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

Abstract

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

Description

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

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

[0002] <Cross-reference to related applications>

[0003] This application claims the benefit of Korean Patent Application No. 10-2023-0106297, filed with the Korean Intellectual Property Office on August 14, 2023, the entire contents of which are incorporated herein by reference.

[0004] 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.

[0005] Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting device of this structure, electrons and holes injected from the two electrodes combine in the organic thin film, forming pairs and then disappearing, emitting light. The organic thin film may be composed of a single layer or multiple layers, as needed.

[0006] The material of the organic thin film may have a light-emitting function as needed. For example, the organic thin film material may be a compound that can form a light-emitting layer on its own, or a compound that can act as a host or dopant in a host-dopant light-emitting layer. In addition, the material of the organic thin film may be a compound that can perform roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection.

[0007] To improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of materials for organic thin films is continuously required.

[0008] [Prior Art Literature]

[0009] (Patent Document 1) U.S. Patent No. 4,356,429

[0010] The present specification provides a compound, an organic light-emitting device, and a composition for an organic layer of an organic light-emitting device.

[0011] One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] R1 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; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R",

[0016] R2 is hydrogen; or deuterium,

[0017] L1 to L3 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,

[0018] a is an integer from 0 to 8,

[0019] b is an integer from 0 to 3,

[0020] o, p and q are equal or different and are each independently an integer from 0 to 3,

[0021] r and s are equal to or different from each other and are each independently an integer from 1 to 4,

[0022] If each of a, b, o, p, q, r and s is 2 or more, the substituents in the parentheses are the same or different from each other,

[0023] Ar1 is represented by the following chemical formula A,

[0024] [Chemical Formula A]

[0025]

[0026] In the above chemical formula A,

[0027] is the part connected to the above L2,

[0028] Rk is hydrogen; deuterium; or a substituted or unsubstituted C6 to C60 aryl group,

[0029] X1 is O; S; or C(R5)(R6),

[0030] R4 is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", wherein at least one R4 is a substituted or unsubstituted C6 to C60 aryl group,

[0031] R5 and R6 are the same or different, 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 C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or adjacent groups are combined with each other to form a substituted or unsubstituted ring,

[0032] d is an integer from 1 to 6, and when d is 2 or greater, R4 are identical or different from each other,

[0033] N-Het is represented by the following chemical formula B:

[0034] [Chemical Formula B]

[0035]

[0036] In the above chemical formula B,

[0037] is the part connected to the above L3,

[0038] X2 is CRa or N, X3 is CRb or N, X4 is CRc or N, but at least one of X2 to X4 is N,

[0039] Ar2 and Ar3 are the same or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0040] Ra, Rb and Rc are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; -P(=O)RR'; and -SiRR'R",

[0041] 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; or a substituted or unsubstituted C6 to C60 aryl group.

[0042] 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.

[0043] Another embodiment of the present specification provides a composition for an organic layer comprising the compound and a heterocyclic compound represented by the following chemical formula 2 or 3.

[0044] [Chemical Formula 2]

[0045]

[0046] [Chemical Formula 3]

[0047]

[0048] In the above chemical formulas 2 and 3,

[0049] 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',

[0050] 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,

[0051] 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",

[0052] 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,

[0053] a11 and a12 are integers from 0 to 7, respectively,

[0054] a22 is an integer from 0 to 6,

[0055] a23 is an integer from 0 to 4,

[0056] p11, p12, p22 and p23 are integers from 0 to 4, respectively.

[0057] q11, q12, q22 and q23 are integers from 1 to 4, respectively,

[0058] When a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 are each 2 or more, the substituents in the parentheses are the same or different from each other.

[0059] 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.

[0060] Specifically, the compound of the present invention has a structure represented by Chemical Formula 1, and when a strong donor and a strong acceptor are directly bonded within a molecule, a benzene core that may cause a decrease in lifetime due to HOMO-LUMO overlap is introduced to offset the HOMO-LUMO overlap, thereby improving the lifetime.

[0061] Specifically, by introducing N-carbazole, which acts as a strong donor and is responsible for HOMO within the molecule as the first substituent connected to the benzene core, high hole mobility is achieved and charge transfer within the molecule is smooth, thereby exhibiting high efficiency.

[0062] In addition, as a second substituent connected to the benzene core, Ar1 (represented by chemical formula A) is a tricyclic structure, such as a tricyclic fused ring structure such as dibenzofuran, dibenzothiophene, dimethylfluorenyl, etc., and acts as a sub-donor within the molecule, and can effectively stabilize electrons by increasing the delocalization rate of the HOMO site through expansion of the resonance structure.

[0063] In addition, as a third substituent connected to the benzene core, N-Het (represented by chemical formula B) acts as a strong electron acceptor, introducing an N-containing heteroaryl responsible for LUMO within the molecule, thereby effectively pulling electrons from the first and second substituents described above, i.e., N-carbazole (strong donor) and Ar1 (sub-donor), thereby promoting electron stabilization within the molecule, thereby improving the lifespan.

[0064] Figures 1 to 4 are drawings each exemplifying a laminated structure of an organic light-emitting device according to one embodiment of the present specification.

[0065] [Explanation of symbols]

[0066] 100: Substrate

[0067] 200: Bipolar

[0068] 300: Organic layer

[0069] 301: Hole injection layer

[0070] 302: Hole transport layer

[0071] 303: Electronic barrier layer

[0072] 304: Emissive layer

[0073] 305: Electron transport layer

[0074] 306: Electron injection layer

[0075] 400: Cathode

[0076] Hereinafter, the present specification will be described in more detail.

[0077] 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.

[0078] In this specification, the chemical formula means the position where it is combined.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] In one embodiment of the present application, “when no substituent is indicated in the chemical formula or compound structure” may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the deuterium content may be 0% to 100%.

[0083] In one embodiment of the present application, in the case where “no substituent is indicated in the chemical formula or compound structure,” if the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents are hydrogen, etc., and deuterium is not explicitly excluded, hydrogen and deuterium may be used in combination in the compound.

[0084] In one embodiment of the present application, deuterium is an element having a deuteron, which is one of the isotopes of hydrogen and is composed of one proton and one neutron, as its nucleus, and can be expressed as hydrogen-2, and its element symbol is D or 2 It can also be written as H.

[0085] In one embodiment of the present application, an isotope means an atom having the same atomic number (Z) but a different mass number (A). An isotope can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0086] In one embodiment of the present application, the meaning of the content T% of a specific substituent can be defined as T2 / T1×100 = T% when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2.

[0087] 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.

[0088]

[0089] 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.

[0090] In this specification, the halogen may be fluorine, chlorine, bromine or iodine.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] In this specification, the terphenyl group may be selected from the following structures.

[0099]

[0100] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0101] When the above fluorenyl group is substituted, it may be selected from the following structures, but is not limited thereto.

[0102]

[0103] 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.

[0104] 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.

[0105] 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 to these.

[0106] 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.

[0107] 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.

[0108] 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.

[0109] 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.

[0110] One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[0111] [Chemical Formula 1]

[0112]

[0113] In the above chemical formula 1, the description of each substituent is as described above.

[0114] 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.

[0115] Specifically, the compound of the present invention has a structure represented by Chemical Formula 1, and when a strong donor and a strong acceptor are directly bonded within a molecule, a benzene core that may cause a decrease in lifetime due to HOMO-LUMO overlap is introduced to offset the HOMO-LUMO overlap, thereby improving the lifetime.

[0116] Specifically, by introducing N-carbazole, which acts as a strong donor and is responsible for HOMO within the molecule as the first substituent connected to the benzene core, high hole mobility is achieved and charge transfer within the molecule is smooth, thereby exhibiting high efficiency.

[0117] In addition, as a second substituent connected to the benzene core, Ar1 (represented by chemical formula A) is a tricyclic structure, such as a tricyclic fused ring structure such as dibenzofuran, dibenzothiophene, dimethylfluorenyl, etc., and acts as a sub-donor within the molecule, and can effectively stabilize electrons by increasing the delocalization rate of the HOMO site through expansion of the resonance structure.

[0118] In addition, as a third substituent connected to the benzene core, N-Het (represented by chemical formula B) acts as a strong electron acceptor, introducing an N-containing heteroaryl responsible for LUMO within the molecule, thereby effectively pulling electrons from the first and second substituents described above, i.e., N-carbazole (strong donor) and Ar1 (sub-donor), thereby promoting electron stabilization within the molecule, thereby improving the lifespan.

[0119] 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 1-10.

[0120] [Chemical Formula 1-1]

[0121]

[0122] [Chemical Formula 1-2]

[0123]

[0124] [Chemical Formula 1-3]

[0125]

[0126] [Chemical Formula 1-4]

[0127]

[0128] [Chemical Formula 1-5]

[0129]

[0130] [Chemical Formula 1-6]

[0131]

[0132] [Chemical Formula 1-7]

[0133]

[0134] [Chemical Formula 1-8]

[0135]

[0136] [Chemical Formula 1-9]

[0137]

[0138] [Chemical Formula 1-10]

[0139]

[0140] In the above chemical formulas 1-1 to 1-10, R1, R2, L1 to L3, Ar1, N-Het, a, b, o, p, q, r and s are as defined in the above chemical formula 1.

[0141] In one embodiment of the present specification, the chemical formula A may be represented by any one of the following chemical formulas A-1 to A-7.

[0142] [Chemical Formula A-1]

[0143]

[0144] [Chemical Formula A-2]

[0145]

[0146] [Chemical Formula A-3]

[0147]

[0148] [Chemical Formula A-4]

[0149]

[0150] [Chemical Formula A-5]

[0151]

[0152] [Chemical Formula A-6]

[0153]

[0154] [Chemical Formula A-7]

[0155]

[0156] In the above chemical formulas A-1 to A-7, is a part connected to the above L2, and Rk, R4, X1, and d are as defined in the above chemical formula A.

[0157] In one embodiment of the present specification, R1 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; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)RR'; and -SiRR'R".

[0158] In one embodiment of the present specification, R1 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; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)RR'; and -SiRR'R".

[0159] In one embodiment of the present specification, R1 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; a substituted or unsubstituted C6 to C20 aryl group; -P(=O)RR'; and -SiRR'R".

[0160] In one embodiment of the present specification, R1 may be selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group.

[0161] In one embodiment of the present specification, R1 may be selected from the group consisting of hydrogen; deuterium; a C1 to C20 alkyl group substituted or unsubstituted with deuterium; and a C6 to C20 aryl group substituted or unsubstituted with deuterium.

[0162] In one embodiment of the present specification, R1 may be hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; or a biphenyl group substituted or unsubstituted with deuterium.

[0163] In one embodiment of the present specification, L1 to L3 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.

[0164] In one embodiment of the present specification, L1 to L3 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.

[0165] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently may be a direct bond; or a C6 to C20 arylene group substituted or unsubstituted with deuterium.

[0166] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently may be a direct bond; or a phenylene group substituted or unsubstituted with deuterium.

[0167] In one embodiment of the present specification, Rk may be hydrogen; deuterium; or a substituted or unsubstituted C6 to C40 aryl group.

[0168] In one embodiment of the present specification, Rk may be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group.

[0169] In one embodiment of the present specification, Rk may be hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; or a biphenyl group substituted or unsubstituted with deuterium.

[0170] In one embodiment of the present specification, R4 is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)RR'; and -SiRR'R", wherein at least one R4 may be a substituted or unsubstituted C6 to C40 aryl group.

[0171] In one embodiment of the present specification, R4 is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)RR'; and -SiRR'R", wherein at least one R4 may be a substituted or unsubstituted C6 to C20 aryl group.

[0172] In one embodiment of the present specification, R4 is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group, wherein at least one R4 may be a substituted or unsubstituted C6 to C20 aryl group.

[0173] In one embodiment of the present specification, R4 is hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group, wherein at least one R4 may be a substituted or unsubstituted C6 to C20 aryl group.

[0174] In one embodiment of the present specification, R4 is hydrogen; deuterium; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group, wherein at least one R4 may be a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group.

[0175] In one embodiment of the present specification, R4 is hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; or a biphenyl group substituted or unsubstituted with deuterium, wherein at least one R4 may be a phenyl group substituted or unsubstituted with deuterium; or a biphenyl group substituted or unsubstituted with deuterium.

[0176] In one embodiment of the present specification, R5 and R6 are the same or different, 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 C3 to C40 cycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; and a substituted or unsubstituted C2 to C40 heteroaryl group, or adjacent groups may be combined with each other to form a substituted or unsubstituted C2 to C40 heterocycle; or a substituted or unsubstituted C6 to C40 hydrocarbon ring.

[0177] In one embodiment of the present specification, R5 and R6 are the same or different, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group, or adjacent groups may be combined with each other to form a substituted or unsubstituted C2 to C20 heterocycle; or a substituted or unsubstituted C6 to C20 hydrocarbon ring.

[0178] In one embodiment of the present specification, R5 and R6 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a C1 to C20 alkyl group substituted or unsubstituted with deuterium; and a C6 to C20 aryl group substituted or unsubstituted with deuterium, or adjacent groups may be combined with each other to form a substituted or unsubstituted C6 to C20 hydrocarbon ring.

[0179] In one embodiment of the present specification, R5 and R6 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a methyl group substituted or unsubstituted with deuterium; and a phenyl group substituted or unsubstituted with deuterium, or adjacent groups may be combined with each other to form a fluorene ring substituted or unsubstituted with deuterium.

[0180] In one embodiment of the present specification, X2 may be N, X3 may be CRb, and X4 may be CRc.

[0181] In one embodiment of the present specification, X2 may be CRa, X3 may be N, and X4 may be CRc.

[0182] In one embodiment of the present specification, X2 may be CRa, X3 may be CRb, and X4 may be N.

[0183] In one embodiment of the present specification, X2 and X3 may be N, and X4 may be CRc.

[0184] In one embodiment of the present specification, X3 and X4 may be N, and X2 may be CRa.

[0185] In one embodiment of the present specification, X2 and X4 may be N, and X3 may be CRb.

[0186] In one embodiment of the present specification, X2 to X4 may be N.

[0187] In one embodiment of the present specification, Ar2 and 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; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0188] In one embodiment of the present specification, Ar2 and 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; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0189] In one embodiment of the present specification, Ar2 and Ar3 may be the same as or different from each other, and may each independently be a C6 to C20 aryl group substituted or unsubstituted with deuterium; or a C2 to C20 heteroaryl group substituted or unsubstituted with deuterium.

[0190] In one embodiment of the present specification, Ar2 and Ar3 may be the same as or different from each other, and each independently be a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; a terphenyl group unsubstituted or substituted with deuterium; a triphenyl group unsubstituted or substituted with deuterium; a dibenzofuranyl group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group; or a dibenzothiophene group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group.

[0191] In one embodiment of the present specification, Ra, Rb and Rc are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; -P(=O)RR'; and -SiRR'R".

[0192] In one embodiment of the present specification, Ra, Rb and Rc are the same as or different from each other, and each independently may be selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; -P(=O)RR'; and -SiRR'R".

[0193] In one embodiment of the present specification, R, R' and R" are the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 aryl group.

[0194] 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; or a substituted or unsubstituted C6 to C20 aryl group.

[0195] 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%.

[0196] 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%.

[0197] 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%.

[0198] 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%.

[0199] 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%.

[0200] 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%.

[0201] 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%.

[0202] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following.

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220] 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.

[0221] 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.

[0222] 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).

[0223] 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.

[0224] [Chemical Formula 2]

[0225]

[0226] [Chemical Formula 3]

[0227]

[0228] In the above chemical formulas 2 and 3,

[0229] 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',

[0230] 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,

[0231] 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",

[0232] 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,

[0233] a11 and a12 are integers from 0 to 7, respectively,

[0234] a22 is an integer from 0 to 6,

[0235] a23 is an integer from 0 to 4,

[0236] p11, p12, p22 and p23 are integers from 0 to 4, respectively.

[0237] q11, q12, q22 and q23 are integers from 1 to 4, respectively,

[0238] When a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 are each 2 or more, the substituents in the parentheses are the same or different from each other.

[0239] 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'.

[0240] 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'.

[0241] 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'.

[0242] 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.

[0243] 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.

[0244] 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.

[0245] 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.

[0246] 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.

[0247] 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".

[0248] 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 C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; or -SiRR'R".

[0249] 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 C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; or -SiRR'R".

[0250] 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 C20 heteroaryl group substituted or unsubstituted with deuterium; or -SiRR'R".

[0251] 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 cyano group; a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; a terphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; a 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.

[0252] 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.

[0253] 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%.

[0254] 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%.

[0255] 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%.

[0256] 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%.

[0257] 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%.

[0258] 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%.

[0259] 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%.

[0260] In one embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 2 or 3 may be represented by any one of the following.

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273] 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).

[0274] In one embodiment of the present specification, the light-emitting layer including the compound may additionally include a heterocyclic compound represented by the chemical formula 2 or 3.

[0275] 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).

[0276] 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.

[0277] 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.

[0278] 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.

[0279] In one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0280] In another embodiment of the present specification, the first electrode may be a cathode and the second electrode may be an anode.

[0281] 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).

[0282] 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.

[0283] 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.

[0284] 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.

[0285] 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.

[0286] The stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present disclosure is exemplified in Figures 1 to 4. However, the scope of the present application is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present application.

[0287] 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.

[0288] FIG. 3 and FIG. 4 illustrate a case where the organic layer is multilayered. The organic light-emitting device according to FIG. 3 includes a hole injection layer (301), a hole transport layer (302), a light-emitting layer (304), an electron transport layer (305), and an electron injection layer (306), and the organic light-emitting device according to FIG. 4 includes a hole injection layer (301), a hole transport layer (302), an electron blocking layer (303), a light-emitting layer (304), an electron transport layer (305), and an electron injection layer (306). However, the scope of the present application is not limited by such a laminated structure, and, if necessary, layers other than the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0289] For example, the organic layer may further include a hole transport auxiliary layer, and the hole transport auxiliary layer may be included between the hole transport layer (302) and the electron blocking layer (303) based on the laminated structure.

[0290] 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.

[0291] 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 application, and may be replaced with materials known in the art.

[0292] 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.

[0293] 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.

[0294] 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.

[0295] 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.

[0296] 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.

[0297] For example, LiF is a representative material used in the art, but the present application is not limited thereto.

[0298] 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.

[0299] 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.

[0300] 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.

[0301] 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.

[0302] 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.

[0303] Another embodiment of the present specification provides a composition for an organic layer comprising a compound represented by the above chemical formula 1 and a heterocyclic compound represented by the following chemical formula 2 or 3.

[0304] [Chemical Formula 2]

[0305]

[0306] [Chemical Formula 3]

[0307]

[0308] In the above chemical formulas 2 and 3,

[0309] 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',

[0310] 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,

[0311] 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",

[0312] 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,

[0313] a11 and a12 are integers from 0 to 7, respectively,

[0314] a22 is an integer from 0 to 6,

[0315] a23 is an integer from 0 to 4,

[0316] p11, p12, p22 and p23 are integers from 0 to 4, respectively.

[0317] q11, q12, q22 and q23 are integers from 1 to 4, respectively,

[0318] When a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 are each 2 or more, the substituents in the parentheses are the same or different from each other.

[0319] 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.

[0320] 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.

[0321] 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.

[0322] 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.

[0323] In one embodiment of the present specification, a method for manufacturing an organic light-emitting device is provided, comprising: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, wherein the forming of the organic layer comprises forming one or more organic layers using an organic layer composition comprising a compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 2 or 3.

[0324] 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.

[0325] 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.

[0326] The above pre-mixed material may be referred to as a composition for an organic layer according to one embodiment of the present specification.

[0327] 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.

[0328] Manufacturing example

[0329] <Manufacturing Example 1> Preparation of Compound 1-1

[0330]

[0331] 1) Preparation of compound 1-1-3

[0332] 10 g (47.7 mM) of the above compound 1-1-4, 17.6 g (47.7 mM) of (A) 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane, 42.77 g (2.4 mM) of Pd(PPh3), and 13.19 g (95.4 mM) of K2CO3 were dissolved in 1,4-dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 15.7 g (88.3%) of the target compound 1-1-3 was obtained with methanol.

[0333] 2) Preparation of compound 1-1-2

[0334] 15.7 g (42.1 mM) of the above compound 1-1-3, 16.0 g (63.2 mM) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 31.9 g (2.1 mM) of Pd2(dba), 2.0 g (4.2 mM) of Xphos, and 8.18 g (84.2 mM) 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 14.2 g (72.5%) of the target compound 1-1-2.

[0335] 3) Preparation of compound 1-1-1

[0336] 14.2 g (30.6 mM) of the above compound 1-1-2, 8.2 g (30.6 mM) of (B) 2-chloro-4,6-diphenyl-1,3,5-triazine, 41.8 g (1.53 mM) of Pd(PPh3), and 8.45 g (61.2 mM) of K2CO3 were dissolved in 250 mL / 50 mL of 1,4-dioxane / H2O, and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 16.0 g (92.0%) of the target compound 1-1-1 was obtained with methanol.

[0337] 4) Preparation of compound 1-1

[0338] 16.0 g (28.1 mM) of the above compound 1-1-1, 4.7 g (28.1 M) of (C)9H-carbazole, and 27.5 g (84.3 mM) of Cs2CO3 were dissolved in 160 mL of DMA and refluxed at 180°C for 5 hours. After the reaction was completed, distilled water was added to precipitate a solid, which was then purified by column chromatography (DCM:Hex=1:2) and 16.7 g (83.0%) of the target compound 1-1 was obtained with methanol.

[0339] <Manufacturing Example 2> Preparation of compounds 1-2 to 1-6, 1-14, 1-17, 1-18, 1-33 to 1-36, 1-49, 1-50, 1-57, 1-58, 1-65 to 1-68, 1-71, 1-85 to 1-87, 1-89, 1-90, 1-315, 1-317

[0340] The target compound was synthesized by the same method as in Manufacturing Example 1, except that (A) Intermediate A in Table 1 was used instead of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane in Manufacturing Example 1, (B) Intermediate B was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and (C) Intermediate C was used instead of 9H-carbazole.

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349] <Manufacturing Example 3> Preparation of compound 1-93

[0350]

[0351] 1) Preparation of compound 1-93-3

[0352] 10 g (47.7 mM) of the above compound 1-93-4, 17.6 g (47.7 mM) of (A) 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane, 42.77 g (2.4 mM) of Pd(PPh3), and 13.19 g (95.4 mM) of K2CO3 were dissolved in 1,4-dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 13.0 g (73.0%) of the target compound 1-93-3 was obtained with methanol.

[0353] 2) Preparation of compound 1-93-2

[0354] 13.0 g (34.9 mM) of the above compound 1-93-3, 13.3 g (52.4 mM) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 31.6 g (1.7 mM) of Pd2(dba), 1.6 g (3.4 mM) of Xphos, and 6.8 g (69.8 mM) of KOAc were dissolved in 130 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 14.0 g (86.3%) of the target compound 1-93-2.

[0355] 3) Preparation of compound 1-93-1

[0356] 14.0 g (30.2 mM) of the above compound 1-93-2, 8.1 g (30.2 mM) of (B) 2-chloro-4,6-diphenyl-1,3,5-triazine, 41.7 g (1.51 mM) of Pd(PPh3), and 8.35 g (60.4 mM) of K2CO3 were dissolved in 1,4-dioxane / H2O 140 mL / 40 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 15.6 g (90.8%) of the target compound 1-93-1 was obtained with methanol.

[0357] 4) Preparation of compound 1-93

[0358] 15.6 g (27.4 mM) of the above compound 1-93-1, 4.6 g (27.4 mM) of (C) 9H-carbazole, and 26.8 g (82.3 mM) of Cs2CO3 were dissolved in 160 mL of DMA and refluxed at 180 °C for 5 hours. After the reaction was completed, distilled water was added to precipitate a solid, which was then purified by column chromatography (DCM:Hex = 1:2) and 16.1 g (81.9%) of the target compound 1-93 was obtained with methanol.

[0359] <Manufacturing Example 4> Preparation of compounds 1-94, 1-95, 1-97, 1-109, 1-125, 1-141, 1-142, and 1-160

[0360] The target compound was synthesized in the same manner as in Manufacturing Example 3, except that (A) Intermediate A in Table 2 was used instead of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane in Manufacturing Example 3, (B) Intermediate B was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and (C) Intermediate C was used instead of 9H-carbazole.

[0361]

[0362]

[0363] <Manufacturing Example 5> Preparation of compound 1-179

[0364]

[0365] 1) Preparation of compound 1-179-3

[0366] 10 g (47.7 mM) of the above compound 1-179-4, 17.6 g (47.7 mM) of (A) 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane, 42.77 g (2.4 mM) of Pd(PPh3), and 13.19 g (95.4 mM) of K2CO3 were dissolved in 1,4-dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 15.3 g (73.0%) of the target compound 1-179-3 was obtained with methanol.

[0367] 2) Preparation of compound 1-179-2

[0368] 15.3 g (41.0 mM) of the above compound 1-179-3, 15.6 g (61.6 mM) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 31.9 g (2.1 mM) of Pd2(dba), 2.0 g (4.1 mM) of Xphos, and 8.0 g (82.0 mM) of KOAc were dissolved in 150 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 14.8 g (77.9%) of the target compound 1-179-2.

[0369] 3) Preparation of compound 1-179-1

[0370] 14.8 g (31.9 mM) of the above compound 1-179-2, 8.5 g (31.9 mM) of (B) 2-chloro-4,6-diphenyl-1,3,5-triazine, 41.8 g (1.60 mM) of Pd(PPh3), and 8.82 g (63.8 mM) of K2CO3 were dissolved in 1,4-dioxane / H2O 150 mL / 45 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 16.7 g (92.2%) of the target compound 1-179-1 was obtained with methanol.

[0371] 4) Preparation of compound 1-179

[0372] The compound 1-179-1 16.7 g (29.3 mM), (C) 9H-carbazole 4.9 g (29.3 mM), and Cs2CO3 28.6 g (87.9 mM) were dissolved in 170 mL of DMA and refluxed at 180 °C for 5 hours. After the reaction was completed, distilled water was added to precipitate a solid, which was then purified by column chromatography (DCM:Hex = 1:2) and 17.9 g (85.4%) of the target compound 1-179 was obtained with methanol.

[0373] <Manufacturing Example 6> Preparation of compounds 1-180, 1-181, 1-192, and 1-211

[0374] The target compound was synthesized in the same manner as in Manufacturing Example 5, except that (A) Intermediate A in Table 3 was used instead of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane in Manufacturing Example 5, (B) Intermediate B was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and (C) Intermediate C was used instead of 9H-carbazole.

[0375]

[0376] <Manufacturing Example 7> Preparation of compound 1-227

[0377]

[0378] 1) Preparation of compound 1-227-3

[0379] 10 g (47.7 mM) of the above compound 1-227-4, 17.6 g (47.7 mM) of (A) 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane, 42.77 g (2.4 mM) of Pd(PPh3), and 13.19 g (95.4 mM) of K2CO3 were dissolved in 1,4-dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 15.0 g (84.1%) of the target compound 1-227-3 was obtained with methanol.

[0380] 2) Preparation of compound 1-227-2

[0381] 15.0 g (40.2 mM) of the above compound 1-227-3, 15.3 g (60.3 mM) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 31.8 g (2.0 mM) of Pd2(dba), 1.9 g (4.0 mM) of Xphos, and 7.8 g (80.4 mM) of KOAc were dissolved in 150 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 15.1 g (80.6%) of the target compound 1-227-2.

[0382] 3) Preparation of compound 1-227-1

[0383] 15.1 g (32.5 mM) of the above compound 1-227-2, 8.7 g (32.5 mM) of (B) 2-chloro-4,6-diphenyl-1,3,5-triazine, 41.8 g (1.6 mM) of Pd(PPh3), and 8.98 g (65.0 mM) of K2CO3 were dissolved in 1,4-dioxane / H2O 150 mL / 45 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 16.1 g (87.1%) of the target compound 1-227-1 was obtained with methanol.

[0384] 4) Preparation of compound 1-227

[0385] The compound 1-227-1 16.1 g (28.2 mM), (C) 9H-carbazole 4.7 g (28.2 mM), and Cs2CO3 27.6 g (84.6 mM) were dissolved in 160 mL of DMA and refluxed at 180 °C for 5 hours. After the reaction was completed, distilled water was added to precipitate a solid, which was then purified by column chromatography (DCM:Hex = 1:2) and 18.9 g (93.4%) of the target compound 1-227 was obtained with methanol.

[0386] <Manufacturing Example 8> Preparation of compounds 1-228, 1-260, and 1-261

[0387] The target compound was synthesized in the same manner as in Manufacturing Example 7, except that (A) Intermediate A in Table 4 was used instead of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane in Manufacturing Example 7, (B) Intermediate B was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and (C) Intermediate C was used instead of 9H-carbazole.

[0388]

[0389] <Manufacturing Example 9> Preparation of compound 1-275

[0390]

[0391] 1) Preparation of compound 1-275-3

[0392] The compound 1-275-4 10g (47.7 mM), 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane 17.6 g (47.7 mM), Pd(PPh3) 42.77 g (2.4 mM), and K2CO3 13.19 g (95.4 mM) were dissolved in 1,4-dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 16.0 g (89.9%) of the target compound 1-275-3 was obtained with methanol.

[0393] 2) Preparation of compound 1-275-2

[0394] 16.0 g (42.9 mM) of the above compound 1-275-3, 16.4 g (64.4 mM) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 31.9 g (2.1 mM) of Pd2(dba), 2.0 g (4.2 mM) of Xphos, and 8.3 g (85.8 mM) of KOAc were dissolved in 160 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 17.2 g (86.4%) of the target compound 1-275-2.

[0395] 3) Preparation of compound 1-275-1

[0396] The compound 1-275-2 (17.2 g (37.0 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (9.9 g (37.0 mM), Pd(PPh3) (42.2 g (1.9 mM), K2CO3 (10.2 g (74.0 mM))) was dissolved in 1,4-dioxane / H2O (170 mL / 50 mL) and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex = 1:3) and 17.2 g (81.4%) of the target compound 1-275-1 was obtained with methanol.

[0397] 4) Preparation of compound 1-275

[0398] The compound 1-275-1 17.2 g (30.1 mM), 9H-carbazole 5.0 g (30.1 mM), and Cs2CO3 29.4 g (90.3 mM) were dissolved in 170 mL of DMA and refluxed at 180 °C for 5 hours. After the reaction was completed, distilled water was added to precipitate a solid, which was then purified by column chromatography (DCM:Hex = 1:2) and 19.9 g (91.9%) of the target compound 1-275 was obtained with methanol.

[0399] <Manufacturing Example 10> Preparation of compound 1-281

[0400]

[0401] 1) Preparation of compound 1-281-3

[0402] 10 g (47.7 mM) of the above compound 1-281-4, 17.6 g (47.7 mM) of (A) 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane, 42.77 g (2.4 mM) of Pd(PPh3), and 13.19 g (95.4 mM) of K2CO3 were dissolved in 1,4-dioxane / H2O 100 mL / 30 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 15.0 g (84.3%) of the target compound 1-281-3 was obtained with methanol.

[0403] 2) Preparation of compound 1-281-2

[0404] Compound 1-281-3 15.0 g (40.2 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 15.3 g (60.3 mM), Pd2(dba) 31.8 g (2.0 mM), Xphos 1.9 g (4.0 mM), and KOAc 7.8 g (80.4 mM) were dissolved in 150 mL of 1,4-Dioxane and stirred under reflux for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 15.1 g (91.1%) of the target compound 1-281-2.

[0405] 3) Preparation of compound 1-281-1

[0406] 15.1 g (32.5 mM) of the above compound 1-281-2, 8.7 g (32.5 mM) of (B) 2-chloro-4,6-diphenyl-1,3,5-triazine, 41.8 g (1.6 mM) of Pd(PPh3), and 8.98 g (65.0 mM) of K2CO3 were dissolved in 1,4-dioxane / H2O 150 mL / 45 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 16.6 g (89.9%) of the target compound 1-281-1 was obtained with methanol.

[0407] 4) Preparation of compound 1-281

[0408] The compound 1-281-1 16.6 g (29.1 mM), (C) 9H-carbazole 4.9 g (29.1 mM), and Cs2CO3 28.5 g (87.4 mM) were dissolved in 170 mL of DMA and refluxed at 180 °C for 5 hours. After the reaction was completed, distilled water was added to precipitate a solid, which was then purified by column chromatography (DCM:Hex = 1:2) and 17.6 g (84.3%) of the target compound 1-281 was obtained with methanol.

[0409] <Manufacturing Example 11> Preparation of compound 1-282

[0410] The target compound was synthesized in the same manner as in Manufacturing Example 10, except that (A) Intermediate A of Table 5 was used instead of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane in Manufacturing Example 10, (B) Intermediate B was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and (C) Intermediate C was used instead of 9H-carbazole.

[0411]

[0412] <Manufacturing Example 12> Preparation of compound 1-316

[0413]

[0414] 1) Preparation of compound 1-316-4

[0415] The compound 1-316-5 (10 g (47.7 mM) above) was dissolved in Benzene-d6500 mL, then dissolved in CF3SO3H170 g (1075 mM), and refluxed at 60°C for 1 hour. After the reaction was completed, it was neutralized with D2O and Na2CO3. After neutralization, distilled water and ethyl acetate were added to the mixture and extracted, 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=1:4) and 9.0 g (89.1%) of the target compound 1-316-4 was obtained with methanol.

[0416] 2) Preparation of compound 1-316-3

[0417] The compound 1-316-4 9.0 g (42.6 mM), (A) 4,4,5,5-tetramethyl-2-(9-phenyldibenzo [b,d]furan-3-yl)-1,3,2-dioxaborolane 15.8 g (42.6 mM), Pd(PPh3) 42.46 g (2.13 mM), K2CO3 11.78 g (85.2 mM) were dissolved in 1,4-dioxane / H2O 90 mL / 27 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 17.5 g (91.2%) of the target compound 1-316-3 was obtained with methanol.

[0418] 3) Preparation of compound 1-316-2

[0419] 17.5 g (46.7 mM) of the above compound 1-316-3, 17.8 g (70.1 mM) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 32.1 g (2.3 mM) of Pd2(dba), 2.2 g (4.6 mM) of Xphos, and 9.1 g (93.4 mM) of KOAc were dissolved in 170 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 18.5 g (84.9%) of the target compound 1-316-2.

[0420] 4) Preparation of compound 1-316-1

[0421] The compound 1-316-2 18.5 g (39.7 mM), (B) 2-chloro-4,6-diphenyl-1,3,5-triazine 8.2 g (39.7 mM), Pd(PPh3) 41.8 g (1.98 mM), and K2CO 38.45 g (79.6 mM) were dissolved in 1,4-dioxane / H2O 190 mL / 60 mL and refluxed for 6 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and 17.4 g (76.6%) of the target compound 1-316-1 was obtained with methanol.

[0422] 5) Preparation of compound 1-316

[0423] 17.4 g (30.4 mM) of the above compound 1-316-1, 5.1 g (30.4 mM) of (C) 9H-carbazole-1,2,3,4,5,6,7,8-d, and 29.7 g (91.3 mM) of Cs2CO3 were dissolved in 170 mL of DMA and refluxed at 180 °C for 5 hours. After the reaction was completed, distilled water was added to precipitate a solid, which was then purified by column chromatography (DCM:Hex = 1:2) and 19.8 g (89.7%) of the target compound 1-316 was obtained with methanol.

[0424] <Manufacturing Example 13> Preparation of compounds 1-318 and 1-319

[0425] The target compound was synthesized in the same manner as in Manufacturing Example 12, except that (A) Intermediate A of Table 6 was used instead of 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane in Manufacturing Example 12, (B) Intermediate B was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and (C) Intermediate C was used instead of 9H-carbazole-1,2,3,4,5,6,7,8-d8.

[0426]

[0427] Compounds were prepared using the same method as the above manufacturing examples, and the results of their synthesis are shown in Tables 7 and 8 below. Table 7 shows the measured values ​​from FD-mass spectrometry (FD-MS), and Table 8 shows the NMR values.

[0428] Compound FD-MS Compound FD-MS 1-1 m / z = 716.26 (C 51 H 32 N4O=716.83)1-2m / z=716.26 (C 51 H 32 N4O=716.83)1-3m / z=716.26 (C 51 H 32 N4O=716.83)1-4m / z=716.26 (C 51 H 32N4O=716.83)1-5m / z=716.26 (C 51 H 32 NQ4O=716.83)1-6m / z=716.26 (C 51 H 32 N4O=716.83)1-14m / z=716.26 (C 51 H 32 N4O=716.83)1-17m / z= 732.23 (C 51 H 32 N4S= 732.89)1-18m / z= 732.23 (C 51 H 32 N4S= 732.89)1-33m / z= 742.31 (C 54 H 38 N4=742.91)1-34m / z= 742.31 (C 54 H 38 N4=742.91)1-35m / z= 742.31 (C 54 H 38 N4=742.91)1-36m / z= 742.31 (C 54 H 38 N4=742.91)1-49m / z= 792.29 (C 57 H 36 N4O=792.92)1-50m / z= 792.29 (C 57 H 36 N4O=792.92)1-57m / z= 792.29 (C 57 H 36 N4O=792.92)1-58m / z= 792.29 (C 57 H 36 N4O=792.92)1-65m / z= 868.32 (C 63 H 40 N4O=869.04)1-66m / z= 868.32 (C 63 H 40 N4O=869.02)1-67m / z= 792.29 (C 57 H 36 N4O=792.92)1-68m / z= 792.29 (C 57 H 36 N4O=792.92)1-85m / z= 868.32 (C 63 H 40N4O=869.02)1-86m / z= 792.29 (C 57 H 36 N4O=792.92)1-87m / z= 868.32 (C 63 H 40 N4O=869.02)1-89m / z= 884.30 (C 63 H 40 N4S=885.10)1-90m / z= 884.30 (C 63 H 40 N4S=885.10)1-93m / z=716.26 (C 51 H 32 N4O=716.83)1-94m / z=716.26 (C 51 H 32 N4O=716.83)1-95m / z=716.26 (C 51 H 32 N4O=716.83)1-97m / z=716.26 (C 51 H 32 N4O=716.83)1-109m / z= 732.23 (C 51 H 32 N4S= 732.89)1-125m / z= 742.31 (C 54 H 38 N4=742.91)1-141m / z=792.29 (C 57 H 36 N4O=792.92)1-142m / z= 792.29 (C 57 H 36 N4O=792.92)1-160m / z=868.32 (C 63 H 40 N4O=869.02)1-179m / z=716.26 (C 51 H 32 N4O=716.83)1-180m / z=716.26 (C 51 H 32 N4O=716.83)1-181m / z=716.26 (C 51 H 32 N4O=716.83)1-192m / z=716.26 (C 51 H 32 N4O=716.83)1-211m / z=742.31 (C 54 H38 N4=742.91)1-227m / z=716.26 (C 51 H 32 N4O=716.83)1-228m / z=716.26 (C 51 H 32 N4O=716.83)1-260m / z=742.31 (C 54 H 38 N4=742.91)1-261m / z=742.31 (C 54 H 38 N4=742.91)1-275m / z=716.26 (C 51 H 32 N4O=716.83)1-281m / z=716.26 (C 51 H 32 N4O=716.83)1-282m / z=716.26 (C 51 H 32 N4O=716.83)1-315m / z=722.30 (C 51 H 26 D6N4O=722.88)1-316m / z=725.31 (C 51 H23D9N4O=725.90)1-317m / z=733.36 (C 51 H 15 D 17 N4O=733.95)1-318m / z=736.38 (C 51 H 12 D 20 N4O=736.97)1-319m / z=744.43 (C 51 H4D 28 N4O=745.01)

[0429] 화합물번호 1H NMR(CDCl3, 400MHz)1-1δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-7.94(m, 5H), 7.82-7.76(m, 5H), 7.69(d, 1H), 7.58-7.41(m, 13H), 7.20-7.16(m, 2H)1-2δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-7.75(m, 12H), 7.58-7.35(m, 12H), 7.20-7.16(m, 2H)1-3δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-7.94(m, 6H), 7.82-7.75(m, 6H), 7.58-7.35(m, 12H), 7.20-7.16(m, 2H)1-4δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-7.94(m, 7H), 7.82(d, 1H), 7.76(s, 1H), 7.58-7.35(m, 15H), 7.20-7.16(m, 2H)1-5δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-8.08(m, 2H), 8.01-7.94(m, 3H), 7.94-7.79(m, 3H), 7.58-7.31(m, 15H), 7.20-7.16(m, 2H)1-6δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-8.08(m, 2H), 8.01-7.79(m, 8H), 7.69(d, 1H), 7.58-7.35(m, 13H), 7.20-7.161-14δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-7.94(m, 6H), 7.82(d, 1H), 7.69(d, 1H), 7.58-7.35(m, 16H), 7.20-7.16(m, 2H)1-17δ = 8.55(d, 1H), 8.36(d, 4H), 8.19-7.94(m, 10H), 7.79(d, 2H), 7.68(t, 1H), 7.58-7.35(m, 12H), 7.20-7.16(m, 2H)1-18δ = 8.55(d, 1H), 8.36(d, 4H), 8.24-8.08(m, 8H), 8.01-7.94(m, 3H), 7.75(d, 2H), 7.58-7.35(m, 12H), 7.20-7.16(m, 2H)1-33δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-8.08(m, 3H), 8.01-7.89(m, 3H), 7.79-7.78(m, 4H), 7.58-7.35(m, 14H), 7.20-7.16(m, 2H), 1.69(s, 6H)1-34δ = 8.55(d, 1H), 8.36(d, 4H), 8.19-8.18(m, 2H), 8.11-8.08(m, 3H), 8.01-7.89(m, 3H), 7.78-7.68(m, 5H), 7.58-7.35(m, 12H), 7.20-7.16(m, 2H), 1.69(s, 6H)1-35δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-8.08(m, 4H), 8.01-7.89(m, 4H), 7.78-7.75(m, 4H), 7.58-7.35(m, 12H), 7.20-7.16(m, 2H), 1.69(s, 6H)1-36δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-8.08(m, 3H), 8.01-7.89(m, 4H), 7.78(d, 1H), 7.68(d, 1H), 7.58-7.35(m, 15H), 7.20-7.16(m, 2H), 1.69(s, 6H)1-49δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-7.94(m, 5H), 7.82-7.69(m, 6H), 7.58-7.35(m, 13H), 7.25-7.16(m, 6H)1-50δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-7.75(m, 14H), 7.58-7.35(m, 14H), 7.20-7.16(m, 2H)1-57δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-7.75(m, 11H), 7.58-7.35(m, 13H), 7.25-7.16(m, 6H)1-58δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-8.08(m, 2H), 8.01-7.93(m, 5H), 7.75-7.73(m, 3H), 7.58-7.31(m, 17H), 7.20-7.16(m, 2H)1-65δ = 8.55(d, 1H), 8.36(d, 2H), 8.19(d, 1H), 8.11-7.75(m, 18H), 7.61-7.35(m, 14H), 7.25-7.16(m, 4H)1-66δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H),8.11-7.75(m, 18H), 7.60-7.35(m, 14H), 7.25-7.16(m, 4H)1-67δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.11-7.94(m, 7H), 7.82-7.75(m, 8H), 7.58-7.35(m, 13H), 7.25-7.16(m, 4H)1-68δ = 8.55(d, 1H), 8.38-8.36(m, 3H), 8.19(d, 1H), 8.11-7.94(m, 6H), 7.82-7.69(m, 9H), 7.61-7.35(m, 14H), 7.20-7.16(m, 2H)1-71δ = 8.55(d, 1H), 8.38(d, 1H), 8.19(d, 1H), 8.11-7.82(m, 8H), 7.82-7.69(m, 11H), 7.58-7.35(m, 14H), 7.25-7.16(m, 4H)1-85δ = 8.55(d, 1H), 8.36-8.29(m, 5H), 8.08-7.94(m, 7H), 7.82-7.75(m, 6H), 7.58-7.35(m, 12H), 7.19-7.16(m, 5H)1-86δ = 8.55(d, 1H), 8.36-8.31(m, 5H), 8.11-7.75(m, 13H), 7.51-7.35(m, 16H), 7.16(t, 1H)1-87δ = 8.55(d, 1H), 8.36(m, 4H), 8.11-7.89(m, 7H), 7.82-7.69(m, 9H), 7.57-7.35(m, 14H), 7.16(t, 1H)1-89δ = 8.36-8.08(m, 13H), 8.01-7.99(m, 3H), 7.89(s, 2H), 7.77-7.75(m, 7H), 7.50-7.41(m, 15H)1-90δ = 8.55(d, 1H), 8.36(d, 4H), 8.11-7.94(m, 8H), 7.79-7.68(m, 10H), 7.50-7.35(m, 16H), 7.16(t, 1H)1-93δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d, 1H), 8.10(d, 1H), 8.03-8.02(m, 2H), 7.94(d, 1H), 7.82-7.76(m, 5H), 7.69(d, 1H), 7.57-7.35(m, 13H), 7.20-7.16(m, 2H)1-94δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d,1H), 8.10(d, 1H), 8.03-8.02(m, 2H), 7.94-7.75(m, 8H), 7.58-7.35(m, 12H), 7.20-7.16(m, 2H)1-95δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d, 1H), 8.10-8.02(m, 4H), 7.94(d, 1H), 7.82-7.75(m, 6H), 7.57-7.35(m, 12H), 7.20-7.16(m, 2H)1-97δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d, 1H), 8.10(d, 1H), 8.02-7.94(m, 3H), 7.86-7.79(m, 4H), 7.58-7.35(m, 15H), 7.20-7.16(m, 2H)1-109δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.20-8.02(m, 7H), 7.94(m, 2H), 7.79(d, 2H), 7.68(t, 1H), 7.57-7.35(m, 12H), 7.20-7.16(m, 2H)1-125δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d, 1H), 8.10(m, 2H), 8.02(d, 1H), 7.94-7.89(m, 2H), 7.79-7.78(m, 4H), 7.58-7.35(m, 14H), 7.20-7.16(m, 2H), 1.69(s, 6H)1-141δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d, 1H), 8.10(d, 1H), 8.03-8.02(m, 2H), 7.94(d, 1H), 7.82-7.69(m, 6H), 7.57-7.35(m, 13H), 7.25-7.16(m, 6H)1-142δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d, 1H), 8.10(d, 1H), 8.08-8.02(m, 2H), 7.94-7.73(m, 10H), 7.61-7.35(m, 14H), 7.20-7.16(m, 2H)1-160δ = 8.55(d, 1H), 8.40(s, 1H), 8.19(d, 1H), 8.10-7.94(m, 8H), 7.82-7.69(m, 10H), 7.58-7.35(m, 13H), 7.25-7.16(m, 6H)1-179δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d, 1H), 8.10(d, 1H), 8.03(d, 1H), 7.94-7.92(m, 2H), 7.82-7.76(m, 5H), 7.69(d, 1H), 7.58-7.35(m, 13H), 7.20-7.16(m, 2H)1-180δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d, 1H), 8.10(d, 1H), 8.03(d, 1H), 7.94-7.75(m, 9H), 7.58-7.35(m, 12H), 7.20-7.16(m, 2H)1-181δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d, 1H),8.10-8.03(m, 3H), 7.94-7.92(m, 2H), 7.82-7.75(m, 6H), 7.58-7.35(m, 12H), 7.20-7.16(m, 2H)1-192δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d, 1H), 8.10-8.02(m, 3H), 7.94-7.92(m, 2H), 7.82(d, 1H), 7.69(d, 1H), 7.58-7.35(m, 16H), 7.20-7.16(d, 2H)1-211δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d, 1H), 8.10-8.09(m, 2H), 7.94-7.89(m, 3H), 7.79-7.78(m, 4H), 7.58-7.35(m, 14H), 7.20-7.16(m, 2H), 1.69(s, 6H)1-227δ = 8.55(d, 1H), 8.36-8.31(m, 6H), 8.19(d, 1H), 8.03(d, 1H), 7.94-7.90(m, 2H), 7.82-7.76(m, 5H), 7.69(d, 1H), 7.58-7.35(m, 13H), 7.20-7.16(m, 2H)1-228δ = 8.55(d, 1H), 8.36-8.31(m, 6H), 8.19(d, 1H), 8.03(d, 1H), 7.94-7.75(m, 9H), 7.58-7.35(m, 12H), 7.20-7.16(m, 2H)1-260δ = 8.55(d, 1H), 8.36-8.31(m, 6H), 8.19-8.18(m, 2H), 8.09(d, 1H), 7.94-7.89(m, 3H), 7.78-7.68(m, 5H), 7.58-7.35(m, 12H), 7.20-7.16(m, 2H), 1.69(s, 6H)1-261δ = 8.55(d, 1H), 8.36-8.31(m, 6H), 8.19(d, 1H), 8.09(m, 2H), 7.94-7.89(m, 4H), 7.78-7.75(m, 4H), 7.58-7.35(m, 12H), 7.20-7.16(m, 2H), 1.69(s, 6H)1-275δ = 8.55(d, 1H), 8.40-8.36(m, 5H), 8.19(d, 1H), 8.10(d, 1H), 8.03-8.02(m, 2H), 7.94(d, 1H), 7.82-7.76(m, 5H), 7.69(d, 1H), 7.58-7.35(m, 13H), 7.20-7.16(m, 2H)1-281δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.03-7.94(m, 4H), 7.82-7.69(m, 7H), 7.58-7.35(m, 13H), 7.20-7.16(m, 2H)1-282δ = 8.55(d, 1H), 8.36(d, 4H), 8.19(d, 1H), 8.03-7.69(m, 12H), 7.50-7.35(m, 12H), 7.20-7.16(m, 2H)1-315δ = 8.36(d, 4H); 8.11-8.01(m, 4H), 7.82-7.76(m, 5H), 7.69(d, 1H), 7.50-7.41(m, 10H)1-316δ = 8.36(d, 4H), 8.03(d, 1H), 7.82-7.76(m, 5H), 7.69(d, 1H), 7.50-7.41(m, 10H)1-317δ = 8.36(d, 4H), 8.11-8.01(m, 3H), 7.50-7.41(m, 6H)1-318δ = 8.36(d, 4H), 7.50-7.41(m, 6H).

[0430] <Manufacturing Example 14> Preparation of Compound 2-1

[0431]

[0432] 1) Preparation of compound 2-1-1

[0433] In a reaction flask, 10 g (49.59 mmol) of 3-bromo-9H-carbazole, 24.2 g (148.77 mmol) of (a) 2-bromobenzene-1-ylium, 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. Heated at 135℃ for 15 hours.

[0434] After the reaction was completed, the mixture was extracted with methylene chloride (MC) and water, and purified by column chromatography to obtain 14 g (yield 98%) of compound 2-1-1.

[0435] 2) Preparation of compound 2-1

[0436] 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.

[0437] 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 compound 2-1.

[0438] <Manufacturing Example 15> Manufacture of compounds 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-11, 2-16, 2-19, 2-20, 2-21, 2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-32, 2-33, 2-34, 2-38, 2-40, 2-41, 2-42, 2-43, 2-45, 2-46, 2-48, 2-49, 2-50, 2-51, 2-52, 2-55, 2-57 and 2-60

[0439] The target compound was synthesized by the same method as in Manufacturing Example 14, except that compound a of Table 9 below was used instead of 2-bromobenzene-1-ylium (a) in Manufacturing Example 14, and compound b of Table 9 below was used instead of (9-phenyl-9H-carbozol-3-yl)boronic acid (b).

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457] <Manufacturing Example 16> Preparation of compound 2-61

[0458]

[0459] 1) Preparation of compound 2-61-4

[0460] 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.

[0461] 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.

[0462] 2) Preparation of compound 2-61-3

[0463] 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.

[0464] 3) Preparation of compound 2-61-2

[0465] 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.

[0466] 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.

[0467] 4) Preparation of compound 2-61-1

[0468] 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.

[0469] 5) Preparation of compound 2-61

[0470] 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.

[0471] Afterwards, the temperature was lowered to room temperature, and the resulting solid was washed with distilled water and methanol to obtain 13 g (yield 85%) of compound 2-61.

[0472] <Manufacturing Example 17> Preparation of compounds 2-62, 2-63, 2-64, 2-65, 2-66, 2-68, 2-69, 2-70, 2-74, 2-75, 2-81, 2-82, 2-83, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-92, 2-100, and 2-102

[0473] The target compound was synthesized in the same manner as in Manufacturing Example 16, except that compound c of Table 10 below was used instead of bromobenzene (c) in Manufacturing Example 16, and compound d of Table 10 below was used instead of bromobenzene (d).

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482]

[0483]

[0484]

[0485] Compounds were prepared in the same manner as the above manufacturing examples, and the results of their synthesis are shown in Tables 11 and 12 below. Table 11 shows the measured values ​​of FD-MS (Field desorption mass spectrometry), and Table 12 shows the measured values ​​of FD-MS (Field desorption mass spectrometry). 1 This is the measured value of H NMR (CDCl3, 400 MHz).

[0486] Compound number FD-MS Compound number FD-MS 2-1 m / z = 484.59 (C 36 H 24 N2 = 484.19) 2-2 m / z = 560.69 (C 42 H 28 N2 = 560.23) 2-3 m / z = 560.69 (C 42 H 28 N2 = 560.23) 2-4 m / z = 560.69 (C 42 H 28 N2 = 560.23) 2-5 m / z = 636.78 (C 48 H 32 N2 = 636.26) 2-6 m / z = 636.78 (C 48 H 32 N2 = 636.26) 2-7 m / z = 636.78 (C 48 H 32 N2 = 636.26) 2-8 m / z = 543.65 (C 40 H 26 N2 = 543.21) 2-9 m / z = 543.65 (C 40 H 26 N2 = 543.21) 2-10 m / z = 600.75 (C 45 H 35 N2 = 600.26) 2-11 m / z = 600.75 (C 45 H 35 N2 = 600.26) 2-12 m / z = 724.89 (C 55 H 36 N2 = 724.29) 2-13 m / z = 724.89 (C 55 H 36 N2 = 724.29) 2-14 m / z = 724.89 (C 55 H 36 N2 = 724.29) 2-15 m / z = 724.89 (C 55 H 36 N2 = 724.29) 2-16 m / z = 634.77 (C 48 H 30 N2 = 634.24) 2-17 m / z = 509.60 (C 37 H 23 N3 = 509.19) 2-18 m / z = 742.98 (C 54 H 38N2Si=742.28)2-19m / z= 636.78(C 48 H 32 N2=636.26)2-20m / z= 636.78(C 48 H 32 N2=636.26)2-21m / z= 636.78(C 48 H 32 N2=636.26)2-22m / z= 712.88(C 54 H 36 N2=712.29)2-23m / z= 712.88(C 54 H 36 N2=712.29)2-24m / z= 712.88(C 54 H 36 N2=712.29)2-25m / z= 710.86(C 54 H 34 N2=710.27)2-26m / z= 712.88(C 54 H 36 N2=712.29)2-27m / z= 712.88(C 54 H 36 N2=712.29)2-28m / z= 712.88(C 54 H 36 N2=712.29)2-29m / z= 712.88(C 54 H 36 N2=712.29)2-30m / z= 712.88(C 54 H 36 N2=712.29)2-31m / z= 710.86(C 54 H 34 N2=710.27)2-32m / z= 636.78(C 48 H 32 N2=636.26)2-33m / z= 712.88(C 54 H 36 N2=712.29)2-34m / z= 712.88(C 54 H 36 N2=712.29)2-35m / z= 788.97(C 60 H 40 N2=788.32)2-36m / z= 686.84(C 52 H 34 N2=686.27)2-37m / z= 788.97(C60 H 40 N2=788.32)2-38m / z= 788.97(C 60 H 40 N2=788.32)2-39m / z= 686.84(C 52 H 34 N2=686.27)2-40m / z= 686.84(C 52 H 34 N2=686.27)2-41m / z= 494.65(C 36 H 14 D 10 N2=494.26)2-42m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-43m / z= 574.77(C 41 H 14 D 14 N2=574.31)2-44m / z= 650.86(C 48 H 14 D 16 N2=650.34)2-45m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-46m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-47m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-48m / z=654.89(C 48 H 14 D 18 N2=654.37)2-49m / z= 654.89(C 48 H 14 D 18 N2=654.37)2-50m / z: 734.43(C 54 H 14 D 22 N2=735.03)2-51m / z= 735.01(C 54 H 14 D 22 N2=734.43)2-52m / z= 735.01(C 54 H 14 D 22N2=734.43)2-53m / z= 730.98(C 54 H 14 D 20 N2=730.40)2-54m / z= 735.01(C 54 H 14 D 22 N2=734.43)2-55m / z=735.01(C 54 H 14 D 22 N2=734.43)2-56m / z= 815.13(C 60 H 14 D 26 N2=814.48)2-57m / z= 815.13(C 60 H 14 D 26 N2=814.48)2-58m / z= 815.13(C 60 H 14 D 26 N2=814.48)2-59m / z= 815.13(C 60 H 14 D 26 N2=814.48)2-60m / z= 666.86(C 48 H 14 D 16 N2O=666.34)2-61m / z= 498.68(C 36 H 10 D 14 N2=498.28)2-62m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-63m / z= 574.77(C 41 H 14 D 14 N2=574.31)2-64m / z= 648.85(C 48 H 16 D 14 N2=648.33)2-65m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-66m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-67m / z= 650.87(C 48 H18 D 14 N2=650.34)2-68m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-69m / z= 650.87(C 48 H 18 D 14 N2=650.34)2-70m / z=726.38(C 54 H 22 D 14 N2=726.98)2-71m / z= 726.96(C 54 H 22 D 14 N2=726.38)2-72m / z= 726.96(C 54 H 22 D 14 N2=726.38)2-73m / z= 724.95(C 54 H 20 D 14 N2=724.36)2-74m / z= 726.96(C 54 H 22 D 14 N2=726.38)2-75m / z= 726.96(C 54 H 22 D 14 N2=726.38)2-76m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-77m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-78m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-79m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-80m / z= 803.06(C 60 H 26 D 14 N2=802.41)2-81m / z= 508.74(C 36 D 24 N2=508.34)2-82m / z= 668.98(C 48D 32 N2=668.46)2-83m / z= 588.86(C 42 D 28 N2=588.40)2-84m / z= 664.95(C 48 D 30 N2=664.43)2-85m / z= 668.98(C 48 D 32 N2=668.46)2-86m / z= 668.98(C 48 D 32 N2=668.46)2-87m / z= 668.98(C 48 D 32 N2=668.46)2-88m / z= 668.98(C 48 D 32 N2=668.46)2-89m / z= 668.98(C 48 D 32 N2=668.46)2-90m / z= 748.518(C 54 D 36 N2=749.12)2-91m / z= 749.10(C 54 D 36 N2=748.51)2-92m / z= 749.10(C 54 D 36 N2=748.51)2-93m / z= 745.07(C 54 D 34 N2=744.49)2-94m / z= 749.10(C 54 D 36 N2=748.51)2-95m / z= 749.10(C 54 D 36 N2=748.51)2-96m / z= 829.22(C 60 D 40 N2=828.57)2-97m / z= 829.22(C 60 D 40 N2=828.57)2-98m / z= 829.22(C 60 D 40 N2=828.57)2-99m / z= 829.22(C 60 D 40 N2=828.57)2-100m / z= 680.95(C 48 D 30N2O=680.42)2-101m / z= 697.02(C 48 D 30 N2S=696.40)2-102m / z=829.22(C 60 D 40 N2=828.57)2-103m / z= 632.95(C 45 D 32 N2=632.46)2-104m / z= 713.07(C 51 D 36 N2=712.51)

[0487] Compound number 1H NMR(CDCl3, 400MHz)2-1δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.62-7.50(m, 12H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-2δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 6H), 7.80-7.77(m, 2H), 7.62-7.35(m, 10H), 7.20-7.16(m, 6H)2-3δ =8.55(d, 1H), 8.18-8.09(m, 3H), 8.00-7.87(m, 3H), 7.77(s, 2H), 7.58-7.25(m, 18H)2-4δ =8.55(d, 1H), 8.18-8.12(m, 2H), 8.00-7.84(m, 3H), 7.79-7.77(m, 4H), 7.68-7.25(m, 22H)2-5δ =8.55(d, 1H), 8.30(d, 1H), 8.21-8.13(m, 3H), 7.99-7.89(m, 4H), 7.77-7.35(m, 17H), 7.25-7.16(m, 6H)2-6δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.94-7.89(m, 8H), 7.77-7.75(m, 3H), 7.62-7.35(m, 11H), 7.25-7.16(m, 6H)2-7δ =8.55(d, 1H), 8.18-8.09(m, 4H), 8.00-7.94(m, 2H), 7.87(m, 1H), 7.77(m, 2H), 7.69-7.63(m, 2H), 7.52-7.25(m, 20H)2-11δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 5H), 7.77(d, 1H), 7.58-7.28(m, 16H), 1.69(s, 6H)2-16δ =9.05(s, 1H), 8.55(d, 1H), 8.33-8.13(m, 7H), 7.99-7.89(m, 5H), 7.77-7.50(m, 13H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-19δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 8H), 7.80-7.77(m, 3H), 7.58(d, 1H), 7.50-7.35(m, 6H), 7.20-7.16(m, 10H)2-20δ =8.55(d, 1H), 8.30(d, 1H), 8.21-8.13(m, 3H), 7.99-7.89(m, 6H), 7.80-7.35(m, 15H), 7.20-7.16(6H)2-21δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2h), 7.99-7.89(m, 10H), 7.80-7.75(m, 4H), 7.50-7.35(m, 8H), 7.20-7.16(m, 6H)2-22δ =8.55(d, 1H), 8.30(d, 1H), 8.21-8.13(m, 3H), 7.99-7.89(m, 6H), 7.80-7.35(m, 15H), 7.25-7.16(10H)2-23δ =8.55(d, 1H), 8.30(d, 1H), 8.19-8.13(m, 2h), 7.99-7.89(m, 10H), 7.80-7.75(m, 4H), 7.50-7.35(m, 8H), 7.25-7.16(m, 10H)2-26δ =8.55(m, 1H), 8.30(d, 1H), 8.21-8.13(m, 4h), 7.99-7.89(m, 4H), 7.77-7.35(m, 20H), 7.25-7.16(6H)2-27δ =8.55(m, 1H), 8.30(d, 1H), 8.21-8.13(m, 4h), 7.99-7.89(m, 4H), 7.77-7.35(m, 20H), 7.20-7.16(2H)2-28δ =8.55(m, 1H), 8.18-8.09(m, 3H), 8.00-8.79(m, 2H), 7.87(m, 1H), 7.79-7.77(m, 4H), 7.69-7.63(m, 4H), 7.52-7.25(m, 12H)2-29δ =8.55(m, 1H), 8.18-8.09(m, 3H), 8.00-7.94(m, 2H0, 7.87(m, 1H), 7.87(m, 1H), 7.79-7.77(m, 4H), 7.69-7.63(m, 4H), 7.52-7.25(m, 21H)2-30δ =8.55(m, 1H), 8.31-8.30(m, 3H), 8.21-8.13(m, 3h), 7.99-7.89(m, 3H), 7.75-7.35(m, 22H), 7.20-7.16(m, 2H)2-32δ =8.55(m, 1H), 8.18-8.12(m, 2H), 8.00-7.87(m, 3H), 7.79-7.77(m, 6H), 7.69-7.63(m, 6H), 7.52-7.25(m, 14H)2-33δ =8.55(m, 1H), 8.30(d, 1H), 8.21-8.13(m, 3H), 7.99-7.89(m, 8H), 7.77-7.35(m, 17H), 7.25-7.16(6H)2-34δ =8.55(m, 1H), 8.18-8.12(m, 2H), 8.00-7.87(m, 3H), 7.79-7.77(m, 6H), 7.67-7.63(m, 6H), 7.52-7.25(m, 18H)2-38δ =8.55(m, 1H), 8.18-8.12(m, 2H), 8.05-7.87(m, 6H), 7.79-7.77(m, 4H), 7.69-7.63(m, 4H), 7.52-7.25(m, 23H)2-40δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 8.03-7.75(m, 15H), 7.58-7.35(m, 9H), 7.25-7.16(m, 6H)2-41δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-42δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-43δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-45δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-46δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-48δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-49δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-50δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-51δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-52δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-55δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-57δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-60δ =8.55(m, 1H), 8.30(d, 1H), 8.19-8.13(m, 2H), 7.99-7.89(m, 4H), 7.77(d, 1H), 7.58-7.50(m, 2H), 7.35(t, 1H), 7.20-7.16(m, 2H)2-61δ =7.62-7.50(m, 10H)2-62δ =7.79(m, 4H), 7.68(m. 4H), 7.52-7.41(m, 10H)2-63δ =8.21(s, 1H) 7.75-7.41(m, 13H)2-64δ =9.05(s, 1H), 8.33-8.25(m, 4H), 7.94(d, 1H), 7.70-7.50(m, 10H)2-65δ =7.79(m, 2H), 7.70-7.68(m, 3H), 7.58-7.41(m, 13H)2-66δ =7.92-7.91(m, 4H), 7.75(d, 2H), 7.62-7.41(m, 8H), 7.25(s, 4H)2-68δ =8.21(s, 2H), 7.75-7.60(m, 8H), 7.49-7.41(8H)2-69δ =8.21(s, 1H), 7.92-7.91(m, 4H), 7.75-7.60(m, 6H), 7.49-7.41(m, 7H)2-70δ =8.21(s, 1H), 7.94-7.91(m, 5H), 7.75-7.61(m, 9H), 7.49-7.41(m, 7H)2-74δ =7.94-7.91(m, 9H), 7.75-7.73(m, 5H), 7.61(d, 2H), 7.49-7.41(m, 6H)2-75δ =7.92-7.91(m, 8H), 7.75(d, 4H), 7.49-7.41(m, 6H), 7.25(s, 4H).

[0488] <Manufacturing Example 18> Preparation of Compound 3-1

[0489] 1) Preparation of compound 3-1-1

[0490]

[0491] In a reaction flask, (a) 10 g (39.0 mmol) of 5,8-dihydroindolo[2,3-c]carbazole, (b) 6.12 g (39.0 mmol) of 1-bromobenzene, 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.

[0492] 2) Preparation of compound 3-1

[0493] 7.3 g (22.0 mmol) of the above compound 3-1-1, 3.8 g (24.2 mmol) of (C) 1-bromobenzene, 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) were added, and then 70 mL of toluene was added and heated at 135°C for 15 hours. After the reaction was completed, the mixture was extracted with methylene chloride (MC) and water, and purified by column chromatography to obtain 8.3 g (yield 93%) of compound 3-1.

[0494] <Manufacturing Example 19> Preparation of compounds 3-4, 3-5, 3-22, 3-23, 3-32, 3-35, 3-41, 3-61, 3-69, and 3-77

[0495] The target compound was synthesized by the same method as in Manufacturing Example 18, except that intermediate A of Table 13 below was used instead of (a), intermediate B of Table 13 below was used instead of (b), and intermediate C of Table 13 below was used instead of (c).

[0496]

[0497]

[0498]

[0499]

[0500] 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-MS (Field desorption mass spectrometry), and Table 15 shows the measured values ​​of 1 This is the measured value of H NMR (CDCl3, 400 MHz).

[0501] Compound number FD-MS Compound number FD-MS3-1 m / z = 408.16 (C 30 H 20 N2=408.50)3-4m / z= 560.23(C 42 H 28 N2=560.70)3-5m / z=m / z=560.23(C 42 H 28 N2=560.70)3-22m / z=m / z=560.23(C 42 H 28 N2=560.70)3-23m / z= m / z= 560.23(C 42 H 28 N2=560.70)3-32m / z=m / z=560.23(C 42 H 28 N2=560.70)3-35m / z=m / z=560.23(C 42 H 28 N2=560.70)3-41m / z=m / z=560.23(C 42 H 28 N2=560.70)3-61m / z= 578.34(C 42 H 10 D 18 N2=578.81)3-69m / z= 570.29(C 42 H 18 D 10 N2=570.76)3-77m / z= 588.40(C 42 D 28 N2=588.87)

[0502] Compound number 1H NMR(CDCl3, 400MHz)3-1δ = 8.55(2H, d), 7.94(2H, d), 7.62-7.35(14H, m), 7.16(2H, d)3-4δ = 8.55(2H, d), 7.94-7.91(10H, m), 7.75(4H, d), 7.49-7.35(10H, m), 7.16(2H, t)3-5δ = 8.55(2H, d), 8.21(1H, s), 7.94-7.91(6H, m), 7.75-7.35(16H, m), 7.26(1H, d), 7.16(2H, t)3-22δ = 8.55(1H, d), 8.19(1H, d), 7.94-7.91(9H, m), 7.75(4H, d), 7.58-7.35(11H, m), 7.20-7.16(2H, m)3-23δ = 8.55(1H, d), 8.21-8.19(2H, m), 7.94-7.91(5H, m), 7.75-7.35(18H, m), 7.20-7.16(2H, m)3-32δ = 8.55(1H, d), 8.19(1H, d), 7.94-7.91(9H, m), 7.75(4H, d), 7.58-7.35(11H, m), 7.20-7.16(2H, m)3-35δ = 8.55(1H, d), 8.21-8.19(2H, m), 7.94-7.91(5H, m), 7.68-7.35(18H, m), 7.20-7.16(2H, m)3-41δ = 8.55(2H, d), 7.94-7.91(10H, m), 7.84(2H, d), 7.75(4H, d), 7.49-7.35(8H, m), 7.16(2H, t)3-61δ = 8.55(2H, d), 7.94(2H, d), 7.42-7.35(4H, m), 7.16(2H, t)3-69δ = 7.92-7.91(8H, m), 7.75(4H, d), 7.49-7.41(6H, m)

[0503] <실험예 1>

[0504] 1) 유기 발광 소자의 제작

[0505] 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.

[0506] 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).

[0507] 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 400Å. Then, BCP(Bathocuproine) was deposited to 60Å as a hole-blocking layer, and Alq3 was deposited to 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.

[0508] 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.

[0509] 2) Driving voltage and luminous efficiency of organic light-emitting devices

[0510] 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 (cd / A), T 90 was measured.

[0511] 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.

[0512] Compound Compound Driving voltage (V) Efficiency (cd / A) Color coordinates (x, y) Lifespan (T) 90) Comparative Example 1 Ref. 14.8246.1(0.239, 0.710)42 Comparative Example 2 Ref. 25.0146.4(0.248, 0.712)37 Comparative Example 3 Ref. 34.7943.9(0.247, 0.711)93 Comparative Example 4 Ref. 44.6134.8(0.243, 0.713)88 Comparative Example 5 Ref. 54.7238.9(0.246, 0.717)76 Comparative Example 6 Ref. 65.4530.3(0.254, 0.716)7 Comparative Example 7 Ref. 75.2544.5(0.254, 0.711)39Comparative Example 8Ref. 85.2445.3(0.251, 0.715)87Comparative Example 9Ref. 95.3332.6(0.241, 0.711)44Comparative Example 10Ref. 104.3227.3(0.243, 0.714)25Comparative Example 11Ref. 114.7650.9(0.239, 0.710)39Comparative Example 12Ref. 125.3432.9(0.255, 0.720)16Example 11-14.2165.0(0.245, 0.715)188Example 21-24.4469.3(0.241, 0.713)162Example 31-34.3562.2(0.247, 0.711)190Example 41-44.3470.8(0.243, 0.713)149Example 51-54.6776.9(0.241, 0.716)126Example 61-64.5681.6(0.241, 0.721)144Example 71-144.4773.4(0.239, 0.713)169Example 81-174.2760.2(0.243, 0.712)173Example 91-184.3168.9(0.240, 0.710)160Example 101-334.4063.1(0.241, 0.711)181Example 111-344.4860.9(0.241, 0.716)152Example 121-354.2559.3(0.243, 0.721)179Example 131-364.4772.1(0.244, 0.715)155Example 141-494.2363.4(0.237, 0.713)192 Example 151-504.3368.7(0.246, 0.714)164 Example 161-574.5974.4(0.243, 0.720)139 Example 171-584.6370.8(0.241, 0.716)146Example 181-654.4264.9(0.241, 0.716)157Example 191-664.6876.1(0.244, 0.715)139Example 201-674.2260.8(0.239, 0.714)187Example 211-684.3163.4(0.245, 0.713)196Example 221-714.2061.9(0.244, 0.712)185Example 231-854.5979.9(0.241, 0.710)120Example 241-864.6580.3(0.243, 0.721)131 Example 251-874.2058.0(0.241, 0.715)129 Example 261-894.2356.3(0.239, 0.721)167 Example 271-904.2357.0(0.241, 0.716)186 Example 281-934.3561.7(0.251, 0.725)171 Example 291-944.4269.2(0.246, 0.717)159 Example 301-954.3959.9(0.238, 0.714)165 Example 311-974.4367.7(0.243, 0.721)163 Example 321-1094.4057.4(0.240, 0.711)162 Example 331-1254.3059.9(0.241, 0.716)170 Example 341-1414.2360.0(0.238, 0.711)188 Example 351-1424.3270.8(0.243, 0.711)158 Example 361-1604.2955.3(0.242, 0.714)183 Example 371-1794.3471.0(0.245, 0.715)166 Example 381-1804.5075.3(0.241, 0.713)147 Example 391-1814.3166.1(0.247, 0.711)170 Example 401-1924.4675.4(0.239, 0.713)135 Example 411-2114.3768.6(0.241, 0.711)169 Example 421-2274.5573.7(0.245, 0.715)145 Example 431-2284.6170.4(0.241, 0.713)104 Example 441-2604.5672.0(0.245, 0.715)123 Example 451-2614.4067.9(0.241, 0.713)133 Example 461-2754.4269.3(0.245, 0.715)142 Example 471-2814.2462.0(0.239, 0.710)173 Example 481-2824.5272.7(0.241, 0.713)130 Example 491-3154.1865.4(0.244, 0.714)198 Example 501-3164.1665.8(0.245, 0.714)217 Example 511-3174.1566.4(0.245, 0.715)222 Example 521-3184.1267.1(0.244, 0.714)229 Example 531-3194.1765.7(0.245, 0.715)206.

[0513]

[0514] The compounds used in each of Comparative Examples 1 to 12 are as described above.

[0515] As can be seen from the results in Table 16 above, it was confirmed that Examples 1 to 53, 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 12, 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.

[0516] Specifically, compounds Ref. 1, Ref. 2, Ref. 7, and Ref. 11 used in Comparative Examples 1, 2, 7, and 11 have a structure in which the 4th carbon of the group corresponding to Ar1 in the above chemical formula 1 is connected to the benzene core, and exhibited high operating voltage, low efficiency, and short lifetime. Such a structure has strong steric hindrance based on the same plane, and the molecular structure may be distorted to resolve this. However, it is believed that the distorted molecular structure weakens the resonance structure, and thus electrons and holes in the molecule cannot be effectively stabilized, resulting in a deteriorated lifetime. In addition, compound Ref. 3 used in Comparative Example 3 exhibited a short lifetime because it could not stabilize electrons due to a limited resonance structure. On the other hand, it is believed that the compound of the present invention has an improved lifetime by increasing the delocalization rate of the HOMO site by expanding the resonance structure, thereby effectively stabilizing electrons.

[0517] Compounds Ref. 4, Ref. 5 and Ref. 9 used in Comparative Examples 4, 5 and 9, respectively, have a group corresponding to Ar1 of the above chemical formula 1 that is hydrogen or a phenyl group that does not correspond to the above chemical formula A, which is judged to have a weak role as a sub-donor group within the molecule, which does not effectively transfer charges within the molecule, resulting in a deterioration in luminescence efficiency. In addition, in the case of Comparative Examples 6 and 12, it is judged that the HT characteristic was enhanced, so that the hole mobility was too fast, resulting in a charge imbalance, which resulted in an extreme decrease in the lifespan.

[0518] In the case of Comparative Example 10, it is judged that the HT characteristic was weakened, the electron mobility was relatively fast, and the drive increased and the efficiency decreased due to the imbalance in charge mobility.

[0519] Therefore, Comparative Examples 4, 5, 6, 9, 10 and 12 showed a deterioration in device performance due to an imbalance in electron and charge mobility.

[0520] Thermal stability in devices is a critical factor in ensuring operational stability. The glass transition temperature (Tg) is significantly influenced by the molecular weight of the molecule. A higher molecular weight results in a higher Tg, which is beneficial for device stability. Comparative Examples 1, 2, 3, 4, 5, and 9 exhibit low molecular weights. In contrast, the present invention demonstrated improved thermal stability and superior lifespan characteristics based on its high molecular weight, as demonstrated by Chemical Formula A.

[0521] Experimental Example 2

[0522] 1) Fabrication of organic light-emitting devices

[0523] 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. 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 deposition.

[0524] 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).

[0525] On top of that, a light-emitting layer was thermally vacuum deposited as follows.

[0526] The light-emitting layer was deposited at 400Å in one space by pre-mixing one heterocyclic compound having the structure of chemical formula 1 as a host and one heterocyclic compound having the structure of chemical formula 2 or 3 according to Table 17 below, and the green phosphorescent dopant was deposited by doping Ir(ppy)3 at 7% of the thickness of the light-emitting layer deposition.

[0527] Afterwards, BCP was deposited to a thickness of 60Å as a hole blocking layer, and Alq3 was deposited to a thickness of 200Å as an electron transport layer on top of it. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200Å on the electron injection layer to form a cathode, thereby manufacturing an organic light-emitting device.

[0528] 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.

[0529] 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.

[0530] 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.

[0531] Composition ratio (N / P) Driving voltage (V) Luminous efficacy (cd / A) CIE (x, y) Lifespan (T 90) Comparative Example 13 Ref. 1 : 2-83 1 : 14.4154.3(0.239, 0.710) 76 Comparative Example 141 : 24.5656.3(0.239, 0.710) 92 Comparative Example 151 : 34.5958.4(0.239, 0.710) 101 Comparative Example 16 Ref. 3 : 2-100 1 : 14.5147.1(0.247, 0.711) 152 Comparative Example 171 : 24.5449.4(0.247, 0.711) 161 Comparative Example 181 : 34.5751.9(0.247, 0.711) 168 Comparative Example 19 Ref. 5 : 2-831 : 15.1540.7(0.246, 0.717)121Comparative Example 201 : 25.2442.4(0.246, 0.717)129Comparative Example 211 : 35.2944.1(0.246, 0.717)131Comparative Example 22Ref.7 : 2-321 : 15.0157.7(0.246, 0.717)75Comparative Example 231 : 25.0959.9(0.246, 0.717)88Comparative Example 241 : 35.1961.7(0.246, 0.717)91Comparative Example 25Ref. 11: 2-1001: 14.3950.9(0.243, 0.709)108Comparative Example 261: 24.4352.2(0.241, 0.709)121Comparative Example 271: 34.5854.3(0.239, 0.709)145Example 541-1: 2-1001: 13.9167.0(0.245, 0.715)381Example 551: 23.9869.2(0.245, 0.715)398Example 561: 34.0972.3(0.245, 0.715)413Example 571-1: 2-321: 13.9566.7(0.245, 0.715)295 Example 581: 24.0168.9(0.245, 0.715)301 Example 591: 34.1271.8(0.245, 0.715)312 Example 601-2: 2-891: 14.0174.3(0.238, 0.711)243 Example 611: 24.1277.4(0.238, 0.711)267 Example 621: 34.2079.1(0.238, 0.711)301 Example 631-2: 3-41: 13.8771.7(0.234, 0.711)266 Example 641: 23.9272.6 (0.232, 0.714)273 Example 651: 33.9974.4 (0.230, 0.716)313 Example 661-3: 2-1001: 13.9264.3 (0.247, 0.711)365 Example 671: 24.0367.6 (0.247, 0.711)388 Example 681: 34.1269.1 (0.247, 0.711)396 Example 691-3: 3-321: 13.7761.3 (0.241, 0.715)373 Example 701: 23.8163.2(0.241, 0.715)387 Example 711: 33.9864.7(0.241, 0.715)401 Example 721-6: 2-31: 14.1785.1(0.237, 0.711)200 Example 731: 24.2589.3(0.237, 0.715)221 Example 741: 34.3493.1(0.239, 0.715)243 Example 751-49: 2-821: 14.8265.8(0.237, 0.713)383 Example 761: 23.9867.0(0.237, 0.713)399Example 771: 34.0768.2(0.237, 0.713)413Example 781-57: 2-831: 14.3183.4(0.241, 0.714)251Example 791: 24.4385.0(0.241, 0.714)277Example 801: 34.5687.7(0.241, 0.714)293Example 811-68: 2-31: 13.7964.1(0.245, 0.713)378Example 821: 23.9365.9(0.245, 0.713)384Example 831: 34.0467.7(0.245, 0.713)396Example 841-87: 2-831: 13.7660.1(0.241, 0.715)253Example 851: 23.8861.2(0.241, 0.715)267Example 861: 34.0163.7(0.241, 0.715)281Example 871-93: 2-891: 13.8963.4(0.251, 0.725)333Example 881: 24.0364.6(0.251, 0.725)342 Example 891: 34.1165.3(0.251, 0.725)356 Example 901-97: 2-831: 14.1181.3(0.241, 0.710)237 Example 911: 24.2482.6(0.241, 0.710)255 Example 921: 34.3384.4(0.241, 0.710)274 Example 931-97: 3-771: 13.9976.4(0.240, 0.710)241 Example 941: 24.0678.8(0.239, 0.711)267 Example 951: 34.2480.1(0.239, 0.711)288Example 961-125: 2-1001: 13.8460.9(0.241, 0.716)322Example 971: 23.9262.0(0.241, 0.716)343Example 981: 34.0663.7(0.241, 0.716)359Example 991-142: 2-831: 13.88.71.7(0.243, 0.711)308Example 1001: 23.9673.5(0.243, 0.711)314Example 1011: 34.0675.1(0.243, 0.711)322Example 1021-160: 2-891: 13.9057.3(0.242, 0.714)356Example 1031: 23.9959.4(0.242, 0.714)377Example 1041: 34.0960.8(0.242, 0.714)390Example 1051-228:2-831: 14.2172.4(0.241, 0.713)198Example 1061: 24.2875.2(0.241, 0.713)214Example 1071: 34.4077.8(0.241, 0.713)234Example 1081-281: 3-771: 13.8764.1(0.239, 0.710)317Example 1091: 23.9865.3(0.239, 0.710)335Example 1101: 34.0867.7(0.239, 0.710)371Example 1111-282: 3-771: 14.1175.6(0.241, 0.713)248Example 1121: 24.2678.2(0.241, 0.713)269Example 1131: 34.3480.1(0.241, 0.713)293.

[0532]

[0533] The compounds used in Comparative Examples 13 to 27 are as described above.

[0534] From the results in Table 17 above, when the compound of formula 1 and the heterocyclic compound of formula 2 were simultaneously included, or when the compound of formula 1 and the heterocyclic compound of formula 3 were simultaneously included, better efficiency and lifespan effects were observed. From the above results, it can be expected that an exciplex phenomenon will occur when both compounds are simultaneously included.

[0535] The above exciplex phenomenon is a phenomenon in which energy of the size of the HOMO levels of the donor (P-type host) and the LUMO level of the acceptor (N-type host) is released through electron exchange between two molecules. When the exciplex phenomenon between two molecules occurs, Reverse Intersystem Crossing (RISC) occurs, which can increase the fluorescence internal quantum efficiency to 100%.

[0536] When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as hosts in 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.

[0537] In the present invention, it was confirmed that when a heterocyclic compound represented by the above chemical formula 2 or 3 was used as a donor and a compound represented by the above chemical formula 1 was used as an acceptor as a light-emitting layer host, better device characteristics were exhibited. In particular, when deuterium was substituted, further improvement in lifespan characteristics could be confirmed. This is a result shown by the substitution of deuterium as described in the results of Table 17, and this suggests that even if they have similar structures, the characteristics of the compound may vary depending on the substitution of deuterium.

[0538] In addition, as can be seen from the results of Table 17 above, the organic light-emitting devices of Examples 54 to 113, which used a combination of the compound represented by Chemical Formula 1 of the present invention and the heterocyclic compound represented by Chemical Formula 2 or 3 as a light-emitting layer material (particularly, a green phosphorescent host), had lower operating voltages and significantly improved luminous efficiency and lifespans compared to the organic light-emitting devices of Comparative Examples 13 to 27 that did not satisfy the combination.

[0539] As described above in Experimental Example 1, each of the compounds Ref. 1, 3, 5, 7 and 11 used in Comparative Examples 13 to 27 did not meet the conditions of the present invention, and therefore, even when a heterocyclic compound represented by Chemical Formula 2 or 3 was combined therewith, it was confirmed that the driving voltage increased and the luminous efficiency and / or lifespan deteriorated.

[0540] 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, R1 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; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", R2 is hydrogen; or deuterium, L1 to L3 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, a is an integer from 0 to 8, b is an integer from 0 to 3, o, p and q are equal or different and are each independently an integer from 0 to 3, r and s are equal to or different from each other and are each independently an integer from 1 to 4, If each of a, b, o, p, q, r and s is 2 or more, the substituents in the parentheses are the same or different from each other, Ar1 is represented by the following chemical formula A, [Chemical Formula A] In the above chemical formula A, is the part connected to the above L2, Rk is hydrogen; deuterium; or a substituted or unsubstituted C6 to C60 aryl group, X1 is O; S; or C(R5)(R6), R4 is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; and -SiRR'R", wherein at least one R4 is a substituted or unsubstituted C6 to C60 aryl group, R5 and R6 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 C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or adjacent groups are combined with each other to form a substituted or unsubstituted ring, d is an integer from 1 to 6, and when d is 2 or greater, R4 are identical or different from each other, N-Het is represented by the following chemical formula B: [Chemical Formula B] In the above chemical formula B, is the part connected to the above L3, X2 is CRa or N, X3 is CRb or N, X4 is CRc or N, but at least one of X2 to X4 is N, Ar2 and Ar3 are the same or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, Ra, Rb and Rc are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; -P(=O)RR'; and -SiRR'R", The above R, R' and R" are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group.

2. In claim 1, The above chemical formula A is a compound represented by any one of the following chemical formulas A-1 to A-7: [Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] [Chemical Formula A-4] [Chemical Formula A-5] [Chemical Formula A-6] [Chemical Formula A-7] In the above chemical formulas A-1 to A-7, is the part connected to the above L2, Rk, R4, X1, and d are as defined in the above chemical formula A.

3. In claim 1, A compound wherein R1 is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group.

4. In claim 1, A compound wherein L1 to L3 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

5. In claim 1, A compound wherein R4 is hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group, wherein at least one R4 is a substituted or unsubstituted C6 to C20 aryl group.

6. In claim 1, A compound wherein R5 and R6 are the same or different, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; and a substituted or unsubstituted C6 to C20 aryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C20 hydrocarbon ring.

7. In claim 1, A compound wherein Ar2 and Ar3 are the same or different and each independently represent a substituted or unsubstituted C6 to C20 aryl group.

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

17. In claim 16, A composition for an organic layer, 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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