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

Abstract

The present specification aims to provide a compound represented by Chemical Formula 1, an organic light-emitting device, and a composition for an organic layer of an organic light-emitting device. When the compound described in the present specification is used in an organic light-emitting device, it can lower the driving voltage of the device, improve luminous efficiency, and improve the lifespan characteristics of the device.

Description

Technology Field

[0001] This specification relates to compounds, organic light-emitting diodes, and compositions for organic layers of organic light-emitting diodes. Background Technology

[0002] Light-emitting elements are a type of self-emissive display element that has the advantages of a wide viewing angle, excellent contrast, and fast response speed.

[0003] An organic light-emitting diode has a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting diode with such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs and then annihilate, emitting light. The organic thin film can be composed of a single layer or multiple layers as needed.

[0004] The materials of organic thin films may possess luminescence capabilities as needed. For example, compounds capable of independently constituting an emissive layer may be used as organic thin film materials, or compounds capable of acting as a host or dopant in a host-dopant emissive layer may be used. Furthermore, compounds capable of performing functions such as hole injection, hole transport, electron blocking, electron transport, and electron injection may also be used as organic thin film materials.

[0005] To improve the performance, lifespan, or efficiency of organic light-emitting diodes, the development of organic thin film materials is continuously required. Prior art literature

[0006] U.S. Patent No. 4,356,429 The problem to be solved

[0007] The present specification aims to provide a compound, an organic light-emitting device, and a composition for an organic layer of an organic light-emitting device. means of solving the problem

[0008] One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] 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",

[0013] R2 is hydrogen; or deuterium, and

[0014] L1 to L3 are identical or different from one another and are each independently directly bonded; substituted or unsubstituted C6 to C60 arylene groups; or substituted or unsubstituted C2 to C60 heteroarylene groups, and

[0015] a is an integer from 0 to 8, and

[0016] b is an integer from 0 to 3, and

[0017] o, p, and q are identical or different from each other and are each independently integers from 0 to 3, and

[0018] r and s are identical or different from each other and are each independently integers from 1 to 4, and

[0019] If each of a, b, o, p, q, r, and s is 2 or more, the substituents within the parentheses are identical or different from each other, and

[0020] Ar1 is represented by the following chemical formula A, and

[0021] [Chemical Formula A]

[0022]

[0023] In the above chemical formula A,

[0024] is the part connected to the above L2, and

[0025] Rk is hydrogen; deuterium; or a substituted or unsubstituted C6 to C60 aryl group, and

[0026] X1 is O; S; or C(R5)(R6), and

[0027] 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, and

[0028] R5 and R6 are identical 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 to form a substituted or unsubstituted ring, and

[0029] d is an integer from 1 to 6, and if d is 2 or greater, R4 are identical or different from each other, and

[0030] N-Het is represented by the following chemical formula B, and

[0031] [Chemical Formula B]

[0032]

[0033] In the above chemical formula B,

[0034] is the part connected to the above L3, and

[0035] X2 is CRa or N, X3 is CRb or N, and X4 is CRc or N, wherein at least one of X2 to X4 is N,

[0036] Ar2 and Ar3 are identical or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and

[0037] Ra, Rb, and Rc are identical or different from each other and are each independently selected from the group consisting of hydrogen; deuterium; halogen; -CN; substituted or unsubstituted C1 to C60 alkyl groups; substituted or unsubstituted C2 to C60 alkenyl groups; substituted or unsubstituted C2 to C60 alkynyl groups; substituted or unsubstituted C1 to C60 alkoxy groups; substituted or unsubstituted C3 to C60 cycloalkyl groups; substituted or unsubstituted C2 to C60 heterocycloalkyl groups; -P(=O)RR'; and -SiRR'R",

[0038] The above R, R' and R" are identical or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group.

[0039] Another embodiment of the present specification provides an organic light-emitting device comprising a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise the compound.

[0040] Another embodiment of the present specification provides a composition for an organic layer comprising the above compound and a heterocyclic compound represented by the following chemical formula 2 or 3.

[0041] [Chemical Formula 2]

[0042]

[0043] [Chemical Formula 3]

[0044]

[0045] In the above chemical formulas 2 and 3,

[0046] R11, R12, R22 and R23 are identical or different from one another and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0047] L11, L12, L22 and L23 are identical or different from one another and are each independently directly bonded; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and

[0048] Ar11, Ar12, Ar22 and Ar23 are identical or different from one another, and each independently is a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R",

[0049] The above R, R' and R" are identical or different from each other and are each independently 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, and

[0050] a11 and a12 are integers from 0 to 7, respectively, and

[0051] a22 is an integer from 0 to 6, and

[0052] a23 is an integer from 0 to 4, and

[0053] p11, p12, p22, and p23 are each integers from 0 to 4, and

[0054] q11, q12, q22, and q23 are each integers from 1 to 4, and

[0055] If a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22, and q23 are each 2 or more, the substituents within the parentheses are identical or different from each other. Effects of the invention

[0056] When the compound of Formula 1 described in this specification is used in an organic light-emitting device, it may have low driving voltage, high luminous efficiency, and / or long lifespan characteristics.

[0057] Specifically, the compound of the present invention has a structure represented by Chemical Formula 1, and can improve lifespan by introducing a benzene core, which can cause a reduction in lifespan due to the overlap of HOMO-LUMO when a strong donor and a strong acceptor are directly bonded within the molecule, thereby offsetting the overlap of HOMO-LUMO.

[0058] Specifically, as a first substituent connected to the benzene core, N-carbazole is introduced, which acts as a strong donor and is responsible for the HOMO within the molecule, thereby enabling high efficiency by having high hole mobility and smooth charge transfer within the molecule.

[0059] In addition, as a second substituent connected to the benzene core, Ar1 (represented by chemical formula A) has a tricyclic structure and acts as a sub-donor within the molecule, such as dibenzofuran, dibenzothiophene, and dimethylfluorenyl, and can effectively stabilize electrons by increasing the delocalization rate of the HOMO site through the expansion of the resonance structure.

[0060] In addition, as a third substituent connected to the benzene core, N-Het (represented by chemical formula B) acts as a strong electron acceptor and introduces an N-containing heteroaryl responsible for LUMO within the molecule, thereby effectively attracting electrons from the first and second substituents mentioned above, namely N-carbazole (strong donor) and Ar1 (sub-donor), thereby promoting electron stabilization within the molecule and improving the lifespan. Brief explanation of the drawing

[0061] FIGS. 1 to 4 are drawings illustrating exemplary stacked structures of organic light-emitting diodes according to one embodiment of the present specification. Specific details for implementing the invention

[0062] The present specification will be described in more detail below.

[0063] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0064] In this specification, of the chemical formula means the position where it is combined.

[0065] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0066] In this specification, “substituted or unsubstituted” means one or more substituents selected from the group consisting of deuterium; halogen group; cyano group; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; C2 to C60 heteroaryl group; silyl group; phosphine oxide group; and amine group, or one or more substituents selected from the exemplified substituents connected to a substituent.

[0067] In this specification, “where 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 Since H (Deuterium) is an isotope of hydrogen, some hydrogen atoms can be deuterium.

[0068] In one embodiment of the present application, “where no substituents are indicated in the chemical formula or compound structure” may mean that all positions where substituents may be present are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium isotopes, and in this case, the content of deuterium may be 0% to 100%.

[0069] In one embodiment of the present application, where “substituents are not indicated in the chemical formula or compound structure,” the deuterium content is 0%, the hydrogen content is 100%, and all substituents do not explicitly exclude hydrogen or other deuterium, hydrogen and deuterium may be used in a mixture in the compound.

[0070] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, an element having a deuteron as its nucleus, consisting of one proton and one neutron, and can be represented as hydrogen-2, and its element symbol is D or2 It can also be written as H.

[0071] In one embodiment of the present application, an isotope, which means an atom having the same atomic number (Z) but different mass number (A), can also be interpreted as an element having the same number of protons but different number of neutrons.

[0072] 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 a basic compound may have is defined as T1 and the number of specific substituents among them is defined as T2.

[0073] in other words, Taking the phenyl group represented by as an example, the deuterium content of 20% here can be expressed as 20% when the total number of substituents the phenyl group can have is 5 (T1 in the formula) and the number of deuteriums among them is 1 (T2 in the formula). That is, a deuterium content of 20% in the phenyl group can be represented by the following structural formula.

[0074]

[0075] In addition, in one embodiment of the present specification, the “phenyl group having 0% deuterium content” may mean a phenyl group that does not contain deuterium atoms, i.e., has five hydrogen atoms.

[0076] In this specification, the halogen may be fluorine, chlorine, bromine, or iodine.

[0077] In this specification, the alkyl group comprises a straight or branched chain having 1 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, more specifically 1 to 20. 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, There are 2,2-dimethylheptyl groups, 1-ethyl-propyl groups, 1,1-dimethyl-propyl groups, isohexyl groups, 2-methylpentyl groups, 4-methylhexyl groups, 5-methylhexyl groups, etc., but are not limited to these.

[0078] In this specification, the alkenyl group comprises a straight chain or a branched chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically 2 to 20. Specific examples include vinyl groups, 1-propenyl groups, isopropenyl groups, 1-butenyl groups, 2-butenyl groups, 3-butenyl groups, 1-pentenyl groups, 2-pentenyl groups, 3-pentenyl groups, 3-methyl-1-butenyl groups, 1,3-butadienyl groups, allyl groups, 1-phenylvinyl-1-yl groups, 2-phenylvinyl-1-yl groups, 2,2-diphenylvinyl-1-yl groups, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl groups, 2,2-bis(diphenyl-1-yl)vinyl-1-yl groups, stilbenyl groups, styrenyl groups, etc., but are not limited to these.

[0079] In this specification, the alkynyl group comprises a straight or branched chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically 2 to 20.

[0080] In this specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferred to have 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.

[0081] In this specification, the cycloalkyl group comprises a monocyclic or polycyclic group having 3 to 60 carbon atoms and may be further substituted by other substituents. Here, polycyclic means a group in which the 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 other types of ring groups, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, there are cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, 3-methylcyclopentyl groups, 2,3-dimethylcyclopentyl groups, cyclohexyl groups, 3-methylcyclohexyl groups, 4-methylcyclohexyl groups, 2,3-dimethylcyclohexyl groups, 3,4,5-trimethylcyclohexyl groups, 4-tert-butylcyclohexyl groups, cycloheptyl groups, cyclooctyl groups, etc., but are not limited to these.

[0082] In this specification, the heterocycloalkyl group comprises O, S, Se, N, or Si as a heteroatom, comprises a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic means a group in which the 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 other types of ring groups, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0083] In this specification, the aryl group comprises a monocyclic or polycyclic group having 6 to 60 carbon atoms and may be further substituted by other substituents. Here, polycyclic means a group in which the 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 other types of ring groups, such as cycloalkyl groups, heterocycloalkyl groups, heteroaryl groups, etc. The aryl group comprises a spiro group. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the above aryl groups include, but are not limited to, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, anthryl groups, chrysenyl groups, phenanthrenyl groups, perylenyl groups, fluoranthenyl groups, triphenylenyl groups, phenalenyl groups, pyrenyl groups, tetracenyl groups, pentacenyl groups, fluorenyl groups, indenyl groups, acenaphthylenyl groups, benzofluorenyl groups, spirobifluorenyl groups, 2,3-dihydro-1H-indenyl groups, and condensation rings thereof.

[0084] In this specification, the terphenyl group may be selected from the following structures.

[0085]

[0086] In this specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

[0087] When the above fluorenyl group is substituted, it may be selected from the following structures, but is not limited thereto.

[0088]

[0089] In this specification, the heteroaryl group comprises S, O, Se, N, or Si as a heteroatom and comprises a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic group means a group in which the 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 a different type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.Specific examples of the above heteroaryl groups include pyridyl group, pyrrolyl group, pyrimidyl group, pyridazolyl group, furanyl group, thiophene group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazolyl group, oxazolyl group, thiazolyl group, deoxynyl group, triazolyl group, tetrazolyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozoliryl group, naphthalidyl group, acrridinyl group, phenanthridinyl group, imidazopyridinyl group, diazanaphthalenyl group, Triazindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophen group, benzofuran group, dibenzothiophen group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzocazolyl group, dibenzocazolyl group, phenazinyl group, dibenzosilol group, dihydrophenazinyl group, phenoxazinyl group, phenantridyl 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, phenantrazinyl group, phenothiathiazinyl group, Examples include phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, benzo[c][1,2,5]thiadiazolyl group, 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5,10-dihydrodibenzo[b,e][1,4]azacillinyl group, pyrazolo[1,5-c]quinazolinyl group, pyrido[1,2-b]indazolyl group, pyrido[1,2-a]imidazo[1,2-e]indolinyl group, 5,11-dihydroindeno[1,2-b]carbazolyl group, but are not limited to these.

[0090] In the present specification, the silyl group is a substituent comprising Si and said Si atom directly connected as a radical, and is represented as -Si(R101)(R102)(R103), where R101 to R103 are identical or different from each other and may each be a substituent consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group.

[0091] Specific examples of silyl groups include (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), etc., are included, but are not limited to these.

[0092] In this specification, the phosphine oxide group is represented as -P(=O)(R104)(R105), and R104 and R105 are identical or different from each other and may each be a substituent consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group. Specifically, it may be substituted with an alkyl group or an aryl group, and the alkyl group and aryl group may be applied according to the examples described above. For example, the phosphine oxide group may include a dimethylphosphine oxide group, a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, etc., but is not limited thereto.

[0093] In this specification, the amine group is represented as -N(R106)(R107), and R106 and R107 are identical or different from each other and may each be a substituent consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group. The amine group may be selected from the group consisting of -NH2; monoalkylamine group; monoarylamine group; monoheteroarylamine group; dialkylamine group; diarylamine group; diheteroarylamine group; alkylarylamine group; alkylheteroarylamine group; and arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above amine groups include, but are not limited to, methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, dibiphenylamine, anthracenylamine, 9-methyl-anthracenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, triphenylamine, biphenylnaphthylamine, phenylbiphenylamine, biphenylfluorenylamine, phenyltriphenyllenylamine, biphenyltriphenyllenylamine, etc.

[0094] In this specification, the examples of aryl groups described above may be applied, except that the arylene group is a divalent group.

[0095] In this specification, the examples of the aforementioned heteroaryl groups may be applied, except that the heteroarylen group is a divalent group.

[0096] One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[0097] [Chemical Formula 1]

[0098]

[0099] In the above chemical formula 1, the description of each substituent is as described above.

[0100] When the compound according to the above embodiment is used in an organic light-emitting device, it may have low driving voltage, high luminous efficiency, and / or long lifespan characteristics.

[0101] Specifically, the compound of the present invention has a structure represented by Chemical Formula 1, and can improve lifespan by introducing a benzene core, which can cause a reduction in lifespan due to the overlap of HOMO-LUMO when a strong donor and a strong acceptor are directly bonded within the molecule, thereby offsetting the overlap of HOMO-LUMO.

[0102] Specifically, as a first substituent connected to the benzene core, N-carbazole is introduced, which acts as a strong donor and is responsible for the HOMO within the molecule, thereby enabling high efficiency by having high hole mobility and smooth charge transfer within the molecule.

[0103] In addition, as a second substituent connected to the benzene core, Ar1 (represented by chemical formula A) has a tricyclic structure and acts as a sub-donor within the molecule, such as dibenzofuran, dibenzothiophene, and dimethylfluorenyl, and can effectively stabilize electrons by increasing the delocalization rate of the HOMO site through the expansion of the resonance structure.

[0104] In addition, as a third substituent connected to the benzene core, N-Het (represented by chemical formula B) acts as a strong electron acceptor and introduces an N-containing heteroaryl responsible for LUMO within the molecule, thereby effectively attracting electrons from the first and second substituents mentioned above, namely N-carbazole (strong donor) and Ar1 (sub-donor), thereby promoting electron stabilization within the molecule and improving the lifespan.

[0105] In one embodiment of the present specification, the formula 1 may be represented by any one of the following formulas 1-1 to 1-10.

[0106] [Chemical Formula 1-1]

[0107]

[0108] [Chemical Formula 1-2]

[0109]

[0110] [Chemical Formula 1-3]

[0111]

[0112] [Chemical Formula 1-4]

[0113]

[0114] [Chemical Formula 1-5]

[0115]

[0116] [Chemical Formula 1-6]

[0117]

[0118] [Chemical Formula 1-7]

[0119]

[0120] [Chemical Formula 1-8]

[0121]

[0122] [Chemical Formula 1-9]

[0123]

[0124] [Chemical Formula 1-10]

[0125]

[0126] 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.

[0127] In one embodiment of the present specification, the formula A may be represented by any one of the following formulas A-1 to A-7.

[0128] [Chemical Formula A-1]

[0129]

[0130] [Chemical Formula A-2]

[0131]

[0132] [Chemical Formula A-3]

[0133]

[0134] [Chemical Formula A-4]

[0135]

[0136] [Chemical Formula A-5]

[0137]

[0138] [Chemical Formula A-6]

[0139]

[0140] [Chemical Formula A-7]

[0141]

[0142] In the above chemical formulas A-1 to A-7, is the part connected to the above L2, and Rk, R4, X1, and d are as defined in the above chemical formula A.

[0143] 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".

[0144] 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".

[0145] 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".

[0146] 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.

[0147] 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.

[0148] 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.

[0149] In one embodiment of the present specification, L1 to L3 may be identical or different from one another and each independently directly bonded; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0150] In one embodiment of the present specification, L1 to L3 may be identical or different from one another and each independently directly bonded; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0151] In one embodiment of the present specification, L1 to L3 may be identical or different from one another and each independently directly bonded; or may be C6 to C20 arylene groups substituted or unsubstituted with deuterium.

[0152] In one embodiment of the present specification, L1 to L3 may be identical or different from one another and each independently directly bonded; or may be phenylene groups substituted or unsubstituted with deuterium.

[0153] In one embodiment of the present specification, Rk may be hydrogen; deuterium; or a substituted or unsubstituted C6 to C40 aryl group.

[0154] In one embodiment of the present specification, Rk may be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group.

[0155] 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.

[0156] 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.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] In one embodiment of the present specification, R5 and R6 are identical or different from each other and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted 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 to form a substituted or unsubstituted C2 to C40 heterocycle; or a substituted or unsubstituted C6 to C40 hydrocarbon ring.

[0163] In one embodiment of the present specification, R5 and R6 are identical or different from each other 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 combine to form a substituted or unsubstituted C2 to C20 heterocycle; or a substituted or unsubstituted C6 to C20 hydrocarbon ring.

[0164] In one embodiment of the present specification, R5 and R6 may be identical or different from each other and each independently selected from the group consisting of hydrogen; deuterium; C1 to C20 alkyl groups substituted or unsubstituted with deuterium; and C6 to C20 aryl groups substituted or unsubstituted with deuterium, or adjacent groups may be combined to form a substituted or unsubstituted C6 to C20 hydrocarbon ring.

[0165] In one embodiment of the present specification, R5 and R6 may be identical or different from each other and 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 to form a fluorene ring substituted or unsubstituted with deuterium.

[0166] In one embodiment of the present specification, X2 may be N, X3 may be CRb, and X4 may be CRc.

[0167] In one embodiment of the present specification, X2 may be CRa, X3 may be N, and X4 may be CRc.

[0168] In one embodiment of the present specification, X2 may be CRa, X3 may be CRb, and X4 may be N.

[0169] In one embodiment of the present specification, X2 and X3 are N, and X4 may be CRc.

[0170] In one embodiment of the present specification, X3 and X4 may be N, and X2 may be CRa.

[0171] In one embodiment of the present specification, X2 and X4 are N, and X3 may be CRb.

[0172] In one embodiment of the present specification, X2 to X4 may be N.

[0173] In one embodiment of the present specification, Ar2 and Ar3 may be identical or different from each other and each independently substituted or unsubstituted C6 to C40 aryl groups; or substituted or unsubstituted C2 to C40 heteroaryl groups.

[0174] In one embodiment of the present specification, Ar2 and Ar3 may be identical or different from each other and each independently substituted or unsubstituted C6 to C20 aryl groups; or substituted or unsubstituted C2 to C20 heteroaryl groups.

[0175] In one embodiment of the present specification, Ar2 and Ar3 may be identical or different from each other and may each be an aryl group of C6 to C20 that is independently substituted or unsubstituted with deuterium; or a heteroaryl group of C2 to C20 that is substituted or unsubstituted with deuterium.

[0176] In one embodiment of the present specification, Ar2 and Ar3 may be the same or different from each other and may each independently be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a triphenyl group substituted or unsubstituted with deuterium; a dibenzofuranyl group substituted or unsubstituted with deuterium, a methyl group, or a phenyl group; or a dibenzothiophene group substituted or unsubstituted with deuterium, a methyl group, or a phenyl group.

[0177] In one embodiment of the present specification, Ra, Rb and Rc are the same or different from each other and may each independently be selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted 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".

[0178] In one embodiment of the present specification, Ra, Rb and Rc are the same or different from each other and may each independently be selected from the group consisting of hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted 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".

[0179] In one embodiment of the present specification, R, R' and R" are identical 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.

[0180] In one embodiment of the present specification, R, R' and R" are identical or different from each other and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; or a substituted or unsubstituted C6 to C20 aryl group.

[0181] In one embodiment of the present specification, the deuterium content of the compound of Formula 1 may be 0% or 1% to 100%.

[0182] In one embodiment of the present specification, the deuterium content of the compound of Formula 1 may be 0% or 10% to 100%.

[0183] In one embodiment of the present specification, the deuterium content of the compound of Formula 1 may be 0% or 20% to 100%.

[0184] In one embodiment of the present specification, the deuterium content of the compound of Formula 1 may be 0% or 30% to 100%.

[0185] In one embodiment of the present specification, the deuterium content of the compound of Formula 1 may be 0% or 60% to 100%.

[0186] In one embodiment of the present specification, the deuterium content of the compound of Formula 1 may be 0% or 80% to 100%.

[0187] In one embodiment of the present specification, the deuterium content of the compound of Formula 1 may be 0% or 90% to 100%.

[0188] In one embodiment of the present specification, the formula 1 may be represented by any one of the following.

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206] In addition, by introducing various substituents into the structure of Chemical Formula 1, compounds having the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport layer materials, hole transport auxiliary layer materials, light-emitting layer materials, electron transport layer materials, electron transport auxiliary layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, materials that satisfy the conditions required for each organic layer can be synthesized.

[0207] In addition, by introducing various substituents into the structure of Chemical Formula 1 above, the energy band gap can be finely controlled, while at the same time, the properties at the interface between organic materials can be improved and the applications of the material can be varied.

[0208] Another embodiment of the present specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise the compound (represented by Chemical Formula 1).

[0209] In another embodiment of the present specification, the organic layer comprising the compound may further comprise a heterocyclic compound represented by the following chemical formula 2 or 3.

[0210] [Chemical Formula 2]

[0211]

[0212] [Chemical Formula 3]

[0213]

[0214] In the above chemical formulas 2 and 3,

[0215] R11, R12, R22 and R23 are identical or different from one another and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0216] L11, L12, L22 and L23 are identical or different from one another and are each independently directly bonded; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and

[0217] Ar11, Ar12, Ar22 and Ar23 are identical or different from one another, and each independently is a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R",

[0218] The above R, R' and R" are identical or different from each other and are each independently 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, and

[0219] a11 and a12 are integers from 0 to 7, respectively, and

[0220] a22 is an integer from 0 to 6, and

[0221] a23 is an integer from 0 to 4, and

[0222] p11, p12, p22, and p23 are each integers from 0 to 4, and

[0223] q11, q12, q22, and q23 are each integers from 1 to 4, and

[0224] If a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22, and q23 are each 2 or more, the substituents within the parentheses are identical or different from each other.

[0225] In one embodiment of the present specification, R11, R12, R22 and R23 are identical or different from one another and may each independently be selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C40 alkyl group; substituted or unsubstituted C2 to C40 alkenyl group; substituted or unsubstituted C2 to C40 alkynyl group; substituted or unsubstituted C1 to C40 alkoxy group; substituted or unsubstituted C3 to C40 cycloalkyl group; substituted or unsubstituted C2 to C40 heterocycloalkyl group; substituted or unsubstituted C6 to C40 aryl group; substituted or unsubstituted C2 to C40 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0226] In one embodiment of the present specification, R11, R12, R22 and R23 are identical or different from one another and may each independently be selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C2 to C20 alkenyl group; substituted or unsubstituted C2 to C20 alkynyl group; substituted or unsubstituted C1 to C20 alkoxy group; substituted or unsubstituted C3 to C20 cycloalkyl group; substituted or unsubstituted C2 to C20 heterocycloalkyl group; substituted or unsubstituted C6 to C40 aryl group; substituted or unsubstituted C2 to C20 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0227] In one embodiment of the present specification, R11, R12, R22 and R23 are identical or different from one another and each may be independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0228] In one embodiment of the present specification, R11, R12, R22 and R23 may be the same or different from one another and may each independently be hydrogen; or deuterium.

[0229] In one embodiment of the present specification, L11, L12, L22 and L23 may be identical or different from one another and may each be independently directly bonded; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0230] In one embodiment of the present specification, L11, L12, L22 and L23 may be identical or different from one another and may each be independently directly bonded; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0231] In one embodiment of the present specification, L11, L12, L22 and L23 may be identical or different from one another and may each be independently directly bonded; an arylene group of C6 to C20 substituted or unsubstituted with deuterium; or a heteroarylene group of C2 to C20 substituted or unsubstituted with deuterium.

[0232] In one embodiment of the present specification, L11, L12, L22 and L23 may be identical or different from one another and each independently directly bonded; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; a dibenzofuranilene group substituted or unsubstituted with deuterium; or a dibenzothiophenylene group substituted or unsubstituted with deuterium.

[0233] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 are identical or different from one another and each may 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".

[0234] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 are identical or different from one another and each may 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".

[0235] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 are identical or different from one another and each may 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".

[0236] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 are identical or different from one another and each may 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".

[0237] In one embodiment of the present specification, Ar11, Ar12, Ar22 and Ar23 may be identical or different from one another and may each independently be a cyano group; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a triphenylenyl group substituted or unsubstituted with deuterium; a fluorenyl group substituted or unsubstituted with deuterium, a methyl group, or a phenyl group; a spirobifluorenyl group substituted or unsubstituted with deuterium; a dibenzofuranyl group substituted or unsubstituted with deuterium or a phenyl group; a dibenzothiophenyl group substituted or unsubstituted with deuterium or a phenyl group; or a triphenylsilyl group substituted or unsubstituted with deuterium.

[0238] In one embodiment of the present specification, the contents of R, R', and R" defined in Formula 2 or 3 may be applied as they are to R, R', and R" of Formula 1 described above.

[0239] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 2 or 3 may be 0% or 1% to 100%.

[0240] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 2 or 3 may be 0% or 10% to 100%.

[0241] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 2 or 3 may be 0% or 20% to 100%.

[0242] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 2 or 3 may be 0% or 30% to 100%.

[0243] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 2 or 3 may be 0% or 60% to 100%.

[0244] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 2 or 3 may be 0% or 80% to 100%.

[0245] In one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by Formula 2 or 3 may be 0% or 90% to 100%.

[0246] In one embodiment of the present specification, the heterocyclic compound represented by Formula 2 or 3 may be represented by any one of the following.

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260] In one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise the compound (represented by Chemical Formula 1).

[0261] In one embodiment of the present specification, the light-emitting layer comprising the compound may further comprise a heterocyclic compound represented by Formula 2 or 3.

[0262] In one embodiment of the present specification, the organic layer comprises one or more layers selected from a hole transport layer, a hole transport assist layer, and an electron blocking layer, and one or more layers selected from the hole transport layer, the hole transport assist layer, and the electron blocking layer may comprise the compound (represented by Chemical Formula 1).

[0263] In one embodiment of the present specification, one or more layers selected from a hole transport layer, a hole transport assisting layer, and an electron blocking layer containing the compound may additionally include a heterocyclic compound represented by Formula 2 or 3.

[0264] In one embodiment of the present specification, the organic light-emitting device may further include one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport assist layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0265] 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 stacked. For example, the organic light-emitting device of the present invention may have a structure comprising a hole injection layer, a hole transport layer, a hole transport assist layer, a light-emitting layer, an electron transport layer, an electron transport assist layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0266] In one embodiment of the present specification, the first electrode may be an anode and the second electrode may be a cathode.

[0267] In another embodiment of the present specification, the first electrode may be a negative electrode and the second electrode may be a positive electrode.

[0268] An organic light-emitting device according to one embodiment of the present specification can be manufactured by 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 Chemical Formula 1 (additionally, a heterocyclic compound represented by Chemical Formula 2 or 3).

[0269] The compound represented by Chemical Formula 1 (additionally, the heterocyclic compound represented by Chemical Formula 2 or 3) can be formed as an organic layer by vacuum deposition as well as solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0270] 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 Formula 1 (additionally, a heterocyclic compound represented by Formula 2 or 3) may be used as a material for the red organic light-emitting device. For example, the compound represented by Formula 1 (additionally, a heterocyclic compound represented by Formula 2 or 3) may be included in the hole transport layer, hole transport assist layer, electron blocking layer, or light-emitting layer of the red organic light-emitting device.

[0271] 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 Formula 1 (additionally, a heterocyclic compound represented by Formula 2 or 3) may be used as a material for the green organic light-emitting device. For example, the compound represented by Formula 1 (additionally, a heterocyclic compound represented by Formula 2 or 3) may be included in the hole transport layer, hole transport assist layer, electron blocking layer, or light-emitting layer of the green organic light-emitting device.

[0272] 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 Formula 1 (additionally, a heterocyclic compound represented by Formula 2 or 3) may be used as a material for the blue organic light-emitting device. For example, the compound represented by Formula 1 (additionally, a heterocyclic compound represented by Formula 2 or 3) may be included in the hole transport layer, hole transport assist layer, electron blocking layer, or light-emitting layer of the blue organic light-emitting device.

[0273] FIGS. 1 to 4 illustrate the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present specification. However, the scope of the present application is not intended to be limited by these figures, and structures of organic light-emitting devices known in the art may be applied to the present application.

[0274] According to FIG. 1, an organic light-emitting device is shown in which an anode (200), an organic layer (300), and a cathode (400) are sequentially stacked on a substrate (100). However, the structure is not limited to this, and an organic light-emitting device in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate may be implemented as shown in FIG. 2.

[0275] FIGS. 3 and 4 illustrate a case where the organic layer is multilayer. 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 stacked structure, and, if necessary, the remaining layers excluding the light-emitting layer may be omitted, or other necessary functional layers may be added.

[0276] For example, the organic layer may further include a hole transport assist layer, and the hole transport assist layer may be included between the hole transport layer (302) and the electron blocking layer (303) based on the stacked structure.

[0277] The organic layer comprising the compound of Formula 1 and / or the heterocyclic compound of Formula 2 or 3 may additionally include other materials as needed.

[0278] In an organic light-emitting device according to one embodiment of the present specification, materials other than the compound of Formula 1 and / or the heterocyclic compound of Formula 2 or 3 are exemplified below, but these are for illustrative purposes only and are not intended to limit the scope of the present application and may be replaced with materials known in the art.

[0279] Materials with a relatively large work function can be used as anode materials, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the above anode materials include 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, but are not limited to these.

[0280] Materials with a relatively low work function can be used as cathode materials, and metals, metal oxides, or conductive polymers can be used. Specific examples of the above cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0281] As the hole injection material, known hole injection materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or starburst-type amine derivatives described in the document [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), or polyaniline / dodecylbenzenesulfonic acid, which is a soluble conductive polymer, or Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate) can be used.

[0282] In addition to compounds represented by the above chemical formula 1 and / or heterocyclic compounds of the above chemical formula 2 or 3, pyrazolin derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc., may be used as hole transport materials, and low molecular weight or high molecular weight materials may also be used.

[0283] As electron transport materials, metal complexes of oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives, etc., may be used, and not only low molecular weight materials but also high molecular weight materials may be used.

[0284] For example, LiF is commonly used as an electron injection material in the industry, but the present application is not limited thereto.

[0285] In addition to the compound of Formula 1 and / or the heterocyclic compound of Formula 2 or 3, red, green, or blue light-emitting materials may be used as light-emitting materials, and if necessary, two or more light-emitting materials may be mixed and used. In this case, two or more light-emitting materials may be deposited and used as individual sources, or they may be pre-mixed and deposited as a single source. Additionally, fluorescent materials may be used as light-emitting materials, but phosphorescent materials may also be used. As light-emitting materials, a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used alone, but materials in which a host material and a dopant material participate in light emission together may also be used.

[0286] When using a mixture of hosts for light-emitting materials, hosts of the same series may be mixed, or hosts of different series may be mixed. For example, two or more types of materials, such as N-type host materials or P-type host materials, may be selected and used as the host material for the light-emitting layer.

[0287] An organic light-emitting device according to one embodiment of the present specification may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0288] According to one embodiment of the present specification, the compound of Formula 1 and / or the heterocyclic compound of Formula 2 or 3 may operate in organic electronic devices, including organic solar cells, organic photosensitive materials, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.

[0289] In addition, by introducing various substituents into the structure of the compound of Formula 1 and / or the heterocyclic compound of Formula 2 or 3, the energy band gap can be finely tuned, while at the same time, the properties at the interface between organic materials can be improved and the uses of the material can be diversified.

[0290] Another embodiment of the present specification provides a composition for an organic layer comprising a compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 or 3 below.

[0291] [Chemical Formula 2]

[0292]

[0293] [Chemical Formula 3]

[0294]

[0295] In the above chemical formulas 2 and 3,

[0296] R11, R12, R22 and R23 are identical or different from one another and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR'.

[0297] L11, L12, L22 and L23 are identical or different from one another and are each independently directly bonded; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and

[0298] Ar11, Ar12, Ar22 and Ar23 are identical or different from one another, and each is an independently substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R",

[0299] The above R, R' and R" are identical or different from each other and are each independently 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, and

[0300] a11 and a12 are integers from 0 to 7, respectively, and

[0301] a22 is an integer from 0 to 6, and

[0302] a23 is an integer from 0 to 4, and

[0303] p11, p12, p22, and p23 are each integers from 0 to 4, and

[0304] q11, q12, q22, and q23 are each integers from 1 to 4, and

[0305] If a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22, and q23 are each 2 or more, the substituents within the parentheses are identical or different from each other.

[0306] In one embodiment of the present specification, the definition of the substituent of Chemical Formula 2 or 3 may be applied as described in the organic light-emitting device.

[0307] In one embodiment of the present specification, the weight ratio of the compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 or 3 may be 1:10 to 10:1.

[0308] In one embodiment of the present specification, the weight ratio of the compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 or 3 may be 1:5 to 5:1.

[0309] In one embodiment of the present specification, the weight ratio of the compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 or 3 may be 1:3 to 3:1.

[0310] In one embodiment of the present specification, a method for manufacturing an organic light-emitting device is provided, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layers, wherein the step of forming the organic layers includes forming one or more organic layers using a composition for an organic layer comprising a compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 or 3.

[0311] 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 is formed by pre-mixing a compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 or 3 and using a thermal vacuum deposition method.

[0312] The above pre-mixed means mixing the materials first and placing them in a single container to mix the compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or 3 (optional additional compounds) before depositing them on an organic layer.

[0313] The above-mentioned pre-mixed material may be referred to as a composition for an organic layer according to one embodiment of this specification.

[0314] The present specification is described in more detail below through examples, but these are for illustrative purposes only and are not intended to limit the scope of the present application.

[0316] Preparation Example

[0317] <Preparation Example 1> Preparation of Compound 1-1

[0318]

[0319] 1) Preparation of Compound 1-1-3

[0320] 10 g (47.7 mM) of the above compound 1-1-4, (A) 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 100 mL / 30 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

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

[0322] 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 complete, distilled water and DCM were added at room temperature for extraction; the organic layer was dried with MgSO4, and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 14.2 g (72.5%) of the target compound 1-1-2.

[0323] 3) Preparation of Compound 1-1-1

[0324] 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 complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

[0325] 4) Preparation of Compound 1-1

[0326] 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 complete, distilled water was added to precipitate the solid, and the mixture was purified by column chromatography (DCM:Hex=1:2) to obtain 16.7 g (83.0%) of the target compound 1-1 with methanol.

[0328] <Preparation Example 2> Preparation of Compounds 1-2~1-6, 1-14, 1-17, 1-18, 1-33~1-36, 1-49, 1-50, 1-57, 1-58, 1-65~1-68, 1-71, 1-85~1-87, 1-89, 1-90, 1-315, 1-317

[0329] The target compound was synthesized by the same method as in Preparation Example 1, except that intermediate A of Table 1 below was used instead of (A) 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane, intermediate B was used instead of (B) 2-chloro-4,6-diphenyl-1,3,5-triazine, and intermediate C was used instead of (C) 9H-carbazole.

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0339] <Preparation Example 3> Preparation of Compound 1-93

[0340]

[0341] 1) Preparation of Compound 1-93-3

[0342] 10 g (47.7 mM) of the above compound 1-93-4, (A) 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 100 mL / 30 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

[0343] 2) Preparation of Compound 1-93-2

[0344] 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 complete, distilled water and DCM were added at room temperature for extraction; the organic layer was dried with 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.

[0345] 3) Preparation of Compound 1-93-1

[0346] 14.0 g (30.2 mM) of the above compound 1-93-2, (B) 8.1 g (30.2 mM) of 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 140 mL / 40 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

[0347] 4) Preparation of Compound 1-93

[0348] 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 complete, distilled water was added to precipitate the solid, and the mixture was purified by column chromatography (DCM:Hex=1:2) to obtain 16.1 g (81.9%) of the target compound 1-93 with methanol.

[0350] <Preparation Example 4> Preparation of Compounds 1-94, 1-95, 1-97, 1-109, 1-125, 1-141, 1-142 and 1-160

[0351] The target compound was synthesized by the same method as in Preparation Example 3, except that in Preparation Example 3 above, intermediate A of Table 2 below was used instead of (A) 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane, intermediate B was used instead of (B) 2-chloro-4,6-diphenyl-1,3,5-triazine, and intermediate C was used instead of (C) 9H-carbazole.

[0352]

[0353]

[0355] <Preparation Example 5> Preparation of Compound 1-179

[0356]

[0357] 1) Preparation of Compound 1-179-3

[0358] 10 g (47.7 mM) of the above compound 1-179-4, (A) 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 100 mL / 30 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

[0359] 2) Preparation of Compound 1-179-2

[0360] 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 complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) to obtain 14.8g (77.9%) of the target compound 1-179-2.

[0361] 3) Preparation of Compound 1-179-1

[0362] 14.8 g (31.9 mM) of the above compound 1-179-2, (B) 8.5 g (31.9 mM) of 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 150 mL / 45 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

[0363] 4) Preparation of Compound 1-179

[0364] 16.7 g (29.3 mM) of the above compound 1-179-1, 4.9 g (29.3 mM) of (C)9H-carbazole, and 28.6 g (87.9 mM) of Cs2CO3 were dissolved in 170 mL of DMA and refluxed at 180 °C for 5 hours. After the reaction was complete, distilled water was added to precipitate the solid, and the mixture was purified by column chromatography (DCM:Hex=1:2) to obtain 17.9 g (85.4%) of the target compound 1-179 with methanol.

[0366] <Preparation Example 6> Preparation of Compounds 1-180, 1-181, 1-192 and 1-211

[0367] The target compound was synthesized by the same method as in Preparation Example 5, except that in Preparation Example 5 above, intermediate A of Table 3 below was used instead of (A) 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane, intermediate B was used instead of (B) 2-chloro-4,6-diphenyl-1,3,5-triazine, and intermediate C was used instead of (C) 9H-carbazole.

[0368]

[0370] <Preparation Example 7> Preparation of Compound 1-227

[0371]

[0372] 1) Preparation of Compound 1-227-3

[0373] 10 g (47.7 mM) of the above compound 1-227-4, (A) 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 100 mL / 30 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

[0374] 2) Preparation of Compound 1-227-2

[0375] 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 complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:2) to obtain 15.1g (80.6%) of the target compound 1-227-2.

[0376] 3) Preparation of Compound 1-227-1

[0377] 15.1 g (32.5 mM) of the above compound 1-227-2, (B) 8.7 g (32.5 mM) of 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 150 mL / 45 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

[0378] 4) Preparation of Compound 1-227

[0379] 16.1 g (28.2 mM) of the above compound 1-227-1, 4.7 g (28.2 mM) of (C)9H-carbazole, and 27.6 g (84.6 mM) of Cs2CO3 were dissolved in 160 mL of DMA and refluxed at 180 °C for 5 hours. After the reaction was complete, distilled water was added to precipitate the solid, and the mixture was purified by column chromatography (DCM:Hex=1:2) to obtain 18.9 g (93.4%) of the target compound 1-227 with methanol.

[0381] <Preparation Example 8> Preparation of Compounds 1-228, 1-260 and 1-261

[0382] The target compound was synthesized by the same method as in Preparation Example 7, except that in Preparation Example 7 above, intermediate A of Table 4 below was used instead of (A) 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane, intermediate B was used instead of (B) 2-chloro-4,6-diphenyl-1,3,5-triazine, and intermediate C was used instead of (C) 9H-carbazole.

[0383]

[0385] <Preparation Example 9> Preparation of Compound 1-275

[0386]

[0387] 1) Preparation of Compound 1-275-3

[0388] 10 g (47.7 mM) of the above compound 1-275-4, 17.6 g (47.7 mM) of 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 100 mL / 30 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4, followed by the removal of the solvent using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3), and 16.0 g (89.9%) of the target compound 1-275-3 was obtained using methanol.

[0389] 2) Preparation of Compound 1-275-2

[0390] 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 complete, distilled water and DCM were added at room temperature for extraction; the organic layer was dried with MgSO4, and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 17.2 g (86.4%) of the target compound 1-275-2.

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

[0392] 17.2 g (37.0 mM) of the above compound 1-275-2, 9.9 g (37.0 mM) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 42.2 g (1.9 mM) of Pd(PPh3), and 10.2 g (74.0 mM) of K2CO3 were dissolved in 170 mL / 50 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4, followed by the removal of the solvent using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3), and 17.2 g (81.4%) of the target compound 1-275-1 was obtained using methanol.

[0393] 4) Preparation of Compound 1-275

[0394] 17.2 g (30.1 mM) of the above compound 1-275-1, 5.0 g (30.1 mM) of 9H-carbazole, and 29.4 g (90.3 mM) of Cs2CO3 were dissolved in 170 mL of DMA and refluxed at 180 °C for 5 hours. After the reaction was complete, distilled water was added to precipitate the solid, and the mixture was purified by column chromatography (DCM:Hex=1:2) to obtain 19.9 g (91.9%) of the target compound 1-275 with methanol.

[0396] <Preparation Example 10> Preparation of Compound 1-281

[0397]

[0398] 1) Preparation of Compound 1-281-3

[0399] 10 g (47.7 mM) of the above compound 1-281-4, (A) 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 100 mL / 30 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

[0400] 2) Preparation of Compound 1-281-2

[0401] 15.0 g (40.2 mM) of compound 1-281-3, 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 complete, distilled water and DCM were added at room temperature for extraction; the organic layer was dried with 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.

[0402] 3) Preparation of Compound 1-281-1

[0403] 15.1 g (32.5 mM) of the above compound 1-281-2, (B) 8.7 g (32.5 mM) of 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 150 mL / 45 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

[0404] 4) Preparation of Compound 1-281

[0405] 16.6 g (29.1 mM) of the above compound 1-281-1, 4.9 g (29.1 mM) of (C)9H-carbazole, and 28.5 g (87.4 mM) of Cs2CO3 were dissolved in 170 mL of DMA and refluxed at 180 °C for 5 hours. After the reaction was complete, distilled water was added to precipitate the solid, and the mixture was purified by column chromatography (DCM:Hex=1:2) to obtain 17.6 g (84.3%) of the target compound 1-281 with methanol.

[0407] <Preparation Example 11> Preparation of Compound 1-282

[0408] The target compound was synthesized by preparing it in the same manner as in Preparation Example 10, except that in Preparation Example 10 above, intermediate A of Table 5 below was used instead of (A) 4,4,5,5-tetramethyl-2-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,2-dioxaborolane, intermediate B was used instead of (B) 2-chloro-4,6-diphenyl-1,3,5-triazine, and intermediate C was used instead of (C) 9H-carbazole.

[0409]

[0411] <Preparation Example 12> Preparation of Compound 1-316

[0412]

[0413] 1) Preparation of Compound 1-316-4

[0414] 10 g (47.7 mM) of the above compound 1-316-5 was dissolved in 6500 mL of Benzene-d, then dissolved in 170 g (1075 mM) of CF3SO3H, and refluxed at 60°C for 1 hour. When the reaction was complete Subsequently, it was neutralized with D2O and Na2CO3. After neutralization, distilled water and ethyl acetate were added to the mixture for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

[0415] 2) Preparation of Compound 1-316-3

[0416] 9.0 g (42.6 mM) of the above compound 1-316-4, (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), and K2CO3 11.78 g (85.2 mM) were dissolved in 90 mL / 27 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

[0417] 3) Preparation of Compound 1-316-2

[0418] 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 complete, distilled water and DCM were added at room temperature for extraction; the organic layer was dried with MgSO4, and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 18.5 g (84.9%) of the target compound 1-316-2.

[0419] 4) Preparation of Compound 1-316-1

[0420] 18.5 g (39.7 mM) of the above compound 1-316-2, (B) 8.2 g (39.7 mM) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 41.8 g (1.98 mM) of Pd(PPh3), and 8.45 g (79.6 mM) of K2CO3 were dissolved in 190 mL / 60 mL of 1,4-dioxane / H2O and refluxed for 6 hours. After the reaction was complete, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product 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.

[0421] 5) Preparation of Compound 1-316

[0422] 17.4 g (30.4 mM) of the above compound 1-316-1, 85.1 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 complete, distilled water was added to precipitate the solid, and the mixture was purified by column chromatography (DCM:Hex=1:2) to obtain 19.8 g (89.7%) of the target compound 1-316 with methanol.

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

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

[0426]

[0427] Compounds were prepared in the same manner as the above preparation examples, and the results of the synthesis confirmation are shown in Tables 7 and 8 below. Table 7 shows the measured values ​​from the FD-mass spectrometer (FD-MS: Field desorption mass spectrometry), and Table 8 below shows the NMR values.

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

[0429] Compound number 1 H NMR(CDCl3, 400MHz) 1-1 δ = 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) 1-2 δ = 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) 1-3 δ = 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) 1-4 δ = 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) 1-5 δ = 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) 1-6 δ = 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), 7.20-7.16 1-14 δ = 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) 1-17 δ = 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) 1-18 δ = 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) 1-33 δ = 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) 1-34 δ = 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) 1-35 δ = 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) 1-36 δ = 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) 1-49 δ = 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) 1-50 δ = 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) 1-57 δ = 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) 1-58 δ = 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) 1-65 δ = 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) 1-66 δ = 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) 1-67 δ = 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) 1-68 δ = 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) 1-71 δ = 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) 1-85 δ = 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) 1-86 δ = 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) 1-87 δ = 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) 1-89 δ = 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) 1-90 δ = 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) 1-93 δ = 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) 1-94 δ = 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) 1-95 δ = 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) 1-97 δ = 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) 1-109 δ = 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) 1-125 δ = 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) 1-141 δ = 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) 1-142 δ = 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) 1-160 δ = 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) 1-179 δ = 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) 1-180 δ = 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) 1-181 δ = 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) 1-192 δ = 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) 1-211 δ = 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) 1-227 δ = 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) 1-228 δ = 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) 1-260 δ = 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) 1-261 δ = 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) 1-275 δ = 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) 1-281 δ = 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) 1-282 δ = 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) 1-315 δ = 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) 1-316 δ = 8.36(d, 4H), 8.03(d, 1H), 7.82-7.76(m, 5H), 7.69(d, 1H), 7.50-7.41(m, 10H) 1-317 δ = 8.36(d, 4H), 8.11-8.01(m, 3H), 7.50-7.41(m, 6H) 1-318 δ = 8.36(d, 4H), 7.50-7.41(m, 6H)

[0431] <Preparation Example 14> Preparation of Compound 2-1

[0432]

[0433] 1) Preparation of Compound 2-1-1

[0434] 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 to a reaction flask, and 100 mL of toluene was added. It was heated at 135℃ for 15 hours.

[0435] After the reaction was finished, the compound 2-1-1 was extracted with methylene chloride (MC) and water, then purified by column chromatography to obtain 14 g (yield 98%).

[0436] 2) Preparation of Compound 2-1

[0437] 14 g (43.4 mmol) of compound 2-1-1, (b) 14.9 g (52 mmol) of (9-phenyl-9H-carbazol-3-yl)boronic acid, 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 added to a reaction flask, and then 140 mL of 1,4-dioxane and 35 mL of distilled water were added and stirred at 120°C for 4 hours.

[0438] Afterwards, the temperature was lowered to room temperature and the resulting solid was washed with distilled water and methanol to obtain 17g of compound 2-1 (yield 80%).

[0440] <Preparation Example 15> Preparation 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

[0441] The target compound was synthesized by the same method as in Preparation Example 14, except that compound a of Table 9 below was used instead of 2-bromobenzene-1-ylium (a) in Preparation Example 14, and compound b of Table 9 below was used instead of (9-phenyl-9H-carbozol-3-yl)boronic acid (b).

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0460] <Preparation Example 16> Preparation of Compound 2-61

[0461]

[0462] 1) Preparation of Compound 2-61-4

[0463] 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.

[0464] After the reaction was completed, the mixture was neutralized with D2O, and then extracted at room temperature with an aqueous solution of sodium carbonate (Na2CO3) and dichloromethane (DCM). The organic layer was dried with anhydrous magnesium sulfate (MgSO4), and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (dichloromethane:hexane = 1:2) and recrystallized with methanol to obtain 10 g of the target compound 2-61-4 (yield 98%).

[0465] 2) Preparation of Compound 2-61-3

[0466] After adding 10 g (39.5 mmol) of the above compound 2-61-4, 12.4 g (79 mmol) of bromobenzene(c)(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), 100 mL of toluene was added and heated at 135°C for 15 hours. After the reaction was finished, the compound 2-61-3 was extracted with methylene chloride (MC) and water, then purified by column chromatography to obtain 11 g (yield 84%).

[0467] 3) Preparation of Compound 2-61-2

[0468] 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.

[0469] After the reaction was completed, the mixture was neutralized with D2O, and then extracted at room temperature with an aqueous solution of sodium carbonate (Na2CO3) and dichloromethane (DCM). The organic layer was dried with anhydrous magnesium sulfate (MgSO4) and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (dichloromethane:hexane = 1:2) and recrystallized with methanol to obtain 9 g of the target compound 2-61-2 (yield 87%).

[0470] 4) Preparation of Compound 2-61-1

[0471] After adding 9 g (41.3 mmol) of the above compound 2-61-2, 12.9 g (82.5 mmol) of bromobenzene (d)(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 finished, the compound 2-61-1 was extracted with methylene chloride (MC) and water, then purified by column chromatography to obtain 10 g (yield 82%).

[0472] 5) Preparation of Compound 2-61

[0473] 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 140 mL of 1,4-dioxane and 35 mL of distilled water were added and stirred at 120°C for 4 hours.

[0474] Afterwards, the temperature was lowered to room temperature and the resulting solid was washed with distilled water and methanol to obtain 13g of compound 2-61 (yield 85%).

[0476] <Preparation 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

[0477] The target compound was synthesized in the same manner as in Preparation Example 16, except that compound c of Table 10 below was used instead of bromobenzene (c) in Preparation Example 16 below, and compound d of Table 10 below was used instead of bromobenzene (d).

[0478]

[0479]

[0480]

[0481]

[0482]

[0483]

[0484]

[0485]

[0486]

[0487]

[0488]

[0490] Compounds were prepared in the same manner as the above preparation examples, and the results of confirming their synthesis are shown in Tables 11 and 12 below. Table 11 shows the measured values ​​from Field Desorption Mass Spectrometry (FD-MS), and Table 12 is 1 This is the measured value of H NMR (CDCl3, 400 MHz).

[0491] 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 38 N2Si=742.28) 2-19 m / z= 636.78(C 48 H 32 N2=636.26) 2-20 m / z= 636.78(C 48 H 32 N2=636.26) 2-21 m / z= 636.78(C 48 H 32 N2=636.26) 2-22 m / z= 712.88(C 54 H 36 N2=712.29) 2-23 m / z= 712.88(C 54 H 36 N2=712.29) 2-24 m / z= 712.88(C 54 H 36 N2=712.29) 2-25 m / z= 710.86(C 54 H 34 N2=710.27) 2-26 m / z= 712.88(C 54 H 36 N2=712.29) 2-27 m / z= 712.88(C 54 H 36 N2=712.29) 2-28 m / z= 712.88(C 54 H 36 N2=712.29) 2-29 m / z= 712.88(C 54 H 36 N2=712.29) 2-30 m / z= 712.88(C 54 H 36 N2=712.29) 2-31 m / z= 710.86(C 54 H 34 N2=710.27) 2-32 m / z= 636.78(C 48 H 32 N2=636.26) 2-33 m / z= 712.88(C 54 H 36 N2=712.29) 2-34 m / z= 712.88(C 54 H 36 N2=712.29) 2-35 m / z= 788.97(C 60 H 40 N2=788.32) 2-36 m / z= 686.84(C 52 H 34 N2=686.27) 2-37 m / z= 788.97(C 60 H 40 N2=788.32) 2-38 m / z= 788.97(C 60 H 40 N2=788.32) 2-39 m / z= 686.84(C 52 H 34 N2=686.27) 2-40 m / z= 686.84(C 52 H 34 N2=686.27) 2-41 m / z= 494.65(C 36 H 14 D 10 N2=494.26) 2-42 m / z= 654.89(C 48 H 14 D 18 N2=654.37) 2-43 m / z= 574.77(C 41 H 14 D 14 N2=574.31) 2-44 m / z= 650.86(C 48 H 14 D 16 N2=650.34) 2-45 m / z= 654.89(C 48 H 14 D 18 N2=654.37) 2-46 m / z= 654.89(C 48 H 14 D 18 N2=654.37) 2-47 m / z= 654.89(C 48 H 14 D 18 N2=654.37) 2-48 m / z=654.89(C 48 H 14 D 18 N2=654.37) 2-49 m / z= 654.89(C 48 H 14 D 18 N2=654.37) 2-50 m / z: 734.43(C 54 H 14 D 22 N2=735.03) 2-51 m / z= 735.01(C 54 H 14 D 22 N2=734.43) 2-52 m / z= 735.01(C 54 H 14 D 22 N2=734.43) 2-53 m / z= 730.98(C 54 H 14 D 20 N2=730.40) 2-54 m / z= 735.01(C 54 H 14 D 22 N2=734.43) 2-55 m / z=735.01(C 54 H 14 D 22 N2=734.43) 2-56 m / z= 815.13(C 60 H 14 D 26 N2=814.48) 2-57 m / z= 815.13(C 60 H 14 D 26 N2=814.48) 2-58 m / z= 815.13(C 60 H 14 D 26 N2=814.48) 2-59 m / z= 815.13(C 60 H 14 D 26 N2=814.48) 2-60 m / z= 666.86(C 48 H 14 D 16 N2O=666.34) 2-61 m / z= 498.68(C 36 H 10 D 14 N2=498.28) 2-62 m / z= 650.87(C 48 H 18 D 14 N2=650.34) 2-63 m / z= 574.77(C 41 H 14 D 14 N2=574.31) 2-64 m / z= 648.85(C 48 H 16 D 14 N2=648.33) 2-65 m / z= 650.87(C 48 H 18 D 14 N2=650.34) 2-66 m / z= 650.87(C 48 H 18 D 14 N2=650.34) 2-67 m / z= 650.87(C 48 H 18 D 14 N2=650.34) 2-68 m / z= 650.87(C 48 H 18 D 14 N2=650.34) 2-69 m / z= 650.87(C 48 H 18 D 14 N2=650.34) 2-70 m / z=726.38(C 54 H 22 D 14 N2=726.98) 2-71 m / z= 726.96(C 54 H 22 D 14 N2=726.38) 2-72 m / z= 726.96(C 54 H 22 D 14 N2=726.38) 2-73 m / z= 724.95(C 54 H 20 D 14 N2=724.36) 2-74 m / z= 726.96(C 54 H 22 D 14 N2=726.38) 2-75 m / z= 726.96(C 54 H 22 D 14 N2=726.38) 2-76 m / z= 803.06(C 60 H 26 D 14 N2=802.41) 2-77 m / z= 803.06(C 60 H 26 D 14 N2=802.41) 2-78 m / z= 803.06(C 60 H 26 D 14 N2=802.41) 2-79 m / z= 803.06(C 60 H 26 D 14 N2=802.41) 2-80 m / z= 803.06(C 60 H 26 D 14 N2=802.41) 2-81 m / z= 508.74(C 36 D 24 N2=508.34) 2-82 m / z= 668.98(C 48 D 32 N2=668.46) 2-83 m / z= 588.86(C 42 D 28 N2=588.40) 2-84 m / z= 664.95(C 48 D 30 N2=664.43) 2-85 m / z= 668.98(C 48 D 32 N2=668.46) 2-86 m / z= 668.98(C 48 D 32 N2=668.46) 2-87 m / z= 668.98(C 48 D 32 N2=668.46) 2-88 m / z= 668.98(C 48 D 32 N2=668.46) 2-89 m / z= 668.98(C 48 D 32 N2=668.46) 2-90 m / z= 748.518(C 54 D 36 N2=749.12) 2-91 m / z= 749.10(C 54 D 36 N2=748.51) 2-92 m / z= 749.10(C 54 D 36 N2=748.51) 2-93 m / z= 745.07(C 54 D 34 N2=744.49) 2-94 m / z= 749.10(C 54 D 36 N2=748.51) 2-95 m / z= 749.10(C 54 D 36 N2=748.51) 2-96 m / z= 829.22(C 60 D 40 N2=828.57) 2-97 m / z= 829.22(C 60 D 40 N2=828.57) 2-98 m / z= 829.22(C 60 D 40 N2=828.57) 2-99 m / z= 829.22(C 60 D 40 N2=828.57) 2-100 m / z= 680.95(C 48 D 30 N2O=680.42) 2-101 m / z= 697.02(C 48 D 30 N2S=696.40) 2-102 m / z= 829.22(C 60 D 40 N2=828.57) 2-103 m / z= 632.95(C 45 D 32 N2=632.46) 2-104 m / z= 713.07(C 51 D 36 N2=712.51)

[0492] Compound number 1 H NMR(CDCl3, 400MHz) 2-1 δ =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) 2-2 δ =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) 2-3 δ =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) 2-4 δ =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) 2-5 δ =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) 2-6 δ =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) 2-7 δ =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) 2-11 δ =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) 2-16 δ =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) 2-19 δ =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) 2-20 δ =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) 2-21 δ =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) 2-22 δ =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) 2-23 δ =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) 2-26 δ =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) 2-27 δ =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) 2-28 δ =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) 2-29 δ =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) 2-30 δ =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) 2-32 δ =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) 2-33 δ =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) 2-34 δ =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) 2-38 δ =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) 2-40 δ =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) 2-41 δ =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) 2-42 δ =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) 2-43 δ =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) 2-45 δ =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) 2-46 δ =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) 2-48 δ =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) 2-49 δ =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) 2-50 δ =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) 2-51 δ =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) 2-52 δ =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) 2-55 δ =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) 2-57 δ =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) 2-60 δ =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) 2-61 δ =7.62-7.50(m, 10H) 2-62 δ =7.79(m, 4H), 7.68(m. 4H), 7.52-7.41(m, 10H) 2-63 δ =8.21(s, 1H) 7.75-7.41(m, 13H) 2-64 δ =9.05(s, 1H), 8.33-8.25(m, 4H), 7.94(d, 1H), 7.70-7.50(m, 10H) 2-65 δ =7.79(m, 2H), 7.70-7.68(m, 3H), 7.58-7.41(m, 13H) 2-66 δ =7.92-7.91(m, 4H), 7.75(d, 2H), 7.62-7.41(m, 8H), 7.25(s, 4H) 2-68 δ =8.21(s, 2H), 7.75-7.60(m, 8H), 7.49-7.41(8H) 2-69 δ =8.21(s, 1H), 7.92-7.91(m, 4H), 7.75-7.60(m, 6H), 7.49-7.41(m, 7H) 2-70 δ =8.21(s, 1H), 7.94-7.91(m, 5H), 7.75-7.61(m, 9H), 7.49-7.41(m, 7H) 2-74 δ =7.94-7.91(m, 9H), 7.75-7.73(m, 5H), 7.61(d, 2H), 7.49-7.41(m, 6H) 2-75 δ =7.92-7.91(m, 8H), 7.75(d, 4H), 7.49-7.41(m, 6H), 7.25(s, 4H)

[0494] <Preparation Example 18> Preparation of Compound 3-1

[0495] 1) Preparation of Compound 3-1-1

[0496]

[0497] After adding (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) to a reaction flask, add 100 mL of toluene. It was heated at 135℃ for 15 hours. After the reaction was complete, it was extracted with methylene chloride (MC) and water, and then purified by column chromatography to obtain 7.3g (yield 56%) of compound 3-1-1.

[0498] 2) Preparation of Compound 3-1

[0499] After adding 7.3g (22.0mmol) of the above compound 3-1-1, 3.8g (24.2mmol) of 1-bromobenzene, 1.01g (1.1mmol) of Tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.52mL (3.9mmol) of Tri-tert-butylphosphine (P(t-Bu)3), and 4.23g (44.0mmol) of Sodium tert-butoxide (NatOBu), 70mL of toluene was added and heated at 135℃ for 15 hours. After the reaction was finished, the compound 3-1 was extracted with methylene chloride (MC) and water, and then purified by column chromatography to obtain 8.3 g (yield 93%).

[0501] <Preparation 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

[0502] The target compound was synthesized by preparing it in the same manner as in Preparation Example 18, except that intermediate A of Table 13 below was used instead of (a) in Preparation Example 18 below, intermediate B of Table 13 below was used instead of (b) and intermediate C of Table 13 below was used instead of (c).

[0503]

[0504]

[0505]

[0506]

[0508] Compounds were prepared using the same method as the above preparation examples, and the results of confirming their synthesis are shown in Tables 14 and 15 below. Table 14 shows the measured values ​​from Field Desorption Mass Spectrometry (FD-MS), and Table 15 is 1 This is the measured value of H NMR (CDCl3, 400 MHz).

[0509] Compound number FD-MS Compound number FD-MS 3-1 m / z= 408.16(C 30 H 20 N2=408.50) 3-4 m / z= 560.23(C 42 H 28 N2=560.70) 3-5 m / z= m / z= 560.23(C 42 H 28 N2=560.70) 3-22 m / z= m / z= 560.23(C 42 H 28 N2=560.70) 3-23 m / z= m / z= 560.23(C 42 H 28 N2=560.70) 3-32 m / z= m / z= 560.23(C 42 H 28 N2=560.70) 3-35 m / z= m / z= 560.23(C 42 H 28 N2=560.70) 3-41 m / z= m / z= 560.23(C 42 H 28 N2=560.70) 3-61 m / z= 578.34(C 42 H 10 D 18 N2=578.81) 3-69 m / z= 570.29(C 42 H 18 D 10 N2=570.76) 3-77 m / z= 588.40(C 42 D 28 N2=588.87)

[0510] Compound number 1 H NMR(CDCl3, 400MHz) 3-1 δ = 8.55(2H, d), 7.94(2H, d), 7.62-7.35(14H, m), 7.16(2H, d) 3-4 δ = 8.55(2H, d), 7.94-7.91(10H, m), 7.75(4H, d), 7.49-7.35(10H, m), 7.16(2H, t) 3-5 δ = 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) 3-22 δ = 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) 3-23 δ = 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) 3-32 δ = 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) 3-35 δ = 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) 3-41 δ = 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) 3-61 δ = 8.55(2H, d), 7.94(2H, d), 7.42-7.35(4H, m), 7.16(2H, t) 3-69 δ = 7.92-7.91(8H, m), 7.75(4H, d), 7.49-7.41(6H, m)

[0512] <Experimental Example 1>

[0513] 1) Fabrication of Organic Light Emitting Diodes

[0514] A glass substrate coated with a thin film of ITO to a thickness of 1,500 Å was cleaned with distilled water ultrasonics. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then UVO treatment was performed using UV light in a UV cleaner for 5 minutes. Subsequently, the substrate was transferred to a plasma cleaner (PT), and plasma treatment was performed under vacuum to remove the ITO work function and residual film, after which it was transferred to a thermal evaporation equipment for organic deposition.

[0515] 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), was formed on the above ITO transparent electrode (anode).

[0516] An emissive layer was thermally vacuum deposited on top of it as follows. For the emissive layer, the compound listed in Table 16 below was used as the host, and Ir(ppy)3 (tris(2-phenylpyridine)iridium) was used as the green phosphorescent dopant. The host was doped with 7% Ir(ppy)3 and deposited to a thickness of 400 Å. Subsequently, BCP (Bathocuproine) was deposited as a hole blocking layer to a thickness of 60 Å, and Alq3 was deposited as an electron transport layer to a thickness of 200 Å on top of it. Finally, an electron injection layer was formed by depositing lithium fluoride (LiF) to a thickness of 10 Å on the electron transport layer, and then an aluminum (Al) cathode was formed by depositing an aluminum cathode to a thickness of 1200 Å on the electron injection layer to form a cathode, thereby fabricating an organic light-emitting device.

[0517] Meanwhile, all organic compounds required for OLED device fabrication are 10 each for each material -8 ~10 -6 It was purified by vacuum sublimation under torr and used for OLED fabrication.

[0519] 2) Driving voltage and luminous efficiency of organic light-emitting diodes

[0520] The electroluminescence (EL) characteristics of the organic light-emitting diode fabricated as described above were measured using MaxScience's M7000, and based on the measurement results, the reference brightness was 6,000 cd / m² using a lifetime measurement device (M6000) manufactured by MaxScience 2 When, T 90 Measured.

[0521] The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light-emitting diode manufactured according to the present invention are as shown in Table 16 below.

[0522] compound compound Driving voltage (V) Efficiency (cd / A) Color coordinates (x, y) Lifespan (T 90 ) Comparative Example 1 Ref. 1 4.82 46.1 (0.239, 0.710) 42 Comparative Example 2 Ref. 2 5.01 46.4 (0.248, 0.712) 37 Comparative Example 3 Ref. 3 4.79 43.9 (0.247, 0.711) 93 Comparative Example 4 Ref. 4 4.61 34.8 (0.243, 0.713) 88 Comparative Example 5 Ref. 5 4.72 38.9 (0.246, 0.717) 76 Comparative Example 6 Ref. 6 5.45 30.3 (0.254, 0.716) 7 Comparative Example 7 Ref. 7 5.25 44.5 (0.254, 0.711) 39 Comparative Example 8 Ref. 8 5.24 45.3 (0.251, 0.715) 87 Comparative Example 9 Ref. 9 5.33 32.6 (0.241, 0.711) 44 Comparative Example 10 Ref. 10 4.32 27.3 (0.243, 0.714) 25 Comparative Example 11 Ref. 11 4.76 50.9 (0.239, 0.710) 39 Comparative Example 12 Ref. 12 5.34 32.9 (0.255, 0.720) 16 Example 1 1-1 4.21 65.0 (0.245, 0.715) 188 Example 2 1-2 4.44 69.3 (0.241, 0.713) 162 Example 3 1-3 4.35 62.2 (0.247, 0.711) 190 Example 4 1-4 4.34 70.8 (0.243, 0.713) 149 Example 5 1-5 4.67 76.9 (0.241, 0.716) 126 Example 6 1-6 4.56 81.6 (0.241, 0.721) 144 Example 7 1-14 4.47 73.4 (0.239, 0.713) 169 Example 8 1-17 4.27 60.2 (0.243, 0.712) 173 Example 9 1-18 4.31 68.9 (0.240, 0.710) 160 Example 10 1-33 4.40 63.1 (0.241, 0.711) 181 Example 11 1-34 4.48 60.9 (0.241, 0.716) 152 Example 12 1-35 4.25 59.3 (0.243, 0.721) 179 Example 13 1-36 4.47 72.1 (0.244, 0.715) 155 Example 14 1-49 4.23 63.4 (0.237, 0.713) 192 Example 15 1-50 4.33 68.7 (0.246, 0.714) 164 Example 16 1-57 4.59 74.4 (0.243, 0.720) 139 Example 17 1-58 4.63 70.8 (0.241, 0.716) 146 Example 18 1-65 4.42 64.9 (0.241, 0.716) 157 Example 19 1-66 4.68 76.1 (0.244, 0.715) 139 Example 20 1-67 4.22 60.8 (0.239, 0.714) 187 Example 21 1-68 4.31 63.4 (0.245, 0.713) 196 Example 22 1-71 4.20 61.9 (0.244, 0.712) 185 Example 23 1-85 4.59 79.9 (0.241, 0.710) 120 Example 24 1-86 4.65 80.3 (0.243, 0.721) 131 Example 25 1-87 4.20 58.0 (0.241, 0.715) 129 Example 26 1-89 4.23 56.3 (0.239, 0.721) 167 Example 27 1-90 4.23 57.0 (0.241, 0.716) 186 Example 28 1-93 4.35 61.7 (0.251, 0.725) 171 Example 29 1-94 4.42 69.2 (0.246, 0.717) 159 Example 30 1-95 4.39 59.9 (0.238, 0.714) 165 Example 31 1-97 4.43 67.7 (0.243, 0.721) 163 Example 32 1-109 4.40 57.4 (0.240, 0.711) 162 Example 33 1-125 4.30 59.9 (0.241, 0.716) 170 Example 34 1-141 4.23 60.0 (0.238, 0.711) 188 Example 35 1-142 4.32 70.8 (0.243, 0.711) 158 Example 36 1-160 4.29 55.3 (0.242, 0.714) 183 Example 37 1-179 4.34 71.0 (0.245, 0.715) 166 Example 38 1-180 4.50 75.3 (0.241, 0.713) 147 Example 39 1-181 4.31 66.1 (0.247, 0.711) 170 Example 40 1-192 4.46 75.4 (0.239, 0.713) 135 Example 41 1-211 4.37 68.6 (0.241, 0.711) 169 Example 42 1-227 4.55 73.7 (0.245, 0.715) 145 Example 43 1-228 4.61 70.4 (0.241, 0.713) 104 Example 44 1-260 4.56 72.0 (0.245, 0.715) 123 Example 45 1-261 4.40 67.9 (0.241, 0.713) 133 Example 46 1-275 4.42 69.3 (0.245, 0.715) 142 Example 47 1-281 4.24 62.0 (0.239, 0.710) 173 Example 48 1-282 4.52 72.7 (0.241, 0.713) 130 Example 49 1-315 4.18 65.4 (0.244, 0.714) 198 Example 50 1-316 4.16 65.8 (0.245, 0.714) 217 Example 51 1-317 4.15 66.4 (0.245, 0.715) 222 Example 52 1-318 4.12 67.1 (0.244, 0.714) 229 Example 53 1-319 4.17 65.7 (0.245, 0.715) 206

[0523]

[0524] The compounds used in Comparative Examples 1 to 12, respectively, are as described above.

[0526] As can be seen from the results of Table 16 above, it was confirmed that the organic light-emitting devices of Examples 1 to 53, which use the compound represented by Formula 1 of the present invention as a light-emitting layer material (in particular, a green phosphorescent host), have a lower driving voltage and significantly improved light-emitting efficiency and lifespan compared to Comparative Examples 1 to 12, which do not use the compound represented by Formula 1 of the present invention as a light-emitting layer material.

[0527] 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 carbon at position 4 of the group corresponding to Ar1 in Chemical Formula 1 is connected to a benzene core, and exhibited high driving voltage, low efficiency, and short lifetime. Such structures have strong steric hindrance based on the same plane, and the molecular structure may be twisted to resolve this. However, it is determined that the twisted molecular structure weakens the resonance structure, thereby failing to effectively stabilize electrons and holes within the molecule, and consequently, the lifetime deteriorated. Furthermore, in the case of compound Ref. 3 used in Comparative Example 3, it exhibited a short lifetime because it failed to stabilize electrons due to a limited resonance structure. On the other hand, it is determined that the compounds of the present invention have improved lifetime by effectively stabilizing electrons through the expansion of the resonance structure, which increases the delocalization rate of homo sites.

[0528] Compounds Ref. 4, Ref. 5, and Ref. 9 used in Comparative Examples 4, 5, and 9 each have a group corresponding to Ar1 in Chemical Formula 1 that is hydrogen or a phenyl group that does not correspond to Chemical Formula A. It is determined that this acts weakly as a sub-donor group within the molecule, failing to effectively transfer charges within the molecule, and consequently, the luminescence efficiency has deteriorated. Additionally, in the case of Comparative Examples 6 and 12, the HT characteristics are enhanced, causing the hole mobility to be too fast, which leads to charge imbalance and an extreme reduction in lifetime.

[0529] In the case of Comparative Example 10, it is determined that the HT characteristics were weakened and the electron mobility was relatively fast, so the driving increased and the efficiency decreased due to the imbalance in charge mobility.

[0530] Accordingly, Comparative Examples 4, 5, 6, 9, 10, and 12 showed a degradation in device performance due to an imbalance in electron and charge mobility.

[0531] Thermal stability is an important factor in providing operational stability in a device. The glass transition temperature (Tg) is greatly influenced by the molecular weight of the molecule; the larger the molecular weight, the higher the glass transition temperature, which is advantageous for device stability. Comparative Examples 1, 2, 3, 4, 5, and 9 have low molecular weights. On the other hand, the present invention confirmed that thermal stability is improved and excellent lifespan characteristics are exhibited based on a high molecular weight through Formula A.

[0533] <Experimental Example 2>

[0534] 1) Fabrication of Organic Light Emitting Diodes

[0535] A glass substrate coated with a thin film of ITO to a thickness of 1,500 Å was cleaned with distilled water ultrasonics. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then UVO treatment was performed using UV light in a UV cleaner for 5 minutes. Subsequently, the substrate was transferred to a plasma cleaner (PT), and plasma treatment was performed under vacuum to remove the ITO work function and residual film, after which it was transferred to a thermal evaporation equipment for organic deposition.

[0536] 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), was formed on the above ITO transparent electrode (anode).

[0537] A light-emitting layer was thermally vacuum deposited on top of it as follows.

[0538] According to Table 17 below, the emissive layer was deposited at a thickness of 400 Å in one park by pre-mixing one heterocyclic compound having the structure of Formula 1 and one heterocyclic compound having the structure of Formula 2 or 3 as hosts, and the green phosphorescent dopant was deposited by doping 7% of the emissive layer deposition thickness with Ir(ppy)3.

[0539] Subsequently, BCP was deposited as a hole blocking layer at a thickness of 60 Å, and Alq3 was deposited as an electron transport layer at a thickness of 200 Å on top of it. Finally, an electron injection layer was formed by depositing lithium fluoride (LiF) to a thickness of 10 Å on the electron transport layer, and then an aluminum (Al) cathode was formed by depositing an aluminum cathode to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby fabricating an organic light-emitting diode.

[0540] Meanwhile, all organic compounds required for OLED device fabrication are 10 each for each material -8 ~10 -6 It was purified by vacuum sublimation under torr and used for OLED fabrication.

[0542] The electroluminescence (EL) characteristics of the organic light-emitting diode fabricated as described above were measured using MaxScience's M7000, and based on the measurement results, the reference brightness was 6,000 cd / m² using a lifetime measurement device (M6000) manufactured by MaxScience. 2 When, T 90 Measured.

[0543] The driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light-emitting diode manufactured according to the present invention were measured and are as shown in Table 17 below.

[0544] furtherance Ratio (N / P) Driving voltage (V) Luminous efficiency (cd / A) CIE(x, y) Lifespan (T 90 ) Comparative Example 13 Ref.1 : 2-83 1 : 1 4.41 54.3 (0.239, 0.710) 76 Comparative Example 14 1 : 2 4.56 56.3 (0.239, 0.710) 92 Comparative Example 15 1 : 3 4.59 58.4 (0.239, 0.710) 101 Comparative Example 16 Ref.3 : 2-100 1 : 1 4.51 47.1 (0.247, 0.711) 152 Comparative Example 17 1 : 2 4.54 49.4 (0.247, 0.711) 161 Comparative Example 18 1 : 3 4.57 51.9 (0.247, 0.711) 168 Comparative Example 19 Ref.5 : 2-83 1 : 1 5.15 40.7 (0.246, 0.717) 121 Comparative Example 20 1 : 2 5.24 42.4 (0.246, 0.717) 129 Comparative Example 21 1 : 3 5.29 44.1 (0.246, 0.717) 131 Comparative Example 22 Ref.7 : 2-32 1 : 1 5.01 57.7 (0.246, 0.717) 75 Comparative Example 23 1 : 2 5.09 59.9 (0.246, 0.717) 88 Comparative Example 24 1 : 3 5.19 61.7 (0.246, 0.717) 91 Comparative Example 25 Ref. 11 : 2-100 1 : 1 4.39 50.9 (0.243, 0.709) 108 Comparative Example 26 1 : 2 4.43 52.2 (0.241, 0.709) 121 Comparative Example 27 1 : 3 4.58 54.3 (0.239, 0.709) 145 Example 54 1-1 : 2-100 1 : 1 3.91 67.0 (0.245, 0.715) 381 Example 55 1 : 2 3.98 69.2 (0.245, 0.715) 398 Example 56 1 : 3 4.09 72.3 (0.245, 0.715) 413 Example 57 1-1 : 2-32 1 : 1 3.95 66.7 (0.245, 0.715) 295 Example 58 1 : 2 4.01 68.9 (0.245, 0.715) 301 Example 59 1 : 3 4.12 71.8 (0.245, 0.715) 312 Example 60 1-2 : 2-89 1 : 1 4.01 74.3 (0.238, 0.711) 243 Example 61 1 : 2 4.12 77.4 (0.238, 0.711) 267 Example 62 1 : 3 4.20 79.1 (0.238, 0.711) 301 Example 63 1-2 : 3-4 1 : 1 3.87 71.7 (0.234, 0.711) 266 Example 64 1 : 2 3.92 72.6 (0.232, 0.714) 273 Example 65 1 : 3 3.99 74.4 (0.230, 0.716) 313 Example 66 1-3 : 2-100 1 : 1 3.92 64.3 (0.247, 0.711) 365 Example 67 1 : 2 4.03 67.6 (0.247, 0.711) 388 Example 68 1 : 3 4.12 69.1 (0.247, 0.711) 396 Example 69 1-3 : 3-32 1 : 1 3.77 61.3 (0.241, 0.715) 373 Example 70 1 : 2 3.81 63.2 (0.241, 0.715) 387 Example 71 1 : 3 3.98 64.7 (0.241, 0.715) 401 Example 72 1-6 : 2-3 1 : 1 4.17 85.1 (0.237, 0.711) 200 Example 73 1 : 2 4.25 89.3 (0.237, 0.715) 221 Example 74 1 : 3 4.34 93.1 (0.239, 0.715) 243 Example 75 1-49 : 2-82 1 : 1 4.82 65.8 (0.237, 0.713) 383 Example 76 1 : 2 3.98 67.0 (0.237, 0.713) 399 Example 77 1 : 3 4.07 68.2 (0.237, 0.713) 413 Example 78 1-57 : 2-83 1 : 1 4.31 83.4 (0.241, 0.714) 251 Example 79 1 : 2 4.43 85.0 (0.241, 0.714) 277 Example 80 1 : 3 4.56 87.7 (0.241, 0.714) 293 Example 81 1-68 : 2-3 1 : 1 3.79 64.1 (0.245, 0.713) 378 Example 82 1 : 2 3.93 65.9 (0.245, 0.713) 384 Example 83 1 : 3 4.04 67.7 (0.245, 0.713) 396 Example 84 1-87 : 2-83 1 : 1 3.76 60.1 (0.241, 0.715) 253 Example 85 1 : 2 3.88 61.2 (0.241, 0.715) 267 Example 86 1 : 3 4.01 63.7 (0.241, 0.715) 281 Example 87 1-93 : 2-89 1 : 1 3.89 63.4 (0.251, 0.725) 333 Example 88 1 : 2 4.03 64.6 (0.251, 0.725) 342 Example 89 1 : 3 4.11 65.3 (0.251, 0.725) 356 Example 90 1-97 : 2-83 1 : 1 4.11 81.3 (0.241, 0.710) 237 Example 91 1 : 2 4.24 82.6 (0.241, 0.710) 255 Example 92 1 : 3 4.33 84.4 (0.241, 0.710) 274 Example 93 1-97 : 3-77 1 : 1 3.99 76.4 (0.240, 0.710) 241 Example 94 1 : 2 4.06 78.8 (0.239, 0.711) 267 Example 95 1 : 3 4.24 80.1 (0.239, 0.711) 288 Example 96 1-125 : 2-100 1 : 1 3.84 60.9 (0.241, 0.716) 322 Example 97 1 : 2 3.92 62.0 (0.241, 0.716) 343 Example 98 1 : 3 4.06 63.7 (0.241, 0.716) 359 Example 99 1-142 : 2-83 1 : 1 3.88. 71.7 (0.243, 0.711) 308 Example 100 1 : 2 3.96 73.5 (0.243, 0.711) 314 Example 101 1 : 3 4.06 75.1 (0.243, 0.711) 322 Example 102 1-160 : 2-89 1 : 1 3.90 57.3 (0.242, 0.714) 356 Example 103 1 : 2 3.99 59.4 (0.242, 0.714) 377 Example 104 1 : 3 4.09 60.8 (0.242, 0.714) 390 Example 105 1-228 :2-83 1 : 1 4.21 72.4 (0.241, 0.713) 198 Example 106 1 : 2 4.28 75.2 (0.241, 0.713) 214 Example 107 1 : 3 4.40 77.8 (0.241, 0.713) 234 Example 108 1-281 : 3-77 1 : 1 3.87 64.1 (0.239, 0.710) 317 Example 109 1 : 2 3.98 65.3 (0.239, 0.710) 335 Example 110 1 : 3 4.08 67.7 (0.239, 0.710) 371 Example 111 1-282 : 3-77 1 : 1 4.11 75.6 (0.241, 0.713) 248 Example 112 1 : 2 4.26 78.2 (0.241, 0.713) 269 Example 113 1 : 3 4.34 80.1 (0.241, 0.713) 293

[0545]

[0546] The compounds used in Comparative Examples 13 to 27, respectively, are as described above.

[0548] In the results of Table 17 above, superior efficiency and lifespan effects were observed when the compound of Formula 1 and the heterocyclic compound of Formula 2 were included simultaneously, or when the compound of Formula 1 and the heterocyclic compound of Formula 3 were included simultaneously. From the above results, it can be expected that the exciplex phenomenon occurs when the two compounds are included simultaneously.

[0549] The exciplex phenomenon described above is a phenomenon in which energy 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 occurs between two molecules, Reverse Intersystem Crossing (RISC) takes place, which can increase the fluorescence internal quantum efficiency to 100%.

[0550] When a donor (p-host) with good hole transport capability and an acceptor (n-host) with good electron transport capability are used as hosts for the emissive layer, holes are injected into the p-host and electrons are injected into the n-host, which can lower the driving voltage and thereby help improve the lifespan.

[0551] In the present invention, it was confirmed that superior device characteristics are exhibited when a heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 is used as the donor and a compound represented by Chemical Formula 1 is used as the acceptor. In particular, additional improvement in lifetime characteristics can be observed when deuterium is substituted. This result was obtained through the substitution of deuterium as described in the results of Table 17, and it suggests that even if compounds have similar structures, their characteristics can differ depending on the substitution of deuterium.

[0552] In addition, as can be seen from the results of Table 17 above, it was confirmed that the organic light-emitting devices of Examples 54 to 113, which used a combination of the compound represented by Formula 1 of the present invention and the heterocyclic compound represented by Formula 2 or 3 as a light-emitting layer material (in particular, a green phosphorescent host), had a lower driving voltage and significantly improved luminous efficiency and lifespan compared to the organic light-emitting devices of Comparative Examples 13 to 27, which did not satisfy the above combination.

[0553] As explained in Experimental Example 1 above, since each of the compounds Ref. 1, 3, 5, 7 and 11 used in Comparative Examples 13 to 27 does not meet the conditions of the present invention, it was confirmed that even if a heterocyclic compound represented by Formula 2 or 3 is combined with them, the driving voltage increases and the luminous efficiency and / or lifespan deteriorates.

[0555] The present invention is not limited to the above embodiments and can be manufactured in various different forms, and those skilled in the art will understand that the invention can be implemented in other specific forms without changing the technical concept or essential features of the invention. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive. Explanation of the symbols

[0556] 100: Substrate 200: Anode 300: Organic layer 301: Hole injection layer 302: Precision Transport Layer 303: Electronic blocking layer 304: Emissive layer 305: Electron transport layer 306: Electron injection layer 400: Cathode

Claims

Claim 1 Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R1 is 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'; Selected from the group consisting of and -SiRR'R", R2 is hydrogen; or deuterium, L1 to L3 are identical or different from each other and are each independently directly bonded; a C6 to C60 arylene group that is substituted or unsubstituted; or a C2 to C60 heteroarylene group that is substituted or unsubstituted, a is an integer from 0 to 8, b is an integer from 0 to 3, o, p, and q are identical or different from each other and are each independently integers from 0 to 3, r and s are identical or different from each other and are each independently integers from 1 to 4, and where each of a, b, o, p, q, r, and s is 2 or more, the substituents in parentheses are identical 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), and R4 is hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; Selected from the group consisting of and -SiRR'R", wherein at least one of Rk and R4 is a substituted or unsubstituted C6 to C60 aryl group, R5 and R6 are identical 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 bonded to each other to form a substituted or unsubstituted ring, d is an integer of 1, and N-Het is represented by the following chemical formula B, [Chemical Formula B] In the above chemical formula B, ... is a portion connected to the above L3, X2 is CRa or N, X3 is CRb or N, X4 is CRc or N, wherein at least one of X2 to X4 is N, Ar2 and Ar3 are identical or different from each other and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and Ra, Rb and Rc are identical or different from each other and are each independently hydrogen; deuterium; halogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; -P(=O)RR'; Selected from the group consisting of and -SiRR'R", wherein R, R' and R" are identical or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group. Claim 2 The compound of claim 1, wherein the chemical formula A is represented by any one of the following chemical formulas A-1 to A-3: [Chemical formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] In the above chemical formulas A-1 to A-3, is the part connected to the above L2, and Rk, R4, X1, and d are as defined in the above chemical formula A. Claim 3 A compound according to claim 1, 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. Claim 4 A compound according to claim 1, wherein L1 to L3 are identical or different from one another and each independently directly bonded; or are substituted or unsubstituted C6 to C20 arylene groups. Claim 5 delete Claim 6 A compound according to claim 1, wherein R5 and R6 are identical or different from each other 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 combined to form a substituted or unsubstituted C6 to C20 hydrocarbon ring. Claim 7 A compound according to claim 1, wherein Ar2 and Ar3 are identical or different from each other and are each independently substituted or unsubstituted C6 to C20 aryl groups. Claim 8 A compound according to claim 1, wherein the deuterium content of the compound of formula 1 is 0% or 1% to 100%. Claim 9 A compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following: . Claim 10 An organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound according to any one of claims 1 to 4 and 6 to 9. Claim 11 An organic light-emitting device according to claim 10, wherein the organic layer comprising the compound 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 identical or different from one another and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; Selected from the group consisting of -SiRR'R"; -P(=O)RR'; and -NRR', wherein L11, L12, L22 and L23 are identical or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and Ar11, Ar12, Ar22 and Ar23 are identical or different from each other and are each independently a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R", and wherein R, R' and R" are identical or different from each other and are each independently 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 It is a heteroaryl group, a11 and a12 are each integers from 0 to 7, a22 is an integer from 0 to 6, a23 is an integer from 0 to 4, p11, p12, p22 and p23 are each integers from 0 to 4, q11, q12, q22 and q23 are each integers from 1 to 4, and when a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 are each 2 or more, the substituents in parentheses are the same or different from each other. Claim 12 An organic light-emitting device according to claim 11, wherein the deuterium content of the heterocyclic compound represented by formula 2 or 3 is 0% or 1% to 100%. Claim 13 An organic light-emitting device according to claim 11, wherein the heterocyclic compound represented by formula 2 or 3 is represented by any one of the following: . Claim 14 An organic light-emitting device according to claim 10, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound. Claim 15 The organic light-emitting device of claim 10 further comprises 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 assist layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. Claim 16 Composition for an organic layer comprising a compound according to any one of claims 1 to 4 and 6 to 9 and a heterocyclic compound represented by the following formula 2 or 3: [Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, R11, R12, R22, and R23 are identical or different from one another and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; Selected from the group consisting of -SiRR'R"; -P(=O)RR'; and -NRR', wherein L11, L12, L22 and L23 are identical or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and Ar11, Ar12, Ar22 and Ar23 are identical or different from each other and are each independently a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or SiRR'R", and wherein R, R' and R" are identical or different from each other and are each independently 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 It is a heteroaryl group, a11 and a12 are each integers from 0 to 7, a22 is an integer from 0 to 6, a23 is an integer from 0 to 4, p11, p12, p22 and p23 are each integers from 0 to 4, q11, q12, q22 and q23 are integers from 1 to 4, and when a11, a12, a22, a23, p11, p12, p22, p23, q11, q12, q22 and q23 are each 2 or more, the substituents in parentheses are the same or different from each other. Claim 17 A composition for an organic layer according to claim 16, wherein the weight ratio of the compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 or 3 is 1:10 to 10:1.

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