two or more adjacent groups combine with each other to form a substituted or unsubstituted ring,

[0019] The above R, R' and R" are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0020] a is an integer from 0 to 2,

[0021] Each of b and c is an integer from 0 to 4,

[0022] d is an integer from 0 to 5,

[0023] Each m and n is an integer from 0 to 4,

[0024] If each of a, b, c, d, m and n is an integer greater than or equal to 2, the substituents within the parentheses are the same or different.

[0025] Another embodiment of the present specification provides an organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the compound.

[0026] Another embodiment of the present specification provides a composition for an organic layer of an organic light-emitting device comprising the compound and a heterocyclic compound represented by the following chemical formula 2 or 3.

[0027] [Chemical Formula 2]

[0028]

[0029] [Chemical Formula 3]

[0030]

[0031] In the above chemical formulas 2 and 3,

[0032] R11, R12, R22 and R23 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR',

[0033] L11, L12, L22 and L23 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0034] Ar11, Ar12, Ar22 and Ar23 are the same or different from each other, and each independently represents a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R",

[0035] The above R, R' and R" are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0036] Each of a11 and a12 is an integer from 0 to 7,

[0037] a22 is an integer from 0 to 6,

[0038] a23 is an integer from 0 to 4,

[0039] Each of p11, p12, p22 and p23 is an integer from 0 to 4,

[0040] Each of q11, q12, q22 and q23 is an integer from 1 to 4,

[0041] When each of a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 is 2 or more, the substituents in the parentheses are the same or different from each other.

[0042] The compound of chemical formula 1 described herein may have low driving voltage, high luminous efficiency, and / or long life characteristics when used in an organic light-emitting device.

[0043] Specifically, with the benzene core as the center, the first substituent (N of carbazole directly bonded to the benzene core) acts as a strong donor and HOMO within the molecule, and the second substituent (heterocycle composed of X1 to X3) acts as a LUMO within the molecule, and as a strong electron acceptor, effectively pulls electrons from the strong donor of the carbazole and the bonded sub-donor of the benzene core to stabilize electrons within the molecule and thereby improve the lifetime. In particular, when both the strong donor of the first substituent and the strong acceptor of the second substituent are directly bonded within the molecule, a decrease in lifetime may occur due to the overlap of HOMO-LUMO, but the overlap of HOMO-LUMO can be offset by introducing the benzene core between them.

[0044] In addition, since the second and fourth substituents (phenyl groups) are fixed and positioned Para to the benzene core, the electrons are stabilized by the expansion of the LUMO, which can further improve the lifespan. In addition, as the third substituent (Ar3) is added to the benzene core, the HOMO and LUMO are separated, and the second or third substituent positioned ortho or meta to the first substituent causes them to become spatially closer, which can efficiently cause charge transfer, thereby increasing the efficiency.

[0045] That is, the compound represented by the above chemical formula 1 can have its n-type characteristics strengthened by bonding a benzene core-centered, a substituent of an azine group (second substituent) and a phenyl group (fourth substituent) in a para form, and further bonding a carbazole group (first substituent) and Ar3. In addition, when a heterocyclic compound of the above chemical formula 2 of the above chemical formula 2 or the above chemical formula 3 of the above chemical formula 3 with enhanced donor characteristics of the above chemical formula 2 or the above chemical formula 3 having a specific substituent and a biscarbazole type and a fused type are included together with the compound of the above chemical formula 1 and applied to an organic light-emitting device, the driving voltage of the device can be further lowered, the luminous efficiency can be further improved, and the thermal stability can be further secured, thereby further improving the lifespan characteristics of the device.

[0046] Figures 1 to 3 are drawings each exemplifying a laminated structure of an organic light-emitting device according to one embodiment of the present specification.

[0047] 100: Substrate

[0048] 200: Bipolar

[0049] 300: Organic layer

[0050] 301: Hole injection layer

[0051] 302: Hole transport layer

[0052] 303: Emissive layer

[0053] 304: Hole-locking layer

[0054] 305: Electron transport layer

[0055] 306: Electron injection layer

[0056] 400: Cathode

[0057] Hereinafter, the present specification will be described in more detail.

[0058] In this specification, when a part is said to "include" a component, this means that it may include other components, but not to the exclusion of other components, unless specifically stated otherwise.

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

[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 specification, “when no substituent is indicated in the chemical formula or compound structure” may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the deuterium content may be 0% to 100%.

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

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

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

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

[0069]

[0070] Additionally, in one embodiment of the present specification, “a phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain a deuterium atom, i.e., has 5 hydrogen atoms.

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

[0072] In the present specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 40 carbon atoms, and more specifically 1 to 20 carbon atoms. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, Examples include, but are not limited to, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

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

[0075] In the present specification, the alkoxy group may be straight chain, branched chain, or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.

[0076] In the present specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The cycloalkyl group may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. Specifically, there are, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc.

[0077] In the present specification, the heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

[0078] In the present specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. The aryl group includes a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the above aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof.

[0079] In this specification, the terphenyl group may be selected from the following structures.

[0080]

[0081] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0082] When the above fluorenyl group is substituted, it may be selected from the following structures, but is not limited thereto.

[0083]

[0084] In the present specification, the heteroaryl group includes S, O, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic ring means a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.Specific examples of the above heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a deoxynyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinozolinyl group, a naphthyridyl group, an acridinyl group, a phenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenyl group, Triazindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole) group, dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiathiazinyl group, Examples thereof include, but are not limited to, a phthalazinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzo[c][1,2,5]thiadiazolyl group, a 2,3-dihydrobenzo[b]thiophene group, a 2,3-dihydrobenzofuran group, a 5,10-dihydrodibenzo[b,e][1,4]azasilinyl group, a pyrazolo[1,5-c]quinazolinyl group, a pyrido[1,2-b]indazolyl group, a pyrido[1,2-a]imidazo[1,2-e]indolinyl group, and a 5,11-dihydroindeno[1,2-b]carbazolyl group.

[0085] In the present specification, when the substituent is a carbazole group, it means that it is bonded to the nitrogen or carbon of the carbazole.

[0086] In the present specification, when a carbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole.

[0087] In the present specification, the benzocarbazole group may have any of the following structures.

[0088]

[0089] In the present specification, the dibenzocarbazole group may have any of the following structures.

[0090]

[0091] In the present specification, the naphthobenzofuran group may have any of the following structures.

[0092]

[0093] In the present specification, the naphthobenzothiophene group may have any of the following structures.

[0094]

[0095] In the present specification, a silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -Si(R101)(R102)(R103), and R101 to R103 are the same as or different from each other, and may each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group.

[0096] A specific example of a cylinder is (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), but is not limited thereto.

[0097] In the present specification, the phosphine oxide group is represented by -P(=O)(R104)(R105), and R104 and R105 are the same or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. Specifically, it can be substituted with an alkyl group or an aryl group, and the above-described examples can be applied to the alkyl group and the aryl group. For example, the phosphine oxide group includes, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like.

[0098] In the present specification, the amine group is represented by -N(R106)(R107), and R106 and R107 are the same or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. The amine group can be selected from the group consisting of -NH2; a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group.

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

[0100] In this specification, the heteroarylene group may be applied to the examples of the heteroaryl group described above, except that it is a divalent group.

[0101] As used herein, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

[0102] Hydrocarbon rings and heterocycles that adjacent groups can form include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles, and structures exemplified by the aforementioned cycloalkyl groups, aryl groups, heterocycloalkyl groups, and heteroaryl groups can be applied to the rings, except that they are not monovalent groups.

[0103] One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[0104] [Chemical Formula 1]

[0105]

[0106] In the above chemical formula 1, the description of each substituent is as described above.

[0107] The compound according to the above embodiment may have low driving voltage, high luminous efficiency, and / or long life characteristics when used in an organic light-emitting device.

[0108] Specifically, with the benzene core as the center, the first substituent (N of carbazole directly bonded to the benzene core) acts as a strong donor and HOMO within the molecule, and the second substituent (heterocycle composed of X1 to X3) acts as a LUMO within the molecule, and as a strong electron acceptor, effectively pulls electrons from the strong donor of the carbazole and the bonded sub-donor of the benzene core to stabilize electrons within the molecule and thereby improve the lifetime. In particular, when both the strong donor of the first substituent and the strong acceptor of the second substituent are directly bonded within the molecule, a decrease in lifetime may occur due to the overlap of HOMO-LUMO, but the introduction of the benzene core between them can offset the overlap of HOMO-LUMO.

[0109] In addition, since the second and fourth substituents (phenyl groups) are fixed and positioned Para to the benzene core, the electrons are stabilized by the expansion of the LUMO, which can further improve the lifespan. In addition, as the third substituent (Ar3) is added to the benzene core, the HOMO and LUMO are separated, and the second or third substituent positioned ortho or meta to the first substituent causes them to become spatially closer, which can efficiently cause charge transfer, thereby increasing the efficiency.

[0110] That is, the compound represented by the above chemical formula 1 can have its n-type characteristics strengthened by bonding a benzene core-centered, a substituent of an azine group (second substituent) and a phenyl group (fourth substituent) in a para form, and further bonding a carbazole group (first substituent) and Ar3. In addition, when a heterocyclic compound of the above chemical formula 2 of the above chemical formula 2 or the above chemical formula 3 of the above chemical formula 3 with enhanced donor characteristics of the above chemical formula 2 or the above chemical formula 3 having a specific substituent and a biscarbazole type and a fused type are included together with the compound of the above chemical formula 1 and applied to an organic light-emitting device, the driving voltage of the device can be further lowered, the luminous efficiency can be further improved, and the thermal stability can be further secured, thereby further improving the lifespan characteristics of the device.

[0111] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-6.

[0112] [Chemical Formula 1-1]

[0113]

[0114] [Chemical Formula 1-2]

[0115]

[0116] [Chemical Formula 1-3]

[0117]

[0118] [Chemical Formula 1-4]

[0119]

[0120] [Chemical Formula 1-5]

[0121]

[0122] [Chemical Formula 1-6]

[0123]

[0124] In the above chemical formulas 1-1 to 1-6,

[0125] Each of X1 to X3, L1, L2, Ar1 to Ar3, R1 to R4, a, b, c, d, m and n are as defined in the above chemical formula 1.

[0126] In one embodiment of the present specification, Ra may be selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; -P(=O)R R'; and -SiR R'R".

[0127] In one embodiment of the present specification, Ra may be selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; -P(=O)R R'; and -SiR R'R".

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

[0129] In one embodiment of the present specification, X2 may be N, and X1 and X3 may each be CRa.

[0130] In one embodiment of the present specification, X3 may be N, and X1 and X2 may each be CRa.

[0131] In one embodiment of the present specification, X1 and X2 may be N, and X3 may be CRa.

[0132] In one embodiment of the present specification, X2 and X3 may be N, and X1 may be CRa.

[0133] In one embodiment of the present specification, X1 and X3 may be N, and X2 may be CRa.

[0134] In one embodiment of the present specification, X1 to X3 may all be N.

[0135] In one embodiment of the present specification, Ar1 to Ar3 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group including at least one heteroatom selected from O and S; or a combination thereof.

[0136] In one embodiment of the present specification, Ar1 to Ar3 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group including at least one heteroatom selected from O and S; or a combination thereof.

[0137] In one embodiment of the present specification, Ar1 to Ar3 may be the same as or different from each other, and may each independently be a C6 to C20 aryl group unsubstituted or substituted with deuterium; a C2 to C20 heteroaryl group containing at least one heteroatom selected from O and S and unsubstituted or substituted with deuterium or an aryl group; or a combination thereof.

[0138] In one embodiment of the present specification, Ar1 to Ar3 may be the same or different from each other, and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a combination thereof.

[0139] In one embodiment of the present specification, Ar1 to Ar3 may be the same as or different from each other, and 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; a dibenzofuranyl group substituted or unsubstituted with deuterium or a phenyl group; a dibenzothiophenyl group substituted or unsubstituted with deuterium or a phenyl group; or a combination thereof.

[0140] In one embodiment of the present specification, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0141] In one embodiment of the present specification, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0142] In one embodiment of the present specification, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group containing at least one heteroatom selected from O and S.

[0143] In one embodiment of the present specification, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted dibenzofuranylene group; or a substituted or unsubstituted dibenzothiophenylene group.

[0144] In one embodiment of the present specification, R1 and R4 are the same or different from each other, and can each independently be selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0145] In one embodiment of the present specification, R1 and R4 are the same or different from each other, and can each independently be selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0146] In one embodiment of the present specification, R1 and R4 are the same or different from each other, and each independently may be hydrogen or deuterium.

[0147] In one embodiment of the present specification, R2 and R3 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR', or two or more adjacent groups may combine with each other to form a substituted or unsubstituted ring.

[0148] In one embodiment of the present specification, R2 and R3 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 aromatic heterocycle.

[0149] In one embodiment of the present specification, R2 and R3 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 aromatic heterocycle.

[0150] In one embodiment of the present specification, R2 and R3 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a C6 to C30 aryl group unsubstituted or substituted with deuterium; and a C2 to C30 heteroaryl group containing at least one heteroatom selected from N, O, and S and unsubstituted or substituted with deuterium, or two or more adjacent groups may combine with each other to form a C6 to C30 aromatic hydrocarbon ring unsubstituted or substituted with deuterium, or a C2 to C30 aromatic heterocycle containing at least one heteroatom selected from N, O, and S and unsubstituted or substituted with deuterium or an aryl group.

[0151] In one embodiment of the present specification, R2 and R3 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted indole ring; a substituted or unsubstituted benzofuran ring; or a substituted or unsubstituted benzothiophene ring.

[0152] In one embodiment of the present specification, R2 and R3 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted N-carbazole group; a substituted or unsubstituted dibenzofuranyl group; and a substituted or unsubstituted dibenzothiophenyl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted indole ring; a substituted or unsubstituted benzofuran ring; or a substituted or unsubstituted benzothiophene ring.

[0153] In one embodiment of the present specification, R2 and R3 are the same or different, and are each independently selected from the group consisting of hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a carbazole group substituted or unsubstituted with deuterium; a dibenzofuranyl group substituted or unsubstituted with deuterium; and a dibenzothiophenyl group substituted or unsubstituted with deuterium, or two or more adjacent groups may combine with each other to form an indole ring substituted or unsubstituted with deuterium or a phenyl group; a benzofuran ring substituted or unsubstituted with deuterium; or a benzothiophene ring substituted or unsubstituted with deuterium.

[0154] In one embodiment of the present specification, R, R' and R" are the same as or different from each other, and each independently may be hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0155] In one embodiment of the present specification, R, R' and R" are the same as or different from each other, and each independently may be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0156] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 1% to 100%.

[0157] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 10% to 100%.

[0158] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 20% to 100%.

[0159] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 30% to 100%.

[0160] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 60% to 100%.

[0161] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 80% to 100%.

[0162] In one embodiment of the present specification, the deuterium content of the compound of the chemical formula 1 may be 0% or 90% to 100%.

[0163] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following.

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180] In addition, by introducing various substituents into the structure of the above chemical formula 1, a compound having the unique characteristics of the introduced substituent can be synthesized. For example, by introducing a substituent mainly used in hole injection layer material, hole transport layer material, hole transport auxiliary layer material, light emitting layer material, electron transport layer material, electron transport auxiliary layer material, and charge generation layer material used in the manufacture of organic light emitting devices into the above core structure, a material satisfying the conditions required for each organic layer can be synthesized.

[0181] In addition, by introducing various substituents into the structure of the above chemical formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic substances and changing the use of the material in various ways.

[0182] Another embodiment of the present specification provides an organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the compound (represented by Chemical Formula 1).

[0183] In another embodiment of the present specification, the organic layer including the compound may additionally include a heterocyclic compound represented by the following chemical formula 2 or 3.

[0184] [Chemical Formula 2]

[0185]

[0186] [Chemical Formula 3]

[0187]

[0188] In the above chemical formulas 2 and 3,

[0189] R11, R12, R22 and R23 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR',

[0190] L11, L12, L22 and L23 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0191] Ar11, Ar12, Ar22 and Ar23 are the same or different from each other, and each independently represents a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R",

[0192] The above R, R' and R" are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0193] Each of a11 and a12 is an integer from 0 to 7,

[0194] a22 is an integer from 0 to 6,

[0195] a23 is an integer from 0 to 4,

[0196] Each of p11, p12, p22 and p23 is an integer from 0 to 4,

[0197] Each of q11, q12, q22 and q23 is an integer from 1 to 4,

[0198] When each of a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 is 2 or more, the substituents in the parentheses are the same or different from each other.

[0199] In one embodiment of the present specification, R11, R12, R22 and R23 are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0200] In one embodiment of the present specification, R11, R12, R22 and R23 are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0201] In one embodiment of the present specification, R11, R12, R22 and R23 are the same as or different from each other, and can each independently be selected from the group consisting of hydrogen; deuterium; halogen; cyano group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0202] In one embodiment of the present specification, R11, R12, R22 and R23 are the same or different from each other, and may each independently be hydrogen or deuterium.

[0203] In one embodiment of the present specification, L11, L12, L22 and L23 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0204] In one embodiment of the present specification, L11, L12, L22 and L23 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0205] In one embodiment of the present specification, L11, L12, L22 and L23 may be the same as or different from each other, and may each independently be a direct bond; a C6 to C20 arylene group substituted or unsubstituted with deuterium; or a C2 to C20 heteroarylene group substituted or unsubstituted with deuterium.

[0206] In one embodiment of the present specification, L11, L12, L22 and L23 may be the same as or different from each other, and may each independently be a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; a dibenzofuranylene group substituted or unsubstituted with deuterium; or a dibenzothiophenylene group substituted or unsubstituted with deuterium.

[0207] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 may be the same as or different from each other, and may each independently be a cyano group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or SiRR'R".

[0208] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 may be the same as or different from each other, and may each independently be a cyano group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or SiRR'R".

[0209] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 may be the same as or different from each other, and may each independently be a cyano group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C6 to C30 heteroaryl group; or SiRR'R".

[0210] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 may be the same as or different from each other, and may each independently be a cyano group; a C6 to C20 aryl group substituted or unsubstituted with deuterium; a C2 to C30 heteroaryl group substituted or unsubstituted with deuterium; or SiRR'R".

[0211] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 may be the same as or different from each other, and each independently be a phenyl group unsubstituted or substituted with deuterium or a cyano group; a biphenyl group unsubstituted or substituted with deuterium; a terphenyl group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; a triphenylenyl group unsubstituted or substituted with deuterium; a fluorenyl group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; a spirobifluorenyl group unsubstituted or substituted with deuterium; a dibenzofuranyl group unsubstituted or substituted with deuterium or a phenyl group; a dibenzothiophenyl group unsubstituted or substituted with deuterium or a phenyl group; or a triphenylsilyl group unsubstituted or substituted with deuterium.

[0212] In one embodiment of the present specification, R, R' and R" defined in the chemical formula 2 or 3 may be applied as is to R, R' and R" of the chemical formula 1 described above.

[0213] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0%, or 1% to 100%.

[0214] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0% or 10% to 100%.

[0215] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0% or 20% to 100%.

[0216] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0% or 30% to 100%.

[0217] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0% or 60% to 100%.

[0218] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0% or 80% to 100%.

[0219] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the chemical formula 2 or 3 may be 0% or 90% to 100%.

[0220] In one embodiment of the present specification, the heterocyclic compound represented by the chemical formula 2 or 3 may be represented by any one of the following.

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233] In addition, by introducing various substituents into the structure of the above chemical formula 2 or 3, a heterocyclic compound having the unique characteristics of the introduced substituent can be synthesized. For example, by introducing a substituent mainly used in hole injection layer materials, hole transport layer materials, hole transport auxiliary layer materials, light emitting layer materials, electron transport layer materials, electron transport auxiliary layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices into the core structure, a material satisfying the conditions required for each organic layer can be synthesized.

[0234] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound (represented by Chemical Formula 1).

[0235] In one embodiment of the present specification, the light-emitting layer including the compound (represented by Chemical Formula 1) may additionally include a heterocyclic compound represented by Chemical Formula 2 or 3.

[0236] In one embodiment of the present specification, the organic layer includes at least one layer selected from a hole transport layer, a hole transport auxiliary layer, and an electron blocking layer, and at least one layer selected from the hole transport layer, the hole transport auxiliary layer, and the electron blocking layer may include the compound (represented by Chemical Formula 1).

[0237] In one embodiment of the present specification, at least one layer selected from the hole transport layer, hole transport auxiliary layer, and electron blocking layer including the compound may additionally include a heterocyclic compound represented by the chemical formula 2 or 3.

[0238] In one embodiment of the present specification, the organic light-emitting device may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0239] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0240] In one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0241] In another embodiment of the present specification, the first electrode may be a cathode and the second electrode may be an anode.

[0242] An organic light-emitting device according to one embodiment of the present specification can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using a compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3).

[0243] The compound represented by the above chemical formula 1 (in addition, the heterocyclic compound represented by the above chemical formula 2 or 3) can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0244] In another embodiment of the present specification, the organic light-emitting device may be a red organic light-emitting device, and the compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3) may be used as a material of the red organic light-emitting device. For example, the compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3) may be included in a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, or a light-emitting layer of the red organic light-emitting device.

[0245] In another embodiment of the present specification, the organic light-emitting device may be a green organic light-emitting device, and the compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3) may be used as a material of the green organic light-emitting device. For example, the compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3) may be included in a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, or a light-emitting layer of the green organic light-emitting device.

[0246] In one embodiment of the present specification, the organic light-emitting device may be a blue organic light-emitting device, and the compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3) may be used as a material of the blue organic light-emitting device. For example, the compound represented by the chemical formula 1 (additionally, a heterocyclic compound represented by the chemical formula 2 or 3) may be included in a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, or a light-emitting layer of the blue organic light-emitting device.

[0247] 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 disclosure is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present disclosure.

[0248] 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.

[0249] 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 specification is not limited by such a laminated structure, and, if necessary, layers other than the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0250] For example, the organic layer may further include a hole transport auxiliary layer, and the hole transport auxiliary layer may be included between the hole transport layer (302) and the light-emitting layer (303) based on the laminated structure.

[0251] The organic layer including the compound of the above chemical formula 1 and / or the heterocyclic compound of the above chemical formula 2 or 3 may additionally include other substances as needed.

[0252] In an organic light-emitting device according to one embodiment of the present specification, materials other than the compound of the chemical formula 1 and / or the heterocyclic compound of the chemical formula 2 or 3 are exemplified below, but these are only for exemplification and are not intended to limit the scope of the present specification, and may be replaced with materials known in the art.

[0253] 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.

[0254] 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.

[0255] 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.

[0256] In addition to the compound represented by the above chemical formula 1 and / or the heterocyclic compound represented by the above chemical formula 2 or 3, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used as a hole transport material, and a low-molecular-weight or high-molecular-weight material may also be used.

[0257] 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.

[0258] LiF is a representative example used in the art as an electron injection material, but is not limited thereto.

[0259] As a light-emitting material, in addition to the compound of the above chemical formula 1 and / or the heterocyclic compound of the above chemical formula 2 or 3, a red, green or blue light-emitting material may be used, and if necessary, two or more light-emitting materials may be mixed and used. At this time, two or more light-emitting materials may be deposited and used as individual sources, or may be premixed and deposited and used as a single source. In addition, a fluorescent material may be used as the light-emitting material, but it may also be used as a phosphorescent material. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used as the light-emitting material, but materials in which both a host material and a dopant material participate in light emission may also be used.

[0260] 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.

[0261] 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.

[0262] The compound of the above chemical formula 1 and / or the heterocyclic compound of the above chemical formula 2 or 3 according to an embodiment of the present specification can function in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, etc., by a similar principle to that applied to organic light-emitting devices.

[0263] In addition, by introducing various substituents into the structure of the compound of the above chemical formula 1 and / or the heterocyclic compound of the above chemical formula 2 or 3, it is possible to finely control the energy band gap, while improving the properties at the interface between organic substances and diversifying the uses of the material.

[0264] Another embodiment of the present specification provides a composition for an organic layer of an organic light-emitting device, comprising a compound represented by the above chemical formula 1 and a heterocyclic compound represented by the following chemical formula 2 or 3.

[0265] [Chemical Formula 2]

[0266]

[0267] [Chemical Formula 3]

[0268]

[0269] In the above chemical formulas 2 and 3,

[0270] R11, R12, R22 and R23 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR',

[0271] L11, L12, L22 and L23 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0272] Ar11, Ar12, Ar22 and Ar23 are the same or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R",

[0273] The above R, R' and R" are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0274] Each of a11 and a12 is an integer from 0 to 7,

[0275] a22 is an integer from 0 to 6,

[0276] a23 is an integer from 0 to 4,

[0277] Each of p11, p12, p22 and p23 is an integer from 0 to 4,

[0278] Each of q11, q12, q22 and q23 is an integer from 1 to 4,

[0279] When each of a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 is 2 or more, the substituents in the parentheses are the same or different from each other.

[0280] In one embodiment of the present specification, the definition of the substituent of the chemical formula 2 or 3 can be applied as described in the organic light-emitting device.

[0281] In one embodiment of the present specification, the weight ratio of the compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 2 or 3 may be 1:10 to 10:1.

[0282] In one embodiment of the present specification, the weight ratio of the compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 2 or 3 may be 1:5 to 5:1.

[0283] In one embodiment of the present specification, the weight ratio of the compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 2 or 3 may be 1:3 to 3:1.

[0284] In one embodiment of the present specification, a method for manufacturing an organic light-emitting device is provided, comprising: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, wherein the forming of the organic layer comprises forming one or more organic layers using a composition for an organic layer of an organic light-emitting device, the composition including a compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 2 or 3.

[0285] In one embodiment of the present specification, a method for manufacturing an organic light-emitting device is provided, wherein the step of forming the organic layer comprises pre-mixing a compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 2 or 3 and forming the organic layer using a thermal vacuum deposition method.

[0286] The above pre-mixing means that the compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 2 or 3 (optionally, other additional compounds) are mixed in one container before being deposited on the organic layer.

[0287] The above-mentioned pre-mixed material may be referred to as a composition for an organic layer of an organic light-emitting device according to one embodiment of the present specification.

[0288] 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.

[0289] Manufacturing example

[0290] <Manufacturing Example 1> Manufacturing of target compound 1-1, etc.

[0291]

[0292] 1) Preparation of compound 1-1-3

[0293] 10 g (31.51 mmol) of the above compound 1-1-4, 12.8 g (34.66 mmol) of (A) 9H-carbazole, and 8.71 g (63.02 mmol) of Cs2CO3 were dissolved in 100 mL of DMA and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 13.1 g (96.07%) of the target compound 1-1-3 was obtained with methanol.

[0294] 2) Preparation of compound 1-1-2

[0295] 13.1 g (30.27 mmol) of the above compound 1-1-3, 4.14 g (33.3 mmol) of (B) phenyl boronic acid, 41.75 g (1.51 mmol) of Pd(PPh3), and 8.37 g (60.54 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the product, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) and 10.8 g (92.98%) of the target compound 1-1-2 was obtained with methanol.

[0296] 3) Preparation of compound 1-1-1

[0297] 10.8 g (30.47 mmol) of the above compound 1-1-2, 11.61 g (45.7 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 31.4 g (1.52 mmol) of Pd2(dba), 1.45 g (3.05 mmol) of Xphos, and 5.98 g (60.94 mmol) of KOAc were dissolved in 150 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) to obtain 10.5 g (77.09%) of the target compound 1-1-1.

[0298] 4) Preparation of target compound 1-1

[0299] 10.5 g (19.61 mmol) of the above compound 1-1-1, 5 g (18.68 mmol) of (C) 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.03 g (0.89 mmol) of Pd(PPh3), and 5.16 g (37.35 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, methanol was added to precipitate a solid and filtered. The solid was purified by column chromatography (DCM:Hex=1:1) and 10.5 g (89.7%) of the target compound 1-1 was obtained with methanol.

[0300] Hereinafter, the target compounds of Table 1 below were synthesized in the same manner as the target compound 1-1, except that instead of (A) 9H-carbazole, intermediate A of Table 1 below was used, instead of (B) phenyl boronic acid, intermediate B of Table 1 below was used, and instead of (C) 2-chloro-4,6-diphenyl-1,3,5-triazine, intermediate C of Table 1 below was used.

[0301]

[0302]

[0303] <Manufacturing Example 2> Manufacturing of target compounds 1-2, etc.

[0304]

[0305] 1) Preparation of compound 1-2-3

[0306] 10 g (31.51 mmol) of the above compound 1-2-4, 12.8 g (34.66 mmol) of (A) 9H-carbazole, and 8.71 g (63.02 mmol) of Cs2CO3 were dissolved in 100 mL of DMA and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and the target compound 1-2-3 10.8 (79.2%) was obtained with methanol.

[0307] 2) Preparation of compound 1-2-2

[0308] The compound 1-2-3 10.8 (24.96 mmol), (B) phenyl boronic acid 3.42 g (7.45 mmol), Pd(PPh3) 41.44 g (1.25 mmol), and K2CO3 6.9 g (49.91 mmol) were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) and 8.7 g (81.08%) of the target compound 1-2-2 was obtained with methanol.

[0309] 3) Preparation of compound 1-2-1

[0310] The compound 1-2-2 8.7 g (20.24 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 7.71 g (30.35 mmol), Pd2(dba) 30.93 g (1.01 mmol), Xphos 0.96 g (2.02 mmol), and KOAc 5.59 g (40.47 mmol) were dissolved in 100 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) to obtain 7.7 g (72.97%) of the target compound 1-2-1.

[0311] 4) Preparation of target compound 1-2

[0312] The compound 1-2-1 7.7 g (14.77 mmol), (C) 2-chloro-4,6-diphenyl-1,3,5-triazine 4 g (14.94 mmol), Pd(PPh3) 40.86 g (0.75 mmol), and K2CO3 4.13 g (29.88 mmol) were dissolved in 1,4-Dioxane / H2O 80 mL / 24 mL and refluxed for 6 hours. After the reaction was completed, methanol was added to precipitate a solid and filtered. The solid was purified by column chromatography (DCM:Hex=1:1) and 6.4 g (68.34%) of the target compound 1-2 was obtained with methanol.

[0313] Hereinafter, the target compounds of Table 2 below were synthesized in the same manner as the target compounds 1-2 above, except that instead of (A) 9H-carbazole, intermediate A of Table 2 below was used, instead of (B) phenyl boronic acid, intermediate B of Table 2 below was used, and instead of (C) 2-chloro-4,6-diphenyl-1,3,5-triazine, intermediate C of Table 2 below was used.

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322] <Manufacturing Example 3> Manufacturing of target compounds 1-3, etc.

[0323]

[0324] 1) Preparation of compound 1-3-3

[0325] 10 g (31.51 mmol) of the above compound 1-3-4, 12.8 g (34.66 mmol) of (A) 9H-carbazole, and 8.71 g (63.02 mmol) of Cs2CO3 were dissolved in 100 mL of DMA and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and the target compound 1-3-3 12.5 (91.67%) was obtained with methanol.

[0326] 2) Preparation of compound 1-3-2

[0327] The compound 1-3-3 10.8 (24.96 mmol), (B) phenyl boronic acid 3.42 g (7.45 mmol), Pd(PPh3) 41.44 g (1.25 mmol), and K2CO3 6.9 g (49.91 mmol) were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) and 8.7 g (81.08%) of compound 1-3-2 was obtained with methanol.

[0328] 3) Preparation of compound 1-3-1

[0329] 10.4 g (24.19 mmol) of the above compound 1-3-2, 9.21 g (36.28 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 31.11 g (1.21 mmol) of Pd2(dba), 1.15 g (2.42 mmol) of Xphos, and 6.69 g (48.38 mmol) of KOAc were dissolved in 100 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) to obtain 9.7 g (76.9%) of the target compound 1-3-1.

[0330] 4) Preparation of target compounds 1-3

[0331] The compound 1-3-1 9.7 g (18.68 mmol), (C) 2-chloro-4,6-diphenyl-1,3,5-triazine 5 g (18.68 mmol), Pd(PPh3) 41.08 g (0.93 mmol), and K2CO3 5.16 g (37.35 mmol) were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, methanol was added to precipitate a solid and filtered. The solid was purified by column chromatography (DCM:Hex=1:1), and 8 g (68.34%) of the target compound 1-3 was obtained with methanol.

[0332] Hereinafter, the target compounds of Table 3 were synthesized in the same manner as in the preparation of target compounds 1-3, except that intermediate A of Table 3 below was used instead of (A) 9H-carbazole, intermediate B of Table 3 below was used instead of (B) phenyl boronic acid, and intermediate C of Table 3 below was used instead of (C) 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0333] However, in the case of target compound 1-298, 4'-chloro-5'-fluoro-1,1':2',1"-biphenyl-3',6'-d2 was used instead of the compound 1-3-4 as a material corresponding to starting material 1-298-4.

[0334]

[0335]

[0336]

[0337] <Manufacturing Example 4> Manufacturing of target compounds 1-4, etc.

[0338]

[0339] 1) Preparation of compound 1-4-3

[0340] 10 g (31.51 mmol) of the above compound 1-4-4, 12.8 g (34.66 mmol) of (A) 9H-carbazole, and 8.71 g (63.02 mmol) of Cs2CO3 were dissolved in 100 mL of DMA and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 13.1 g (96.07%) of the target compound 1-4-3 was obtained with methanol.

[0341] 2) Preparation of compound 1-4-2

[0342] 13.1 g (30.27 mmol) of the compound 1-4-3, 4.14 g (33.3 mmol) of (B) phenyl boronic acid, 41.75 g (1.51 mmol) of Pd(PPh3), and 8.37 g (60.54 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the product, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) and 10.8 g (92.98%) of the target compound 1-4-2 was obtained with methanol.

[0343] 3) Preparation of compound 1-4-1

[0344] 10.8 g (30.47 mmol) of the above compound 1-4-2, 11.61 g (45.7 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 31.4 g (1.52 mmol) of Pd2(dba), 1.45 g (3.05 mmol) of Xphos, and 5.98 g (60.94 mmol) of KOAc were dissolved in 150 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) to obtain 10.5 g (77.09%) of the target compound 1-4-1.

[0345] 4) Preparation of target compounds 1-4

[0346] 10.5 g (19.61 mmol) of the above compound 1-4-1, 5 g (18.68 mmol) of (C) 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.03 g (0.89 mmol) of Pd(PPh3), and 5.16 g (37.35 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, methanol was added to precipitate a solid, which was then filtered. The solid was purified by column chromatography (DCM:Hex=1:1), and 10.5 g (89.7%) of the target compound 1-4 was obtained with methanol.

[0347] Hereinafter, the target compounds of Table 4 below were synthesized in the same manner as target compounds 1-4, except that intermediate A of Table 4 below was used instead of (A) 9H-carbazole, intermediate B of Table 4 below was used instead of (B) phenyl boronic acid, and intermediate C of Table 4 below was used instead of (C) 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0348]

[0349]

[0350]

[0351] <Manufacturing Example 5> Manufacturing of target compounds 1-5, etc.

[0352]

[0353] 1) Preparation of compound 1-5-3

[0354] 10 g (31.51 mmol) of the above compound 1-5-4, 12.8 g (34.66 mmol) of (A) 9H-carbazole, and 8.71 g (63.02 mmol) of Cs2CO3 were dissolved in 100 mL of DMA and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and the target compound 1-5-3 12.5 (91.67%) was obtained with methanol.

[0355] 2) Preparation of compound 1-5-2

[0356] 12.5 g (30.27 mmol) of the above compound 1-5-3, 3.95 g (31.77 mmol) of (B) phenyl boronic acid, 41.67 g (1.44 mmol) of Pd(PPh3), and 7.98 g (57.77 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the product, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) and 10.4 g (83.74%) of the target compound 1-5-2 was obtained with methanol.

[0357] 3) Preparation of compound 1-5-1

[0358] Compound 1-5-2 10.4 g (24.19 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 9.21 g (36.28 mmol), Pd2(dba) 31.11 g (1.21 mmol), Xphos 1.15 g (2.42 mmol), KOAc 6.69 g (48.38 mmol) were dissolved in 100 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) to obtain 9.7 g (76.9%) of the target compound 1-5-1.

[0359] 4) Preparation of target compounds 1-5

[0360] The compound 1-5-1 9.7 g (18.68 mmol), (C) 2-chloro-4,6-diphenyl-1,3,5-triazine 5 g (18.68 mmol), Pd(PPh3) 41.08 g (0.93 mmol), K2CO3 5.16 g (37.35 mmol) were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, methanol was added to precipitate a solid and filtered. The solid was purified by column chromatography (DCM:Hex=1:1) and 8 g (68.34%) of the target compound 1-5 was obtained with methanol.

[0361] Hereinafter, the target compounds of Table 5 below were synthesized in the same manner as target compounds 1-5, except that intermediate A of Table 5 below was used instead of (A) 9H-carbazole, intermediate B of Table 5 below was used instead of (B) phenyl boronic acid, and intermediate C of Table 5 below was used instead of (C) 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0362]

[0363]

[0364] <Manufacturing Example 6> Manufacturing of compounds 1-6, etc.

[0365]

[0366] 1) Preparation of compound 1-6-3

[0367] 10 g (31.51 mmol) of the above compound 1-6-4, 12.8 g (34.66 mmol) of (A) 9H-carbazole, and 8.71 g (63.02 mmol) of Cs2CO3 were dissolved in 100 mL of DMA and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and the target compound 1-6-3 10.8 (79.2%) was obtained with methanol.

[0368] 2) Preparation of compound 1-6-2

[0369] The compound 1-6-3 10.8 (24.96 mmol), (B) phenyl boronic acid 3.42 g (7.45 mmol), Pd(PPh3) 41.44 g (1.25 mmol), and K2CO3 6.9 g (49.91 mmol) were dissolved in 1,4-Dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) and 8.7 g (81.08%) of the target compound 1-6-2 was obtained with methanol.

[0370] 3) Preparation of compound 1-6-1

[0371] Compound 1-6-2 8.7 g (20.24 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 7.71 g (30.35 mmol), Pd2(dba) 30.93 g (1.01 mmol), Xphos 0.96 g (2.02 mmol), and KOAc 5.59 g (40.47 mmol) were dissolved in 100 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) to obtain 7.7 g (72.97%) of the target compound 1-6-1.

[0372] 4) Preparation of target compounds 1-6

[0373] The compound 1-6-1 7.7 g (14.77 mmol), (C) 2-chloro-4,6-diphenyl-1,3,5-triazine 4 g (14.94 mmol), Pd(PPh3) 40.86 g (0.75 mmol), and K2CO3 4.13 g (29.88 mmol) were dissolved in 1,4-Dioxane / H2O 80 mL / 24 mL and refluxed for 6 hours. After the reaction was completed, methanol was added to precipitate a solid and filtered. The solid was purified by column chromatography (DCM:Hex=1:1) and 6.4 g (68.34%) of the target compound 1-6 was obtained with methanol.

[0374] Hereinafter, the target compound was synthesized by the same method as the target compound 1-6, except that intermediate A of Table 6 below was used instead of (A) 9H-carbazole, intermediate B of Table 6 below was used instead of (B) phenyl boronic acid, and intermediate C of Table 6 below was used instead of (C) 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0375] However, for target compounds 1-300 and 1-301, 2-bromo-4-chloro-6-fluoro-1,1'-biphenyl-2',3,3',4',5,5',6'-d7 was used instead of the compound 1-6-4 as the material corresponding to the starting materials 1-300-4 and 1-301-4, respectively, and for target compound 1-304, 2-bromo-4-chloro-6-fluoro-1,1'-biphenyl-2',3,3',4',5,5'-d6 was used as the material corresponding to 1-304-4.

[0376]

[0377]

[0378]

[0379] Compounds were manufactured using the same method as the above manufacturing examples, and the results of their synthesis are shown in Tables 7 and 8 below, respectively. Table 7 shows the measured values ​​of FD-MS (Field desorption mass spectrometry), and Table 8 shows the measured values ​​of 1 This is the measured value of H NMR (CDCl3, 400 MHz).

[0380] 화합물번호FD-MS화합물번호FD-MS1-1m / z = 626.25 (C45H30N4, 626.76)1-153m / z = 808.27 (C57H36N4S, 809.00)1-2m / z = 626.25 (C45H30N4, 626.76)1-154m / z = 808.27 (C57H36N4S, 809.00)1-3m / z = 626.25 (C45H30N4, 626.76)1-159m / z = 808.27 (C57H36N4S, 809.00)1-4m / z = 626.25 (C45H30N4, 626.76)1-162m / z = 808.27 (C57H36N4S, 809.00)1-5m / z = 626.25 (C45H30N4, 626.76)1-167m / z = 732.23 (C51H32N4S, 732.90)1-6m / z = 626.25 (C45H30N4, 626.76)1-169m / z = 791.30 (C57H37N5, 791.96)1-7m / z = 702.28 (C51H34N4, 702.86)1-171m / z = 791.30 (C57H37N5, 791.96)1-8m / z = 702.28 (C51H34N4, 702.86)1-176m / z = 732.23 (C51H32N4S, 732.90)1-9m / z = 702.28 (C51H34N4, 702.86)1-177m / z = 791.30 (C57H37N5, 791.96)1-10m / z = 702.28 (C51H34N4, 702.86)1-180m / z = 791.30 (C57H37N5, 791.96)1-14m / z = 778.31 (C57H38N4, 778.96)1-185m / z = 702.28 (C51H34N4, 702.86)1-19m / z = 778.31 (C57H38N4, 778.96)1-188m / z = 778.31 (C57H38N4, 778.96)1-26m / z = 792.29 (C57H36N4O, 792.94)1-191m / z = 778.31 (C57H38N4, 778.96)1-27m / z = 792.29 (C57H36N4O, 792.94)1-193m / z = 778.31 (C57H38N4, 778.96)1-32m / z = 792.29 (C57H36N4O, 792.94)1-197m / z = 778.31 (C57H38N4, 778.96)1-34m / z = 792.29 (C57H36N4O, 792.94)1-203m / z = 716.26 (C51H32N4O, 716.84)1-38m / z = 808.27 (C57H36N4S, 809.00)1-210m / z = 792.29 (C57H36N4O, 792.94)1-41m / z = 808.27 (C57H36N4S, 809.00)1-215m / z = 792.29 (C57H36N4O, 792.94)1-45m / z = 808.27 (C57H36N4S, 809.00)1-218m / z = 792.29 (C57H36N4O, 792.94)1-49m / z = 808.27 (C57H36N4S, 809.00)1-221m / z = 808.27 (C57H36N4S, 809.00)1-53m / z = 791.30 (C57H37N5, 791.96)1-223m / z = 808.27 (C57H36N4S, 809.00)1-54m / z = 791.30 (C57H37N5, 791.96)1-232m / z = 808.27 (C57H36N4S, 809.00)1-57m / z = 702.28 (C51H34N4, 702.86)1-239m / z = 792.29 (C57H36N4O, 792.94)1-60m / z = 778.31 (C57H38N4, 778.96)1-240m / z = 792.29 (C57H36N4O, 792.94)1-61m / z = 778.31 (C57H38N4, 778.96)1-248m / z = 792.29 (C57H36N4O, 792.94)1-67m / z = 778.31 (C57H38N4, 778.96)1-253m / z = 792.29 (C57H36N4O, 792.94)1-70m / z = 716.26 (C51H32N4O, 716.84)1-250m / z = 792.29 (C57H36N4O, 792.94)1-73m / z = 732.23 (C51H32N4S, 732.90)1-265m / z = 808.27 (C57H36N4S, 809.00)1-79m / z = 792.29 (C57H36N4O, 792.94)1-266m / z = 808.27 (C57H36N4S, 809.00)1-85m / z = 792.29 (C57H36N4O, 792.94)1-271m / z = 808.27 (C57H36N4S, 809.00)1-92m / z = 808.27 (C57H36N4S, 809.00)1-274m / z = 808.27 (C57H36N4S, 809.00)1-97m / z = 808.27 (C57H36N4S, 809.00)1-279m / z = 808.27 (C57H36N4S, 809.00)1-99m / z = 808.27 (C57H36N4S, 809.00)1-282m / z = 808.27 (C57H36N4S, 809.00)1-102m / z = 716.26 (C51H32N4O, 716.84)1-285m / z = 808.27 (C57H36N4S, 809.00)1-105m / z = 732.23 (C51H32N4S, 732.90)1-290m / z = 702.28 (C51H34N4, 702.86)1-111m / z = 792.29 (C57H36N4O, 792.94)1-291m / z = 702.28 (C51H34N4, 702.86)1-116m / z = 792.29 (C57H36N4O, 792.94)1-292m / z = 702.28 (C51H34N4, 702.86)1-117m / z = 792.29 (C57H36N4O, 792.94)1-293m / z = 656.44 (C45D30N4, 656.95)1-124m / z = 792.29 (C57H36N4O, 792.94)1-298m / z = 636.31 (C45H20D10N4, 636.82)1-132m / z = 792.29 (C57H36N4O, 792.94)1-299m / z = 636.31 (C45H20D10N4, 636.82)1-135m / z = 792.29 (C57H36N4O, 792.94)1-300m / z = 816.44 (C57H12D24N4O, 817.09)1-137m / z = 792.29 (C57H36N4O, 792.94)1-301m / z = 762.42 (C51H2D30N4S, 763.09)1-141m / z = 808.27 (C57H36N4S, 809.00)1-304m / z = 816.44 (C57H12D24N4O, 817.09)1-146m / z = 808.27 (C57H36N4S, 809.00)1-309m / z = 796.34 (C57H32D5N5, 796.99).

[0381] 화합물번호 1H NMR (CDCl3, 400MHz)1-1δ = 8.55(1H, s), 8.36(4H, d), 8.2(1H, d), 8.19(1H, d), 8.11(1H, d), 7.94(1H, d), 7.79(2H, d), 7.58(1H, d), 7.51(2H, d), 7.5(7H, dd), 7.46(4H, d), 7.41(2H, d), 7.35(1H, dd), 7.2(1H, dd), 7.16(1H, s),1-2δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 7.94(1H, d), 7.79(2H, d), 7.75(2H, d), 7.58(1H, d), 7.5(7H, dd), 7.49(2H, d), 7.46(2H, d), 7.41(2H, dd), 7.35(1H, dd), 7.2(1H, s), 7.16 (1H, t),1-3δ = 8.59(1H, s), 8.55(1H, d), 8.36(4H, d), 8.27(1H, d), 8.19(1H, d), 7.94(1H, d), 7.79(4H, d), 7.58(1H, d), 7.5(7H, d), 7.46(4H, dd), 7.41(2H, d), 7.35(1H, d), 7.2(1H, dd), 7.16(1H, dd),1-4δ = 8.55(1H, s), 8.36(4H, d), 8.2(1H, d), 8.19(1H, d), 8.11(1H, d), 7.94(1H, d), 7.58(1H, d), 7.51(2H, d), 7.5(7H, d), 7.46(2H, dd), 7.41(2H, d), 7.35(1H, d), 7.2(1H, dd), 7.19(4H, dd), 7.16(1H, s),1-5δ = 8.59(1H, s), 8.55(1H, d), 8.36(4H, d), 8.27(1H, d), 8.19(1H, d), 7.94(1H, d), 7.79(2H, d), 7.58(1H, d), 7.5(7H, d), 7.46(2H, dd), 7.41(2H, d), 7.35(1H, d), 7.2(1H, dd), 7.19(4H, dd), 7.16(1H, s),1-6δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 7.94(1H, d), 7.79(2H, d), 7.58(1H, d), 7.51(2H, d), 7.5(7H, dd), 7.46(4H, d), 7.41(2H, d), 7.35(1H, dd), 7.2(1H, dd), 7.16(1H, s),1-7δ = 8.55(1H, s), 8.36(4H, d), 8.29(1H, d), 8.2(1H, d), 8.11(1H, d), 8.06(1H, d), 7.94(1H, d), 7.79(2H, d), 7.51(2H, d), 7.5(6H, dd), 7.48(1H, d), 7.46(4H, d), 7.41(3H, dd), 7.35(1H, dd), 7.19(4H, s), 7.16 (1H, t),1-8δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.31(1H, d), 8.09(1H, d), 7.94(1H, d), 7.91(1H, d), 7.79(2H, d), 7.75(4H, d), 7.74(1H, dd), 7.5(6H, d), 7.49(4H, d), 7.46(2H, dd), 7.41(3H, dd), 7.35(1H, s), 7.16 (1H, t),1-9δ = 8.59(1H, s), 8.55(1H, d), 8.36(4H, d), 8.27(1H, d), 7.99(1H, d), 7.94(1H, d), 7.89(1H, d), 7.79(4H, d), 7.77(1H, d), 7.75(2H, dd), 7.5(6H, d), 7.49(2H, d), 7.46(4H, dd), 7.41(3H, dd), 7.35(1H, s), 7.16 (1H, t),1-10δ = 8.55(1H, s), 8.36(4H, d), 8.2(1H, d), 8.11(1H, d), 7.94(1H, d), 7.91(1H, d), 7.79(2H, d), 7.68(1H, d), 7.56(1H, d), 7.51(2H, dd), 7.5(6H, d), 7.46(4H, d), 7.41(3H, dd), 7.35(1H, dd), 7.19(4H, s), 7.16 (1H, t),1-14δ = 8.65(1H, s), 8.5(1H, d), 8.42(1H, d), 8.36(4H, d), 8.29(1H, d), 8.09(1H, d), 8.06(1H, d), 7.79(2H, d), 7.75(2H, d), 7.5(6H, dd), 7.49(2H, d), 7.48(1H, d), 7.46(2H, dd), 7.44(1H, dd), 7.41(4H, s), 7.19 (8H, t),1-19δ = 8.36(4H, s), 8.3(1H, d), 8.2(1H, d), 8.13(1H, d), 8.11(1H, d), 7.99(1H, d), 7.89(2H, d), 7.79(2H, d), 7.77(1H, d), 7.75(4H, dd), 7.51(2H, d), 7.5(6H, d), 7.49(4H, dd), 7.46(4H, dd), 7.41(4H, s),1-26δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.31(1H, d), 8.09(1H, d), 8.03(1H, d), 7.98(1H, d), 7.94(1H, d), 7.91(1H, d), 7.82(1H, dd), 7.79(2H, d), 7.76(1H, d), 7.75(2H, dd), 7.74(1H, dd), 7.54(1H, s), 7.5 (6H, t), 7.49 (2H, t), 7.46 (2H, dd), 7.41 (2H, dd), 7.39 (1H, t), 7.35 (1H, d), 7.31 (1H, d), 7.16 (1H, d),1-27δ = 8.59(1H, s), 8.55(1H, d), 8.36(4H, d), 8.27(1H, d), 8.03(1H, d), 7.99(1H, d), 7.98(1H, d), 7.94(1H, d), 7.89(1H, d), 7.82(1H, dd), 7.79(4H, d), 7.77(1H, d), 7.76(1H, dd), 7.54(1H, dd), 7.5(6H, s), 7.46 (4H, t), 7.41 (2H, t), 7.39 (1H, dd), 7.35 (1H, dd), 7.31 (1H, t), 7.16 (1H, d),1-32δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.09(1H, d), 7.98(1H, d), 7.94(1H, d), 7.91(1H, d), 7.88(1H, d), 7.83(1H, d), 7.79(3H, dd), 7.75(2H, d), 7.68(1H, d), 7.56(1H, dd), 7.54(1H, dd), 7.5(6H, s), 7.49 (2H, t), 7.46 (2H, t), 7.41 (2H, dd), 7.39 (1H, dd), 7.35 (1H, t), 7.31 (1H, d), 7.16 (1H, d),1-34δ = 8.55(1H, s), 8.36(4H, d), 8.31(1H, d), 8.2(1H, d), 8.11(1H, d), 7.98(1H, d), 7.94(1H, d), 7.91(1H, d), 7.82(1H, d), 7.74(1H, dd), 7.69(1H, d), 7.57(1H, d), 7.54(1H, dd), 7.51(2H, dd), 7.5(6H, s), 7.46 (2H, t), 7.41 (2H, t), 7.39 (1H, dd), 7.35 (1H, dd), 7.31 (1H, t), 7.19 (4H, d), 7.16 (1H, d),1-38δ = 8.55(2H, s), 8.5(1H, d), 8.45(1H, d), 8.36(4H, d), 8.32(1H, d), 8.31(1H, d), 8.09(1H, d), 7.94(1H, d), 7.93(1H, d), 7.91(1H, dd), 7.79(2H, d), 7.75(2H, d), 7.74(1H, dd), 7.7(1H, dd), 7.56(1H, s), 7.5 (6H, t), 7.49 (3H, t), 7.46 (2H, dd), 7.41 (2H, dd), 7.35 (1H, t), 7.16 (1H, d),1-41δ = 8.55(1H, s), 8.45(1H, d), 8.36(4H, d), 8.29(1H, d), 8.24(1H, d), 8.2(2H, d), 8.17(1H, d), 8.11(1H, d), 8.06(1H, d), 7.94(1H, dd), 7.93(1H, d), 7.79(2H, d), 7.56(1H, dd), 7.51(2H, dd), 7.5(6H, s), 7.49 (1H, t), 7.48 (1H, t), 7.46 (4H, dd), 7.41 (2H, dd), 7.35 (1H, t), 7.16 (1H, d),1-45δ = 8.55(1H, s), 8.5(1H, d), 8.45(1H, d), 8.36(4H, d), 8.29(1H, d), 8.12(2H, d), 8.09(1H, d), 8.06(1H, d), 7.99(1H, d), 7.94(1H, dd), 7.93(1H, d), 7.79(2H, d), 7.56(1H, dd), 7.51(2H, dd), 7.5(6H, s), 7.49 (1H, t), 7.48 (1H, t), 7.46 (4H, dd), 7.41 (2H, dd), 7.35 (1H, t), 7.16 (1H, d),1-49δ = 8.55(1H, s), 8.5(1H, d), 8.45(1H, d), 8.36(4H, d), 8.29(1H, d), 8.09(1H, d), 8.06(1H, d), 8.03(1H, d), 7.94(2H, d), 7.93(1H, dd), 7.79(2H, d), 7.75(2H, d), 7.68(1H, dd), 7.56(1H, dd), 7.5(6H, s), 7.49 (3H, t), 7.48 (1H, t), 7.46 (2H, dd), 7.41 (2H, dd), 7.35 (1H, t), 7.16 (1H, d),1-53δ = 8.55(2H, s), 8.36(4H, d), 8.2(1H, d), 8.19(1H, d), 8.15(1H, d), 8.11(1H, d), 7.94(2H, d), 7.79(2H, d), 7.58(1H, d), 7.51(2H, dd), 7.5(7H, d), 7.46(4H, d), 7.43(1H, dd), 7.41(2H, dd), 7.38(1H, s), 7.35 (2H, t), 7.2 (1H, t), 7.16 (2H, dd),1-54δ = 8.59(1H, s), 8.55(2H, d), 8.36(4H, d), 8.27(1H, d), 8.26(1H, d), 8.19(1H, d), 7.94(2H, d), 7.79(4H, d), 7.58(1H, d), 7.52(1H, dd), 7.5(7H, d), 7.46(4H, d), 7.41(2H, dd), 7.35(2H, dd), 7.3(1H, s), 7.2 (1H, t), 7.16 (2H, t),1-57δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 7.96(2H, d), 7.94(1H, d), 7.79(2H, d), 7.6(2H, d), 7.58(1H, dd), 7.51(2H, d), 7.5(7H, d), 7.46(4H, dd), 7.41(2H, dd), 7.35(1H, s), 7.2 (1H, t), 7.16 (1H, t),1-60δ = 8.59(1H, s), 8.55(1H, d), 8.36(4H, d), 8.27(1H, d), 8.19(1H, d), 7.96(4H, d), 7.94(1H, d), 7.79(4H, d), 7.6(4H, d), 7.58(1H, dd), 7.5(7H, d), 7.46(4H, d), 7.41(2H, dd), 7.35(1H, dd), 7.2(1H, s), 7.16 (1H, t),1-61δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 7.96(2H, d), 7.94(2H, d), 7.75(4H, d), 7.73(1H, d), 7.61(2H, dd), 7.6(2H, d), 7.58(1H, d), 7.5(7H, dd), 7.49(4H, dd), 7.41(2H, s), 7.35 (1H, t), 7.2 (1H, t), 7.16 (1H, dd),1-67δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 7.94(2H, d), 7.75(4H, d), 7.73(1H, d), 7.61(2H, d), 7.58(1H, dd), 7.5(7H, d), 7.49(4H, d), 7.41(2H, dd), 7.35(1H, dd), 7.25(4H, s), 7.2 (1H, t), 7.16 (1H, t),1-70δ = 8.59(1H, s), 8.55(1H, d), 8.36(4H, d), 8.27(1H, d), 8.19(1H, d), 8.03(1H, d), 7.98(1H, d), 7.94(1H, d), 7.82(1H, d), 7.76(1H, dd), 7.58(1H, d), 7.54(1H, d), 7.5(7H, dd), 7.41(1H, dd), 7.39(1H, s), 7.35 (1H, t), 7.31 (1H, t), 7.2 (1H, dd), 7.19 (4H, dd), 7.16 (1H, t),1-73δ = 8.55(2H, s), 8.5(1H, d), 8.45(1H, d), 8.36(4H, d), 8.32(1H, d), 8.19(1H, d), 8.09(1H, d), 7.94(1H, d), 7.93(1H, d), 7.75(2H, dd), 7.7(1H, d), 7.58(1H, d), 7.56(1H, dd), 7.5(7H, dd), 7.49(3H, s), 7.41 (1H, t), 7.35 (1H, t), 7.2 (1H, dd), 7.16 (1H, dd),1-79δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 8.08(1H, d), 8.02(1H, d), 7.98(1H, d), 7.94(1H, d), 7.75(2H, dd), 7.58(1H, d), 7.54(1H, d), 7.51(1H, dd), 7.5(7H, dd), 7.49(2H, s), 7.41 (1H, t), 7.39 (1H, t), 7.35 (1H, dd), 7.31 (1H, dd), 7.25 (4H, t), 7.2 (1H, d), 7.16 (1H, d),1-85δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 7.98(1H, d), 7.94(1H, d), 7.88(1H, d), 7.83(1H, d), 7.79(1H, dd), 7.75(2H, d), 7.58(1H, d), 7.54(1H, dd), 7.5(7H, dd), 7.49(2H, s), 7.41 (1H, t), 7.39 (1H, t), 7.35 (1H, dd), 7.31 (1H, dd), 7.25 (4H, t), 7.2 (1H, d), 7.16 (1H, d),1-92δ = 8.55(1H, s), 8.45(1H, d), 8.36(4H, d), 8.24(1H, d), 8.2(2H, d), 8.19(1H, d), 8.17(1H, d), 8.11(1H, d), 7.96(2H, d), 7.94(1H, dd), 7.93(1H, d), 7.6(2H, d), 7.58(1H, dd), 7.56(1H, dd), 7.5(7H, s), 7.49 (1H, t), 7.41 (1H, t), 7.35 (1H, dd), 7.2 (1H, dd), 7.19 (4H, t), 7.16 (1H, d),1-97δ = 8.55(1H, s), 8.45(1H, d), 8.36(4H, d), 8.2(1H, d), 8.19(1H, d), 8.12(2H, d), 8.11(1H, d), 7.99(1H, d), 7.94(1H, d), 7.93(1H, dd), 7.79(2H, d), 7.58(1H, d), 7.56(1H, dd), 7.5(7H, dd), 7.49(1H, s), 7.46 (2H, t), 7.41 (1H, t), 7.35 (1H, dd), 7.25 (4H, dd), 7.2 (1H, t), 7.16 (1H, d),1-99δ = 8.55(1H, s), 8.5(1H, d), 8.45(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 8.03(1H, d), 7.94(3H, d), 7.93(1H, d), 7.75(2H, dd), 7.73(1H, d), 7.68(1H, d), 7.61(2H, dd), 7.58(1H, dd), 7.56(1H, s), 7.5 (7H, t), 7.49 (3H, t), 7.41 (1H, dd), 7.35 (1H, dd), 7.2 (1H, t), 7.16 (1H, d),1-102δ = 8.59(1H, s), 8.55(1H, d), 8.36(4H, d), 8.27(1H, d), 8.19(1H, d), 8.03(1H, d), 7.98(1H, d), 7.94(1H, d), 7.82(1H, d), 7.76(1H, dd), 7.58(1H, d), 7.54(1H, d), 7.5(7H, dd), 7.41(1H, dd), 7.39(1H, s), 7.35 (1H, t), 7.31 (1H, t), 7.2 (1H, dd), 7.19 (4H, dd), 7.16 (1H, t),1-105δ = 8.55(2H, s), 8.5(1H, d), 8.45(1H, d), 8.36(4H, d), 8.32(1H, d), 8.19(1H, d), 8.09(1H, d), 7.94(1H, d), 7.93(1H, d), 7.75(2H, dd), 7.7(1H, d), 7.58(1H, d), 7.56(1H, dd), 7.5(7H, dd), 7.49(3H, s), 7.41 (1H, t), 7.35 (1H, t), 7.2 (1H, dd), 7.16 (1H, dd),1-111δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 8.03(1H, d), 7.94(1H, d), 7.82(2H, d), 7.79(2H, d), 7.76(1H, dd), 7.75(2H, d), 7.69(1H, d), 7.58(1H, dd), 7.57(1H, dd), 7.5(7H, s), 7.49 (2H, t), 7.46 (2H, t), 7.41 (2H, dd), 7.35 (1H, dd), 7.2 (1H, t), 7.16 (1H, d),1-116δ = 8.59(1H, s), 8.55(1H, d), 8.36(4H, d), 8.27(1H, d), 8.19(1H, d), 7.94(1H, d), 7.88(1H, d), 7.83(1H, d), 7.82(1H, d), 7.79(3H, dd), 7.75(2H, d), 7.69(1H, d), 7.58(1H, dd), 7.57(1H, dd), 7.5(7H, s), 7.49 (2H, t), 7.46 (2H, t), 7.41 (2H, dd), 7.35 (1H, dd), 7.2 (1H, t), 7.16 (1H, d),1-117δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 7.94(1H, d), 7.88(2H, d), 7.83(2H, d), 7.79(2H, d), 7.75(4H, dd), 7.58(1H, d), 7.5(7H, d), 7.49(4H, dd), 7.41(2H, dd), 7.35(1H, s), 7.2 (1H, t), 7.16 (1H, t),1-124δ = 8.55(1H, s), 8.36(2H, d), 8.2(1H, d), 8.19(1H, d), 8.11(1H, d), 8.03(1H, d), 7.94(1H, d), 7.82(2H, d), 7.76(1H, d), 7.75(2H, dd), 7.69(1H, d), 7.58(1H, d), 7.57(1H, dd), 7.51(2H, dd), 7.5(4H, s), 7.49 (2H, t), 7.46 (2H, t), 7.41 (3H, dd), 7.35 (1H, dd), 7.2 (1H, t), 7.19 (4H, d), 7.16 (1H, d),1-132δ = 8.59(1H, s), 8.55(1H, d), 8.36(4H, d), 8.27(1H, d), 8.19(1H, d), 8.08(1H, d), 8.02(1H, d), 7.94(1H, d), 7.88(1H, d), 7.83(1H, dd), 7.79(1H, d), 7.58(1H, d), 7.51(3H, dd), 7.5(7H, dd), 7.46(2H, s), 7.41 (2H, t), 7.35 (1H, t), 7.2 (1H, dd), 7.19 (4H, dd), 7.16 (1H, t),1-135δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.19(1H, d), 8.13(1H, d), 8.09(1H, d), 8.01(1H, d), 7.98(1H, d), 7.94(1H, d), 7.75(2H, dd), 7.58(1H, d), 7.54(1H, d), 7.51(2H, dd), 7.5(7H, dd), 7.49(2H, s), 7.46 (2H, t), 7.41 (2H, t), 7.39 (1H, dd), 7.35 (1H, dd), 7.31 (1H, t), 7.2 (1H, d), 7.16 (1H, d),1-137δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 7.98(1H, d), 7.94(1H, d), 7.86(1H, d), 7.81(1H, d), 7.75(2H, dd), 7.58(1H, d), 7.54(1H, d), 7.51(2H, dd), 7.5(7H, dd), 7.49(2H, s), 7.46 (2H, t), 7.41 (2H, t), 7.39 (1H, dd), 7.35 (1H, dd), 7.31 (1H, t), 7.2 (1H, d), 7.16 (1H, d),1-141δ = 8.55(2H, s), 8.5(1H, d), 8.36(4H, d), 8.32(1H, d), 8.19(1H, d), 8.09(1H, d), 8.03(1H, d), 7.94(2H, d), 7.79(2H, d), 7.75(2H, dd), 7.7(1H, d), 7.68(1H, d), 7.58(1H, dd), 7.5(7H, dd), 7.49(2H, s), 7.46 (2H, t), 7.41 (2H, t), 7.35 (1H, dd), 7.2 (1H, dd), 7.16 (1H, t),1-146δ = 8.59(1H, s), 8.55(1H, d), 8.36(4H, d), 8.27(1H, d), 8.24(1H, d), 8.2(1H, d), 8.19(1H, d), 8.17(1H, d), 8.12(2H, d), 7.99(1H, dd), 7.94(1H, d), 7.79(2H, d), 7.75(2H, dd), 7.58(1H, dd), 7.5(7H, s), 7.49 (2H, t), 7.46 (2H, t), 7.41 (2H, dd), 7.35 (1H, dd), 7.2 (1H, t), 7.16 (1H, d),1-153δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.24(2H, d), 8.2(2H, d), 8.19(1H, d), 8.17(2H, d), 8.09(1H, d), 7.94(1H, d), 7.75(4H, dd), 7.58(1H, d), 7.5(7H, d), 7.49(4H, dd), 7.41(2H, dd), 7.35(1H, s), 7.2 (1H, t), 7.16 (1H, t),1-154δ = 8.55(1H, s), 8.36(4H, d), 8.24(1H, d), 8.2(2H, d), 8.19(1H, d), 8.17(1H, d), 8.12(2H, d), 8.11(1H, d), 7.99(1H, d), 7.94(1H, dd), 7.75(2H, d), 7.58(1H, d), 7.5(7H, dd), 7.49(2H, dd), 7.41(2H, s), 7.35 (1H, t), 7.2 (1H, t), 7.19 (4H, dd), 7.16 (1H, dd),1-159δ = 8.55(3H, s), 8.5(1H, d), 8.36(4H, d), 8.32(2H, d), 8.19(1H, d), 8.09(1H, d), 7.94(1H, d), 7.75(2H, d), 7.7(2H, d), 7.58(1H, dd), 7.51(2H, d), 7.5(7H, d), 7.49(2H, dd), 7.46(2H, dd), 7.41(2H, s), 7.35 (1H, t), 7.2 (1H, t), 7.16 (1H, dd),1-162δ = 8.59(1H, s), 8.55(2H, d), 8.36(4H, d), 8.32(1H, d), 8.27(1H, d), 8.19(1H, d), 8.03(1H, d), 7.94(2H, d), 7.7(1H, d), 7.68(1H, dd), 7.58(1H, d), 7.51(2H, d), 7.5(7H, dd), 7.46(2H, dd), 7.41(2H, s), 7.35 (1H, t), 7.2 (1H, t), 7.19 (4H, dd), 7.16 (1H, dd),1-167δ = 8.55(1H, s), 8.5(1H, d), 8.45(1H, d), 8.36(4H, d), 8.09(1H, d), 7.96(1H, d), 7.94(1H, d), 7.93(1H, d), 7.79(2H, d), 7.56(1H, dd), 7.51(2H, d), 7.5(6H, d), 7.49(1H, dd), 7.46(4H, dd), 7.41(2H, s), 7.35 (1H, t), 7.31 (1H, t), 7.16 (1H, dd),1-169δ = 8.55(1H, s), 8.36(4H, d), 8.2(1H, d), 8.19(1H, d), 8.11(1H, d), 7.94(1H, d), 7.79(2H, d), 7.62(2H, d), 7.58(2H, d), 7.55(1H, dd), 7.51(2H, d), 7.5(9H, d), 7.46(4H, dd), 7.41(2H, dd), 7.4(1H, s), 7.35 (1H, t), 7.2 (1H, t), 7.16 (1H, dd),1-171δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 7.94(1H, d), 7.79(2H, d), 7.75(2H, d), 7.62(2H, d), 7.58(2H, dd), 7.55(1H, d), 7.5(9H, d), 7.49(2H, dd), 7.46(2H, dd), 7.41(2H, s), 7.4 (1H, t), 7.35 (1H, t), 7.2 (1H, dd), 7.16 (1H, dd),1-176δ = 8.59(1H, s), 8.55(1H, d), 8.45(1H, d), 8.36(4H, d), 8.27(1H, d), 8.08(1H, d), 7.94(1H, d), 7.93(1H, d), 7.8(1H, d), 7.79(4H, dd), 7.56(1H, d), 7.5(6H, d), 7.49(1H, dd), 7.46(4H, dd), 7.41(2H, s), 7.35 (1H, t), 7.16 (1H, t),1-177δ = 8.55(1H, s), 8.36(4H, d), 8.2(1H, d), 8.19(1H, d), 8.11(1H, d), 7.94(1H, d), 7.79(2H, d), 7.62(2H, d), 7.58(2H, d), 7.55(1H, dd), 7.51(2H, d), 7.5(9H, d), 7.46(4H, dd), 7.41(2H, dd), 7.4(1H, s), 7.35 (1H, t), 7.2 (1H, t), 7.16 (1H, dd),1-180δ = 8.55(2H, s), 8.36(4H, d), 8.2(1H, d), 8.12(1H, d), 8.11(1H, d), 7.94(2H, d), 7.62(2H, d), 7.58(1H, d), 7.51(2H, d), 7.5(8H, dd), 7.46(2H, d), 7.41(2H, d), 7.35(2H, dd), 7.19(4H, dd), 7.18(1H, s), 7.16 (2H, t),1-185δ = 8.55(1H, s), 8.5(1H, d), 8.36(2H, d), 8.19(1H, d), 8.09(1H, d), 7.96(2H, d), 7.94(1H, d), 7.79(2H, d), 7.75(4H, d), 7.58(1H, dd), 7.5(4H, d), 7.49(4H, d), 7.46(2H, dd), 7.41(3H, dd), 7.35(1H, s), 7.25 (2H, t), 7.2 (1H, t), 7.16 (1H, dd),1-188δ = 8.59(1H, s), 8.55(1H, d), 8.36(2H, d), 8.27(1H, d), 8.19(1H, d), 7.96(2H, d), 7.94(1H, d), 7.79(2H, d), 7.75(2H, d), 7.6(2H, dd), 7.58(1H, d), 7.5(4H, d), 7.49(2H, dd), 7.46(2H, dd), 7.41(3H, s), 7.35 (1H, t), 7.25 (4H, t), 7.2 (1H, dd), 7.19 (4H, dd), 7.16 (1H, t),1-191δ = 8.55(1H, s), 8.5(1H, d), 8.38(1H, d), 8.36(2H, d), 8.19(1H, d), 8.09(1H, d), 7.94(2H, d), 7.79(2H, d), 7.75(4H, d), 7.73(1H, dd), 7.61(1H, d), 7.58(1H, d), 7.5(4H, dd), 7.49(4H, dd), 7.46(2H, s), 7.41 (3H, t), 7.35 (1H, t), 7.25 (4H, dd), 7.2 (1H, dd), 7.16 (1H, t),1-193δ = 8.55(1H, s), 8.5(1H, d), 8.36(2H, d), 8.19(1H, d), 8.09(1H, d), 7.96(2H, d), 7.94(2H, d), 7.79(2H, d), 7.75(2H, d), 7.73(1H, dd), 7.61(2H, d), 7.58(1H, d), 7.51(2H, dd), 7.5(4H, dd), 7.49(2H, s), 7.46 (4H, t), 7.41 (3H, t), 7.35 (1H, dd), 7.25 (2H, dd), 7.2 (1H, t), 7.16 (1H, d),1-197δ = 8.55(1H, s), 8.5(1H, d), 8.19(1H, d), 8.09(1H, d), 7.96(4H, d), 7.94(1H, d), 7.79(4H, d), 7.75(4H, d), 7.6(2H, d), 7.58(1H, dd), 7.5(1H, d), 7.49(4H, d), 7.46(4H, dd), 7.41(4H, dd), 7.35(1H, s), 7.25 (2H, t), 7.2 (1H, t), 7.16 (1H, dd),1-203δ = 8.55(1H, s), 8.5(1H, d), 8.36(2H, d), 8.19(1H, d), 8.09(1H, d), 8.03(1H, d), 7.98(1H, d), 7.94(1H, d), 7.82(1H, d), 7.79(2H, dd), 7.76(1H, d), 7.75(2H, d), 7.58(1H, dd), 7.54(1H, dd), 7.5(4H, s), 7.49 (2H, t), 7.46 (2H, t), 7.41 (2H, dd), 7.39 (1H, dd), 7.35 (1H, t), 7.31 (1H, d), 7.2 (1H, d), 7.16 (1H, d),1-210δ = 8.55(1H, s), 8.38(1H, d), 8.36(2H, d), 8.2(1H, d), 8.19(1H, d), 8.11(1H, d), 7.98(1H, d), 7.94(2H, d), 7.82(1H, d), 7.73(1H, dd), 7.69(1H, d), 7.61(1H, d), 7.58(1H, dd), 7.57(1H, dd), 7.54(1H, s), 7.51 (2H, t), 7.5 (4H, t), 7.46 (2H, dd), 7.41 (2H, dd), 7.39 (1H, t), 7.35 (1H, d), 7.31 (1H, d), 7.2 (1H, d),1-215δ = 8.55(1H, s), 8.5(1H, d), 8.36(2H, d), 8.19(1H, d), 8.09(1H, d), 8.03(1H, d), 7.98(1H, d), 7.96(2H, d), 7.94(1H, d), 7.82(1H, dd), 7.79(2H, d), 7.76(1H, d), 7.75(2H, dd), 7.6(2H, dd), 7.58(1H, s), 7.54 (1H, t), 7.5 (4H, t), 7.49 (2H, dd), 7.46 (2H, dd), 7.41 (2H, t), 7.39 (1H, d), 7.35 (1H, d), 7.31 (1H, d),1-218δ = 8.59(1H, s), 8.55(1H, d), 8.36(2H, d), 8.27(1H, d), 8.19(1H, d), 8.08(1H, d), 8.02(1H, d), 7.98(1H, d), 7.96(2H, d), 7.94(1H, dd), 7.79(2H, d), 7.6(2H, d), 7.58(1H, dd), 7.54(1H, dd), 7.51(1H, s), 7.5 (4H, t), 7.46 (2H, t), 7.41 (2H, dd), 7.39 (1H, dd), 7.35 (1H, t), 7.31 (1H, d), 7.2 (1H, d), 7.19 (4H, d),1-221δ = 8.55(1H, s), 8.5(1H, d), 8.45(1H, d), 8.36(2H, d), 8.19(1H, d), 8.09(1H, d), 8.03(1H, d), 7.96(2H, d), 7.94(2H, d), 7.93(1H, dd), 7.79(2H, d), 7.75(2H, d), 7.68(1H, dd), 7.6(2H, dd), 7.58(1H, s), 7.56 (1H, t), 7.5 (4H, t), 7.49 (3H, dd), 7.46 (2H, dd), 7.41 (2H, t), 7.35 (1H, d), 7.2 (1H, d), 7.16 (1H, d),1-223δ = 8.55(1H, s), 8.5(1H, d), 8.45(1H, d), 8.36(2H, d), 8.19(1H, d), 8.09(1H, d), 8.03(1H, d), 7.96(2H, d), 7.94(2H, d), 7.93(1H, dd), 7.79(2H, d), 7.68(1H, d), 7.58(1H, dd), 7.56(1H, dd), 7.51(2H, s), 7.5 (4H, t), 7.49 (1H, t), 7.46 (4H, dd), 7.41 (2H, dd), 7.35 (1H, t), 7.25 (2H, d), 7.2 (1H, d), 7.16 (1H, d),1-232δ = 8.59(1H, s), 8.55(2H, d), 8.45(1H, d), 8.36(2H, d), 8.32(1H, d), 8.27(1H, d), 8.19(1H, d), 7.96(2H, d), 7.94(1H, d), 7.93(1H, dd), 7.79(4H, d), 7.7(1H, d), 7.58(1H, dd), 7.56(1H, dd), 7.5(4H, s), 7.49 (1H, t), 7.46 (4H, t), 7.41 (2H, dd), 7.35 (1H, dd), 7.25 (2H, t), 7.2 (1H, d), 7.16 (1H, d),1-239δ = 8.55(1H, s), 8.5(1H, d), 8.36(2H, d), 8.19(1H, d), 8.09(1H, d), 8.07(1H, d), 7.98(1H, d), 7.94(1H, d), 7.89(1H, d), 7.79(2H, dd), 7.75(2H, d), 7.65(2H, d), 7.58(1H, dd), 7.55(2H, dd), 7.54(1H, s), 7.5 (4H, t), 7.49 (2H, t), 7.46 (2H, dd), 7.41 (3H, dd), 7.39 (1H, t), 7.35 (1H, d), 7.31 (1H, d), 7.2 (1H, d),1-240δ = 8.55(1H, s), 8.36(2H, d), 8.2(1H, d), 8.19(1H, d), 8.11(1H, d), 7.94(1H, d), 7.88(1H, d), 7.83(1H, d), 7.82(1H, d), 7.79(1H, dd), 7.75(2H, d), 7.69(1H, d), 7.58(1H, dd), 7.57(1H, dd), 7.51(2H, s), 7.5 (4H, t), 7.49 (2H, t), 7.46 (2H, dd), 7.41 (3H, dd), 7.35 (1H, t), 7.2 (1H, d), 7.19 (4H, d), 7.16 (1H, d),1-248δ = 8.59(1H, s), 8.55(1H, d), 8.36(2H, d), 8.27(1H, d), 8.19(1H, d), 8.03(1H, d), 7.94(1H, d), 7.88(1H, d), 7.83(1H, d), 7.82(1H, dd), 7.79(3H, d), 7.76(1H, d), 7.75(2H, dd), 7.58(1H, dd), 7.5(4H, s), 7.49 (2H, t), 7.46 (2H, t), 7.41 (3H, dd), 7.35 (1H, dd), 7.2 (1H, t), 7.19 (4H, d), 7.16 (1H, d),1-253δ = 8.55(1H, s), 8.5(1H, d), 8.36(2H, d), 8.19(1H, d), 8.09(1H, d), 7.98(1H, d), 7.94(1H, d), 7.86(1H, d), 7.81(1H, d), 7.79(2H, dd), 7.75(2H, d), 7.58(1H, d), 7.54(1H, dd), 7.51(2H, dd), 7.5(4H, s), 7.49 (2H, t), 7.46 (4H, t), 7.41 (3H, dd), 7.39 (1H, dd), 7.35 (1H, t), 7.31 (1H, d), 7.2 (1H, d), 7.16 (1H, d),1-250δ = 8.55(1H, s), 8.5(1H, d), 8.36(2H, d), 8.19(1H, d), 8.09(1H, d), 7.98(1H, d), 7.94(1H, d), 7.93(1H, d), 7.87(1H, d), 7.79(2H, dd), 7.75(2H, d), 7.58(1H, d), 7.54(1H, dd), 7.51(2H, dd), 7.5(4H, s), 7.49 (2H, t), 7.46 (4H, t), 7.41 (3H, dd), 7.39 (1H, dd), 7.35 (1H, t), 7.31 (1H, d), 7.2 (1H, d), 7.16 (1H, d),1-265δ = 8.55(1H, s), 8.5(1H, d), 8.45(1H, d), 8.36(2H, d), 8.19(1H, d), 8.13(1H, d), 8.11(1H, d), 8.09(1H, d), 7.94(1H, d), 7.93(1H, dd), 7.79(4H, d), 7.75(2H, d), 7.58(1H, dd), 7.56(1H, dd), 7.5(4H, s), 7.49 (3H, t), 7.46 (4H, t), 7.41 (3H, dd), 7.35 (1H, dd), 7.2 (1H, t), 7.16 (1H, d),1-266δ = 8.55(1H, s), 8.45(1H, d), 8.36(2H, d), 8.3(1H, d), 8.2(1H, d), 8.19(1H, d), 8.11(1H, d), 8.01(1H, d), 7.94(1H, d), 7.93(1H, dd), 7.79(2H, d), 7.58(1H, d), 7.56(1H, dd), 7.51(2H, dd), 7.5(4H, s), 7.49 (1H, t), 7.46 (4H, t), 7.41 (3H, dd), 7.35 (1H, dd), 7.2 (1H, t), 7.19 (4H, d), 7.16 (1H, d),1-271δ = 8.55(2H, s), 8.5(1H, d), 8.36(2H, d), 8.19(1H, d), 8.12(2H, d), 8.09(1H, d), 7.99(1H, d), 7.94(1H, d), 7.92(1H, d), 7.79(2H, dd), 7.75(4H, d), 7.7(1H, d), 7.58(1H, dd), 7.5(4H, dd), 7.49(4H, s), 7.46 (2H, t), 7.41 (3H, t), 7.35 (1H, dd), 7.2 (1H, dd), 7.16 (1H, t),1-274δ = 8.59(1H, s), 8.55(1H, d), 8.45(1H, d), 8.36(2H, d), 8.27(1H, d), 8.19(1H, d), 8.11(1H, d), 8.09(1H, d), 7.94(1H, d), 7.93(1H, dd), 7.79(4H, d), 7.58(1H, d), 7.56(1H, dd), 7.5(4H, dd), 7.49(1H, s), 7.46 (4H, t), 7.41 (3H, t), 7.35 (1H, dd), 7.2 (1H, dd), 7.19 (4H, t), 7.16 (1H, d),1-279δ = 8.55(1H, s), 8.5(1H, d), 8.45(1H, d), 8.36(2H, d), 8.34(1H, d), 8.19(1H, d), 8.13(1H, d), 8.09(1H, d), 7.94(1H, d), 7.93(1H, dd), 7.79(4H, d), 7.58(1H, d), 7.56(1H, dd), 7.51(2H, dd), 7.5(4H, s), 7.49 (1H, t), 7.46 (6H, t), 7.41 (3H, dd), 7.35 (1H, dd), 7.2 (1H, t), 7.16 (1H, d),1-282δ = 8.59(1H, s), 8.55(2H, d), 8.36(2H, d), 8.32(1H, d), 8.27(1H, d), 8.19(1H, d), 8.03(1H, d), 7.94(2H, d), 7.79(2H, d), 7.7(1H, dd), 7.68(1H, d), 7.58(1H, d), 7.51(2H, dd), 7.5(4H, dd), 7.46(4H, s), 7.41 (3H, t), 7.35 (1H, t), 7.2 (1H, dd), 7.19 (4H, dd), 7.16 (1H, t),1-285δ = 8.55(3H, s), 8.5(1H, d), 8.36(2H, d), 8.32(1H, d), 8.19(1H, d), 8.09(1H, d), 7.94(1H, d), 7.92(1H, d), 7.79(2H, d), 7.75(2H, dd), 7.7(2H, d), 7.58(1H, d), 7.51(2H, dd), 7.5(4H, dd), 7.49(2H, s), 7.46 (4H, t), 7.41 (3H, t), 7.35 (1H, dd), 7.2 (1H, dd), 7.16 (1H, t),1-290δ = 8.55(1H, s), 8.36(4H, d), 8.2(1H, d), 8.19(1H, d), 8.11(1H, d), 7.96(2H, d), 7.94(1H, d), 7.79(2H, d), 7.6(2H, d), 7.58(1H, dd), 7.51(2H, d), 7.5(7H, d), 7.46(4H, dd), 7.41(2H, dd), 7.35(1H, s), 7.2 (1H, t), 7.16 (1H, t),1-291δ = 8.55(1H, s), 8.5(1H, d), 8.38(1H, d), 8.36(4H, d), 8.19(1H, d), 8.09(1H, d), 7.94(2H, d), 7.79(2H, d), 7.75(2H, d), 7.73(1H, dd), 7.61(1H, d), 7.58(1H, d), 7.5(7H, dd), 7.49(2H, dd), 7.46(2H, s), 7.41 (2H, t), 7.35 (1H, t), 7.2 (1H, dd), 7.16 (1H, dd),1-292δ = 8.59(1H, s), 8.55(1H, d), 8.36(4H, d), 8.27(1H, d), 8.19(1H, d), 7.96(2H, d), 7.94(1H, d), 7.79(4H, d), 7.58(1H, d), 7.5(7H, dd), 7.46(4H, d), 7.41(2H, d), 7.35(1H, dd), 7.25(2H, dd), 7.2(1H, s), 7.16 (1H, t),1-298δ = 8.36(4H, s), 7.51(4H, d), 7.5(6H, d), 7.46(4H, d), 7.41(2H, d),1-299δ = 8.55(1H, s), 8.5(1H, d), 8.45(1H, d), 8.36(4H, d), 8.32(1H, d), 8.09(1H, d), 7.93(1H, d), 7.75(2H, d), 7.7(1H, d), 7.56(1H, dd), 7.5(6H, d), 7.49(3H, d), 7.41(1H, dd),1-300δ = 8.43(1H, s), 8.01(1H, d), 7.98(1H, d), 7.77(1H, d), 7.7(1H, d), 7.67(1H, d), 7.61(1H, d), 7.54(1H, d), 7.52(1H, d), 7.41(1H, dd), 7.39(1H, d), 7.31(1H, d),1-301δ = 7.77(1H, s), 7.52(1H, d),1-304δ = 8.36(2H, s), 7.77(1H, d), 7.67(2H, d), 7.61(1H, d), 7.52(1H, d), 7.5(3H, d), 7.49(1H, d), 7.42(1H, d),1-309δ = 8.55(1H, s), 8.5(1H, d), 8.36(4H, d), 8.09(1H, d), 7.94(1H, d), 7.81(1H, d), 7.79(2H, d), 7.75(2H, d), 7.72(1H, d), 7.67(1H, dd), 7.5(7H, d), 7.49(2H, d), 7.46(2H, dd), 7.41(3H, dd), 7.38(1H, s), 7.35 (1H, t), 7.16 (1H, t),.

[0382] <Manufacturing Example 7> Manufacturing of compound 2-1, etc.

[0383] 1) Preparation of compound 2-1-1

[0384] In a reaction flask, 10 g (49.59 mmol) of 3-bromo-9H-carbazole, 24.2 g (148.77 mmol) of 2-bromobenzene-1-ylium (a), 2.27 g (2.48 mmol) of Tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 2.42 mL (9.92 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 9.53 g (99.18 mmol) of sodium tert-butoxide (NatOBu) were added, and then 100 mL of toluene was added. It was heated at 135℃ for 15 hours. After the reaction was completed, it was extracted with methylene chloride (MC) and water, and purified by column chromatography to obtain 14 g (yield 98%) of compound 2-1-1.

[0385] 2) Preparation of target compound 2-1

[0386] In a reaction flask, 14 g (43.4 mmol) of the compound 2-1-1, 14.9 g (52 mmol) of (9-phenyl-9H-carbazol-3-yl)boronic acid (b), 2.5 g (2.17 mmol) of tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4, and 17.9 g (130 mmol) of potassium carbonate (K2CO3) were placed, and then 140 mL of 1,4-dioxane and 35 mL of distilled water were added, and the mixture was stirred at 120°C for 4 hours.

[0387] After that, the temperature was lowered to room temperature, and the resulting solid was washed with distilled water and methanol to obtain 17 g (80% yield) of the target compound 2-1.

[0388] Hereinafter, the target compound of Table 9 below was prepared in the same manner as the target compound 2-1, except that compound a of Table 9 below was used instead of the above 2-bromobenzene-1-ylium (a), and compound b of Table 9 below was used instead of (9-phenyl-9H-carbozol-3-yl)boronic acid (b).

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400] <Manufacturing Example 8> Manufacture of target compound 2-61, etc.

[0401]

[0402] 1) Preparation of compound 2-61-4

[0403] 10 g (40.23 mmol) of 3-bromo-9H-carbazole, 1,000 mL of D6-benzene, and 170 g (1,075 mmol) of triflic acid (CF3SO3H) were added and stirred at 50°C.

[0404] After the reaction was completed, the mixture was neutralized with D2O, extracted with aqueous sodium carbonate (Na2CO3) solution and dichloromethane (DCM) at room temperature, and the organic layer was dried over anhydrous magnesium sulfate (MgSO4) and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (dichloromethane:hexane = 1:2) and recrystallized from methanol to obtain 10 g (yield 98%) of the target compound 2-61-4.

[0405] 2) Preparation of compound 2-61-3

[0406] 10 g (39.5 mmol) of the above compound 2-61-4, 12.4 g (79 mmol) of bromobenzene, 1.81 g (1.98 mmol) of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 1.93 mL (7.9 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 11.4 g (118.51 mmol) of sodium tert-butoxide (NatOBu) were added, and then 100 mL of toluene was added and heated at 135°C for 15 hours. After the reaction was completed, the mixture was extracted with methylene chloride (MC) and water, and purified by column chromatography to obtain 11 g (yield 84%) of compound 2-61-3.

[0407] 3) Preparation of compound 2-61-2

[0408] 10 g (47.3 mmol) of 9H-carbazol-3-ylboronic acid, 1,000 mL of D6-benzene, and 170 g (1,075 mmol) of triflic acid (CF3SO3H) were added and stirred at 50°C.

[0409] After the reaction was completed, the mixture was neutralized with D2O, extracted with aqueous sodium carbonate (Na2CO3) solution and dichloromethane (DCM) at room temperature, and the organic layer was dried over anhydrous magnesium sulfate (MgSO4) and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (dichloromethane:hexane = 1:2) and recrystallized from methanol to obtain 9 g (yield 87%) of the target compound 2-61-2.

[0410] 4) Preparation of compound 2-61-1

[0411] After adding 9 g (41.3 mmol) of the above compound 2-61-2, 12.9 g (82.5 mmol) of bromobenzene, 1.89 g (2.06 mmol) of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 2 mL (8.25 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 7.93 g (82.574 mmol) of sodium tert-butoxide (NatOBu), 100 mL of toluene was added and heated at 135°C for 10 hours. After the reaction was completed, the mixture was extracted with methylene chloride (MC) and water, and purified by column chromatography to obtain 10 g (yield 82%) of compound 2-61-1.

[0412] 5) Preparation of target compound 2-61

[0413] 10 g (30.37 mmol) of the above compound 2-61-3, 17.87 g (60.75 mmol) of the above compound 2-61-1, 1.39 g (1.52 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) and 12.59 g (91.13 mmol) of potassium carbonate (K2CO3) were added, and then added to 140 mL of 1,4-dioxane and 35 mL of distilled water, and stirred at 120°C for 4 hours.

[0414] After that, the temperature was lowered to room temperature, and the resulting solid was washed with distilled water and methanol to obtain 13 g (85% yield) of the target compound 2-61.

[0415] Hereinafter, the target compounds of Table 10 below were each synthesized in the same manner as the target compound 2-61, except that compound c of Table 10 below was used instead of the bromobenzene (c) and compound d of Table 10 below was used instead of the bromobenzene (d).

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424] <Manufacturing Example 9> Manufacture of target compound 2-82, etc.

[0425]

[0426] 10 g (15.7 mmol) of the above compound 2-82-1 (compound 2-32), 1,000 mL of D6-benzene, and 170 g (1,075 mmol) of triflic acid (CF3SO3H) were added and stirred at 50°C.

[0427] After the reaction was completed, the mixture was neutralized with D2O, extracted with aqueous sodium carbonate (Na2CO3) solution and dichloromethane (DCM) at room temperature, and the organic layer was dried over anhydrous magnesium sulfate (MgSO4) and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (dichloromethane:hexane = 1:2) and recrystallized from methanol to obtain 10.0 g (yield 95%) of the target compound 2-82.

[0428] Below, compounds were manufactured using the same method as the above manufacturing examples, and the results of their synthesis are shown in Tables 11 and 12. Table 11 shows the measured values ​​of FD-MS, and Table 12 shows the measured values ​​of FD-MS. 1 This is the measured value of H NMR (CDCl3, 400 MHz).

[0429] Compound number FD-MS Compound number FD-MS2-1 m / z = 484.59 (C 36 H 24 N2=484.19)2-2m / z= 560.69(C 42 H 28 N2=560.23)2-3m / z= 560.69(C 42 H 28 N2=560.23)2-4m / z= 560.69(C 42 H 28 N2=560.23)2-5m / z= 636.78(C 48 H 32 N2=636.26)2-6m / z= 636.78(C 48 H 32 N2=636.26)2-7m / z= 636.78(C 48 H 32 N2=636.26)2-8m / z= 543.65(C 40 H 26N2=543.21)2-9m / z= 543.65(C 40 H 26 N2=543.21)2-10m / z= 600.75(C 45 H 35 N2=600.26)2-11m / z= 600.75(C 45 H 35 N2=600.26)2-12m / z= 724.89(C 55 H 36 N2=724.29)2-13m / z= 724.89(C 55 H 36 N2=724.29)2-14m / z= 724.89(C 55 H 36 N2=724.29)2-15m / z= 724.89(C 55 H 36 N2=724.29)2-16m / z= 634.77(C 48 H 30 N2=634.24)2-17m / z= 509.60(C 37 H 23 N3=509.19)2-18m / z= 742.98(C 54 H 38 N2Si=742.28)2-19m / z= 636.78(C 48 H 32 N2=636.26)2-20m / z= 636.78(C 48 H 32 N2=636.26)2-21m / z= 636.78(C 48 H 32 N2=636.26)2-22m / z= 712.88(C 54 H 36 N2=712.29)2-23m / z= 712.88(C 54 H 36 N2=712.29)2-24m / z= 712.88(C 54 H 36 N2=712.29)2-25m / z= 710.86(C 54 H 34 N2=710.27)2-26m / z= 712.88(C 54 H 36 N2=712.29)2-27m / z= 712.88(C54 H 36 N2=712.29)2-28m / z= 712.88(C 54 H 36 N2=712.29)2-29m / z= 712.88(C 54 H 36 N2=712.29)2-30m / z= 712.88(C 54 H 36 N2=712.29)2-31m / z= 710.86(C 54 H 34 N2=710.27)2-32m / z= 636.78(C 48 H 32 N2=636.26)2-33m / z= 712.88(C 54 H 36 N2=712.29)2-34m / z= 712.88(C 54 H 36 N2=712.29)2-35m / z= 788.97(C 60 H 40 N2=788.32)2-36m / z= 686.84(C 52 H 34 N2=686.27)2-37m / z= 788.97(C 60 H 40 N2=788.32)2-38m / z= 788.97(C 60 H 40 N2=788.32)2-39m / z= 686.84(C 52 H 34 N2=686.27)2-40m / z= 686.84(C 52 H 34 N2=686.27)2-41m / z= 494.65(C 36 H 14 D 10 N2=494.26)2-42m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-43m / z= 574.77(C 41 H 14 D 14 N2=574.31)2-44m / z= 650.86(C 48 H 14 D 16N2=650.34)2-45m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-46m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-47m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-48m / z=654.89(C 48 H 14 D 18 N2=654.37)2-49m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-50m / z: 734.43(C 54 H 14 D 22 N2=735.03)2-51m / z= 735.01(C 54 H 14 D 22 N2=734.43)2-52m / z= 735.01(C 54 H 14 D 22 N2=734.43)2-53m / z= 730.98(C 54 H 14 D 20 N2=730.40)2-54m / z= 735.01(C 54 H 14 D 22 N2=734.43)2-55m / z=735.01(C 54 H 14 D 22 N2=734.43)2-56m / z= 815.13(C 60 H 14 D 26 N2=814.48)2-57m / z= 815.13(C 60 H 14 D 26 N2=814.48)2-58m / z= 815.13(C 60 H 14 D 26 N2=814.48)2-59m / z= 815.13(C 60 H14 D 26 N2=814.48)2-60m / z= 666.86(C 48 H 14 D 16 N2O=666.34)2-61m / z= 498.68(C 36 H 10 D 14 N2=498.28)2-62m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-63m / z= 574.77(C 41 H 14 D 14 N2=574.31)2-64m / z= 648.85(C 48 H 16 D 14 N2=648.33)2-65m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-66m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-67m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-68m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-69m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-70m / z=726.38(C 54 H 22 D 14 N2=726.98)2-71m / z= 726.96(C 54 H 22 D 14 N2=726.38)2-72m / z= 726.96(C 54 H 22 D 14 N2=726.38)2-73m / z= 724.95(C 54 H 20 D 14N2=724.36)2-74m / z= 726.96(C 54 H 22 D 14 N2=726.38)2-75m / z= 726.96(C 54 H 22 D 14 N2=726.38)2-76m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-77m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-78m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-79m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-80m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-81m / z= 508.74(C 36 D 24 N2=508.34)2-82m / z= 668.98(C 48 D 32 N2=668.46)2-83m / z= 588.86(C 42 D 28 N2=588.40)2-84m / z= 664.95(C 48 D 30 N2=664.43)2-85m / z= 668.98(C 48 D 32 N2=668.46)2-86m / z= 668.98(C 48 D 32 N2=668.46)2-87m / z= 668.98(C 48 D 32 N2=668.46)2-88m / z= 668.98(C 48 D 32 N2=668.46)2-89m / z= 668.98(C 48 D 32 N2=668.46)2-90m / z= 748.518(C 54D 36 N2=749.12)2-91m / z= 749.10(C 54 D 36 N2=748.51)2-92m / z= 749.10(C 54 D 36 N2=748.51)2-93m / z= 745.07(C 54 D 34 N2=744.49)2-94m / z= 749.10(C 54 D 36 N2=748.51)2-95m / z= 749.10(C 54 D 36 N2=748.51)2-96m / z= 829.22(C 60 D 40 N2=828.57)2-97m / z= 829.22(C 60 D 40 N2=828.57)2-98m / z= 829.22(C 60 D 40 N2=828.57)2-99m / z= 829.22(C 60 D 40 N2=828.57)2-100m / z= 680.95(C 48 D 30 N2O=680.42)2-101m / z= 697.02(C 48 D 30 N2S=696.40)2-102m / z= 829.22(C 60 D 40 N2=828.57)2-103m / z= 632.95(C 45 D 32 N2=632.46)2-104m / z= 713.07(C 51 D 36 N2=712.51)

[0430] compound no 1H NMR(CDCl3, 400MHz)2-1δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.62-7.50(m, 12H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-2δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 6H), 7.80-7.77(m, 2H), 7.62-7.35(m, 10H), 7.20-7.16(m, 6H)2-3δ =8.55(d, 1H), 8.18-8.09(m, 3H), 8.00-7.87(m, 3H), 7.77(s, 2H), 7.58-7.25(m, 18H)2-4δ =8.55(d, 1H), 8.18-8.12(m, 2H), 8.00-7.84(m, 3H), 7.79-7.77(m, 4H), 7.68-7.25(m, 22H)2-5δ =8.55(d, 1H), 8.30(d, 1H), 8.21-8.13(m, 3H), 7.99-7.89(m, 4H), 7.77-7.35(m, 17H), 7.25-7.16(m, 6H)2-6δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.94-7.89(m, 8H), 7.77-7.75(m, 3H), 7.62-7.35(m, 11H), 7.25-7.16(m, 6H)2-7δ =8.55(d, 1H), 8.18-8.09(m, 4H), 8.00-7.94(m, 2H), 7.87(m, 1H), 7.77(m, 2H), 7.69-7.63(m, 2H), 7.52-7.25(m, 20H)2-11δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 5H), 7.77(d, 1H), 7.58-7.28(m, 16H), 1.69(s, 6H)2-16δ =9.05(s, 1H), 8.55(d, 1H), 8.33-8.13(m, 7H), 7.99-7.89(m, 5H), 7.77-7.50(m, 13H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-19δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 8H), 7.80-7.77(m, 3H), 7.58(d, 1H), 7.50-7.35(m, 6H), 7.20-7.16(m, 10H)2-20δ =8.55(d, 1H), 8.30(d, 1H), 8.21-8.13(m, 3H), 7.99-7.89(m, 6H), 7.80-7.35(m, 15H), 7.20-7.16(6H)2-21δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2h), 7.99-7.89(m, 10H), 7.80-7.75(m, 4H), 7.50-7.35(m, 8H), 7.20-7.16(m, 6H)2-22δ =8.55(d, 1H), 8.30(d, 1H), 8.21-8.13(m, 3H), 7.99-7.89(m, 6H), 7.80-7.35(m, 15H), 7.25-7.16(10H)2-23δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2h), 7.99-7.89(m, 10H), 7.80-7.75(m, 4H), 7.50-7.35(m, 8H), 7.25-7.16(m, 10H)2-26δ =8.55(m, 1H), 8.30(d, 1H), 8.21-8.13(m, 4h), 7.99-7.89(m, 4H), 7.77-7.35(m, 20H), 7.25-7.16(6H)2-27δ =8.55(m, 1H), 8.30(d, 1H), 8.21-8.13(m, 4h), 7.99-7.89(m, 4H), 7.77-7.35(m, 20H), 7.20-7.16(2H)2-28δ =8.55(m, 1H), 8.18-8.09(m, 3H), 8.00-8.79(m, 2H), 7.87(m, 1H), 7.79-7.77(m, 4H), 7.69-7.63(m, 4H), 7.52-7.25(m, 12H)2-29δ =8.55(m, 1H), 8.18-8.09(m, 3H), 8.00-7.94(m, 2H0, 7.87(m, 1H), 7.87(m, 1H), 7.79-7.77(m, 4H), 7.69-7.63(m, 4H), 7.52-7.25(m, 21H)2-30δ =8.55(m, 1H), 8.31-8.30(m, 3H), 8.21-8.13(m, 3h), 7.99-7.89(m, 3H), 7.75-7.35(m, 22H), 7.20-7.16(m, 2H)2-32δ =8.55(m, 1H), 8.18-8.12(m, 2H), 8.00-7.87(m, 3H), 7.79-7.77(m, 6H), 7.69-7.63(m, 6H), 7.52-7.25(m, 14H)2-33δ =8.55(m, 1H), 8.30(d, 1H), 8.21-8.13(m, 3H), 7.99-7.89(m, 8H), 7.77-7.35(m, 17H), 7.25-7.16(6H)2-34δ =8.55(m, 1H), 8.18-8.12(m, 2H), 8.00-7.87(m, 3H), 7.79-7.77(m, 6H), 7.67-7.63(m, 6H), 7.52-7.25(m, 18H)2-38δ =8.55(m, 1H), 8.18-8.12(m, 2H), 8.05-7.87(m, 6H), 7.79-7.77(m, 4H), 7.69-7.63(m, 4H), 7.52-7.25(m, 23H)2-40δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 8.03-7.75(m, 15H), 7.58-7.35(m, 9H), 7.25-7.16(m, 6H)2-41δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-42δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-43δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-45δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-46δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-48δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-49δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-50δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-51δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-52δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-55δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-57δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-60δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-61δ =7.62-7.50(m, 10H)2-62δ =7.79(m, 4H), 7.68(m. 4H), 7.52-7.41(m, 10H)2-63δ =8.21(s, 1H) 7.75-7.41(m, 13H)2-64δ =9.05(s, 1H), 8.33-8.25(m, 4H), 7.94(d, 1H), 7.70-7.50(m, 10H)2-65δ =7.79(m, 2H), 7.70-7.68(m, 3H), 7.58-7.41(m, 13H)2-66δ =7.92-7.91(m, 4H), 7.75(d, 2H), 7.62-7.41(m, 8H), 7.25(s, 4H)2-68δ =8.21(s, 2H), 7.75-7.60(m, 8H), 7.49-7.41(8H)2-69δ =8.21(s, 1H), 7.92-7.91(m, 4H), 7.75-7.60(m, 6H), 7.49-7.41(m, 7H)2-70δ =8.21(s, 1H), 7.94-7.91(m, 5H), 7.75-7.61(m, 9H), 7.49-7.41(m, 7H)2-74δ =7.94-7.91(m, 9H), 7.75-7.73(m, 5H), 7.61(d, 2H), 7.49-7.41(m, 6H)2-75δ =7.92-7.91(m, 8H), 7.75(d, 4H), 7.49-7.41(m, 6H), 7.25(s, 4H).

[0431] <Manufacturing Example 10> Manufacturing of target compound 3-1, etc.

[0432] 1) Preparation of compound 3-1-1

[0433] In a reaction flask, 10 g (39.0 mmol) of 5,8-dihydroindolo[2,3-c]carbazole (a), 6.12 g (39.0 mmol) of 1-bromobenzene (b), 1.79 g (1.95 mmol) of Tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.92 mL (3.9 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 7.50 g (78.0 mmol) of sodium tert-butoxide (NatOBu) were added, and then 100 mL of toluene was added. It was heated at 135℃ for 15 hours. After the reaction was completed, it was extracted with methylene chloride (MC) and water, and purified by column chromatography to obtain 7.3 g (yield 56%) of compound 3-1-1.

[0434] 2) Preparation of target compound 3-1

[0435] After adding 7.3 g (22.0 mmol) of the above compound 3-1-1, 3.8 g (24.2 mmol) of 1-bromobenzene (b), 1.01 g (1.1 mmol) of tris (dibenzylideneacetone) dipalladium (Pd2(dba)3), 0.52 mL (3.9 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 4.23 g (44.0 mmol) of sodium tert-butoxide (NatOBu), 70 mL of toluene was added and heated at 135°C for 15 hours. After the reaction was completed, the mixture was extracted with methylene chloride (MC) and water, and purified by column chromatography to obtain 8.3 g (yield 93%) of target compound 3-1.

[0436] The target compounds of Table 13 below were synthesized in the same manner as the target compound 3-1 above, except that instead of (a), intermediate A of Table 13 below was used, instead of (b), intermediate B of Table 13 below was used, and instead of (c), intermediate C of Table 13 below was used.

[0437]

[0438]

[0439]

[0440] Compounds were prepared in the same manner as the above manufacturing examples, and the results of their synthesis are shown in Tables 14 and 15 below. Table 14 shows the measured values ​​of FD-mass spectrometry (FD-MS), and Table 15 shows the measured values ​​of 1 This is the measured value of H NMR (CDCl3, 400 MHz).

[0441] Compound number FD-MS Compound number FD-MS3-1 m / z = 408.16 (C 30 H 20 N2=408.50)3-4m / z= 560.23(C42 H 28 N2=560.70)3-5m / z= m / z= 560.23(C 42 H 28 N2=560.70)3-22m / z= m / z= 560.23(C 42 H 28 N2=560.70)3-23m / z= m / z= 560.23(C 42 H 28 N2=560.70)3-32m / z= m / z= 560.23(C 42 H 28 N2=560.70)3-35m / z= m / z= 560.23(C 42 H 28 N2=560.70)3-41m / z= m / z= 560.23(C 42 H 28 N2=560.70)3-61m / z= 578.34(C 42 H 10 D 18 N2=578.81)3-69m / z= 570.29(C 42 H 18 D 10 N2=570.76)3-77m / z= 588.40(C 42 D 28 N2=588.87)

[0442] compound no 1H NMR(CDCl3, 400MHz)3-1δ = 8.55(2H, d), 7.94(2H, d), 7.62-7.35(14H, m), 7.16(2H, d)3-4δ = 8.55(2H, d), 7.94-7.91(10H, m), 7.75(4H, d), 7.49-7.35(10H, m), 7.16(2H, t)3-5δ = 8.55(2H, d), 8.21(1H, s), 7.94-7.91(6H, m), 7.75-7.35(16H, m), 7.26(1H, d), 7.16(2H, t)3-22δ = 8.55(1H, d), 8.19(1H, d), 7.94-7.91(9H, m), 7.75(4H, d), 7.58-7.35(11H, m), 7.20-7.16(2H, m)3-23δ = 8.55(1H, d), 8.21-8.19(2H, m), 7.94-7.91(5H, m), 7.75-7.35(18H, m), 7.20-7.16(2H, m)3-32δ = 8.55(1H, d), 8.19(1H, d), 7.94-7.91(9H, m), 7.75(4H, d), 7.58-7.35(11H, m), 7.20-7.16(2H, m)3-35δ = 8.55(1H, d), 8.21-8.19(2H, m), 7.94-7.91(5H, m), 7.68-7.35(18H, m), 7.20-7.16(2H, m)3-41δ = 8.55(2H, d), 7.94-7.91(10H, m), 7.84(2H, d), 7.75(4H, d), 7.49-7.35(8H, m), 7.16(2H, t)3-61δ = 8.55(2H, d), 7.94(2H, d), 7.42-7.35(4H, m), 7.16(2H, t)3-69δ = 7.92-7.91(8H, m), 7.75(4H, d), 7.49-7.41(6H, m)

[0443] <실험예 1> 1) 유기 발광 소자(OLED)의 제작

[0444] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (ultraviolet ozone) for 5 minutes in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), where it was plasma-treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic vapor deposition.

[0445] 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).

[0446] On top of that, a light-emitting layer was thermally vacuum deposited as follows. The light-emitting layer used the compound described in Table 16 as a host, and Ir(ppy)3(tris(2-phenylpyridine)iridium) as a green phosphorescent dopant, and the host was doped with 7% Ir(ppy)3 and deposited to a thickness of 400Å. Then, BCP(Bathocuproine) was deposited to a thickness of 60Å as a hole-blocking layer, and Alq3 was deposited to a thickness of 200Å as an electron-transport layer thereon. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron-transport layer to form an electron-injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1200Å on the electron-injection layer to form a cathode, thereby manufacturing an organic light-emitting device.

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

[0448] 2) Driving voltage and luminous efficiency of organic light-emitting devices

[0449] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using M7000 from MaxScience, and the standard luminance was determined to be 6,000 cd / m using the life measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 When, T 90 was measured.

[0450] The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention were as shown in Table 16 below.

[0451]

[0452]

[0453]

[0454] The compounds used in each of Comparative Examples 1 to 19 are as follows.

[0455]

[0456] As can be seen from the results in Table 16 above, it was confirmed that Examples 1 to 87, which are organic light-emitting devices using the compound represented by Chemical Formula 1 of the present invention as a light-emitting layer material (particularly, a green phosphorescent host), had lower operating voltages and significantly improved luminous efficiency and lifespans compared to Comparative Examples 1 to 19, which are organic light-emitting devices not using the compound represented by Chemical Formula 1 of the present invention as a light-emitting layer material.

[0457] Specifically, the compounds used in the organic light-emitting devices of Examples 1 to 87 have four substituents based on the benzene core, among which the triazine substituent and the phenyl substituent are fixedly bonded in the para direction, and at the remaining positions, the N of the carbazole substituent is bonded to the benzene core and the substituent corresponding to Ar3 is bonded.

[0458] On the other hand, the compounds used in the organic light-emitting devices of Comparative Examples 1 to 4 and 13 to 15 (ref. 1 to ref. 4 and ref. 13 to ref. 15) have three or four substituents based on the benzene core, but the triazine group and the carbazole are bonded in the para direction. In the case of this bonding structure, the HOMO and LUMO overlap and become unstable, so it is judged that the device performance (driving voltage, luminous efficiency, and / or lifespan) of Comparative Examples 1 to 4 is overall degraded.

[0459] In addition, the compounds used in the organic light-emitting devices of Comparative Examples 5 and 6 (ref. 5 and ref. 6) have four substituents based on the benzene core, but two of the substituents are bonded to carbazole. In the case of this bonding structure, it is believed that the HOMO is greatly strengthened due to the strong donor carbazole, causing an imbalance between the HOMO and LUMO, or the efficiency is reduced and the driving voltage is increased due to the strong donor characteristic.

[0460] The compounds used in the organic light-emitting devices of Comparative Examples 7 and 8 (ref. 7 and ref. 8) used a triphenyl core instead of a benzene core, and it appears that they had stronger steric properties than those claimed in the present invention, resulting in lower efficiency and higher operating voltage.

[0461] The compounds used in the organic light-emitting devices of Comparative Examples 9 to 12 (ref. 9 to ref. 12) appear to have greatly enhanced HOMO or LUMO, resulting in a decrease in efficiency and an increase in driving voltage due to an imbalance in charge balance.

[0462] The compounds used in the organic light-emitting devices of Comparative Examples 16 and 17 (ref. 16 and ref. 17) were used as hosts because their intended uses were as materials for electron transport layers and dopants, respectively, and thus their lifespan and efficiency were judged to be poor.

[0463] It is believed that the compound used in the organic light-emitting device of Comparative Example 18 (ref. 18) has a reduced lifetime due to a decrease in LUMO stabilization because the phenyl group is not extended to the linker benzene, unlike in the present claim.

[0464] It is believed that the compound used in the organic light-emitting device of Comparative Example 19 (ref. 19) has a HOMO that is greatly strengthened due to the symmetrical positioning of the strong donor carbazole, causing an imbalance between the HOMO and LUMO, or that the efficiency is reduced and the driving voltage is increased due to the strong donor characteristic.

[0465] Accordingly, the compounds used in the organic light-emitting devices of Examples 1 to 87, carbazole ortho-bonded to triazine or aryl, have high molecular stability due to steric hindrance between substituents. The reason for this high stability is that molecules have various energy levels due to rotational and vibrational motion. In the case of compounds with strong steic, rotation within the molecule is restricted, and at this time, the vibrational energy within the molecule is reduced, thereby increasing the stability of the molecule. This can increase the lifespan of the device. In addition, it increases the efficiency of the device by reducing the non-luminescent energy loss of the molecule. In addition, in the case of the present invention, the carbazole corresponding to the donor and the triazine corresponding to the acceptor are spatially opposite each other. This allows smooth spatial CT to occur by Through Space Charge Transfer, which can increase the efficiency of the device. It is presumed that this is advantageous for both hole and electron transport, and thus the lifespan is judged to be excellent. In addition, it is judged that the efficiency is increased due to the increased spatial distance, which facilitates charge transfer.

[0466] In other words, when the compound corresponding to the chemical formula 1 of the present invention is used as a host for the light-emitting layer, it can be confirmed that the driving voltage, light-emitting efficiency, and lifespan are remarkably excellent.

[0467] Experimental Example 2

[0468] 1) Fabrication of organic light-emitting devices

[0469] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT), where it was plasma-treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0470] A common layer, a hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine), were formed on the ITO transparent electrode (anode).

[0471] On top of that, a light-emitting layer was thermally vacuum deposited as follows.

[0472] The light-emitting layer was deposited in a thickness of 400 Å in one park by pre-mixing one compound having the structure of chemical formula 1 as a host and one heterocyclic compound having the structure of chemical formula 2 or 3 according to Table 17 below, and the green phosphorescent dopant was deposited by doping Ir(ppy)3 at 7% of the thickness of the light-emitting layer deposition.

[0473] Afterwards, BCP was deposited as a hole blocking layer with a thickness of 60 Å, and Alq3 was deposited as an electron transport layer with a thickness of 200 Å on top of it. Finally, lithium fluoride (LiF) was deposited on the electron transport layer with a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer with a thickness of 1,200 Å to form a cathode, thereby manufacturing an organic light-emitting device.

[0474] 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.

[0475] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using MacScience's M7000, and the standard luminance was determined to be 6,000 cd / m using the lifespan measuring equipment (M6000) manufactured by MacScience based on the measurement results. 2 When, T 90 was measured.

[0476] The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention were as shown in Table 17 below.

[0477] [Table 17]

[0478]

[0479]

[0480]

[0481] The compounds used in Comparative Examples 20 to 40 of Table 17 above are the same as those used in Experimental Example 1.

[0482] From the results in Table 17 above, when the compound of formula 1 and the heterocyclic compound of formula 2 were included simultaneously, or when the compound of formula 1 and the heterocyclic compound of formula 3 were included simultaneously (Examples 1-88 to 1-186), better efficiency and lifespan effects were observed. From the above results, it can be expected that an exciplex phenomenon occurs when the two compounds are included simultaneously.

[0483] The above exciplex phenomenon is a phenomenon in which energy of the size of the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) is released due to electron exchange between two molecules. When the exciplex phenomenon occurs between two molecules, Reverse Intersystem Crossing (RISC) occurs, and this can increase the internal quantum efficiency of fluorescence up to 100%. When a donor (p-host) with a good hole transport ability and an acceptor (n-host) with a good electron transport ability are used as a host for the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host, so the driving voltage can be lowered, which can help improve the lifespan. In the present invention, it was confirmed that the heterocyclic compound represented by the chemical formula 2 or 3 acts as a donor (p-host), and the compound represented by the chemical formula 1 acts as an acceptor, and when such a combination is used as a host for the light-emitting layer, excellent device characteristics are exhibited.

[0484] On the other hand, it can be seen that compounds (Comparative Examples 20 to 40) that do not satisfy the structure of Chemical Formula 1 of the present invention have inferior device performance in terms of driving voltage, luminous efficiency, and / or lifespan compared to the example group, even when used in combination with compounds of Chemical Formula 2 or Chemical Formula 3.

[0485] That is, when the compound of chemical formula 1 of the present invention and the compound of chemical formula 2 or 3 are simultaneously used as a host for the light-emitting layer, it can be confirmed that the driving voltage, light-emitting efficiency, and lifespan are remarkably excellent.

[0486] The present invention is not limited to the above-described embodiments, but can be manufactured in a variety of different forms. Those skilled in the art will appreciate that the present invention can be implemented in other specific forms without altering the technical spirit or essential characteristics of the present invention. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X1 to X3 are the same or different from each other, and are each independently N or CRa, and at least one of X1 to X3 is N, Ra is selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; -P(=O)R R'; and -SiR R'R", Ar1 to Ar3 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group containing at least one heteroatom of O and S; or a combination thereof, L1 and L2 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, R1 and R4 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR', R2 and R3 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR', or two or more adjacent groups combine with each other to form a substituted or unsubstituted ring, The above R, R' and R" are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, a is an integer from 0 to 2, Each of b and c is an integer from 0 to 4, d is an integer from 0 to 5, Each m and n is an integer from 0 to 4, If each of a, b, c, d, m and n is an integer greater than or equal to 2, the substituents within the parentheses are the same or different.

2. In claim 1, The above chemical formula 1 is a compound represented by any one of the following chemical formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-1 to 1-6, Each of X1 to X3, L1, L2, Ar1 to Ar3, R1 to R4, a, b, c, d, m and n are as defined in the chemical formula 1.

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

4. In claim 1, A compound wherein Ar1 to Ar3 are the same or different and each independently represent a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group containing at least one heteroatom selected from O and S; or a combination thereof.

5. In claim 1, A compound wherein L1 and L2 are the same or different and each independently a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group containing at least one heteroatom selected from O and S.

6. In claim 1, A compound wherein R1 and R4 are the same or different and each independently hydrogen or deuterium.

7. In claim 1, A compound wherein R2 and R3 are the same or different, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group; and a substituted or unsubstituted C2 to C30 heteroaryl group, or two or more adjacent groups combine with each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 aromatic heterocycle.

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

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

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

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

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

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

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

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

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

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

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