Novel compound and organic light-emitting device comprising same

Abstract

The present invention relates to a novel compound and an organic light-emitting device comprising same. The novel compound of the present invention may be used in a first electrode and a second electrode, or one or more organic material layers disposed between the first electrode and the second electrode, and may be used for an electron transport layer, a hole blocking layer, or a charge generation layer. According to the present invention, it is possible to achieve a low voltage, high efficiency, and a long lifespan of an organic light-emitting device.

Description

Novel compound and organic light-emitting device containing the same

[0001] The present invention relates to a novel compound and an organic light-emitting device comprising the same.

[0002] Recently, the technology of organic light emitting devices (OLEDs), one of the flat panel display devices, has been developing rapidly.

[0003] An organic light-emitting device is a device that has an organic thin film layer including a light-emitting layer between an anode and a cathode, and emits light when holes and electrons injected into the light-emitting layer pair up and then disappear.

[0004] Compounds used in organic light-emitting devices require improved performance.

[0005] The purpose of the present invention is to provide a novel compound and an organic light-emitting device comprising the same.

[0006] The object of the present invention is achieved by a novel compound represented by the following chemical formula 1 and an organic light-emitting device comprising the same.

[0007]

[0008] In the above chemical formula 1,

[0009] Ar1 is a substituted or unsubstituted 1,10-phenanthroline group,

[0010] Ar2 is each independently hydrogen, deuterium, halogen, chloro group (-Cl), bromo group (-Br), cyano group, nitro group, nitrile group, substituted or unsubstituted C1~C30 alkyl group, substituted or unsubstituted C2~C30 alkenyl group, substituted or unsubstituted C1~C30 alkynyl group, substituted or unsubstituted C3~C30 cycloalkyl group, substituted or unsubstituted C2~C30 heterocycloalkyl group, substituted or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 sulfide group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C2~C30 heteroaryl group, substituted or unsubstituted C6~C30 aryloxy group, substituted or unsubstituted C6~C30 arylthio group, substituted or unsubstituted Selected from the group consisting of a C6~C30 amine group, a substituted or unsubstituted arylsilyl group, and a substituted or unsubstituted arylphosphine oxide group,

[0011] L1 and L2 are each independently a direct bond, a substituted or unsubstituted C6~C30 arylene group, or a substituted or unsubstituted C2~C30 heteroarylene group, but are not an anthracenylene group.

[0012] According to the present invention, a novel compound and an organic light-emitting device comprising the same are provided. The novel compound of the present invention can be used in an electron transport layer, a hole blocking layer, or a charge generation layer to realize low voltage, high efficiency, and long life of an organic light-emitting device.

[0013] In this specification, when a part is said to 'include' a certain component, this does not mean that other components are excluded, but rather that other components may be included, unless otherwise specifically stated.

[0014] In this specification, when it is said that a member is located 'on' another member, this includes not only cases where a member is in contact with another member, but also cases where another member exists between the two members.

[0015] In this specification, examples of substituents are described below, but are not limited thereto.

[0016] As used herein, the term "substitution" refers to the replacement of a hydrogen atom bonded to a carbon atom of a compound with another substituent. The position of substitution is not particularly limited as long as it is a position where substitution is possible, and when substitution is made with two or more substituents, the substituents may be the same or different.

[0017] In this specification, the term 'substituted or unsubstituted' means that it is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a chloro group (-Cl), a bromo group (-Br), a cyano group, a nitro group, a nitrile group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthioxy group, an arylthioxy group, an amine group, a phosphine oxide group, an aryl group, and a heteroaryl group, or is substituted with a substituent in which two or more substituents among the substituents selected from the above group are connected, or has no substituents, and the selected substituents may or may not form a ring by combining with each other. The substituent in which two or more substituents are connected may be, as an example, a biphenyl group. That is, the biphenyl group corresponds to an aryl group and may also correspond to a substituent in which two phenyl groups are connected.

[0018] In the present specification, the alkyl group may be straight-chain or branched, and specific examples thereof include 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, 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-ethylpropyl, 1,1-dimethylpropyl, isohexyl, These include, but are not limited to, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0019] In the present specification, specific examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups.

[0020] In the present specification, the aryl group may be monocyclic or polycyclic. In the case of a monocyclic aryl group, specific examples thereof include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. In the case of a polycyclic aryl group, specific examples thereof include, but are not limited to, a naphthyl group, anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a fluorenyl group, etc.

[0021] In the present specification, a heteroaryl group includes at least one atom other than carbon, i.e., a heteroatom, and specifically may include at least one atom selected from the group consisting of O, N, S, and Se. The heteroaryl group may also be monocyclic or polycyclic. Specific examples include a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, a quinazolyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, a pyridoindolyl group, a benzothienopyrimidyl group, an indenocarbazolyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, Examples thereof include, but are not limited to, a dibenzothiophenyl group, a benzofuranyl group, a phenanthridinyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group.

[0022] In the present specification, the amine group may be selected from the group consisting of -NH2, an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group.

[0023] In the chemical formula or structural formula in this specification, * or indicates the binding position.

[0024] The novel compound of the present invention is described below.

[0025] The novel compound of the present invention is represented by the following chemical formula 1.

[0026]

[0027] In the above chemical formula 1,

[0028] Ar1 is a substituted or unsubstituted 1,10-phenanthroline group,

[0029] Ar2 is hydrogen, deuterium, halogen, chloro group (-Cl), bromo group (-Br), cyano group, nitro group, nitrile group, substituted or unsubstituted C1~C30 alkyl group, substituted or unsubstituted C2~C30 alkenyl group, substituted or unsubstituted C1~C30 alkynyl group, C3~C30 cycloalkyl group, C2~C30 heterocycloalkyl group, substituted or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 sulfide group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C2~C30 heteroaryl group, substituted or unsubstituted C6~C30 aryloxy group, substituted or unsubstituted C6~C30 arylthio group, substituted or unsubstituted C6~C30 amine group, substituted or unsubstituted Selected from the group consisting of arylsilyl groups and substituted or unsubstituted arylphosphine oxide groups,

[0030] L1 and L2 are each independently a direct bond, a substituted or unsubstituted C6~C30 arylene group, or a substituted or unsubstituted C2~C30 heteroarylene group, but are not an anthracenylene group.

[0031] As such, the novel compound of the present invention is characterized by having a structure in which a 1,10-phenanthroline group is bonded to the 3-position of 1,5-naphthyridine. The 1,10-phenanthroline group has a nitrogen atom with nucleophilic properties, so it easily bonds to metal cations and has the characteristic of easy electron transfer, and the 1,5-naphthyridine group has a large electron affinity, so the LUMO energy level is lowered, resulting in a small energy gap, and thus not only has excellent electron transport ability but also has excellent durability due to its rigid structure. Therefore, the compound of the present invention combining these has properties such as excellent electron mobility and strong nucleophilicity, making it suitable for application to an N-type charge generation layer, a hole blocking layer, or an electron transport layer of an organic light-emitting device.

[0032] More specifically, the Ar1 may be any one selected from the following structural formulae A-1 to A-4, and structural formula A-1 may be most preferable. That is, when the 1,10-phenanthroline group is bonded to the 3-position of 1,5-naphthyridien, it may be most preferable to bond to the 9-position of the 1,10-phenanthroline group, because it has the effect of preventing structural change due to intramolecular hydrogen bonding, expanding π conjugation, and exhibiting strong nucleophilicity and excellent electron mobility.

[0033]

[0034] In the above structural formulas A-1 to A-4,

[0035] Each R may be independently any one selected from the group consisting of hydrogen, deuterium, halogen, chloro group (-Cl), bromo group (-Br), cyano group, nitro group, nitrile group, substituted or unsubstituted C1~C30 alkyl group, substituted or unsubstituted C3~C30 cycloalkyl group, substituted or unsubstituted C2~C30 heterocycloalkyl group, substituted or unsubstituted C6~C30 aryl group, and substituted or unsubstituted C2~C30 heteroaryl group, and m may be an integer of 0 to 7.

[0036] More specifically, each of the R groups may independently be any one of hydrogen, deuterium, halogen, a chloro group (-Cl), a bromo group (-Br), a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C10 alkyl group, a substituted or unsubstituted C3~C10 cycloalkyl group, a substituted or unsubstituted C2~C10 heterocycloalkyl group, a substituted or unsubstituted C6~C15 aryl group, and a substituted or unsubstituted C2~C15 heteroaryl group.

[0037] In one embodiment, R may be any one of the structural formulae R-1 to R-17 below. In one embodiment, it may be preferable that it be structural formulae R-3, R-9 to R-11, R-16 or R-17.

[0038]

[0039] Meanwhile, the above m may be an integer of 0 to 3, more specifically an integer of 0 to 2, and even more specifically 0 or 1. In one embodiment, when m is 1, the bonding position of the substituent R may be the 2nd position of 1,10-phenanthroline, as in the structural formula A-1-1 below.

[0040]

[0041] Meanwhile, the above Ar2 may be any one selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1~C30 alkyl group, a substituted or unsubstituted C3~C30 cycloalkyl group, a substituted or unsubstituted C2~C30 heterocycloalkyl group, a substituted or unsubstituted C6~C30 aryl group, and a substituted or unsubstituted C2~C30 heteroaryl group, and more specifically, may be any one of hydrogen, deuterium, a substituted or unsubstituted C6~C20 aryl group, and a substituted or unsubstituted C2~C20 heteroaryl group.

[0042] According to one embodiment, Ar2 may be hydrogen, and if not hydrogen, it may be one of the structural formulae B-1 to B-39 below. More specifically, it may be preferably one of the structural formulae B-1 to B-3, B-12 to B-17, B-20 to B-30, and B-33 to B-39. In this way, Ar2 having a different structure from Ar1 may be preferable for application to an organic layer of an organic light-emitting device, particularly an N-type charge generation layer.

[0043]

[0044] Meanwhile, the above L1 and L2 may be independently a direct bond, or may be formed by combining one or two or more selected from the structural formulae L-1 to L-19 below. In the present specification, the meaning of being formed by combining two or more means combining two or more structural formulae that are the same or different from each other, and in one embodiment, the case of combining two structural formulae L-1, the case of combining structural formulae L-1 and L-2, the case of combining two structural formulae L-1 and one L-2, etc. may be included. In one embodiment, L1 and L2 may be the same or different from each other.

[0045]

[0046] In one embodiment, L1 and L2 may be more specifically a direct bond or a combination of one or two of the following structural formulas. In the case of an asymmetric structure among the structural formulas below, the left and right are not fixed and may be changed.

[0047]

[0048] Meanwhile, it is characterized in that L1 and L2 do not contain an anthracenylene group, and furthermore, it may be preferable that not only the linking group but also the entire compound of the present invention does not contain an anthracene or anthracenylene group. This is because anthracene or anthracenylene groups are bulky, and orbitals overlap due to pi-stacking and intermolecular interactions to create new levels, which is not suitable because it lowers efficiency.

[0049] The novel compound of the present invention may be selected from compounds consisting of compounds 1 to 148 below.

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] The novel compound of the present invention described so far is characterized by a structure in which a 1,10-phenanthroline group is bonded to the 3-position with 1,5-naphthyridine as the center, and specific substituents are bonded to the 7-position.

[0058] Meanwhile, the novel compound of the present invention described above can be applied to an organic light-emitting device including a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, and specifically, can be applied to one or more of the organic layers.

[0059] Below, the organic light-emitting device is described in more detail.

[0060] An organic light-emitting device has an organic layer positioned between two electrodes. The organic layer may be composed of one or more organic layers, and specifically, may be composed of one or more layers selected from known organic layers that constitute a light-emitting portion, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0061] The hole injection layer (HIL) is a layer that injects holes from an electrode. The hole injection material is preferably a compound that has the ability to transport holes, has an excellent hole injection effect at the anode, an excellent hole injection effect for the light-emitting layer or light-emitting material, prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material, and has excellent thin film forming ability.

[0062] The hole transport layer (HTL) is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. As the hole transport material, a material with high hole mobility is suitable, as it can transport holes from the anode or the hole injection layer and move them to the light-emitting layer.

[0063] The light-emitting material used in the emission layer (EML) is a material that can emit light in the visible light range by transporting holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them. A material with good quantum efficiency for fluorescence or phosphorescence is preferable. The emission layer may include a host material and a dopant material.

[0064] The electron transport layer (ETL) is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is preferable.

[0065] The electron injection layer (EIL) is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect for a light-emitting layer or light-emitting material, prevents movement of excitons generated in the light-emitting layer to the hole injection layer, and is preferably a compound having excellent thin-film forming ability.

[0066] The organic layer may further include a hole blocking layer (hole blocking layer, HBL). The hole blocking layer may be positioned between the light-emitting layer and the electron transport layer, and reduces the problem of holes from the hole injection layer invading the electron transport layer.

[0067] Among the organic layers of such organic light-emitting devices, the novel compound of the present invention can be particularly applied to an electron transport layer or a hole blocking layer.

[0068] Meanwhile, the composition of the organic light-emitting device can vary. For example, it can be a tandem structure in which two or more light-emitting layers (or light-emitting units) are provided. In the case of a tandem structure, in addition to the above-mentioned organic layers, a charge generation layer (CGL) can be further included as one of the organic layers. Generally, the charge generation layer is composed of multiple layers including an N-type charge generation layer and a P-type charge generation layer, but is not limited thereto and can also be composed of a single layer.

[0069] The novel compound of the present invention can also be applied to a charge generation layer of such a tandem organic light-emitting device, and specifically, can be applied to an N-type charge generation layer.

[0070] Specifically, the N-type charge generation layer may include a host and a dopant, and the novel compound of the present invention may be applied as a host. Here, the dopant may be an alkali metal, an alkali metal compound, an alkaline earth metal, or an alkaline earth metal compound. Specifically, it may be at least one selected from the group consisting of Li, Cs, K, Rb, Mg, Na, Ca, Sr, Eu, and Yb. The ratio of the dopant may be mixed at 1 to 8% relative to the entire 100% of the host.

[0071] An organic light-emitting device in which the novel compound of the present invention is applied to an electron transport layer, a hole blocking layer, or an N-type charge generation layer can realize low voltage, high efficiency, high brightness, and long life.

[0072] The present invention is described in more detail below through synthetic examples, embodiments, and experimental examples.

[0073] Synthesis of compounds

[0074] Synthesis of intermediate-1

[0075]

[0076] 3,7-dibromo-1,5-naphthyridine (15 g, 52.09 mmol), phenanthren-9-ylboronic acid (12.7 g, 57.30 mmol), potassium carbonate (14.4 g, 104.19 mmol), and tetrakis(triphenylphophine)palladium (1.2 g, 1.04 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in toluene at room temperature and reprecipitated with hexanes to obtain intermediate-1 (16.7 g, 83.2%).

[0077] Synthesis of intermediate-2

[0078]

[0079] Intermediate-1 (16.7 g, 43.35 mmol), bis(pinacolato)diboron (13.2 g, 52.02 mmol), potassium acetate (8.5 g, 86.69 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)[1.1 g, 1.30 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 250 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered through silica gel and Celite under reduced pressure, and concentrated under reduced pressure to obtain intermediate-2 (12.3 g, 65.6%).

[0080] Synthetic Example 1. Synthesis of Compound 7

[0081]

[0082] 2-Bromo-1,10-phenanthroline (6.0 g, 23.16 mmol), intermediate-2 (11.0 g, 25.47 mmol), potassium carbonate (6.4 g, 46.31 mmol), and tetrakis(triphenylphophine)palladium (0.5 g, 0.46 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 60 mL of 1,4-dioxane and 30 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was added to toluene and filtered hot to obtain a solid. Monochlorobenzene was added to the obtained solid and filtered hot to obtain solid compound 7 (6.5 g, 57.9%).

[0083] Synthesis of intermediate-3

[0084]

[0085] A round-bottomed flask was charged with 1,3-dibromo-5-chlorobenzene (20 g, 73.98 mmol), bis(pinacolato)diboron (39.5 g, 155.35 mmol), potassium acetate (29.0 g, 295.91 mmol), and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (3.0 g, 3.70 mmol), and the mixture was stirred overnight under reflux in 300 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered through silica gel and Celite under reduced pressure, and concentrated under reduced pressure to obtain intermediate-3 (22.7 g, 84.2%).

[0086] Synthesis of intermediate-4

[0087]

[0088] Intermediate-3 (22.7 g, 62.28 mmol), bromobenzene (20.5 g, 130.79 mmol), potassium carbonate (34.4 g, 249.12 mmol), and tetrakis(triphenylphophine)palladium (3.6 g, 3.11 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 230 mL of 1,4-dioxane and 115 mL of water. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was purified by column chromatography to obtain intermediate-4 (14.1 g, 85.5%).

[0089] Synthesis of intermediate-5

[0090]

[0091] Intermediate-4 (14.1 g, 53.26 mmol), bis(pinacolato)diboron (16.2 g, 63.91 mmol), potassium acetate (10.5 g, 106.52 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.3 g, 1.60 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 220 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered through silica gel and Celite under reduced pressure, and concentrated under reduced pressure to obtain intermediate-5 (17.3 g, 91.2%).

[0092] Synthesis of intermediate-6

[0093]

[0094] In a round-bottomed flask were added 3,7-dibromo-1,5-naphthyridine (12.0 g, 41.68 mmol), intermediate-5 (16.3 g, 45.84 mmol), potassium carbonate (12.7 g, 91.69 mmol), and tetrakis(triphenylphophine)palladium (2.1 g, 1.83 mmol), and the mixture was stirred overnight under reflux in 120 mL of 1,4-dioxane and 60 mL of water. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was purified by column chromatography to obtain intermediate-6 (15.2 g, 83.4%).

[0095] Synthesis of intermediate-7

[0096]

[0097] Intermediate-6 (15.2 g, 34.76 mmol), bis(pinacolato)diboron (10.6 g, 41.71 mmol), potassium acetate (6.8 g, 69.51 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.9 g, 1.04 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 230 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered through silica gel and Celite under reduced pressure, and concentrated under reduced pressure to obtain intermediate-7 (14.6 g, 86.7%).

[0098] Synthesis Example 2. Synthesis of Compound 9

[0099]

[0100] 2-Bromo-1,10-phenanthroline (7.0 g, 27.02 mmol), intermediate-7 (14.4 g, 29.72 mmol), potassium carbonate (7.5 g, 54.03 mmol), and tetrakis(triphenylphophine)palladium (0.6 g, 0.54 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 70 mL of 1,4-dioxane and 35 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 9 (8.3 g, 57.3%).

[0101] Synthesis of intermediate-8

[0102]

[0103] 3,7-dibromo-1,5-naphthyridine (20.0 g, 69.46 mmol), bis(pinacolato)diboron (44.1 g, 173.65 mmol), potassium acetate (27.3 g, 277.84 mmol), and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(2.8 g, 3.47 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 300 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered under reduced pressure through silica gel and celite, and concentrated under reduced pressure to obtain intermediate-8 (20.6 g, 77.6%).

[0104] Synthesis Example 3. Synthesis of Compound 12

[0105]

[0106] 2-Bromo-1,10-phenanthroline (22.4 g, 86.37 mmol), intermediate-8 (15.0 g, 39.26 mmol), potassium carbonate (21.7 g, 157.04 mmol), and tetrakis(triphenylphophine)palladium (2.3 g, 1.96 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 12 (11.3 g, 59.2%).

[0107] Synthesis of intermediate-9

[0108]

[0109] In a round-bottomed flask were added 3,7-dibromo-1,5-naphthyridine (20 g, 69.46 mmol), phenylboronic acid (9.3 g, 76.40 mmol), potassium carbonate (19.2 g, 138.92 mmol), and tetrakis(triphenylphophine)palladium (1.6 g, 1.39 mmol), and the mixture was stirred overnight while refluxing in 200 mL of 1,4-dioxane and 100 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in toluene and recrystallized with acetone to obtain intermediate-9 (15.3 g, 77.3%).

[0110] Synthesis of intermediate-10

[0111]

[0112] Intermediate-9 (15.3 g, 53.66 mmol), bis(pinacolato)diboron (16.4 g, 64.39 mmol), potassium acetate (10.5 g, 107.32 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.3 g, 1.61 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 230 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered through silica gel and Celite under reduced pressure, and concentrated under reduced pressure to obtain intermediate-10 (16.7 g, 93.7%).

[0113] Synthesis of intermediate-11

[0114]

[0115] In a round-bottomed flask, 2,9-dibromo-1,10-phenanthroline (15.0 g, 44.38 mmol), phenylboronic acid (6.0 g, 48.82 mmol), potassium carbonate (12.3 g, 88.76 mmol), and tetrakis(triphenylphophine)palladium (1.0 g, 0.89 mmol) were added and refluxed in 150 mL of 1,4-dioxane and 75 mL of water overnight. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in toluene and recrystallized with acetone to obtain intermediate-11 (12.4 g, 83.4%).

[0116] Synthesis Example 4. Synthesis of Compound 18

[0117]

[0118] Intermediate-11 (12.4 g, 36.99 mmol) and intermediate-10 (13.5 g, 40.69 mmol), potassium carbonate (10.2 g, 73.99 mmol), and tetrakis(triphenylphophine)palladium (1.3 g, 1.11 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 190 mL of 1,4-dioxane and 95 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in dichlorobenzene, and the mixture was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 18 (9.6 g, 56.3%).

[0119] Synthesis of intermediate-12

[0120]

[0121] 2,9-dibromo-1,10-phenanthroline (15.0 g, 44.38 mmol), pyridin-2-ylboronic acid (6.0 g, 48.82 mmol), potassium carbonate (12.3 g, 88.76 mmol), and tetrakis(triphenylphophine)palladium (1.0 g, 0.89 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in toluene and recrystallized with acetone to obtain intermediate-12 (10.6 g, 71.0%).

[0122] Synthetic Example 5. Synthesis of Compound 24

[0123]

[0124] Intermediate-12 (10.6 g, 31.53 mmol) and intermediate-10 (12.6 g, 37.84 mmol), potassium carbonate (6.2 g, 63.06 mmol), and tetrakis(triphenylphophine)palladium (0.7 g, 0.63 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 110 mL of 1,4-dioxane and 55 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 24 (7.2 g, 49.5%).

[0125] Synthesis of intermediate-13

[0126]

[0127] 1-(4-bromophenyl)ethan-1-one (20.0 g, 100.48 mmol), bis(pinacolato)diboron (30.6 g, 120.57 mmol), potassium acetate (19.7 g, 200.95 mmol), and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(2.5 g, 3.01 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 300 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered under reduced pressure through silica gel and celite, and concentrated under reduced pressure to obtain intermediate-13 (23.0 g, 93.0%).

[0128] Synthesis of intermediate-14

[0129]

[0130] In a round-bottomed flask were added 3-bromo-1,5-naphthyridine (15.0 g, 71.75 mmol), intermediate-13 (19.4 g, 78.93 mmol), potassium carbonate (19.8 g, 143.51 mmol), and tetrakis(triphenylphophine)palladium (1.7 g, 1.44 mmol), and the mixture was stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in toluene and recrystallized with acetone to obtain intermediate-14 (13.8 g, 77.5%).

[0131] Synthetic Example 6. Synthesis of Compound 44

[0132]

[0133] Intermediate-14 (13.8 g, 55.58 mmol), 8-aminoquinoline-7-carbaldehyde (12.4 g, 72.25 mmol), and 100 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (12.2 g, 216.76 mmol) was dissolved in 70 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in toluene, filtered through silica gel and Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure and recrystallized from toluene to obtain compound 44 (12.7 g, 59.4%).

[0134] Synthesis of intermediate-15

[0135]

[0136] In a round-bottomed flask were added 3,7-dibromo-1,5-naphthyridine (15.0 g, 52.09 mmol), (4-acetylphenyl)boronic acid (10.3 g, 62.51 mmol), potassium carbonate (21.6 g, 156.28 mmol), and tetrakis(triphenylphophine)palladium (1.2 g, 1.04 mmol), and the mixture was stirred overnight while refluxing in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in toluene and recrystallized with acetone to obtain intermediate-15 (12.6 g, 73.9%).

[0137] Synthesis of intermediate-16

[0138]

[0139] Intermediate-15 (12.6 g, 38.51 mmol) and 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (9.4 g, 46.21 mmol), potassium carbonate (16.0 g, 115.53 mmol), and tetrakis(triphenylphophine)palladium (0.9 g, 0.77 mmol) were added to a round-bottomed flask and stirred overnight while refluxing in 130 mL of 1,4-dioxane and 65 mL of water. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solid was washed with water. The solid was recrystallized in toluene to obtain intermediate-16 (8.3 g, 66.4%).

[0140] Synthetic Example 7. Synthesis of Compound 45

[0141]

[0142] Intermediate-16 (8.3 g, 25.59 mmol), 8-aminoquinoline-7-carbaldehyde (5.7 g, 33.26 mmol), and 60 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (4.3 g, 76.76 mmol) was dissolved in 45 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, filtered through silica gel and Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 45 (6.3 g, 53.5%).

[0143] Synthesis of intermediate-17

[0144]

[0145] Intermediate-15 (15.0 g, 45.85 mmol), phenanthren-9-ylboronic acid (12.4 g, 55.02 mmol), potassium carbonate (19.0 g, 137.54 mmol), and tetrakis(triphenylphophine)palladium (1.1 g, 0.92 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solid was washed with ethanol. The solid was recrystallized in toluene to obtain intermediate-17 (12.4 g, 63.7%).

[0146] Synthetic Example 8. Synthesis of Compound 47

[0147]

[0148] Intermediate-17 (12.4 g, 29.21 mmol), 8-aminoquinoline-7-carbaldehyde (6.5 g, 37.97 mmol), and 90 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (4.9 g, 87.63 mmol) was dissolved in 65 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, filtered through silica gel and Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 47 (9.6 g, 58.6%).

[0149] Synthesis of intermediate-18

[0150]

[0151] Intermediate-15 (15.0 g, 45.85 mmol) and 4,4,5,5-tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane (14.0 g, 55.02 mmol), potassium carbonate (19.0 g, 137.54 mmol), and tetrakis(triphenylphophine)palladium (1.1 g, 0.92 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solid was washed with ethanol. The solid was recrystallized in toluene to obtain intermediate-18 (12.8 g, 74.6%).

[0152] Synthetic Example 9. Synthesis of Compound 48

[0153]

[0154] Intermediate-18 (12.8 g, 34.18 mmol), 8-aminoquinoline-7-carbaldehyde (7.7 g, 44.44 mmol), and 90 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (5.8 g, 102.55 mmol) was dissolved in 65 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, filtered through silica gel and Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 48 (9.4 g, 53.9%).

[0155] Synthesis of intermediate-19

[0156]

[0157] Intermediate-15 (15.0 g, 45.85 mmol), 8-aminoquinoline-7-carbaldehyde (10.3 g, 59.60 mmol), and 105 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (7.7 g, 137.54 mmol) was dissolved in 75 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, filtered through Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain intermediate-19 (13.2 g, 62.1%).

[0158] Synthetic Example 10. Synthesis of Compound 49

[0159]

[0160] Intermediate-19 (13.2 g, 28.49 mmol) and intermediate-5 (12.2 g, 34.19 mmol), potassium carbonate (11.8 g, 85.47 mmol), and tetrakis(triphenylphophine)palladium (0.7 g, 0.57 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 135 mL of 1,4-dioxane and 70 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in dichlorobenzene, and then filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 49 (10.4 g, 59.6%).

[0161] Synthesis of intermediate-20

[0162]

[0163] 1-(3-bromophenyl)ethan-1-one (10.0 g, 50.24 mmol), intermediate-10 (20.0 g, 60.29 mmol), potassium carbonate (20.8 g, 150.72 mmol), and tetrakis(triphenylphophine)palladium (1.2 g, 1.00 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 100 mL of 1,4-dioxane and 50 mL of water. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solid was washed with ethanol. The solid was recrystallized in toluene to obtain intermediate-20 (11.8 g, 72.4%).

[0164] Synthetic Example 11. Synthesis of Compound 56

[0165]

[0166] Intermediate-20 (11.8 g, 36.38 mmol), 8-aminoquinoline-7-carbaldehyde (8.1 g, 47.29 mmol), and 85 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (6.1 g, 109.13 mmol) was dissolved in 60 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methyl. The solid was dissolved in dichlorobenzene, filtered through silica gel and Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 56 (9.6 g, 57.3%).

[0167] Synthesis of intermediate-21

[0168]

[0169] Intermediate-15 (15.0 g, 45.85 mmol), 8-amino-2-phenylquinoline-7-carbaldehyde (14.8 g, 59.60 mmol), and 105 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (7.7 g, 137.54 mmol) was dissolved in 75 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, filtered through Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain intermediate-21 (13.1 g, 53.0%).

[0170] Synthesis Example 12. Synthesis of Compound 71

[0171]

[0172] Intermediate-21 (13.1 g, 24.28 mmol) and intermediate-5 (10.4 g, 29.14 mmol), potassium carbonate (10.1 g, 72.85 mmol), and tetrakis(triphenylphophine)palladium (0.6 g, 0.49 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 135 mL of 1,4-dioxane and 70 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in dichlorobenzene, and then filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 71 (10.7 g, 64.0%).

[0173] Synthesis of intermediate-22

[0174]

[0175] 1-(4-bromonaphthalen-1-yl)ethan-1-one (20.0 g, 80.29 mmol), bis(pinacolato)diboron (24.5 g, 96.34 mmol), potassium acetate (15.8 g, 160.57 mmol), and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(2.0 g, 2.41 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 300 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered under reduced pressure through silica gel and celite, and concentrated under reduced pressure to obtain intermediate-22 (16.7 g, 70.2%).

[0176] Synthesis of intermediate-23

[0177]

[0178] 3-Bromo-1,5-naphthyridine (10.0 g, 47.84 mmol), intermediate-22 (15.6 g, 52.62 mmol), potassium carbonate (13.2 g, 95.67 mmol), and tetrakis(triphenylphophine)palladium (1.1 g, 0.96 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 100 mL of 1,4-dioxane and 50 mL of water. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in toluene and recrystallized with acetone to obtain intermediate-23 (10.6 g, 74.3%).

[0179] Synthesis Example 13. Synthesis of Compound 79

[0180]

[0181] Intermediate-23 (10.6 g, 35.53 mmol), 8-aminoquinoline-7-carbaldehyde (8.0 g, 46.19 mmol), and 75 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (6.0 g, 106.59 mmol) was dissolved in 55 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, filtered through silica gel and Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 79 (9.3 g, 60.2%).

[0182] Synthetic Example 14. Synthesis of Compound 81

[0183]

[0184] 2-(4-bromonaphthalen-1-yl)-1,10-phenanthroline (15.0 g, 38.93 mmol), intermediate-10 (14.2 g, 42.83 mmol), potassium carbonate (10.8 g, 77.87 mmol), and tetrakis(triphenylphophine)palladium (0.9 g, 0.78 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 81 (11.2 g, 56.3%).

[0185] Synthesis of intermediate-24

[0186]

[0187] 3,7-dibromo-1,5-naphthyridine (15.0 g, 52.09 mmol), intermediate-22 (17.0 g, 57.30 mmol), potassium carbonate (14.4 g, 104.19 mmol), and tetrakis(triphenylphophine)palladium (1.2 g, 1.04 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in toluene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in toluene, and recrystallized with acetone to obtain intermediate-24 (14.7 g, 74.8%).

[0188] Synthesis of intermediate-25

[0189]

[0190] Intermediate-24 (14.7 g, 38.97 mmol), phenanthren-9-ylboronic acid (9.5 g, 42.86 mmol), potassium carbonate (10.8 g, 77.93 mmol), and tetrakis(triphenylphophine)palladium (0.9 g, 0.78 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in dichlorobenzene, filtered through silica gel and Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain intermediate-25 (13.6 g, 73.5%).

[0191] Synthesis Example 15. Synthesis of Compound 82

[0192]

[0193] Intermediate-25 (13.6 g, 28.66 mmol), 8-aminoquinoline-7-carbaldehyde (6.4 g, 37.26 mmol), and 100 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (4.8 g, 85.97 mmol) was dissolved in 70 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, filtered through silica gel and Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 82 (9.3 g, 53.1%).

[0194] Synthesis of intermediate-26

[0195]

[0196] 1-Bromo-4-iodonaphthalene (20.0 g, 60.07 mmol), phenylboronic acid (8.1 g, 66.07 mmol), potassium carbonate (16.6 g, 120.13 mmol), and tetrakis(triphenylphophine)palladium (1.4 g, 1.20 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 200 mL of 1,4-dioxane and 100 mL of water. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was purified by column chromatography to obtain intermediate-26 (13.9 g, 81.7%).

[0197] Synthesis of intermediate-27

[0198]

[0199] Intermediate-26 (13.9 g, 49.09 mmol), bis(pinacolato)diboron (15.0 g, 58.90 mmol), potassium acetate (9.6 g, 98.17 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.2 g, 1.47 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 210 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered through silica gel and Celite under reduced pressure, and concentrated under reduced pressure to obtain intermediate-27 (14.9 g, 91.9%).

[0200] Synthesis of intermediate-28

[0201]

[0202] In a round-bottomed flask were added 3,7-dibromo-1,5-naphthyridine (11.0 g, 38.20 mmol), intermediate-27 (13.9 g, 42.02 mmol), potassium carbonate (10.6 g, 76.40 mmol), and tetrakis(triphenylphophine)palladium (0.9 g, 0.76 mmol), and the mixture was stirred overnight under reflux in 110 mL of 1,4-dioxane and 55 mL of water. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was purified by column chromatography to obtain intermediate-28 (12.4 g, 78.9%).

[0203] Synthesis of intermediate-29

[0204]

[0205] Intermediate-28 (12.4 g, 30.15 mmol), bis(pinacolato)diboron (15.0 g, 58.90 mmol), potassium acetate (9.6 g, 98.17 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.2 g, 1.47 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 190 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered through silica gel and Celite under reduced pressure, and concentrated under reduced pressure to obtain intermediate-29 (12.7 g, 27.71%).

[0206] Synthesis of intermediate-30

[0207]

[0208] 1-(3-bromophenyl)ethan-1-one (5.0 g, 25.12 mmol), intermediate-29 (12.7 g, 27.63 mmol), potassium carbonate (7.6 g, 55.26 mmol), and tetrakis(triphenylphophine)palladium (1.3 g, 1.11 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 50 mL of 1,4-dioxane and 25 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with water and ethanol. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and celite under reduced pressure to obtain a filtrate. The filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain intermediate-30 (8.9 g, 78.6%).

[0209] Synthetic Example 16. Synthesis of Compound 105

[0210]

[0211] Intermediate-30 (8.9 g, 19.75 mmol), 8-aminoquinoline-7-carbaldehyde (4.4 g, 25.68 mmol), and 65 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (3.3 g, 59.26 mmol) was dissolved in 45 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, filtered through silica gel and Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 105 (6.4 g, 55.2%).

[0212] Synthesis of intermediate-31

[0213]

[0214] 1-Bromo-4-iodobenzene (15.0 g, 53.02 mmol), intermediate-22 (17.3 g, 58.32 mmol), potassium carbonate (22.0 g, 159.06 mmol), and tetrakis(triphenylphophine)palladium (1.2 g, 1.06 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was purified by column chromatography to obtain intermediate-31 (14.7 g, 85.3%).

[0215] Synthesis of intermediate-32

[0216]

[0217] Intermediate-31 (14.7 g, 45.20 mmol), bis(pinacolato)diboron (13.8 g, 54.24 mmol), potassium acetate (8.9 g, 90.40 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.1 g, 1.36 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 220 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered through silica gel and Celite under reduced pressure, and concentrated under reduced pressure to obtain intermediate-32 (15.8 g, 93.9%).

[0218] Synthesis of intermediate-33

[0219]

[0220] 3-Bromo-1,5-naphthyridin (8.0 g, 38.27 mmol), intermediate-32 (15.7 g, 42.10 mmol), potassium carbonate (15.9 g, 114.81 mmol), and tetrakis(triphenylphophine)palladium (0.9 g, 0.77 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 80 mL of 1,4-dioxane and 40 mL of water. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was purified by column chromatography to obtain intermediate-33 (10.3 g, 71.9%).

[0221] Synthesis Example 17. Synthesis of Compound 130

[0222]

[0223] Intermediate-33 (10.3 g, 27.51 mmol), 8-aminoquinoline-7-carbaldehyde (6.2 g, 35.76 mmol), and 75 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (4.6 g, 82.52 mmol) was dissolved in 55 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methyl. The solid was dissolved in dichlorobenzene, filtered through Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 130 (8.1 g, 57.7%).

[0224] Synthesis of intermediate-34

[0225]

[0226] In a round-bottomed flask were added 1-(2-bromopyrimidin-5-yl)ethan-1-one (20.0 g, 99.49 mmol), bis(pinacolato)diboron (30.3 g, 119.39 mmol), potassium acetate (19.5 g 198.99 mmol), and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(2.4 g, 2.98 mmol), and the mixture was stirred overnight under reflux in 300 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered under reduced pressure through silica gel and celite, and concentrated under reduced pressure to obtain intermediate-34 (22.1 g, 89.08%).

[0227] Synthesis of intermediate-35

[0228]

[0229] In a round-bottomed flask were added 3,7-dibromo-1,5-naphthyridine (20.0 g, 69.46 mmol), intermediate-34 (19.0 g, 76.40 mmol), potassium carbonate (19.2 g, 138.92 mmol), and tetrakis(triphenylphophine)palladium (1.6 g, 1.39 mmol), and the mixture was stirred overnight while refluxing in 200 mL of 1,4-dioxane and 100 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with ethanol. The solid was dissolved in toluene, and the filtrate was filtered under reduced pressure through silica gel and Celite to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in toluene, and recrystallized with acetone to obtain intermediate-35 (18.1 g, 79.2%).

[0230] Synthesis of intermediate-36

[0231]

[0232] Intermediate-35 (18.1 g, 54.99 mmol) and 4,4,5,5-tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane (15.4 g, 60.49 mmol), potassium carbonate (15.2 g, 109.98 mmol), and tetrakis(triphenylphophine)palladium (1.3 g, 1.10 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 180 mL of 1,4-dioxane and 90 mL of water. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the solid was washed with ethanol. The solid was dissolved in toluene, and then filtered under reduced pressure through silica gel and Celite to obtain the filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in toluene, and recrystallized with acetone to obtain intermediate-36 (15.7 g, 75.8%).

[0233] Synthetic Example 18. Synthesis of Compound 131

[0234]

[0235] Intermediate-36 (15.7 g, 41.71 mmol), 8-amino-2-phenylquinoline-7-carbaldehyde (13.5 g, 54.22 mmol), and 110 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (7.0 g, 125.13 mmol) was dissolved in 80 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, filtered through silica gel and Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 131 (12.7 g, 51.7%).

[0236] Synthesis of intermediate-37

[0237]

[0238] 4-Bromo-2,6-diphenylpyridine (20.0 g, 64.48 mmol), bis(pinacolato)diboron (19.6 g, 77.37 mmol), potassium acetate (12.7 g 128.95 mmol), and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.6 g, 1.93 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 300 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered under reduced pressure through silica gel and celite, and concentrated under reduced pressure to obtain intermediate-37 (21.3 g, 92.5%).

[0239] Synthesis of intermediate-38

[0240]

[0241] Intermediate-15 (15.0 g, 45.85 mmol) and intermediate-37 (19.7 g, 55.02 mmol), potassium carbonate (19.0 g, 137.54 mmol), and tetrakis(triphenylphophine)palladium (1.1 g, 0.92 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with ethanol. The solid was dissolved in dichlorobenzene, filtered through silica gel and celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain intermediate-38 (14.7 g, 67.1%).

[0242] Synthetic Example 19. Synthesis of Compound 132

[0243]

[0244] Intermediate-38 (14.7 g, 30.78 mmol), 8-aminoquinoline-7-carbaldehyde (6.9 g, 40.02 mmol), and 105 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (5.2 g, 92.34 mmol) was dissolved in 75 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 132 (11.4 g, 60.3%).

[0245] Synthesis of intermediate-39

[0246]

[0247] 2-Bromo-4,6-diphenylpyrimidine (20.0 g, 64.27 mmol), bis(pinacolato)diboron (19.6 g, 77.13 mmol), potassium acetate (12.6 g 128.54 mmol), and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.6 g, 1.93 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 300 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in dichloromethane, filtered under reduced pressure through silica gel and celite, and concentrated under reduced pressure to obtain intermediate-39 (20.7 g, 89.9%).

[0248] Synthesis of intermediate-40

[0249]

[0250] Intermediate-15 (15.0 g, 45.85 mmol), intermediate-39 (19.7 g, 55.02 mmol), potassium carbonate (19.0 g, 137.54 mmol), and tetrakis(triphenylphophine)palladium (1.1 g, 0.92 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with ethanol. The solid was dissolved in dichlorobenzene, filtered through silica gel and celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain intermediate-40 (15.9 g, 72.5%).

[0251] Synthesis Example 20. Synthesis of Compound 133

[0252]

[0253] Intermediate-40 (15.9 g, 33.22 mmol), 8-aminoquinoline-7-carbaldehyde (7.4 g, 43.19 mmol), and 115 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (5.6 g, 99.67 mmol) was dissolved in 80 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, filtered through silica gel and Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 133 (10.7 g, 52.4%).

[0254] Synthesis of intermediate-41

[0255]

[0256] 2-Chloro-4,6-diphenyl-1,3,5-triazine (20.0 g, 74.70 mmol), bis(pinacolato)diboron (22.8 g, 89.65 mmol), potassium acetate (14.7 g 149.41 mmol), and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.8 g, 2.24 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 300 mL of 1,4-dioxane. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was extracted with ethyl acetate and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to obtain a filtrate. The obtained filtrate was dissolved in toluene, filtered under reduced pressure through silica gel and celite, and concentrated under reduced pressure to obtain intermediate-41 (24.3 g, 90.5%).

[0257] Synthesis of intermediate-42

[0258]

[0259] Intermediate-15 (15.0 g, 45.85 mmol), intermediate-41 (19.8 g, 55.02 mmol), potassium carbonate (19.0 g, 137.54 mmol), and tetrakis(triphenylphophine)palladium (1.1 g, 0.92 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 mL of 1,4-dioxane and 75 mL of water. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the solid was washed with ethanol. The solid was dissolved in dichlorobenzene, and then filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain intermediate-42 (11.2 g, 50.9%).

[0260] Synthetic Example 21. Synthesis of Compound 134

[0261]

[0262] Intermediate-42 (11.2 g, 23.36 mmol), 8-aminoquinoline-7-carbaldehyde (5.2 g, 30.36 mmol), and 80 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (3.9 g, 70.07 mmol) was dissolved in 60 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, and the filtrate was filtered through silica gel and Celite under reduced pressure to obtain a filtrate. The filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 134 (6.7 g, 46.6%).

[0263] Synthetic Example 22. Synthesis of Compound 135

[0264]

[0265] Intermediate-25 (15.0 g, 31.61 mmol), 8-amino-2-phenylquinoline-7-carbaldehyd (10.2 g, 41.09 mmol), and 105 mL of toluene were added to a round-bottomed flask. Potassium hydroxide (5.3 g, 94.82 mmol) was dissolved in 75 mL of ethanol, added dropwise, and stirred under reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, filtered, and the solid was washed with methionine. The solid was dissolved in dichlorobenzene, filtered through silica gel and Celite under reduced pressure, and the filtrate was obtained. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 135 (10.1 g, 46.5%).

[0266] Fabrication of organic light-emitting devices

[0267] Comparative Example 1

[0268] After patterning the ITO substrate to have a light-emitting area of ​​2 mm × 2 mm, it was cleaned with isopropyl alcohol and UV ozone, respectively. Afterwards, the ITO substrate was mounted on the substrate holder of a vacuum deposition device and the vacuum level was set to 1 × 10 -7The pressure was set to 10 torr. Afterwards, plasma treatment was performed for 3 minutes under a N2 atmosphere. Afterwards, the HAT-CN compound was vacuum-deposited to form a first hole injection layer with a thickness of 5 nm. On top of this, the NPB material was deposited with a thickness of 20 nm to form a first hole transport layer. Afterwards, the GH-1 material was used as a host, and the GD-1 material was used as a dopant at a mass ratio of about 10% by vacuum-depositing to form a green first light-emitting layer with a thickness of 20 nm. On this light-emitting layer, the TmPyPb compound was deposited with a thickness of 20 nm to form a first electron transport layer. Afterwards, the Li material was vacuum-deposited with a thickness of 10 nm by vacuum-depositing to a mass ratio of 2% to the BPhen material to form an N-type charge generation layer. Afterwards, the HAT-CN compound was vacuum-deposited with a thickness of 5 nm as a P-type charge generation layer. This material was also used as a second hole injection layer. On this, NPB material was deposited with a thickness of 50 nm to form a second hole transport layer. Thereafter, GH-1 material was used as a host and GD-1 material was used as a dopant, and vacuum deposited with a thickness of 20 nm at a mass ratio of about 10% to form a green second light-emitting layer. On this light-emitting layer, TmPyPb compound was used as a host and Liq compound was used as a dopant, and vacuum deposited with a thickness of 20 nm at a mass ratio of about 33% to form a second electron transport layer. Thereafter, LiF material was vacuum deposited with a thickness of 1 nm as an electron injection layer. Finally, Al was deposited with a thickness of 50 nm to form a cathode, thereby fabricating an organic light-emitting device. The structures of the HAT-CN, NPB, GH-1, GD-1, TmPyPb, BPhen, and Liq materials used previously are shown in Table 1, respectively.

[0269] Table 1

[0270]

[0271] Comparison Example 2

[0272] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Comparative Compound 1 shown in Table 2 below was used instead of the BPhen material as the N-type charge generation layer.

[0273] Table 2

[0274]

[0275] Examples 1 to 22

[0276] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds synthesized in Synthesis Examples 1 to 22 were used instead of the BPhen material as the N-type charge generation layer.

[0277] Experimental Example: Evaluation of Organic Light-Emitting Diodes

[0278] The operating voltage, current efficiency, and lifetime of the previously fabricated organic light-emitting devices were evaluated. The evaluation results are shown in Table 3 below.

[0279] Table 3

[0280]

[0281] As can be seen from the results shown in Table 3 above, examples using the compounds of the present invention as an N-type charge generation layer exhibited lower voltage, higher efficiency, and longer lifespan than comparative examples. Comparative compound 1 contains an anthracenylene group, and since the anthracenylene group is bulky, orbitals overlap due to pi-stacking and intermolecular interactions, creating a new level, which can be confirmed to result in lower efficiency.

[0282] The novel compound of the present invention is characterized by having a structure in which a 1,10-phenanthroline group is bonded to the 3-position of 1,5-naphthyridine. The 1,10-phenanthroline group has a nitrogen atom with nucleophilic properties, so it easily bonds to metal cations and has the characteristic of easy electron transfer, and the 1,5-naphthyridine group has a high electron affinity, so the LUMO energy level is lowered, resulting in a small energy gap, and thus not only has excellent electron transport ability but also has excellent durability due to its rigid structure. Therefore, the compound of the present invention combining these has properties such as excellent electron mobility and strong nucleophilicity, making it suitable for application to an N-type charge generation layer, a hole blocking layer, or an electron transport layer of an organic light-emitting device.

Claims

1. A novel compound represented by the following chemical formula 1: In the above chemical formula 1, Ar1 is a substituted or unsubstituted 1,10-phenanthroline group, Ar2 is hydrogen, deuterium, halogen, chloro group (-Cl), bromo group (-Br), cyano group, nitro group, nitrile group, substituted or unsubstituted C1~C30 alkyl group, substituted or unsubstituted C2~C30 alkenyl group, substituted or unsubstituted C1~C30 alkynyl group, substituted or unsubstituted C3~C30 cycloalkyl group, substituted or unsubstituted C2~C30 heterocycloalkyl group, substituted or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 sulfide group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C2~C30 heteroaryl group, substituted or unsubstituted C6~C30 aryloxy group, substituted or unsubstituted C6~C30 arylthio group, substituted or unsubstituted C6~C30 Selected from the group consisting of an amine group, a substituted or unsubstituted arylsilyl group, and a substituted or unsubstituted arylphosphine oxide group, L1 and L2 are each independently a direct bond, a substituted or unsubstituted C6~C30 arylene group, or a substituted or unsubstituted C2~C30 heteroarylene group, but are not an anthracenylene group.

2. In paragraph 1, A novel compound characterized in that the above Ar1 is one of the following structural formulas A-1 to A-4: In the above structural formulas A-1 to A-4, R is independently any one selected from the group consisting of hydrogen, deuterium, halogen, chloro group (-Cl), bromo group (-Br), cyano group, nitro group, nitrile group, substituted or unsubstituted C1~C30 alkyl group, substituted or unsubstituted C3~C30 cycloalkyl group, substituted or unsubstituted C2~C30 heterocycloalkyl group, substituted or unsubstituted C6~C30 aryl group, and substituted or unsubstituted C2~C30 heteroaryl group, m is an integer from 0 to 7, each independently.

3. In paragraph 2, A novel compound characterized in that the above R is hydrogen or one of the following structural formulae R-1 to R-17:

4. In paragraph 2, The above Ar1 is a novel compound characterized by the following structural formula A-1-1: In the above structural formula A-1-1, R has the same definition as in the above structural formula A-1.

5. In paragraph 1, A novel compound characterized in that the above Ar2 is hydrogen or one of the following structural formulas B-1 to B-39:

6. In paragraph 1, A novel compound characterized in that the above L1 and L2 are each independently a direct bond or are formed by combining one or two or more selected from the structural formulas L-1 to L-19 below:

7. In paragraph 1, The above compound is a novel compound characterized in that it is selected from compounds consisting of compounds 1 to 148 below:

8. First electrode and second electrode; It comprises one or more organic layers disposed between the first electrode and the second electrode, An organic light-emitting device, characterized in that at least one of the organic layers comprises a novel compound according to any one of claims 1 to 7.

9. In paragraph 8, An organic light-emitting device, characterized in that the organic layer containing the compound is an electron transport layer, a hole blocking layer, or a charge generation layer.

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