Organic electroluminescent device using polycyclic aromatic compound

Abstract

The organic electroluminescent device according to the present invention can be driven at low voltage by using compounds with unique structures as hole transport materials and dopant materials in the hole injection layer or hole transport layer and the light emission layer, respectively. It has excellent external quantum efficiency and exhibits efficient light emission characteristics, and therefore can be used in industry for flat panel display devices, flexible display devices, monochrome or white flat panel lighting devices, monochrome or white flexible lighting devices, etc.

Description

Technical Field

[0001] This invention relates to a high-efficiency organic light-emitting device that exhibits significantly improved luminous efficiency by using polycyclic aromatic derivative compounds in its organic layer. Background Technology

[0002] Organic light-emitting devices (OLEDs) are self-emissive devices that emit light when energy is released from excitons formed by the recombination of electrons injected through an electron injection electrode (cathode) and holes injected through a hole injection electrode (anode) in the light-emitting layer. Such OLEDs have attracted considerable attention as a next-generation light source due to their advantages, such as low driving voltage, high brightness, wide viewing angle, and fast response speed, making them suitable for full-color flat panel displays.

[0003] To enable organic light-emitting devices (OLEDs) to exhibit the aforementioned characteristics, the structure of the organic layers within the OLED should be optimized, and the materials constituting each organic layer—namely, hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, or electron blocking materials—should be based on stable and efficient compositions. However, there is an ongoing need to develop organic layer structures and corresponding materials for stable and efficient OLEDs.

[0004] Therefore, there is a ongoing need to develop structures that can improve the light-emitting properties of organic light-emitting devices, as well as to develop new materials that support such structures. Summary of the Invention

[0005] Technical issues

[0006] Therefore, the present invention was made in view of the above problems, and one object of the present invention is to provide a high-efficiency organic light-emitting device that can operate at low voltage and exhibits excellent external quantum efficiency based on compounds for the light-emitting layer and compounds for the hole transport layer or hole injection layer.

[0007] Technical solution

[0008] According to the present invention, the above and other objectives can be achieved by providing an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and a hole injection layer or hole transport layer and a light-emitting layer between the first electrode and the second electrode.

[0009] The organic light-emitting device according to the present invention (i) includes at least one compound represented by [Formula A] or [Formula B] in the hole injection layer or hole transport layer, and (ii) includes a compound represented by [Formula C] or [Formula D] in the light-emitting layer.

[0010]

[0011] At least one of Ar1 and Ar2 is represented by the following [Structure 1]:

[0012] [Structure 1]

[0013]

[0014] The specific structures of [Formula A] and [Formula B], the compounds obtained therefrom, and the limitations of A1, R1 to R3 and Ar1 to Ar2 will be described later.

[0015]

[0016] The specific structures of [Formula C] through [Formula D], the compounds obtained therefrom, and their substituents will be described later.

[0017] Beneficial effects

[0018] The organic light-emitting device according to the present invention can operate at a lower driving voltage and exhibits excellent external quantum efficiency and thus high luminous efficiency by utilizing compounds with characteristic structures as hole transport materials and dopant materials in the hole injection layer or hole transport layer and the light-emitting layer, respectively. Detailed Implementation

[0019] The invention will now be described in detail with reference to the accompanying drawings.

[0020] In one aspect, the present invention relates to an organic light-emitting device, the organic light-emitting device comprising: a first electrode, a second electrode facing the first electrode, and a hole injection layer or hole transport layer and a light-emitting layer between the first electrode and the second electrode, wherein (i) the hole injection layer or hole transport layer comprises at least one compound represented by [Formula A] or [Formula B], and (ii) the light-emitting layer comprises a compound represented by [Formula C] or [Formula D]. Based on this structure, a high-efficiency organic light-emitting device can be obtained.

[0021]

[0022] in

[0023] A1 is selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C50 heteroaryl groups.

[0024] W represents either an oxygen atom (O) or a sulfur atom (S).

[0025] R1 and R2 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C2-C50 heteroaryl, provided that R1 and R2 are bonded to each other to form an alicyclic or aromatic monocyclic or polycyclic ring.

[0026] Ar1 and Ar2 may be identical or different from each other, and each is independently a substituted or unsubstituted C6-C50 aryl and a substituted or unsubstituted C2-C50 heteroaryl, provided that at least one of Ar1 and Ar2 is represented by the following structural formula 1:

[0027] [Structure 1]

[0028]

[0029] in

[0030] R3 is selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C2-C50 heteroaryl.

[0031] R4 is selected from hydrogen, deuterium, cyano, halogen group, hydroxyl, nitro, C1-C24 alkyl, C1-C24 haloalkyl, C1-C24 cycloalkyl, C1-C24 alkenyl, C1-C24 alkynyl, C1-C24 heteroalkyl, C6-C30 aryl, C6-C30 arylalkyl, C2-C30 heteroaryl, C2-C30 heteroarylalkyl, C1-C24 alkoxy, C1-C24 alkylamino, C6-C30 arylamino, C2-C30 heteroarylamino, C1-C24 alkylsilyl, C6-C30 arylsilyl, and C6-C30 aryloxy.

[0032] l is an integer from 0 to 4, provided that when l is 2 or greater, R4 are either the same or different from each other.

[0033] "-*" refers to the sites where nitrogen atoms are bonded at positions Ar1 and Ar2 in [Formula A] or [Formula B].

[0034] According to one embodiment of the invention, R1 and R2 are each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C2-C50 heteroaryl.

[0035] Furthermore, when R1 and R2 bond to each other to form a ring, compounds represented by the following [Structural Formula 2] can be obtained:

[0036] [Structure 2]

[0037]

[0038] in

[0039] Y can be a single bond, an oxygen atom (O), or a sulfur atom (S).

[0040] R5 and R6 are selected from hydrogen, deuterium, cyano, halogen group, hydroxyl, nitro, C1-C24 alkyl, C1-C24 haloalkyl, C1-C24 cycloalkyl, C1-C24 alkenyl, C1-C24 alkynyl, C1-C24 heteroalkyl, C6-C30 aryl, C6-C30 arylalkyl, C2-30 heteroaryl, C2-C30 heteroarylalkyl, C1-C24 alkoxy, C1-C24 alkylamino, C6-C30 arylamino, C2-30 heteroarylamino, C1-C24 alkylsilyl, C6-C30 arylsilyl, and C6-C30 aryloxy, where n and m are each integers from 0 to 4, provided that when n and m are each 2 or greater, R5 and R6 are the same or different from each other.

[0041] According to one embodiment of the present invention, A1 can be represented by the following [Structural Formula 3]:

[0042] [Structure 3]

[0043]

[0044] in

[0045] Z is N or CR, where R is selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C5-C30 arylthio, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C5-C30 arylamino, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C5-C30 arylsilyl, nitro, cyano, and halogen groups.

[0046] R are bonded to each other, or each of them is bonded to an adjacent substituent to form at least one alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atom of the formed alicyclic, aromatic monocyclic or polycyclic ring is substituted with at least one heteroatom selected from (N), sulfur (S) and oxygen (O).

[0047]

[0048] in

[0049] Q1 to Q3 may be the same as or different from each other, and each is independently a substituted or unsubstituted aromatic C6-C50 hydrocarbon ring, or a substituted or unsubstituted C2-C50 aromatic heterocyclic group.

[0050] Y1 to Y3 may be the same as or different from each other, and each is independently selected from N-R1, CR2R3, O, S, Se, and SiR4R5.

[0051] X is selected from B, P, and P=O, and in a preferred embodiment of the invention, X is B, and in this case, a boron (B)-containing polycyclic aromatic derivative compound is used structurally as a dopant in the light-emitting layer of the device to impart high efficiency to the organic light-emitting device.

[0052] R1 to R5 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C5-C30 arylthio, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C5-C30 arylamino, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C5-C30 arylsilyl, nitro, cyano, and halogen groups.

[0053] The conditions are that R1 to R5 are each bonded to rings Q1 to Q3 to further form alicyclic or aromatic monocyclic or polycyclic rings, and R2 and R3 and R4 and R5 are bonded to each other to further form alicyclic or aromatic monocyclic or polycyclic rings.

[0054] According to one embodiment of the invention, [Formula C] or [Formula D] can form framework structures such as [Formula C-1] to [Formula C-3], [Formula D-1] and [Formula D-2], particularly various polycyclic aromatic framework structures. Highly efficient organic light-emitting devices can be achieved by satisfying the required characteristics of compounds for the light-emitting layer of organic light-emitting devices.

[0055]

[0056]

[0057] in

[0058] Z is CR or N, where R are the same or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, nitro, cyano, halogen group and -N(R6)(R7).

[0059] In one embodiment of the present invention, at least one of R is -N(R6)(R7).

[0060] Furthermore, R are bonded to each other, or each of them is bonded to an adjacent substituent to form at least one alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atom of the formed alicyclic, aromatic monocyclic or polycyclic ring is substituted with at least one heteroatom selected from (N), sulfur (S) and oxygen (O).

[0061] R6 and R7 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, and substituted or unsubstituted C2-C50 heteroaryl, provided that R6 and R7 are bonded to each other to form an alicyclic or aromatic monocyclic or polycyclic ring.

[0062] X and Y1 to Y4 are defined as X and Y1 to Y3 in [Equation C] and [Equation D].

[0063] Furthermore, as used herein, the term "substituted" means that the various substituents defined in [Formula A] to [Formula D] are substituted with one or more substituents selected from: deuterium, cyano, halogen group, hydroxyl, nitro, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, heteroalkyl, aryl, arylalkyl, alkylaryl, heteroaryl, heteroarylalkyl, alkoxy, amino, silyl, aryloxy, and mixed aliphatic-aromatic cyclogroups; or substituted with a substituent comprising two or more substituents linked to each other. The term "unsubstituted" in the same definition means without substituents.

[0064] Furthermore, the range of carbon atoms for alkyl or aryl groups in terms such as "substituted or unsubstituted C1-C30 alkyl" and "substituted or unsubstituted C6-C50 aryl" refers to the total number of carbon atoms constituting the alkyl or aryl moiety when the corresponding group is unsubstituted, without considering the number of carbon atoms in the substituents. For example, a phenyl group substituted with butyl at the para-position corresponds to an aryl group having 6 carbon atoms substituted with butyl having 4 carbon atoms.

[0065] Furthermore, as used herein, the phrase "a substituent bonds with an adjacent substituent to form a ring" means that the corresponding substituent bonds with an adjacent substituent to form a substituted or unsubstituted alicyclic or aromatic ring. The term "adjacent substituent" can mean a substituent that substitutes an atom directly bonded to an atom substituted with the corresponding substituent, a substituent spatially located closest to the corresponding substituent, or another substituent that substitutes an atom substituted with the corresponding substituent. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon atom in an aliphatic ring can be considered "adjacent" to each other.

[0066] As used herein, alkyl groups can be linear or branched. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc.

[0067] As used herein, alkenyl groups can include linear or branched alkenyl groups and can also be substituted with other substituents. Specifically, examples of alkenyl groups include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, Matrix, styrene, etc.

[0068] As used herein, the alkynyl group may also include linear or branched alkynyl groups, and may be substituted with other substituents, and examples of substituents may include, but are not limited to, ethynyl, 2-propynyl, etc.

[0069] As used herein, aromatic hydrocarbon rings or aryl groups can be monocyclic or polycyclic; examples of monocyclic aryl groups include phenyl, biphenyl, terphenyl, etc. Examples of aryl groups, including but not limited to naphthyl, anthraceneyl, phenanthryl, pyrene, etc. alkyl, tetraphenyl, The compounds used include methyl, fluorenyl, acenaphathcenyl, triphenylene, fluoranyl, etc., but the scope of this invention is not limited thereto.

[0070] As used herein, an aromatic heterocyclic group or heteroaryl group is an aromatic ring containing at least one heteroatom, and examples include, but are not limited to, thiophene, furanyl, pyrrole, imidazolyl, triazolyl, etc. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Triazolyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, dibenzofuranyl, phenanthrolinel, thiazolyl, iso azole group, Diazole group, thiadiazole group, benzothiazolium group, and phenthiazolium group, etc.

[0071] As used herein, an aliphatic ring refers to a non-aromatic ring containing only carbon and hydrogen atoms, including monocyclic or polycyclic rings, and may be substituted with other substituents. The term "polycyclic" means that a polycyclic group can be directly attached to or fused with at least one other cyclic group, which can be an aliphatic ring or a different type of cyclic group, such as aliphatic heterocyclic groups, aryl, heteroaryl, etc. Specifically, examples include, but are not limited to: cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, adamantyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl; cycloalkanes such as cyclohexane and cyclopentane; and cycloolefins such as cyclohexene and cyclobutene.

[0072] As used herein, an aliphatic heterocycle refers to an aliphatic ring containing at least one of heteroatoms such as O, S, Se, N, and Si, and may include monocyclic or polycyclic rings, and may be substituted with other substituents. The term "polycyclic" means that the polycyclic group can be directly attached to or fused with at least one other cyclic group, and the other cyclic group can be an aliphatic hydrocarbon ring, or different types of cyclic groups, such as aliphatic heterocyclic groups, aryl groups, heteroaryl groups, etc.

[0073] As used herein, a mixed aliphatic-aromatic ring refers to a ring in which two or more rings are connected to each other and fused together, and the aliphatic and aromatic rings are fused together to form a non-aromatic whole, and the polycyclic mixed aliphatic-aromatic ring may contain heteroatoms selected from N, O, P and S in addition to C.

[0074] As used herein, specifically, the alkoxy group can be methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentoxy, isopentoxy, hexoxy, etc., but is not limited to these.

[0075] As used herein, silyl is represented by -SiH3 and can be alkylsilyl, arylsilyl, alkylarylsilyl, arylheteroarylsilyl, etc. Specific examples of silyl include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfuranylsilyl, etc.

[0076] As used herein, the amino group is represented by -NH2, or it can be an alkylamino group, an arylamino group, an arylheteroarylamino group, etc. An arylamino group refers to an amine substituted with an aryl group, an alkylamino group refers to an amine substituted with an alkyl group, and an arylheteroarylamino group refers to an amine substituted with both aryl and heteroaryl groups. For example, arylamino groups include substituted or unsubstituted monoarylamino groups, substituted or unsubstituted diarylamino groups, or substituted or unsubstituted triarylamino groups. The aryl and heteroaryl groups in arylamino groups and arylheteroarylamino groups can be monocyclic aryl or monocyclic heteroaryl, or polycyclic aryl or polycyclic heteroaryl. Arylheteroarylamino groups and arylamino groups containing two or more aryl groups and two or more heteroaryl groups respectively include monocyclic aryl (heteroaryl), polycyclic aryl (heteroaryl), or both monocyclic aryl (heteroaryl) and polycyclic aryl (heteroaryl). Furthermore, the aryl and heteroaryl groups in arylamino and arylheteroarylamino groups can be selected from the examples of the aryl and heteroaryl groups mentioned above.

[0077] As used herein, examples of aryl groups in aryloxy and arylthio groups are the same as those of the aryl groups described above, and specifically, examples of aryloxy groups include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethylphenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenoxy, 4-biphenoxy, 1-naphthoxy, 2-naphthoxy, 4-methyl-1-naphthoxy, 5-methyl-2-naphthoxy, 1-anthraoxy, 2-anthraoxy, 9-anthraoxy, 1-phenanthoxy, 3-phenanthoxy, 9-phenanthoxy, etc., and examples of arylthio groups include, but are not limited to, phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, etc.

[0078] In this invention, examples of halogen groups include fluorine, chlorine, bromine, and iodine.

[0079] More specifically, the compounds represented by [Formula A] or [Formula B] according to the invention are selected from compounds represented by the following formulas that clearly show specific substituents, but these compounds should not be construed as limiting the scope of [Formula A] or [Formula B] according to the invention.

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091] Furthermore, more specifically, the polycyclic aromatic derivative compounds represented by [Formula C] or [Formula D] according to the invention used as dopants for the light-emitting layer are selected from the following compounds that clearly show specific substituents, but these compounds should not be construed as limiting the scope of [Formula C] or [Formula D] according to the invention.

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101] As can be seen from the specific compounds, organic light-emitting materials with the inherent properties of substituents can be synthesized. In particular, dopant materials used in the light-emitting layer can be prepared by forming a polycyclic aromatic structure containing B, P and P=O and introducing substituents. Furthermore, highly efficient organic light-emitting devices can be realized by applying the compounds represented by [Formula A] or [Formula B] according to the present invention to the device.

[0102] Furthermore, in another aspect, the present invention relates to an organic light-emitting device comprising a first electrode, a second electrode, and a hole injection layer and / or a hole transport layer and a light-emitting layer between the first electrode and the second electrode, and the organic light-emitting device can be manufactured using conventional methods and materials for manufacturing devices as follows: using a compound of [Formula A] or [Formula B] in the hole injection layer, the hole transport layer and the functional layer capable of injecting and / or transporting holes, and using a compound of [Formula B] or [Formula C] as a dopant in the light-emitting layer.

[0103] In addition to the light-emitting layer, hole injection layer, hole transport layer, and functional layer capable of injecting and / or transporting holes, the organic light-emitting device according to the present invention may also include an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc., and the organic light-emitting device may use materials for the corresponding layers.

[0104] Specifically, the organic light-emitting device according to the present invention can use the following anthracene derivative compounds as the host compound for the light-emitting layer.

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129] The organic material layer structure of the preferred organic light-emitting device according to the present invention will be described in more detail in the following embodiments.

[0130] Meanwhile, the detailed structure of an organic light-emitting device according to one embodiment of the present invention, the method of manufacturing it, and the materials used for the organic layer will be described below.

[0131] First, the substrate is coated with a material for the anode to form the anode. The substrate used herein is a substrate commonly used in organic light-emitting devices, and is preferably an organic substrate or a transparent plastic substrate with excellent transparency, surface smoothness, operability, and water resistance. Furthermore, the material used for the anode is transparent and has excellent conductivity, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO).

[0132] The hole injection layer is formed on the anode by vacuum thermal evaporation or spin coating using the material for the hole injection layer, and then the hole transport layer is formed on the hole injection layer by vacuum thermal evaporation or spin coating using the material for the hole transport layer.

[0133] The materials used for the hole injection layer can be used without particular restrictions, as long as they are commonly used in the art, and specific examples include 2-TNATA [4,4',4”-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine], TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine], DNTPD [N,N'-diphenyl-N,N'-bis-(4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine], etc.

[0134] Furthermore, the materials used for the hole transport layer are not particularly restricted, as long as they are commonly used in the art, and are, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-bis(naphthyl-1-yl)-N,N'-diphenylbenzidine (α-NPD).

[0135] Subsequently, a hole-assist layer and a light-emitting layer are sequentially stacked on the hole transport layer, and a hole-blocking layer is selectively deposited on the light-emitting layer by vacuum deposition or spin coating to form a thin film. Since the device lifetime and efficiency decrease when holes are introduced to the cathode through the organic light-emitting layer, a material with a very low HOMO (highest occupied molecular orbital) energy level is used to form the hole-blocking layer to prevent this problem. The hole-blocking materials used in this paper are not particularly limited and are typically BAlq, BCP, or TPBI, which have electron transport capabilities and a higher ionization potential than the ionization potential of the light-emitting compound.

[0136] Materials used for hole blocking layers can be BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, Liq, etc., but are not limited to these.

[0137] An electron transport layer is deposited on a hole-blocking layer by vacuum deposition or spin coating, and a metal for forming a cathode is formed on an electron injection layer by vacuum thermal evaporation. Thus, an organic light-emitting device according to one embodiment is completed.

[0138] Here, the metal used to form the cathode can be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. A top-emitting light-emitting device can be obtained by using a transmission cathode utilizing ITO or IZO.

[0139] Materials used in electron transport layers are used to stably transport electrons injected from the cathode and can be known electron transport materials. Examples of known electron transport materials include quinoline derivatives, particularly tris(8-hydroxyquinoline)aluminum (Alq3), TAZ, BAlq, bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), and... Diazole derivatives (PBD, BMD, BND, etc.).

[0140] Furthermore, each of the organic layers can be formed by monomolecular deposition or solution methods. Deposition is a method of forming a thin film by evaporating the material used to form each layer through heating in the presence of a vacuum or low pressure. Solution methods are thin film forming methods that form a thin film by mixing the material used to form each layer with a solvent and forming the mixture by methods such as inkjet printing, roll-to-roll coating, screen printing, spraying, dip coating, or spin coating.

[0141] Furthermore, the organic light-emitting device according to the present invention may further include a light-emitting layer of a blue-emitting, green-emitting, or red-emitting material that emits light in the wavelength range of 380 nm to 800 nm. That is, the light-emitting layer of the present invention comprises a plurality of light-emitting layers, and the blue-emitting, green-emitting, or red-emitting material in the additionally formed light-emitting layer may be a fluorescent material or a phosphorescent material.

[0142] In addition, organic light-emitting devices are used in displays or lighting systems selected from flat panel displays, flexible displays, monochrome or white flat panel lighting systems, monochrome or white flexible lighting systems, vehicle displays, and displays for virtual reality or augmented reality.

[0143] Invention Embodiments

[0144] The invention will now be described in more detail with reference to preferred embodiments. However, it will be apparent to those skilled in the art that these embodiments are provided for illustrative purposes only and should not be construed as limiting the scope of the invention.

[0145] Synthesis Example 1. Synthesis of Equation 5

[0146] Synthetic Example 1-(1): Synthesis of Intermediate 1-a

[0147]

[0148] 4-Bromodibenzofuran (100 g, 0.405 mol), (1R,2R)-cyclohexane-1,2-diamine (46.2 g, 0.404 mol), acetamide (71.7 g, 1.21 mol), copper iodide (I) (77.1 g, 0.404 mol), potassium carbonate (200 g, 0.809 mol), and 1,000 mL of toluene were added to a round-bottom flask, and the mixture was stirred overnight under reflux. After the reaction was complete, the product was filtered through a diatomaceous earth filter and washed with ethyl acetate. The filtrate was extracted with water and ethyl acetate, and the organic layer was separated. The organic layer was dehydrated with magnesium sulfate, filtered, and concentrated under reduced pressure. The result was recrystallized in dichloromethane and petroleum ether to obtain 50 g of <intermediate 1-a> (yield 32%).

[0149] Synthesis Example 1-(2): Synthesis of Intermediate 1-b

[0150]

[0151] Intermediate 1-a (50 g, 0.222 mol) was dissolved in 600 mL of acetic acid in a round-bottom flask and stirred at room temperature. A diluted solution of bromine (11.37 mL, 0.222 mol) in 200 mL of acetic acid was added dropwise to the reaction solution, followed by stirring for approximately 4 hours. After the reaction was complete, the resulting solid was filtered and washed with water. The solid was dissolved in 1,000 mL of tetrahydrofuran / water / ethanol (1:1:1) solution, to which potassium hydroxide (250 g, 1.11 mol) was added, and the mixture was stirred overnight under reflux. After the reaction was complete, the solvent was concentrated under reduced pressure and extracted with ethyl acetate and water. The organic layer was separated, dehydrated with magnesium sulfate, filtered, and concentrated under reduced pressure. The result was recrystallized from ethyl acetate and heptane to obtain 40 g of intermediate 1-b (yield 68%).

[0152] Synthesis Example 1-(3): Synthesis of Intermediate 1-c

[0153]

[0154] Intermediate 1-b (40 g, 0.153 mol), bis(pinacol)diboron (51.7 g, 0.183 mol), and 400 mL of acetonitrile were added to a round-bottom flask and stirred at room temperature. Tert-butyl nitrite (26.2 g, 0.229 mol) was added to the reaction solution in portions, followed by stirring at 80 °C for 2 hours. After the reaction was complete, the product was cooled to room temperature. The reaction solution was concentrated under reduced pressure and separated by column chromatography to obtain 20 g of intermediate 1-c (yield 35%).

[0155] Synthetic Example 1-(4): Synthesis of Intermediate 1-d

[0156]

[0157] Methyl 2-bromobenzoate (15.7 g, 73 mmol), <intermediate 1-c> (32.8 g, 88 mmol), tetrakis(triphenylphosphine)palladium (1.7 g, 0.15 mmol), and potassium carbonate (20.2 g, 146.7 mmol) were added to a round-bottom flask, followed by the addition of 125 mL toluene, 125 mL tetrahydrofuran, and 50 mL water. The reactor temperature was raised to 80 °C and stirred for 10 hours. When the reaction was complete, the reactor temperature was lowered to room temperature, the reaction product was extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 18.6 g of <intermediate 1-d> (yield 67%).

[0158] Synthetic Example 1-(5): Synthesis of Intermediate 1-e

[0159]

[0160] Intermediate 1-d (17.1 g, 45 mmol), sodium hydroxide (2.14 g, 54 mmol), and 170 mL of ethanol were added to a round-bottom flask, and the mixture was stirred under reflux for 48 hours. The reaction was confirmed to be complete by thin-layer chromatography, and the product was then cooled to room temperature. The cooled solution was acidified by adding 2 equimolar amounts of hydrochloric acid dropwise, and the resulting solid was stirred for 30 minutes and then filtered. The product was recrystallized from dichloromethane and n-hexane to obtain 14.2 g of intermediate 1-e (yield 86%).

[0161] Synthetic Example 1-(6): Synthesis of Intermediate 1-f

[0162]

[0163] Intermediate 1-e (14.3 g, 39 mmol) and 145 mL of methanesulfonic acid were added to a round-bottom flask. The temperature was raised to 80 °C, and the mixture was stirred for 3 hours. The reaction was confirmed to be complete by thin-film chromatography, and the reaction product was then cooled to room temperature. The reaction solution was slowly added dropwise to 150 mL of ice water, followed by stirring for 30 minutes. The resulting solid was filtered and washed with water and methanol to obtain 12.0 g of intermediate 1-f (yield 88%).

[0164] Synthetic Example 1-(7): Synthesis of Intermediate 1-g

[0165]

[0166] 2-Bromobiphenyl (8.4 g, 0.036 mol) and 110 mL tetrahydrofuran were added to a round-bottom flask and cooled to -78 °C under a nitrogen atmosphere. At the same temperature, n-butyllithium (19.3 mL, 0.031 mol) was added dropwise to the cooled reaction solution. Intermediate 1-f (9.1 g, 0.026 mol) was added to the reaction solution in portions, followed by stirring at room temperature. The reaction was considered complete by TLC when the color of the reaction solution changed. The reaction was terminated by adding 50 mL H₂O, and the product was extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and recrystallized from acetonitrile to obtain 10.2 g of intermediate 1-f (78% yield).

[0167] Synthetic Example 1-(8): Synthesis of Intermediate 1-h

[0168]

[0169] 10.6 g (0.021 mol) of intermediate 1-h, 120 mL of acetic acid, and 2 mL of sulfuric acid were added to a round-bottom flask, and the mixture was stirred under reflux for 5 hours. When a solid formed, the reaction was confirmed to be complete by thin-film chromatography, and the product was then cooled to room temperature. The resulting solid was filtered, washed with H₂O and methanol, dissolved in monochlorobenzene, filtered through silica gel, concentrated, and cooled to room temperature to obtain 8.6 g of intermediate 1-h (yield 84%).

[0170] Synthesis Example 1-(9): Synthesis of Intermediate 1-i

[0171]

[0172] 3-Bromo-9-phenyl-9H-carbazole (11.3 g, 0.035 mol), 1-naphthylamine (5.6 g, 0.039 mol), tris(dibenzylacetone)dipalladium(0) (0.65 g, 0.0007 mol), sodium tert-butoxide (6.79 g, 0.0706 mol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.44 g, 0.0007 mol), and 100 mL of toluene were added to a round-bottom flask, and the mixture was stirred under reflux for 3 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated, dehydrated with magnesium sulfate, and then concentrated under reduced pressure. The result was separated by column chromatography to obtain 11.3 g <intermediate 1-i> (yield 84%).

[0173] Synthesis Example 1-(10): Synthesis of Equation 5

[0174]

[0175] Intermediate 1-h (4.4 g, 0.009 mol), Intermediate 1-i (5.0 g, 0.013 mol), Palladium(II) acetate (0.08 g, 0.4 mmol), sodium tert-butoxide (3.4 g, 0.035 mol), tri-tert-butylphosphine (0.07 g, 0.4 mmol), and toluene (60 mL) were added to a round-bottom flask, and the mixture was stirred under reflux for 2 hours. After the reaction was complete, the product was cooled to room temperature. The reaction solution was extracted with dichloromethane and water. The organic layer was separated, dehydrated with magnesium sulfate, and then concentrated under reduced pressure. The product was separated and purified by column chromatography and recrystallized from dichloromethane and acetone to obtain 3.3 g of Formula 5 (yield 46%).

[0176] MS (MALDI-TOF): m / z 788.28 [M + ]

[0177] Synthesis Example 2: Synthesis of Equation 8

[0178] Synthesis Example 2-(1): Synthesis of Equation 8

[0179] Formula 8 was synthesized in the same manner as in Synthesis Examples 1-(9) and 1-(10) (yield 44%), except that 2-bromo-9-phenyl-9H-carbazole was used instead of 3-bromo-9-phenyl-9H-carbazole used in Synthesis Example 1-(9), and 2-amino-9,9-dimethylfluorene was used instead of 1-naphthylamine.

[0180] MS (MALDI-TOF): m / z 854.33 [M + ]

[0181] Synthesis Example 3: Synthesis of Equation 47

[0182] Synthetic Example 3-(1): Synthesis of Intermediate 3-a

[0183]

[0184] 4-Dibenzofuranboronic acid (85.0 g, 401 mmol), bismuth(III) nitrate pentahydrate (99.2 g, 200 mmol), and 400 mL of toluene were added to a round-bottom flask, and the mixture was stirred at 70 °C for 3 hours under a nitrogen atmosphere. After the reaction was complete, the product was cooled to room temperature and the resulting solid was filtered off. The filtrate was washed with toluene to obtain 61.5 g of <intermediate 3-a> (yield 72%).

[0185] Synthetic Example 3-(2): Synthesis of Intermediate 3-b

[0186]

[0187] Ethyl cyanoacetate (202.9 g, 1.794 mol) and 500 mL of dimethylformamide were added to a round-bottom flask. Potassium hydroxide (67.10 g, 1.196 mol) and potassium cyanide (38.95 g, 0.598 mol) were then added, followed by 200 mL of dimethylformamide, and the mixture was stirred at room temperature. Intermediate 3-a (127 g, 0.737 mol) was added to the reaction solution in portions, and the mixture was stirred at 50 °C for 72 hours. After the reaction was complete, 200 mL of a 25% aqueous solution of sodium hydroxide was added to the product, and the mixture was stirred under reflux for 3 hours. The product was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and then purified by column chromatography to obtain 20.0 g of intermediate 3-b (yield 16%).

[0188] Synthesis Example 3-(3): Synthesis of intermediate 3-c

[0189]

[0190] Intermediate 3-b (20.0 g, 96 mmol), 600 mL of ethanol, and 170 mL of potassium hydroxide aqueous solution (142.26 g, 2.53 mol) were added to a round-bottom flask, and the mixture was stirred under reflux for 12 hours. When the reaction was complete, the product was cooled to room temperature. 400 mL of 6N hydrochloric acid was added to the reaction solution to acidify the product, and the resulting solid was stirred for 20 minutes, then filtered. The solid was washed with ethanol to obtain 17.0 g of intermediate 3-c (yield 88%).

[0191] Synthetic Example 3-(4): Synthesis of Intermediate 3-d

[0192]

[0193] Intermediate 3-c (17.0 g, 75 mmol) and 15 mL of sulfuric acid were added to a round-bottom flask, and the mixture was stirred under reflux for 72 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated and washed with an aqueous sodium bicarbonate solution. During concentration under reduced pressure, excess methanol was added to the organic layer, and the resulting solid was filtered to obtain 14.0 g of intermediate 3-d (78% yield).

[0194] Synthetic Example 3-(5): Synthesis of Intermediate 3-e

[0195]

[0196] Intermediate 3-d (12 g, 50 mmol), 15 mL hydrochloric acid, and 75 mL water were added to a round-bottom flask, cooled to 0 °C, and stirred for 1 hour. At the same temperature, 38 mL (5.6 g, 81 mmol) of sodium nitrite aqueous solution was added dropwise to the reaction solution, followed by stirring for 1 hour. While maintaining the temperature of the reaction solution at 5 °C or lower, 38 mL of potassium iodide aqueous solution (22.4 g, 135 mmol) was added dropwise. The resulting product was stirred at room temperature for 5 hours. After the reaction was complete, the mixture was washed with sodium thiosulfate aqueous solution and extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography to obtain 11 g of intermediate 3-e (yield 91%).

[0197] Synthetic Example 3-(6): Synthesis of Intermediate 3-f

[0198]

[0199] 1-Bromodibenzofuran (20.0 g, 81 mmol), bis(pinacol)diboron (26.7 g, 105 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (1.3 g, 0.002 mol), potassium acetate (19.9 g, 202 mmol), and 200 mL of 1,4-dioxane were added. The alkane was added to a round-bottom flask, and the mixture was stirred under reflux for 10 hours. The reaction product was concentrated under reduced pressure and then separated by column chromatography. The result was recrystallized from dichloromethane and heptane to obtain 17.0 g of <intermediate 3-f> (yield 70%).

[0200] Synthetic Example 3-(7): Synthesis of Intermediate 3-g

[0201]

[0202] Intermediate 3-g was obtained by the same synthetic method as in Synthetic Example 1-(4) (yield 75%), except that intermediate 3-e was used instead of methyl 2-bromobenzoate and intermediate 3-f was used instead of intermediate 1-c.

[0203] Synthetic Example 3-(8): Synthesis of Intermediate 3-h

[0204]

[0205] Intermediate 3-h was obtained by the same synthesis method as in Synthesis Example 1-(5) (yield 77%), except that intermediate 3-g was used instead of intermediate 1-d.

[0206] Synthesis Example 3-(9): Synthesis of Intermediate 3-i

[0207]

[0208] Intermediate 3-i was obtained by the same synthesis method as in Synthesis Example 1-(6) (yield 94%), except that Intermediate 3-h was used instead of Intermediate 1-e.

[0209] Synthetic Example 3-(10): Synthesis of Intermediate 3-j

[0210]

[0211] Intermediate 3-i (44 g, 122 mmol) and 600 mL of dichloromethane were added to a round-bottom flask and stirred at room temperature. A diluted solution of bromine (13.7 mL, 85 mmol) in 50 mL of dichloromethane was added dropwise, followed by stirring for approximately 3 hours. The reaction product was recrystallized from methanol to obtain 40.7 g of intermediate 3-j (76% yield).

[0212] Synthetic Example 3-(11): Synthesis of Intermediate 3-k

[0213]

[0214] Intermediate 3-k was obtained by the same synthesis method as in Synthesis Example 1-(7) (yield 74%), except that intermediate 3-j was used instead of intermediate 1-f.

[0215] Synthetic Example 3-(12): Synthesis of Intermediate 3-l

[0216]

[0217] Intermediate 3-l was obtained by the same synthesis method as in Synthesis Example 1-(8) (yield 86%), except that intermediate 3-k was used instead of intermediate 1-g.

[0218] Synthesis Example 3-(13): Synthesis of Equation 47

[0219] Formula 47 (yield 45%) was obtained by the same synthesis method as in Synthesis Example 1-(9) and Synthesis Example 1-(10), except that 4-tert-butylaniline was used instead of 1-naphthylamine in Synthesis Example 1-(9), and Intermediate 3-l was used instead of Intermediate 1-h in Synthesis Example 1-(10).

[0220] MS (MALDI-TOF): m / z 884.34 [M + ]

[0221] Synthesis Example 4: Synthesis of Equation 54

[0222] Synthetic Example 4-(1): Synthesis of Intermediate 4-a

[0223]

[0224] Methyl 2-iodobenzoate (19.1 g, 73 mmol), 4-dibenzofuranboronic acid (18.7 g, 88 mmol), tetrakis(triphenylphosphine)palladium (1.7 g, 0.15 mmol), and potassium carbonate (20.2 g, 146.7 mmol) were added to a round-bottom flask, followed by the addition of 125 mL toluene, 125 mL tetrahydrofuran, and 50 mL water. The reactor temperature was raised to 80 °C, and the mixture was stirred for 10 hours. When the reaction was complete, the reactor temperature was lowered to room temperature, the reaction product was extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 9.5 g of <intermediate 4-a> (yield 43%).

[0225] Synthetic Example 4-(2): Synthesis of Intermediate 4-b

[0226]

[0227] Bromobenzene (13.2 g, 83.97 mmol) and 250 mL of tetrahydrofuran were added to a round-bottom flask, and the mixture was stirred at low temperature under a nitrogen atmosphere. Approximately 58 mL of n-butyllithium was slowly added dropwise over 2 hours at -78 °C, followed by the addition of <intermediate 4-a> (9.4 g, 31.1 mmol). After the reaction was complete, 100 mL of water was added, followed by stirring for 30 minutes and extraction to obtain 3.2 g of <intermediate 4-b>.

[0228] (Yield 24%)

[0229] Synthetic Example 4-(3): Synthesis of Intermediate 4-c

[0230]

[0231] Intermediate 4-b (55.0 g, 129 mmol), 500 mL of acetic acid, and 10 mL of sulfuric acid were added to a round-bottom flask, and the mixture was stirred under reflux for 5 hours. After the reaction was complete, the product was cooled to room temperature, and the resulting solid was filtered. The product was washed with methanol to obtain 50 g of intermediate 4-c (yield 95%).

[0232] Synthetic Example 4-(4): Synthesis of Intermediate 4-d

[0233]

[0234] Intermediate 4-c (50 g, 122 mmol) and 600 mL of dichloromethane were added to a round-bottom flask and stirred at room temperature. A diluted solution of bromine (13.7 mL, 85 mmol) in 50 mL of dichloromethane was added dropwise, followed by stirring for approximately 3 hours. The reaction product was recrystallized from methanol to obtain 45 g of intermediate 4-d (76% yield).

[0235] Synthesis Example 4-(5): Synthesis of Equation 54

[0236] Formula 54 (yield 44%) was obtained by the same synthesis method as in Synthesis Example 1-(9) and Synthesis Example 1-(10), except that aniline-2,3,4,5,6-d5 was used instead of 1-naphthylamine in Synthesis Example 1-(9), and intermediate 4-d was used instead of intermediate 1-h in Synthesis Example 1-(10).

[0237] MS (MALDI-TOF): m / z 745.31 [M + ]

[0238] Synthesis Example 5: Synthesis of Equation 52

[0239] Synthesis Example 5-(1): Synthesis of Equation 52

[0240] Formula 52 was obtained by the same synthetic method as in Synthetic Examples 1-(9) and 1-(10) (yield 45%), except that 3-aminodibenzofuran was used instead of 1-naphthylamine in Synthetic Example 1-(9) and Intermediate 4-d was used instead of Intermediate 1-h in Synthetic Example 1-(10).

[0241] MS (MALDI-TOF): m / z 830.29 [M + ]

[0242] Synthesis Example 6: Synthesis of Equation 41

[0243] Synthetic Example 6-(1): Synthesis of Intermediate 6-a

[0244]

[0245] 2-Phenoxyaniline (25.0 g, 0.135 mol), 30 mL of hydrochloric acid, and 150 mL of water were added to a round-bottom flask, cooled to 0 °C, and stirred for 1 hour. At the same temperature, 75 mL (11.2 g, 0.162 mmol) of sodium nitrite aqueous solution was added dropwise to the reaction solution, followed by stirring for 1 hour. While maintaining the temperature of the reaction solution at 5 °C or lower, 75 mL of potassium iodide aqueous solution (44.8 g, 0.270 mol) was added dropwise. The resulting product was stirred at room temperature for 5 hours. After the reaction was complete, the mixture was washed with sodium thiosulfate aqueous solution and extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography to obtain 22.6 g of <intermediate 6-a> (yield 56%).

[0246] Synthetic Example 6-(2): Synthesis of Intermediate 6-b

[0247]

[0248] Intermediate 6-b was obtained by the same synthetic method as in Synthetic Example 1-(7) (yield 70%), except that Intermediate 6-a was used instead of 2-bromobiphenyl used in Synthetic Example 1-(7).

[0249] Synthetic Example 6-(3): Synthesis of Intermediate 6-c

[0250]

[0251] Intermediate 6-c was obtained by the same synthesis method as in Synthesis Example 1-(8) (yield 75%), except that Intermediate 6-b was used instead of Intermediate 1-g used in Synthesis Example 1-(8).

[0252] Synthesis Example 6-(4): Synthesis of Equation 41

[0253] Formula 41 (yield 44%) was obtained by the same synthetic method as in Synthetic Examples 1-(9) and 1-(10), except that 2-bromo-9-phenyl-9H-carbazole was used instead of 3-bromo-9-phenyl-9H-carbazole used in Synthetic Example 1-(9), 4-tert-butylaniline was used instead of 1-naphthylamine, and Intermediate 6-c was used instead of Intermediate 1-h used in Synthetic Example 1-(10).

[0254] MS (MALDI-TOF): m / z 810.32 [M + ]

[0255] Synthesis Example 7: Synthesis of Equation 88

[0256] Synthetic Example 7-(1): Synthesis of Intermediate 7-a

[0257]

[0258] Ethyl cyanoacetate (202.9 g, 1.794 mol) and 500 mL of dimethylformamide were added to a round-bottom flask. Potassium hydroxide (67.1 g, 1.196 mol) and potassium cyanide (38.95 g, 0.598 mol) were then added, followed by 200 mL of dimethylformamide, and the mixture was stirred at room temperature. 4-Nitrobenzofuran (127.5 g, 0.737 mol) was added to the reaction solution in portions, and the mixture was stirred at 50 °C for 72 hours. After the reaction was complete, 200 mL of a 25% aqueous solution of sodium hydroxide was added to the product, and the mixture was stirred under reflux for 3 hours. The product was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and then purified by column chromatography to obtain 20.0 g of <intermediate 7-a> (yield 17%).

[0259] Synthetic Example 7-(2): Synthesis of Intermediate 7-b

[0260]

[0261] Intermediate 7-a (20.0 g, 96 mmol), 600 mL of ethanol, and 170 mL (142.26 g, 2.53 mol) of aqueous potassium hydroxide solution were added to a round-bottom flask, and the mixture was stirred under reflux for 12 hours. When the reaction was complete, the product was cooled to room temperature. 400 mL of 6N hydrochloric acid was added to the reaction solution to acidify the product, and the resulting solid was stirred for 20 minutes, then filtered. The solid was washed with ethanol to obtain 17.0 g of intermediate 7-b (yield 88%).

[0262] Synthetic Example 7-(3): Synthesis of Intermediate 7-c

[0263]

[0264] Intermediate 7-b (17.0 g, 75 mmol) and 15 mL of sulfuric acid were added to a round-bottom flask, and the mixture was stirred under reflux for 72 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated and washed with an aqueous sodium bicarbonate solution. During concentration under reduced pressure, excess methanol was added to the organic layer, and the resulting solid was filtered to obtain 14.0 g of intermediate 7-c (yield 78%).

[0265] Synthetic Example 7-(4): Synthesis of Intermediate 7-d

[0266]

[0267] Intermediate 7-c (14.0 g, 0.058 mmol), 20 mL of hydrochloric acid, and 100 mL of water were added to a round-bottom flask, cooled to 0 °C, and stirred for 1 hour. At the same temperature, 50 mL (7.4 g, 0.116 mol) of sodium nitrite aqueous solution was added dropwise to the reaction solution, followed by stirring for 1 hour. While maintaining the temperature of the reaction solution at 5 °C or lower, 100 mL of potassium iodide aqueous solution (30.0 g, 0.180 mol) was added dropwise. The resulting product was stirred at room temperature for 5 hours. After the reaction was complete, the mixture was washed with sodium thiosulfate aqueous solution and extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and then separated by column chromatography to obtain 9.1 g of intermediate 7-d (yield 48%).

[0268] Synthetic Example 7-(5): Synthesis of Intermediate 7-e

[0269]

[0270] Intermediate 7-d (9.3 g, 25 mmol), 1-dibenzofuranboronic acid (8.3 g, 28 mmol), tetra(triphenylphosphine)palladium (0.6 g, 0.05 mmol), and potassium carbonate (6.7 g, 50 mmol) were added to a round-bottom flask, followed by the addition of 50 mL toluene, 50 mL tetrahydrofuran, and 20 mL water. The reactor temperature was raised to 80 °C and stirred for 10 hours. When the reaction was complete, the reactor temperature was lowered to room temperature, the reaction product was extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 5.3 g of intermediate 7-e (yield 52%).

[0271] Synthetic Example 7-(6): Synthesis of Intermediate 7-f

[0272]

[0273] Bromobenzene (25.5 g, 0.163 mol) and 170 mL of tetrahydrofuran were added to a round-bottom flask, and the resulting product was cooled to -78 °C under a nitrogen atmosphere. Butyllithium (1.6 M) (95.6 mL, 0.153 mol) was slowly added dropwise to the cooled reaction solution. The resulting product was stirred at the same temperature for 1 hour, and <intermediate 7-e> (20.0 g, 0.051 mol) was added, followed by stirring at room temperature for 3 hours. After the reaction was complete, 50 mL of water was added, followed by stirring for 30 minutes. The result was extracted with ethyl acetate and water, and the organic layer was separated and concentrated under reduced pressure. 200 mL of acetic acid and 1 mL of hydrochloric acid were added to the concentrate, followed by stirring at an increased temperature of 80 °C. After the reaction was complete, the mixture was filtered at room temperature and washed with methanol to obtain 20.0 g <intermediate 7-f> (yield 78%).

[0274] Synthetic Example 7-(7): Synthesis of Intermediate 7-g

[0275]

[0276] Intermediate 7-g was obtained by the same synthesis method as in Synthesis Example 3-(10) (yield 55%), except that Intermediate 7-f was used instead of Intermediate 3-i used in Synthesis Example 3-(10).

[0277] Synthesis Example 7-(8): Synthesis of Equation 88

[0278] Formula 88 (yield 46%) was obtained by the same synthesis method as in Synthesis Examples 1-(9) and 1-(10), except that 4-bromo-9-phenyl-9H-carbazole was used instead of 3-bromo-9-phenyl-9H-carbazole used in Synthesis Example 1-(9), and Intermediate 7-g was used instead of Intermediate 1-h used in Synthesis Example 1-(10).

[0279] MS (MALDI-TOF): m / z 956.34 [M + ]

[0280] Synthesis Example 8: Synthesis of Equation 101

[0281] Synthetic Example 8-(1): Synthesis of Intermediate 8-a

[0282]

[0283] Intermediate 1-d (30.5 g, 80 mmol) was added to a round-bottom flask containing 250 mL of tetrahydrofuran, and the temperature was lowered to -78 °C under nitrogen. After 30 minutes, 1.0 M methyl magnesium bromide (210 mL, 240 mmol) was slowly added dropwise. After 1 hour, 1.0 M methyl magnesium bromide (210 mL, 240 mmol) was slowly added dropwise, and the temperature was raised to room temperature. The reaction product was stirred at room temperature for about 2 hours, and an aqueous solution of ammonium chloride was added dropwise. The result was extracted, distilled under reduced pressure, and recrystallized from hexane to obtain 24.4 g of intermediate 8-a (80% yield).

[0284] Synthetic Example 8-(2): Synthesis of Intermediate 8-b

[0285]

[0286] Intermediate 8-a (25.2 g, 66 mmol) was added to a round-bottom flask containing 300 mL of acetic acid, and then stirred at -0 °C for 10 min. 350 mL of phosphoric acid was added, and the mixture was stirred at room temperature for approximately 1 h. The product was neutralized with an aqueous sodium hydroxide solution, extracted, and then concentrated under reduced pressure. The result was separated by column chromatography to obtain 17.5 g of intermediate 8-b (yield 73%).

[0287] Synthesis Example 8-(3): Synthesis of Equation 101

[0288] Formula 101 (yield 45%) was obtained by the same synthetic method as in Synthetic Examples 1-(9) and 1-(10), except that 3-bromo-9-phenyl-9H-carbazole was used instead of 3-bromo-9-phenyl-9H-carbazole used in Synthetic Example 1-(9), 2-naphthylamine was used instead of 1-naphthylamine, and Intermediate 8-b was used instead of Intermediate 1-h used in Synthetic Example 1-(10).

[0289] MS (MALDI-TOF): m / z 716.28 [M] + ]

[0290] Synthesis Example 9: Synthesis of Equation 102

[0291] Synthesis Example 9-(1): Synthesis of Formula 102

[0292] Formula 102 (yield 48%) was obtained by the same synthesis method as in Synthesis Example 1-(9) and Synthesis Example 1-(10), except that aniline was used instead of 1-naphthylamine used in Synthesis Example 1-(9), and Intermediate 8-b was used instead of Intermediate 1-h used in Synthesis Example 1-(10).

[0293] MS (MALDI-TOF): m / z 616.25 [M] + ]

[0294] Synthesis Example 10: Synthesis of Equation 103

[0295] Synthesis Example 10-(1): Synthesis of Equation 103

[0296] Formula 103 (yield 43%) was obtained by the same synthetic method as in Synthetic Examples 1-(9) and 1-(10), except that 2-bromo-9-phenyl-9H-carbazole was used instead of 3-bromo-9-phenyl-9H-carbazole used in Synthetic Example 1-(9), 4-(1-naphthyl)aniline was used instead of 1-naphthylamine, and Intermediate 8-b was used instead of Intermediate 1-h used in Synthetic Example 1-(10).

[0297] MS (MALDI-TOF): m / z 742.30 [M + ]

[0298] Synthesis Example 11: Synthesis of Equation 104

[0299] Synthesis Example 11-(1): Synthesis of Equation 104

[0300] Formula 104 (yield 44%) was obtained by the same synthetic method as in Synthetic Examples 1-(9) and 1-(10), except that 2-bromo-9-phenyl-9H-carbazole was used instead of 3-bromo-9-phenyl-9H-carbazole used in Synthetic Example 1-(9), 2-amino-9,9-dimethylfluorene was used instead of 1-naphthylamine, and Intermediate 8-b was used instead of Intermediate 1-h used in Synthetic Example 1-(10).

[0301] MS (MALDI-TOF): m / z 732.31 [M + ]

[0302] Synthesis Example 12: Synthesis of Equation 91

[0303] Synthetic Example 12-(1): Synthesis of Intermediate 12-a

[0304]

[0305] <Intermediate 12-a>

[0306] Intermediate 12-a was obtained by the same synthetic method as in Synthetic Examples 4-(2) to 4-(4) (yield 70%), except that 1-bromo-4-tert-butylbenzene was used instead of bromobenzene used in Synthetic Example 4-(2).

[0307] Synthesis Example 12-(2): Synthesis of Equation 91

[0308] Formula 91 was obtained (yield 45%) by the same synthetic method as in Synthetic Examples 1-(9) and 1-(10), except that 3-aminodibenzofuran was used instead of 1-naphthylamine, and Intermediate 12-a was used instead of Intermediate 1-h used in Synthetic Example 1-(10).

[0309] MS (MALDI-TOF): m / z 942.42 [M + ]

[0310] <Example of synthesis of [Formula C] or [Formula D]>

[0311] Synthesis Example 1. Synthesis of Compound 1

[0312] Synthesis Example 1-1. Synthesis of <Intermediate 1-a>

[0313] [Reaction Scheme 1]

[0314]

[0315]

[0316] 50 g (423 mmol) of benzofuran and 500 mL of dichloromethane were added to a 1 L reactor and stirred. The reaction product was cooled to -10 °C, and a diluted solution of 67.7 g (423 mmol) of bromine in 100 mL of dichloromethane was added dropwise. The mixture was then stirred at 0 °C for 2 hours. After the reaction was complete, an aqueous solution of sodium thiosulfate was added, followed by stirring and extraction with ethyl acetate and H₂O. The organic layer was concentrated under reduced pressure and recrystallized from ethanol to obtain 100 g of <intermediate 1-a> (yield 93%).

[0317] Synthesis Example 1-2. Synthesis of <Intermediate 1-b>

[0318] Intermediate 1-b is synthesized via the following [reaction scheme 2].

[0319] [Reaction Scheme 2]

[0320]

[0321] 48.6 g (866 mmol) of potassium hydroxide was dissolved in 400 mL of ethanol in a 1 L reactor. A solution of 120 g (433 mmol) of <Intermediate 1-A> in ethanol was added dropwise at 0 °C, followed by stirring under reflux for 2 hours. After the reaction was complete, the ethanol organic layer was concentrated under reduced pressure and extracted with ethyl acetate and water. The result was separated by column chromatography to obtain 42 g of <Intermediate 1-b> (yield 50%).

[0322] Synthesis Example 1-3. Synthesis of <Intermediate 1-c>

[0323] Intermediate 1-c is synthesized via the following [Reaction Scheme 3].

[0324] [Reaction Scheme 3]

[0325]

[0326] 4.5 g (16 mmol) of 1-bromo-3-iodobenzene, 5.8 g (16 mmol) of aniline, 0.1 g (1 mmol) of palladium acetate, 3 g (32 mmol) of sodium tert-butoxide, 0.2 g (1 mmol) of bis(diphenylphosphino)-1,1'-binaphthylene, and 45 mL of toluene were added to a 100 mL reactor, and the mixture was stirred under reflux for 24 hours. After the reaction was complete, the product was filtered, the filtrate was concentrated, and the product was separated by column chromatography to obtain 5.2 g of <intermediate 1-c> (yield 82%).

[0327] Synthesis Example 1-4. Synthesis of <Intermediate 1-d>

[0328] Intermediate 1-d was synthesized via the following [reaction scheme 4].

[0329] [Reaction Scheme 4]

[0330]

[0331] 20 g (98 mmol) of intermediate 1-c, 18.4 g (98 mmol) of intermediate 1-b, 0.5 g (2 mmol) of palladium acetate, 18.9 g (196 mmol) of sodium tert-butoxide, 0.8 g (4 mmol) of tri-tert-butylphosphine, and 200 mL of toluene were added to a 250 mL reactor, and the mixture was stirred under reflux for 5 hours. After the reaction was complete, the product was filtered, the filtrate was concentrated, and the residue was separated by column chromatography to obtain 22 g of intermediate 1-d (yield 75%).

[0332] Synthesis Examples 1-5. Synthesis of <Intermediate 1-e>

[0333] Intermediate 1-e> is synthesized via the following [Reaction Scheme 5].

[0334] [Reaction Scheme 5]

[0335]

[0336] 18.5 g of <intermediate 1-e> was obtained in the same manner as in Synthetic Examples 1-3, except that <intermediate 1-d> was used instead of 1-bromo-4-iodobenzene. (Yield 74.1%)

[0337] Synthesis Examples 1-6. Synthesis of <Intermediate 1-f>

[0338] Intermediate 1-f is synthesized via the following [Reaction Scheme 6].

[0339] [Reaction Scheme 6]

[0340]

[0341] 12 g of <intermediate 1-f> was obtained in the same manner as in Synthetic Examples 1-4, except that <intermediate 1-c> and <intermediate 1-b> were replaced with <intermediate 1-e> and 1-bromo-2-iodobenzene>. (Yield 84.1%)

[0342] Synthesis Examples 1-7. Synthesis of <Compound 1>

[0343] Compound 1 was synthesized using the following [Reaction Scheme 7].

[0344] [Reaction Scheme 7]

[0345]

[0346] 12 g (23 mmol) of <Intermediate 1-f> and 120 mL of tert-butylbenzene were added to a 300 mL reactor. 42.5 mL (68 mmol) of n-butyllithium was added dropwise at -78 °C. The mixture was then stirred at 60 °C for 3 hours. Heptane was then removed by purging with nitrogen at 60 °C. 11.3 g (45 mmol) of boron tribromide was added dropwise at -78 °C. The mixture was then stirred at room temperature for 1 hour, and 5.9 g (45 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. The mixture was then stirred at 120 °C for 2 hours. After the reaction was complete, a sodium acetate solution was added at room temperature, followed by stirring. The result was extracted with ethyl acetate, and the organic layer was concentrated and separated by column chromatography to obtain 0.8 g of <Compound 1> (yield 13%).

[0347] MS (MALDI-TOF): m / z 460.17 [M] + ]

[0348] Synthesis Example 2. Synthesis of Compound 2

[0349] Synthesis Example 2-1. Synthesis of <Intermediate 2-a>

[0350] Intermediate 2-a was synthesized via the following [Reaction Scheme 8].

[0351] [Reaction Scheme 8]

[0352]

[0353] 50 g (373 mmol) of benzothiophene and 500 mL of dichloromethane were added to a 1 L reactor and stirred. The reaction product was cooled to -0 °C, and a diluted solution of 59.5 g (373 mmol) of bromine in 100 mL of chloroform was added dropwise. The mixture was then stirred at room temperature for 4 hours. After the reaction was complete, an aqueous solution of sodium thiosulfate was added, followed by stirring and extraction with ethyl acetate and H₂O. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 70 g of <intermediate 2-a> (yield 91%).

[0354] Synthesis Example 2-2. Synthesis of <Intermediate 2-b>

[0355] Intermediate 2-b was synthesized via the following [reaction scheme 9].

[0356] [Reaction Scheme 9]

[0357]

[0358] 32 g of <intermediate 2-b> was obtained in the same manner as in Synthetic Examples 1-4, except that <intermediate 2-a> was used instead of <intermediate 1-b>. (Yield 75.4%)

[0359] Synthesis Example 2-3. Synthesis of <Intermediate 2-c>

[0360] Intermediate 2-c is synthesized via the following [Reaction Scheme 10].

[0361] [Reaction Scheme 10]

[0362]

[0363] 24.5 g of <intermediate 2-c> was obtained in the same manner as in Synthetic Examples 1-3, except that <intermediate 2-b> was used instead of 1-bromo-4-iodobenzene. (Yield 73.1%)

[0364] Synthesis Example 2-4. Synthesis of <Intermediate 2-d>

[0365] Intermediate 2-d was synthesized via the following [Reaction Scheme 11].

[0366] [Reaction Scheme 11]

[0367]

[0368] 21 g of <intermediate 2-d> was obtained in the same manner as in Synthetic Examples 1-4, except that <intermediate 1-c> and <intermediate 1-b> were replaced with <intermediate 2-c> and 1-bromo-2-iodobenzene>. (Yield 77.5%)

[0369] Synthesis Example 2-5. Synthesis of <Compound 2>

[0370] Compound 2 was synthesized by the following [reaction scheme 12].

[0371] [Reaction Scheme 12]

[0372]

[0373] 1.5 g of <Compound 2> was obtained in the same manner as in Synthetic Examples 1-7, except that <Intermediate 2-d> was used instead of <Intermediate 1-f>. (Yield 10.1%)

[0374] MS (MALDI-TOF): m / z 467.15 [M] + ]

[0375] Synthesis Example 3. Synthesis of Compound 13

[0376] Synthesis Example 3-1. Synthesis of <Intermediate 3-a>

[0377] Intermediate 3-a is synthesized via the following [Reaction Scheme 13].

[0378] [Reaction Scheme 13]

[0379]

[0380] 50 g (177 mmol) of 1-bromo-3-(tert-butyl)-5-iodobenzene, 36.2 g (389 mmol) of aniline, 1.6 g (7 mmol) of palladium acetate, 51 g (530 mmol) of sodium tert-butoxide, 4.4 g (7 mmol) of bis(diphenylphosphine)-1,1'-binaphthylene, and 500 mL of toluene were added to a 1 L reactor, and the mixture was stirred under reflux for 24 hours. After the reaction was complete, the product was filtered. The filtrate was concentrated and separated by column chromatography to obtain 42.5 g of <intermediate 3-a> (yield 50%).

[0381] Synthesis Example 3-2. Synthesis of <Intermediate 3-b>

[0382] Intermediate 3-b was synthesized via the following [Reaction Scheme 14].

[0383] [Reaction Scheme 14]

[0384]

[0385] 11 g (42 mmol) of intermediate 3-a, 20 g (101 mmol) of intermediate 1-b, 1 g (2 mmol) of palladium acetate, 12.2 g (127 mmol) of sodium tert-butoxide, 0.7 g (3 mmol) of tri-tert-butylphosphine, and 150 mL of toluene were added to a 250 mL reactor, and the mixture was stirred under reflux for 5 hours. After the reaction was complete, the product was filtered, the filtrate was concentrated, and then separated by column chromatography to obtain 11 g of intermediate 3-b (yield 65%).

[0386] Synthesis Example 3-3. Synthesis of <Compound 13>

[0387] Compound 13 was synthesized using the following [reaction scheme 15].

[0388] [Reaction Scheme 15]

[0389]

[0390]

[0391] 0.5 g of <Compound 13> was obtained in the same manner as in Synthetic Examples 1-7, except that <Intermediate 3-b> was used instead of <Intermediate 1-f>. (Yield 8%)

[0392] MS (MALDI-TOF): m / z 556.23 [M + ]

[0393] Synthesis Example 4. Synthesis of Compound 65

[0394] Synthesis Example 4-1. Synthesis of <Intermediate 4-a>

[0395] Intermediate 4-a was synthesized via the following [Reaction Scheme 16].

[0396] [Reaction Scheme 16]

[0397]

[0398] 35.6 g of <intermediate 4-a> was obtained in the same manner as in Synthetic Examples 1-3, except that 1-bromo-2,3-dichlorobenzene was used instead of 1-bromo-4-iodobenzene. (Yield 71.2%)

[0399] Synthesis Example 4-2. Synthesis of <Intermediate 4-b>

[0400] Intermediate 4-b was synthesized via the following [Reaction Scheme 17].

[0401] [Reaction Scheme 17]

[0402]

[0403] 60.0 g (355 mmol) of diphenylamine, 100.3 g (355 mmol) of 1-bromo-3-iodobenzene, 0.8 g (4 mmol) of palladium acetate, 2 g (4 mmol) of xantphos, 68.2 g (709 mmol) of sodium tert-butoxide, and 700 mL of toluene were added to a 2 L reactor, and the mixture was stirred under reflux for 2 hours. After the reaction was complete, the resulting product was filtered at room temperature, concentrated under reduced pressure, and separated by column chromatography to obtain 97 g of <intermediate 4-b> (yield 91.2%).

[0404] Synthesis Example 4-3. Synthesis of <Intermediate 4-c>

[0405] Intermediate 4-c was synthesized via the following [Reaction Scheme 18].

[0406] [Reaction Scheme 18]

[0407]

[0408] 31 g of <intermediate 4-c> was obtained in the same manner as in Synthetic Examples 1-4, except that <intermediate 4-a> and <intermediate 4-b> were used instead of <intermediate 1-c> and <intermediate 1-b>. (Yield 77.7%)

[0409] Synthesis Example 4-4. Synthesis of <Intermediate 4-d>

[0410] Intermediate 4-d was synthesized via the following [Reaction Scheme 19].

[0411] [Reaction Scheme 19]

[0412]

[0413] Mix 30g (174mmol) 3-bromoaniline, 25.5g (209mmol) phenylboronic acid, 4g (3mmol) tetrakis(triphenylphosphine)palladium, 48.2g (349mmol) potassium carbonate, and 150mL 1,4-dioxane. Alkane, 150 mL of toluene, and 90 mL of distilled water were added to a 1 L reactor, which was then stirred under reflux for 4 hours. After the reaction was complete, the layers were separated at room temperature, and the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 24 g of <intermediate 4-d> (yield 80%).

[0414] Synthesis Example 4-5. Synthesis of <Intermediate 4-e>

[0415] Intermediate 4-e> is synthesized via the following [Reaction Scheme 20].

[0416] [Reaction Scheme 20]

[0417]

[0418] 31.6 g of <intermediate 4-e> was obtained in the same manner as in Synthetic Examples 1-3, except that <intermediate 4-d> and <intermediate 1-b> were used instead of 1-bromo-4-iodobenzene and aniline. (Yield 68.2%)

[0419] Synthesis Example 4-6. Synthesis of <Intermediate 4-f>

[0420] Intermediate 4-f was synthesized via the following [reaction scheme 21].

[0421] [Reaction Scheme 21]

[0422]

[0423] 21 g of <intermediate 4-f> was obtained in the same manner as in Synthetic Examples 1-4, except that <intermediate 4-c> and <intermediate 4-e> were used instead of <intermediate 1-c> and <intermediate 1-b>. (Yield 67.7%)

[0424] Synthesis Examples 4-7. Synthesis of <Compound 65>

[0425] Compound 65 was synthesized using the following [reaction scheme 22].

[0426] [Reaction Scheme 22]

[0427]

[0428] 21 g (37 mmol) of intermediate 4-f and tert-butylbenzene were added to a 250 mL reactor. 42.4 mL (74 mmol) of n-butyllithium was added dropwise at -78 °C. The mixture was then stirred at 60 °C for 3 hours. Pentane was then removed by nitrogen purging at 60 °C. 7.1 mL (74 mmol) of boron tribromide was added dropwise at -78 °C. The mixture was then stirred at room temperature for 1 hour, and 6 g (74 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. The mixture was then stirred at 120 °C for 2 hours. After the reaction was complete, a sodium acetate solution was added at room temperature, followed by stirring. The result was extracted with ethyl acetate, and the organic layer was concentrated and separated by column chromatography to obtain 2.0 g of compound 65 (yield 17.4%).

[0429] MS (MALDI-TOF): m / z 703.28 [M] + ]

[0430] Synthesis Example 5. Synthesis of Compound 73

[0431] Synthesis Example 5-1. Synthesis of <Intermediate 5-a>

[0432] Intermediate 5-a was synthesized via the following [Reaction Scheme 23].

[0433] [Reaction Scheme 23]

[0434]

[0435] 40 g (236 mmol) of 4-tert-butylaniline was dissolved in 400 mL of dichloromethane in a 1 L reactor and stirred at 0 °C. Then, 42 g (236 mmol) of N-bromosuccinimide was slowly added to the reactor. The reaction product was heated to room temperature and stirred for 4 hours. After the reaction was complete, H₂O was added dropwise at room temperature and the mixture was extracted with dichloromethane. The organic layer was concentrated and separated by column chromatography to obtain 48 g of <intermediate 5-a> (80% yield).

[0436] Synthesis Example 5-2. Synthesis of <Intermediate 5-b>

[0437] Intermediate 5-b was synthesized via the following [Reaction Scheme 24].

[0438] [Reaction Scheme 24]

[0439]

[0440] 80 g (351 mmol) of <intermediate 5-a> and 450 mL of water were added to a 2 L reactor and stirred. 104 mL of sulfuric acid was then added. A solution of 31.5 g (456 mmol) of sodium nitrite in 240 mL of water was added dropwise at 0 °C. The mixture was then stirred at 0 °C for 2 hours. A solution of 116.4 g (701 mmol) of potassium iodide in 450 mL of water was added dropwise at 0 °C. The mixture was then stirred at room temperature for 6 hours. After the reaction was complete, an aqueous solution of sodium thiosulfate was added at room temperature and stirred. The reaction product was extracted with ethyl acetate, and the organic layer was concentrated and separated by column chromatography to obtain 58 g of <intermediate 5-b> (yield 51%).

[0441] Synthesis Example 5-3. Synthesis of <Intermediate 5-c>

[0442] Intermediate 5-c is synthesized via the following [Reaction Scheme 25].

[0443] [Reaction Scheme 25]

[0444]

[0445] 95 g of intermediate 4-c was obtained in the same manner as in Synthesis Example 3-1, except that 4-tert-butylaniline was used instead of aniline. (Yield 80.4%)

[0446] Synthesis Example 5-4. Synthesis of <Intermediate 5-d>

[0447] Intermediate 5-d was synthesized via the following [Reaction Scheme 26].

[0448] [Reaction Scheme 26]

[0449]

[0450] 31 g of <intermediate 5-d> was obtained in the same manner as in Synthetic Examples 1-4, except that <intermediate 5-c> was used instead of <intermediate 1-c>. (Yield 71.5%)

[0451] Synthesis Example 5-5. Synthesis of <Intermediate 5-e>

[0452] Intermediate 5-e> was synthesized via the following [Reaction Scheme 27].

[0453] [Reaction Scheme 27]

[0454]

[0455] 24 g of <intermediate 5-e> was obtained in the same manner as in Synthetic Examples 1-4, except that <intermediate 5-d> and <intermediate 5-b> were used instead of <intermediate 1-c> and <intermediate 1-b>. (Yield 67.1%)

[0456] Synthetic Examples 5-6. Synthesis of <Compound 73>

[0457] Compound 73 was synthesized by the following [reaction scheme 28].

[0458] [Reaction Scheme 28]

[0459]

[0460] 2.4 g of <Compound 73> was obtained in the same manner as in Synthetic Examples 1-7, except that <Intermediate 5-e> was used instead of <Intermediate 1-f>. (Yield 15%)

[0461] MS (MALDI-TOF): m / z 628.36 [M + ]

[0462] Synthesis Example 6. Synthesis of Compound 109

[0463] Synthesis Example 6-1. Synthesis of <Intermediate 6-a>

[0464] Intermediate 6-a is synthesized via the following [reaction scheme 29].

[0465] [Reaction Scheme 29]

[0466]

[0467] 40.0 g (123 mmol) of 1,5-dichloro-2,4-dinitrobenzene, 44.9 g (368 mmol) of phenylboronic acid, 2.8 g (2.5 mmol) of tetrakis(triphenylphosphine)palladium, 50.9 g (368 mmol) of potassium carbonate, and 120 mL of 1,4-diphenylboronic acid were added. Alkane, 200 mL toluene, and 120 mL water were added to a 1 L reactor, which was then stirred under reflux. After the reaction was complete, the product was extracted with water and ethyl acetate, and the organic layer was concentrated and separated by column chromatography to obtain 27.5 g of <intermediate 6-a> (yield 70%).

[0468] Synthesis Example 6-2. Synthesis of <Intermediate 6-b>

[0469] Intermediate 6-b was synthesized via the following [reaction scheme 30].

[0470] [Reaction Scheme 30]

[0471]

[0472] 27.5 g (86 mmol) of intermediate 6-a, 57.8 g (348 mmol) of triphenylphosphine, and 300 mL of dichlorobenzene were added to a 1 L reactor, and the mixture was stirred under reflux for 3 days. After the reaction was complete, the dichlorobenzene was removed, and the residue was separated by column chromatography to obtain 10.8 g of intermediate 6-b (yield 49.0%).

[0473] Synthesis Example 6-3. Synthesis of <Intermediate 6-c>

[0474] Intermediate 6-c is synthesized via the following [reaction scheme 31].

[0475] [Reaction Scheme 31]

[0476]

[0477] 10.8 g (42 mmol) of intermediate 6-b, 11.0 g (10.8 mmol) of intermediate 2-a, 10.7 g (1 mmol) of copper powder, 4.5 g (17 mmol) of 18-crown-6-ether, 34.9 g (253 mmol) of potassium carbonate, and 110 mL of dichlorobenzene were added to a 250 mL reactor, and the mixture was stirred at 180 °C under reflux for 24 hours. After the reaction was complete, the dichlorobenzene was removed, and the residue was separated by column chromatography to obtain 9.5 g of intermediate 6-c (yield 52%).

[0478] Synthesis Example 6-4. Synthesis of <Intermediate 6-d>

[0479] Intermediate 6-d was synthesized via the following [Reaction Scheme 32].

[0480] [Reaction Scheme 32]

[0481]

[0482] 14 g of intermediate 6-d was obtained in the same manner as in synthetic example 6-3, except that intermediate 1-c and intermediate 2-a were replaced with intermediate 6-c and 1-bromo-2-iodobenzene. (Yield 67.1%)

[0483] Synthesis Example 6-5. Synthesis of <Compound 109>

[0484] <Compound 109> was synthesized by the following [Reaction Scheme 33].

[0485] [Reaction Scheme 33]

[0486]

[0487] 2.1 g of <compound 109> was obtained in the same manner as in Synthetic Examples 1-7, except that <intermediate 6-d> was used instead of <intermediate 1-f>. (Yield 14%)

[0488] MS (MALDI-TOF): m / z 472.12 [M + ]

[0489] Synthesis Example 7. Synthesis of Compound 126

[0490] Synthesis Example 7-1. Synthesis of <Intermediate 7-a>

[0491] Intermediate 7-a is synthesized via the following [reaction scheme 34].

[0492] [Reaction Scheme 34]

[0493]

[0494] 30.0 g (150 mmol) of intermediate 2-b, 31.2 g (160 mmol) of phenol, 45.7 g (300 mmol) of potassium carbonate, and 250 mL of NMP were added to a 500 mL reactor, and the mixture was stirred under reflux at 160 °C for 12 hours. After the reaction was complete, the product was cooled to room temperature, and the NMP was distilled off under reduced pressure. The residue was extracted with water and ethyl acetate. The solvent was concentrated under reduced pressure and separated by column chromatography to obtain 22 g of intermediate 7-a (yield 68%).

[0495] Synthesis Example 7-2. Synthesis of <Compound 126>

[0496] <Compound 126> was synthesized by the following [Reaction Scheme 35].

[0497] [Reaction Scheme 35]

[0498]

[0499] 1.2 g of <Compound 126> was obtained in the same manner as in Synthetic Examples 1-7, except that <Intermediate 7-a> was used instead of <Intermediate 1-f>. (Yield 13.4%)

[0500] MS (MALDI-TOF): m / z 401.10 [M + ]

[0501] Synthesis Example 8. Synthesis of Compound 145

[0502] Synthesis Example 8-1. Synthesis of <Intermediate 8-a>

[0503] Intermediate 8-a is synthesized via the following [Reaction Scheme 36].

[0504] [Reaction Scheme 36]

[0505]

[0506] 41.6 g of <intermediate 8-a> was obtained in the same manner as in Synthetic Examples 1-3, except that 2-bromo-5-tert-butyl-1,3-dimethylbenzene and 4-tert-butylaniline were used instead of 1-bromo-3-iodobenzene and aniline. (Yield 88.2%)

[0507] Synthesis Example 8-2. Synthesis of <Intermediate 8-b>

[0508] Intermediate 8-b was synthesized via the following [Reaction Scheme 37].

[0509] [Reaction Scheme 37]

[0510]

[0511] 37.6 g of intermediate 8-b was obtained in the same manner as in Synthesis Example 4-2, except that intermediate 8-a was used instead of diphenylamine. (Yield 78.4%)

[0512] Synthesis Example 8-3. Synthesis of <Intermediate 8-c>

[0513] Intermediate 8-c is synthesized via the following [Reaction Scheme 38].

[0514] [Reaction Scheme 38]

[0515]

[0516] 31.2 g of <intermediate 8-c> was obtained in the same manner as in Synthetic Examples 1-3, except that <intermediate 8-b> and 4-tert-butylaniline were used instead of 1-bromo-3-iodobenzene and aniline. (Yield 74.2%)

[0517] Synthesis Example 8-4. Synthesis of <Intermediate 8-d>

[0518] Intermediate 8-d was synthesized via the following [reaction scheme 39].

[0519] [Reaction Scheme 39]

[0520]

[0521] 30.3 g of <intermediate 8-d> was obtained in the same manner as in Synthetic Examples 1-3, except that 1-bromo-2,3-dichloro-5-ethylbenzene and 4-tert-butylaniline were used instead of 1-bromo-3-iodobenzene and aniline.

[0522] (Yield 89.8%)

[0523] Synthesis Example 8-5. Synthesis of <Intermediate 8-e>

[0524] Intermediate 8-e> is synthesized via the following [reaction scheme 40].

[0525] [Reaction Scheme 40]

[0526]

[0527] 27.4 g of intermediate 8-e was obtained in the same manner as in Synthetic Examples 1-4, except that intermediate 8-d and 3-bromo-5-(tert-butyl)benzothiophene were used instead of intermediates 1-c and 1-b. (Yield 77.1%)

[0528] Synthesis Example 8-6. Synthesis of <Intermediate 8-f>

[0529] Intermediate 8-f is synthesized via the following [reaction scheme 41].

[0530] [Reaction Scheme 41]

[0531]

[0532] 21 g of <intermediate 8-f> was obtained in the same manner as in Synthetic Examples 1-4, except that <intermediate 8-e> and <intermediate 8-c> were used instead of <intermediate 1-c> and <intermediate 1-b>. (Yield 74.1%)

[0533] Synthetic Example 8-7. Synthesis of <Compound 145>

[0534] <Compound 145> was synthesized by the following [reaction scheme 42].

[0535] [Reaction Scheme 42]

[0536]

[0537] 3.4 g of <Compound 145> was obtained in the same manner as in Synthetic Examples 1-7, except that <Intermediate 8-f> was used instead of <Intermediate 1-f>. (Yield 19.4%)

[0538] MS[M] + 979.60

[0539] Synthesis Example 9. Synthesis of Compound 150

[0540] Synthesis Example 9-1. Synthesis of <Intermediate 9-a>

[0541] Intermediate 9-a is synthesized via the following [reaction scheme 43].

[0542] [Reaction Scheme 43]

[0543]

[0544] 32.7 g of <intermediate 9-a> was obtained in the same manner as in Synthetic Examples 1-3, except that bromobenzene-d5 and 4-tert-butylaniline were used instead of 1-bromo-3-iodobenzene and aniline. (Yield 78.2%)

[0545] Synthesis Example 9-2. Synthesis of <Intermediate 9-b>

[0546] Intermediate 9-b was synthesized via the following [Reaction Scheme 44].

[0547] [Reaction Scheme 44]

[0548]

[0549] 34.2 g of intermediate 9-b was obtained in the same manner as in synthetic examples 1-4, except that intermediates 8-e and 9-a were used instead of intermediates 1-c and 1-b. (Yield 84.1%)

[0550] Synthesis Example 9-3. Synthesis of <Compound 150>

[0551] <Compound 150> was synthesized by the following [Reaction Scheme 45].

[0552] [Reaction Scheme 45]

[0553]

[0554] 2.7 g of <Compound 150> was obtained in the same manner as in Synthetic Examples 1-7, except that <Intermediate 9-b> was used instead of <Intermediate 1-f>. (Yield 11.4%)

[0555] MS[M] + 663.39

[0556] Synthesis Example 10. Synthesis of Compound 153

[0557] Synthesis Example 10-1. Synthesis of <Intermediate 10-a>

[0558] Intermediate 10-a was synthesized via the following [Reaction Scheme 46].

[0559] [Reaction Scheme 46]

[0560]

[0561] 25.6 g of <intermediate 10-a> was obtained in the same manner as in Synthetic Examples 1-3, except that 1-bromo-dibenzofuran and 4-tert-butylaniline were used instead of 1-bromo-3-iodobenzene and aniline. (Yield 79.2%)

[0562] Synthesis Example 10-2. Synthesis of <Intermediate 10-b>

[0563] Intermediate 10-b was synthesized via the following [reaction scheme 47].

[0564] [Reaction Scheme 47]

[0565]

[0566] 18.6 g of intermediate 10-b was obtained in the same manner as in synthetic examples 1-4, except that intermediates 8-e and 10-a were used instead of intermediates 1-c and 1-b. (Yield 74.1%)

[0567] Synthetic Example 10-3. Synthesis of <Compound 153>

[0568] <Compound 153> was synthesized by the following [Reaction Scheme 48].

[0569] [Reaction Scheme 48]

[0570]

[0571] 3.4 g of <Compound 153> was obtained in the same manner as in Synthetic Examples 1-7, except that <Intermediate 10-b> was used instead of <Intermediate 1-f>. (Yield 15.4%)

[0572] MS[M] + 748.37

[0573] Examples 1 to 20: Fabrication of Organic Light-Emitting Devices

[0574] The ITO glass was patterned to adjust the luminescent area to 2mm × 2mm, and then washed. The ITO glass was then installed in a vacuum chamber, and the base pressure was set to 1 × 10⁻⁶. -7 Torx, and sequentially deposited 2-TNATA on ITO glass. and the materials for the hole transport layer shown in [Table 1] Then, a mixture of [BH] as the host and the compounds shown in Table 1 below (3 wt%) as dopants was deposited onto... The thickness is increased to form a light-emitting layer. Then, a compound of [Formula E-1] is deposited on the light-emitting layer to a thickness of [thickness missing]. The thickness is increased to form an electron transport layer, and Liq is deposited on the electron transport layer to a thickness of [missing information]. The thickness is such that an electron injection layer is formed, and Al is deposited on the electron injection layer to a thickness of [missing information]. The thickness is increased to form the cathode. Thus, an organic light-emitting device is fabricated. At 10 mA / cm²... 2 The characteristics of organic light-emitting devices were measured.

[0575]

[0576] Comparative Examples 1 to 10

[0577] Organic light-emitting devices were fabricated in the same manner as in the above embodiments, except that [HT1] and [HT2], and [BD1] and [BD2], were used instead of the compounds used as hole transport layer materials and dopant compounds in Examples 1 to 20, respectively. At 10 mA / cm 2 The characteristics of organic light-emitting devices were measured. The structures of [HT1], [HT2], [BD1] and [BD2] are as follows.

[0578]

[0579] [Table 1]

[0580]

[0581]

[0582] [Table 2]

[0583] project Hole transport layer dopant compounds Voltage (V) External quantum efficiency (%) Comparative Example 1 5 BD1 3.8 8.1 Comparative Example 2 47 BD1 3.7 8.2 Comparative Example 3 52 BD1 3.7 8.5 Comparative Example 4 88 BD1 3.8 8.6 Comparative Example 5 104 BD1 3.8 8.8 Comparative Example 6 8 BD2 3.7 7.2 Comparative Example 7 54 BD2 3.8 7.7 Comparative Example 8 41 BD2 3.8 7.4 Comparative Example 9 101 BD2 3.9 7.5 Comparative Example 10 91 BD2 3.8 7.8

[0584] As can be seen from Tables 1 and 2 above, compared with organic light-emitting devices using conventional compounds represented by HT1 and HT2, organic light-emitting devices using conventional compounds represented by BD1 and BD2, and organic light-emitting devices that do not use a combination of materials according to the invention, the organic light-emitting device according to the invention that uses a hole transport material (formula A / B) in the hole transport layer and a dopant material according to the invention (formula C / D) in the light-emitting layer can operate at a lower voltage and exhibit improved luminous efficiency based on a significantly improved external quantum efficiency.

[0585] Industrial applicability

[0586] The organic light-emitting device according to the present invention can operate at a lower driving voltage and exhibit excellent external quantum efficiency and thus high luminous efficiency by utilizing compounds with characteristic structures as hole transport materials and dopant materials in the hole injection layer or hole transport layer and the light-emitting layer, respectively. Therefore, it is industrially applicable to flat panel displays, flexible displays, monochrome or white flat panel lighting systems, monochrome or white flexible lighting systems, vehicle displays, virtual reality or augmented reality displays, etc.

Claims

1. An organic light-emitting device, comprising: First electrode; The second electrode facing the first electrode; as well as Between the first electrode and the second electrode, a hole injection layer or hole transport layer and a light-emitting layer, in (i) The hole injection layer or the hole transport layer comprises at least one compound selected from [Formula A] or [Formula B], and (ii) The luminescent layer comprises a compound represented by either [Formula C] or [Formula D]: [Formula A] [Formula B] in A1 is selected from phenyl, naphthyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, benzofuranyl, and benzothiophenyl. W represents either an oxygen atom (O) or a sulfur atom (S). R1 and R2 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C2-C50 heteroaryl, or R1 and R2 may be bonded to each other to form alicyclic or aromatic monocyclic or polycyclic compounds. Ar1 and Ar2 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6-C50 aryl and a substituted or unsubstituted C2-C50 heteroaryl, and at least one of Ar1 and Ar2 is represented by the following structural formula 1: [Structure 1] in R3 is selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C50 aryl, and substituted or unsubstituted C2-C50 heteroaryl. R4 is selected from hydrogen and deuterium. l is an integer from 0 to 4, and when l is 2 or greater, R4 are either the same or different from each other. "-*" refers to the sites where nitrogen atoms are bonded at positions Ar1 and Ar2 in [Formula A] or [Formula B]. [Formula C] [Formula D] in Q1 to Q3 may be the same as or different from each other, and each is independently a substituted or unsubstituted aromatic C6-C50 hydrocarbon ring, or a substituted or unsubstituted C2-C50 aromatic heterocyclic group; Y1 to Y3 may be the same as or different from each other, and each is independently selected from N-R1, CR2R3, O, S, Se, and SiR4R5; X is selected from B and P, where P=O; and R1 to R5 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylthio, substituted or unsubstituted C5-C30 The group may contain arylthio, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C5-C30 arylamino, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C5-C30 arylsilyl, nitro, cyano, and halogen groups, or R1 to R5 may each be bonded to rings Q1 to Q3 to further form alicyclic or aromatic monocyclic or polycyclic rings, or R2 and R3 and R4 and R5 may be bonded to each other to further form alicyclic or aromatic monocyclic or polycyclic rings. In [Formula A] through [Formula D], "substituted" means substituted with one or more substituents selected from the following: deuterium, cyano, halogen group, hydroxyl, nitro, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, heteroalkyl, aryl, arylalkyl, alkylaryl, heteroaryl, heteroarylalkyl, alkoxy, amino, silyl, aryloxy, and mixed aliphatic-aromatic cycloalcohols; or substituted with a substituent comprising two or more substituents connected to each other.

2. The organic light-emitting device according to claim 1, wherein [Formula C] or [Formula D] is represented by the following [Formula C-1] or [Formula D-1]: [Equation C-1] [Equation D-1] in Z is either CR or N, and Z is either the same as or different from each other, and R is either the same as or different from each other. Each of the following R groups is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C5-C30 arylamino, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C5-C30 arylsilyl, nitro, cyano, halogen groups, and -N(R6)(R7). R are bonded to each other, or each of them is bonded to an adjacent substituent to form at least one alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atom of the formed alicyclic, aromatic monocyclic or polycyclic ring is substituted with at least one heteroatom selected from (N), sulfur (S) and oxygen (O). R6 and R7 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, and substituted or unsubstituted C2-C50 heteroaryl, or R6 and R7 may be bonded to each other to form alicyclic or aromatic monocyclic or polycyclic compounds, and X and Y1 to Y3 are as defined in [Equation C] and [Equation D] above. In [Formula C-1] and [Formula D-1], "substituted" means substituted with one or more substituents selected from: deuterium, cyano, halogen group, hydroxyl, nitro, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, heteroalkyl, aryl, arylalkyl, alkylaryl, heteroaryl, heteroarylalkyl, alkoxy, amino, silyl, aryloxy, and mixed aliphatic-aromatic cycloalcohols; or substituted with a substituent comprising two or more substituents connected to each other.

3. The organic light-emitting device according to claim 1, wherein [Formula C] or [Formula D] is represented by any one of [Formula C-2], [Formula C-3], and [Formula D-2]: [Equation C-2] [Equation C-3] [Equation D-2] in Z is either CR or N, and Z is either the same as or different from each other, and R is either the same as or different from each other. Each of the following R groups is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C50 heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C5-C30 arylamino, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C5-C30 arylsilyl, nitro, cyano, halogen groups, and -N(R6)(R7). R are bonded to each other, or each of them is bonded to an adjacent substituent to form at least one alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atom of the formed alicyclic, aromatic monocyclic or polycyclic ring is substituted with at least one heteroatom selected from (N), sulfur (S) and oxygen (O). R6 and R7 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C3-C30 cycloalkyl, and substituted or unsubstituted C2-C50 heteroaryl, or R6 and R7 may be bonded to each other to form alicyclic or aromatic monocyclic or polycyclic compounds, and X and Y1 to Y4 are defined as X and Y1 to Y3 in [Equation C] and [Equation D] above. In [Formula C-2], [Formula C-3] and [Formula D-2], "substituted" means substituted with one or more substituents selected from: deuterium, cyano, halogen group, hydroxyl, nitro, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, heteroalkyl, aryl, arylalkyl, alkylaryl, heteroaryl, heteroarylalkyl, alkoxy, amino, silyl, aryloxy and mixed aliphatic-aromatic cycloalcohols; or substituted with a substituent comprising two or more substituents connected to each other.

4. The organic light-emitting device according to claim 2, wherein at least one of R is -N(R6)(R7).

5. The organic light-emitting device according to claim 3, wherein at least one of R is -N(R6)(R7).

6. The organic light-emitting device according to claim 1, wherein the compound represented by [Formula A] or [Formula B] is selected from the compound represented by the following formula: 。 7. The organic light-emitting device according to claim 1, wherein the compound represented by [Formula C] or [Formula D] is selected from the compound represented by the following formula: 。 8. The organic light-emitting device according to claim 1, wherein, in addition to the hole injection layer, the hole transport layer and the light-emitting layer, between the first electrode and the second electrode, at least one of the following is selected from the electron injection layer, the electron transport layer, the electron blocking layer, the hole blocking layer and the hole auxiliary layer.

9. The organic light-emitting device according to claim 8, wherein at least one of the layers is formed by deposition or solution processing.

10. The organic light-emitting device according to claim 1, wherein the organic light-emitting device is used in a display or lighting system, the display or lighting system being selected from flat panel displays, flexible displays, monochrome or white flat panel lighting systems, monochrome or white flexible lighting systems, vehicle displays, and displays for virtual reality or augmented reality.

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