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 N-containing heterocyclic ring,

[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.

[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 applied to an electron transport layer, a hole blocking layer, or a charge generation layer, and enables the implementation of 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, halogen group, cyano group, nitro group, nitrile group, alkyl group, cycloalkyl group, alkoxy group, aryloxy group, alkylthioxy group, arylthioxy group, amine group, phosphine oxide group, aryl group and heteroaryl group, or is substituted with a substituent in which two or more 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 according to 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 N-containing heterocyclic ring,

[0029] 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, 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 Selected from the group consisting of an unsubstituted arylsilyl group and a substituted or unsubstituted arylphosphine oxide group,

[0030] L1 and L2 can each independently be a direct bond, a substituted or unsubstituted C6~C30 arylene group, or a substituted or unsubstituted C2~C30 heteroarylene group.

[0031] As such, the novel compound of the present invention is characterized by having a structure in which an N-containing heterocyclic ring is bonded to the 3-position of 1,5-naphthyridine. The N-containing heterocyclic ring containing at least one nitrogen atom N has the characteristic of increasing electron mobility due to the strong nucleophilicity of the nitrogen atom, and the 1,5-naphthyridine group has a large electron affinity, which lowers the LUMO energy level and narrows the energy gap, and thus has excellent electron transport ability, and has excellent durability due to its rigid structure. Therefore, the compound of the present invention combining these has the advantage of easy electron transfer due to characteristics such as excellent electron mobility and strong nucleophilicity.

[0032] Specifically, the above chemical formula 1 may be the following chemical formula 2 or chemical formula 3. Chemical formula 2 represents a case where one 1,5-naphthyridine is bonded to L1, and chemical formula 3 represents a case where two 1,5-naphthyridines are bonded to L1.

[0033]

[0034] In the above chemical formulas 2 and 3, Ar1, Ar2, L1 and L2 have the same definitions as in the above chemical formula 1.

[0035] In the above chemical formula 2, Ar1 and Ar2 may be the same or different. In the above chemical formula 3, Ar1 and Ar2 may also be the same or different, and Ar2 may also be the same or different.

[0036] According to one embodiment, the chemical formula 3 may be the following chemical formula 4.

[0037]

[0038] In the above chemical formula 4, Ar1, Ar2 and L2 are the same as defined in the above chemical formula 1,

[0039] X1 to X3 are each independently N or CH, and L3 may be a direct bond, a substituted or unsubstituted C6~C30 arylene group, or a substituted or unsubstituted C2~C30 heteroarylene group.

[0040] In one embodiment, X1 to X3 may all be CH, X1 to X3 may all be N, only X1 and X3 among X1 to X3 may be N, or only X2 among X1 to X3 may be N. That is, when two 1,5-naphthyridines are bonded to Ar1, they may be bonded using phenylene, triazinylene, pyrimidinylene, or pyridinylene as a linker.

[0041] Meanwhile, according to one embodiment, Ar1 may be any one selected from the following structural formulae A-1 to A-5. That is, Ar1, which is a substituted or unsubstituted N-containing heterocyclic ring, may be any one of a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted pyrazine, a substituted or unsubstituted pyridazine, and a substituted or unsubstituted triazine.

[0042]

[0043] In the above structural formulas A-1 to A-5,

[0044] R1 may be any one substituent independently selected from the group consisting of hydrogen, deuterium, halogen, 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 n may be each independently an integer from 0 to 4.

[0045] According to one embodiment, the structural formula A-1 may be one of the structural formulas A-1-1 to A-1-3 below, the structural formula A-2 may be one of the structural formulas A-2-1 to A-2-3 below, and the structural formula A-4 may be the structural formula A-4-1 or A-4-2 below.

[0046]

[0047] In the above structural formulas A-1-1 to A-1-3, A-2-1 to A-2-3, A-4-1 and A-4-2, R1 and n are as defined in the above structural formulas A-1 to A-5.

[0048] In one embodiment, it may be preferred that Ar1 is of the structural formula A-1, A-2 or A-5.

[0049] Meanwhile, according to one embodiment, each of R1 may independently be a C6 to C18 aryl group or a C2 to C18 heteroaryl group, and more specifically, may be any one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyrazine group, a substituted or unsubstituted pyridazine group, and a substituted or unsubstituted triazine group.

[0050] In one embodiment, n can be 0 to 3, more specifically 0 to 2, and even more specifically 1 or 2.

[0051] In one embodiment, when n is 2, the structural formula Ar1 may be any one of the following structural formulas.

[0052]

[0053] 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.

[0054] In one embodiment, Ar2 may be hydrogen, and if not hydrogen, may be any one of the structural formulae B-1 to B-50 below.

[0055]

[0056]

[0057] Meanwhile, the above L1 to L3 may each independently be 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 a combination of two or more means a combination of two or more identical or different structural formulae, and as an example, the case may include a case where two structural formulae L-1 are combined, a case where structural formulae L-1 and L-2 are combined, a case where two structural formulae L-1 and one L-2 are combined, etc.

[0058]

[0059] According to one embodiment, L1 to L3 may be more specifically a direct bond, one of the structural formulae below, or a combination of two or three. In the case of an asymmetric structure among the structural formulae below, the left and right are not fixed and may be changed.

[0060]

[0061] The novel compound of the present invention may be selected from compounds consisting of compounds 1 to 159 below.

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070] The novel compound of the present invention described so far includes a core structure in which a heterocyclic ring containing at least one nitrogen atom N, such as pyridine, pyrimidine, pyridazine, pyrazine, or triazine, is bonded to the 3-position of 1,5-naphthyridine, and is characterized in that an additional substituent can be bonded to the 7-position of 1,5-naphthyridine. This novel compound of the present invention has a particularly excellent electron transport ability.

[0071] 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.

[0072] Below, the organic light-emitting device is described in more detail.

[0073] 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.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] The organic layer may further include a hole blocking layer (HBL). The HBL may be positioned between the light-emitting layer and the electron transport layer, and reduces the problem of holes in the hole injection layer invading the electron transport layer.

[0080] 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.

[0081] Meanwhile, the configuration of the organic light-emitting device can vary. For example, it can be a tandem structure in which multiple 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.

[0082] 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 a host of an N-type charge generation layer.

[0083] 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 a charge generation layer can realize low voltage, high efficiency, high brightness, and long life.

[0084] The present invention is described in more detail below through synthetic examples, embodiments, and experimental examples.

[0085] Synthesis of compounds

[0086] Synthesis of intermediate-1

[0087]

[0088] 3-Bromopyridine (10.0 g, 63.29 mmol), bis(pinacolato)diboron (19.3 g, 75.95 mmol), potassium acetate (18.6 g, 189.87 mmol), [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.6 g, 1.90 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 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-1 (12.1 g, 93.2%).

[0089] Synthesis of intermediate-2

[0090]

[0091] 3,7-dibromo-1,5-naphthyridine (15.0 g, 52.09 mmol), intermediate-1 (11.8 g, 57.30 mmol), potassium carbonate (21.6 g, 156.28 mmol), and tetrakis(triphenylphophine)palladium (3.0 g, 2.60 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-2 (12.7 g, 85.2%).

[0092] Synthesis of intermediate-3

[0093]

[0094] 1-Bromo-4-iodobenzene (15.0 g, 53.02 mmol), bis(pinacolato)diboron (16.2 g, 63.62 mmol), potassium acetate (15.6 g, 159.06 mmol), [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.3 g, 1.59 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 225 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 (14.3 g, 95.3%).

[0095] Synthesis of intermediate-4

[0096]

[0097] 2-Bromo-4,6-diphenylpyrimidine (10.0 g, 32.14 mmol), intermediate-3 (10.0 g, 35.35 mmol), potassium carbonate (13.3 g, 96.41 mmol), and tetrakis(triphenylphophine)palladium (1.9 g, 1.61 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 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 (7.3 g, 58.7%).

[0098] Synthesis of intermediate-5

[0099]

[0100] Intermediate-4 (7.3 g, 18.85 mmol), bis(pinacolato)diboron (5.7 g, 22.62 mmol), potassium acetate (5.6 g, 56.55 mmol), and [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.5 g, 0.57 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 110 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 (7.2 g, 87.9%).

[0101] Synthetic Example 1. Synthesis of Compound 36

[0102]

[0103] Intermediate-2 (4.0 g, 13.98 mmol) and intermediate-5 (6.7 g, 15.38 mmol), potassium carbonate (5.8 g, 41.94 mmol), and tetrakis(triphenylphophine)palladium (0.8 g, 0.70 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 40 mL of 1,4-dioxane and 20 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 36 (5.0 g, 69.6%).

[0104] Synthesis of intermediate-6

[0105]

[0106] 1-Bromo-3-iodobenzene (15.0 g, 53.02 mmol), bis(pinacolato)diboron (16.2 g, 63.62 mmol), potassium acetate (15.6 g, 159.06 mmol), [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.3 g, 1.59 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 225 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-6 (13.7 g, 91.3%).

[0107] Synthesis of intermediate-7

[0108]

[0109] 2-Bromo-4,6-diphenylpyrimidine (10.0 g, 32.14 mmol), intermediate-6 (10.0 g, 35.35 mmol), potassium carbonate (13.3 g, 96.41 mmol), and tetrakis(triphenylphophine)palladium (1.9 g, 1.61 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 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-7 (7.2 g, 57.9%).

[0110] Synthesis of intermediate-8

[0111]

[0112] Intermediate-7 (7.2 g, 18.59 mmol), bis(pinacolato)diboron (5.7 g, 22.31 mmol), potassium acetate (5.5 g, 55.77 mmol), and [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.5 g, 0.56 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 110 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-8 (7.6 g, 94.1%).

[0113] Synthetic Example 2. Synthesis of Compound 41

[0114]

[0115] Intermediate-2 (4.0 g, 13.98 mmol) and intermediate-8 (6.7 g, 15.38 mmol), potassium carbonate (5.8 g, 41.94 mmol), and tetrakis(triphenylphophine)palladium (0.8 g, 0.70 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 40 mL of 1,4-dioxane and 20 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 41 (4.2 g, 58.5%).

[0116] Synthesis of intermediate-9

[0117]

[0118] 3,7-dibromo-1,5-naphthyridine (15.0 g, 52.09 mmol), phenylboronic acid (7.0 g, 57.30 mmol), potassium carbonate (21.6 g, 156.28 mmol), and tetrakis(triphenylphophine)palladium (3.0 g, 2.6 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-9 (10.6 g, 71.4%).

[0119] Synthetic Example 3. Synthesis of Compound 43

[0120]

[0121] Intermediate-9 (10.6 g, 37.17 mmol) and intermediate-8 (17.8 g, 40.89 mmol), potassium carbonate (15.4 g, 111.52 mmol), and tetrakis(triphenylphophine)palladium (2.1 g, 1.86 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 43 (10.9 g, 57.2%).

[0122] Synthesis of intermediate-10

[0123]

[0124] 1-Bromo-4-iodonaphthalene (15.0 g, 45.05 mmol), bis(pinacolato)diboron (13.7 g, 54.06 mmol), potassium acetate (13.3 g, 135.15 mmol), [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.1 g, 1.35 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 225 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 (13.7 g, 91.3%).

[0125] Synthesis of intermediate-11

[0126]

[0127] 2-Bromo-4,6-diphenylpyrimidine (10.0 g, 32.14 mmol), intermediate-10 (11.8 g, 35.35 mmol), potassium carbonate (13.3 g, 96.41 mmol), and tetrakis(triphenylphophine)palladium (1.9 g, 1.61 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 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-11 (8.0 g, 56.9%).

[0128] Synthesis of intermediate-12

[0129]

[0130] Intermediate-11 (8.0 g, 18.29 mmol), bis(pinacolato)diboron (5.6 g, 21.95 mmol), potassium acetate (5.4 g, 54.88 mmol), and [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.4 g, 0.55 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 120 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-12 (8.1 g, 91.4%).

[0131] Synthetic Example 4. Synthesis of Compound 51

[0132]

[0133] Intermediate-9 (4.0 g, 14.03 mmol), intermediate-12 (7.5 g, 15.43 mmol), potassium carbonate (5.8 g, 42.08 mmol), and tetrakis(triphenylphophine)palladium (0.8 g, 0.70 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 40 mL of 1,4-dioxane and 20 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 51 (5.3 g, 67.1%).

[0134] Synthetic Example 5. Synthesis of Compound 52

[0135]

[0136] Intermediate-1 (5.0 g, 17.47 mmol), intermediate-12 (9.3 g, 19.22 mmol), potassium carbonate (7.2 g, 52.42 mmol), and tetrakis(triphenylphophine)palladium (1.0 g, 0.87 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 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 52 (5.7 g, 58.0%).

[0137] Synthesis of intermediate-13

[0138]

[0139] 5'-Bromo-1,1':3',1''-terphenyl (15.0 g, 48.51 mmol), bis(pinacolato)diboron (14.8 g, 58.21 mmol), potassium acetate (14.3 g, 145.53 mmol), and [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.2 g, 1.46 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 225 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 (15.1 g, 87.4%).

[0140] Synthesis of intermediate-14

[0141]

[0142] 3,7-dibromo-1,5-naphthyridine (10.0 g, 34.73 mmol), intermediate-13 (13.6 g, 38.20 mmol), potassium carbonate (14.4 g, 104.19 mmol), and tetrakis(triphenylphophine)palladium (2.0 g, 1.74 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 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-14 (11.3 g, 74.4%).

[0143] Synthesis of intermediate-15

[0144]

[0145] Intermediate-14 (11.3 g, 25.84 mmol), bis(pinacolato)diboron (7.9 g, 31.01 mmol), potassium acetate (7.6 g, 77.51 mmol), [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.6 g, 0.78 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 170 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-15 (11.9 g, 95.1%).

[0146] Synthetic Example 6. Synthesis of Compound 85

[0147]

[0148] In a round-bottomed flask were added 2-chloro-4,6-diphenyl-1,3,5-triazine (5.0 g, 18.68 mmol), intermediate-15 (10.0 g, 20.54 mmol), potassium carbonate (7.7 g, 56.03 mmol), and tetrakis(triphenylphophine)palladium (1.1 g, 0.93 mmol), and the mixture was stirred overnight while refluxing 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 under reduced pressure through silica gel and Celite to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 85 (6.8 g, 61.7%).

[0149] Synthesis of intermediate-16

[0150]

[0151] 2-Chloro-4,6-diphenyl-1,3,5-triazine (10.0 g, 37.35 mmol), intermediate-3 (11.6 g, 41.09 mmol), potassium carbonate (15.5 g, 112.06 mmol), and tetrakis(triphenylphophine)palladium (2.2 g, 1.87 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 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-16 (8.2 g, 56.5%).

[0152] Synthesis of intermediate-17

[0153]

[0154] Intermediate-16 (8.2 g, 21.12 mmol), bis(pinacolato)diboron (6.4 g, 25.34 mmol), potassium acetate (6.2 g, 63.36 mmol), [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.5 g, 0.63 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 125 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-17 (8.5 g, 92.5%).

[0155] Synthetic Example 7. Synthesis of Compound 95

[0156]

[0157] Intermediate-14 (7.0 g, 16.01 mmol) and intermediate-17 (7.7 g, 17.61 mmol), potassium carbonate (6.6 g, 48.02 mmol), and tetrakis(triphenylphophine)palladium (0.9 g, 48.02 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 under reduced pressure through silica gel and Celite to obtain a filtrate. The filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 95 (7.9 g, 74.1%).

[0158] Synthesis of intermediate-18

[0159]

[0160] 2-Chloro-4,6-diphenyl-1,3,5-triazine (15.0 g, 56.03 mmol), intermediate-6 (17.4 g, 61.63 mmol), potassium carbonate (23.2 g, 168.09 mmol), and tetrakis(triphenylphophine)palladium (3.2 g, 2.80 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 150 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-18 (12.4 g, 57.0%).

[0161] Synthesis of intermediate-19

[0162]

[0163] Intermediate-18 (12.4 g, 31.94 mmol), bis(pinacolato)diboron (9.7 g, 38.32 mmol), potassium acetate (9.4 g, 95.81 mmol), [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.8 g, 0.96 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-19 (12.7 g, 91.3%).

[0164] Synthetic Example 8. Synthesis of Compound 99

[0165]

[0166] 3-Bromo-1,5-naphthyridin (5.0 g, 23.92 mmol), intermediate-19 (11.5 g, 26.31 mmol), potassium carbonate (9.9 g, 71.75 mmol), and tetrakis(triphenylphophine)palladium (1.4 g, 1.20 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 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 99 (7.1 g, 67.9%).

[0167] Synthesis Example 9. Synthesis of Compound 100

[0168]

[0169] Intermediate-9 (10.0 g, 35.07 mmol), intermediate-19 (16.8 g, 38.58 mmol), potassium carbonate (14.5 g, 105.21 mmol), and tetrakis(triphenylphophine)palladium (2.0 g, 1.75 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 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 under reduced pressure through silica gel and Celite to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 100 (11.0 g, 61.1%).

[0170] Synthesis of intermediate-20

[0171]

[0172] Intermediate-9 (20.0 g, 70.14 mmol), intermediate-10 (25.7 g, 77.16 mmol), potassium carbonate (29.1 g, 210.42 mmol), and tetrakis(triphenylphophine)palladium (4.1 g, 3.51 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-20 (15.2 g, 52.7%).

[0173] Synthesis of intermediate-21

[0174]

[0175] Intermediate-20 (15.2 g, 36.96 mmol), bis(pinacolato)diboron (11.3 g, 44.35 mmol), potassium acetate (10.9 g, 110.87 mmol), [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.9 g, 1.11 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-21 (15.3 g, 90.3%).

[0176] Synthesis Example 10. Synthesis of Compound 108

[0177]

[0178] 2-Chloro-4,6-diphenyl-1,3,5-triazine (8.0 g, 29.88 mmol), intermediate-21 (15.1 g, 32.87 mmol), potassium carbonate (12.4 g, 89.65 mmol), and tetrakis(triphenylphophine)palladium (1.7 g, 1.49 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, 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 108 (10.2 g, 78.0%).

[0179] Synthesis of intermediate-22

[0180]

[0181] 1-Bromo-4-iodonaphthalene (15.0 g, 52.61 mmol), intermediate-17 (25.2 g, 57.87 mmol), potassium carbonate (21.8 g, 157.82 mmol), and tetrakis(triphenylphophine)palladium (3.0 g, 2.63 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-22 (16.9 g, 62.4%).

[0182] Synthesis of intermediate-23

[0183]

[0184] Intermediate-22 (16.9 g, 32.85 mmol), bis(pinacolato)diboron (10.0 g, 39.42 mmol), potassium acetate (9.7 g, 98.56 mmol), [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.8 g, 0.99 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 260 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-23 (17.6 g, 95.4%).

[0185] Synthetic Example 11. Synthesis of Compound 117

[0186]

[0187] 3-Bromo-1,5-naphthyridine (5.0 g, 23.92 mmol), intermediate-23 (14.8 g, 26.31 mmol), potassium carbonate (9.9 g, 71.75 mmol), and tetrakis(triphenylphophine)palladium (1.4 g, 1.20 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 under reduced pressure through silica gel and Celite to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 117 (9.3 g, 69.0%).

[0188] Synthesis Example 12. Synthesis of Compound 118

[0189]

[0190] In a round-bottomed flask were added 3,7-dibromo-1,5-naphthyridine (10.0 g, 35.07 mmol), intermediate-19 (33.6 g, 77.16 mmol), potassium carbonate (19.4 g, 140.28 mmol), and tetrakis(triphenylphophine)palladium (2.8 g, 2.45 mmol), and the mixture was stirred overnight under reflux in 100 mL of 1,4-dioxane and 50 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 under reduced pressure through silica gel and Celite to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 118 (15.2 g, 58.2%).

[0191] Synthesis of intermediate-24

[0192]

[0193] 3-Bromo-1,5-naphthyridine (15.0 g, 71.75 mmol), intermediate-3 (22.3 g, 78.93 mmol), potassium carbonate (29.7 g, 215.26 mmol), and tetrakis(triphenylphophine)palladium (4.1 g, 3.59 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-24 (8.7 g, 47.0%).

[0194] Synthetic Example 13. Synthesis of Compound 119

[0195]

[0196] Intermediate-24 (8.7 g, 33.70 mmol) and intermediate-23 (20.8 g, 37.07 mmol), potassium carbonate (14.0 g, 101.11 mmol), and tetrakis(triphenylphophine)palladium (1.9 g, 1.69 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 90 mL of 1,4-dioxane and 45 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 119 (13.2 g, 61.2%).

[0197] Synthesis of intermediate-25

[0198]

[0199] 1-Bromo-4-iodonaphthalene (15.0 g, 45.05 mmol), intermediate-19 (21.6 g, 49.55 mmol), potassium carbonate (18.7 g, 135.15 mmol), and tetrakis(triphenylphophine)palladium (2.6 g, 2.25 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-25 (16.2 g, 69.9%).

[0200] Synthesis of intermediate-26

[0201]

[0202] 3-Bromo-1,5-naphthyridine (15.0 g, 71.75 mmol), bis(pinacolato)diboron (21.9 g, 86.10 mmol), potassium acetate (21.1 g, 215.26 mmol), and [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.8 g, 2.15 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 225 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-26 (16.8 g, 91.4%).

[0203] Synthesis Example 14. Synthesis of Compound 120

[0204]

[0205] Intermediate-25 (15.0 g, 29.16 mmol) and intermediate-26 (8.2 g, 32.07 mmol), potassium carbonate (12.1 g, 87.48 mmol), and tetrakis(triphenylphophine)palladium (1.7 g, 1.46 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 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 120 (11.4 g, 69.4%).

[0206] Synthesis of intermediate-27

[0207]

[0208] Intermediate-9 (15.0 g, 52.61 mmol), bis(pinacolato)diboron (16.0 g, 63.13 mmol), potassium acetate (15.5 g, 157.82 mmol), [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1.3 g, 1.58 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 225 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 (16.1 g, 62.1%).

[0209] Synthesis of intermediate-28

[0210]

[0211] 2,6-dibromonaphthalene (10.0 g, 34.97 mmol), intermediate-27 (12.8 g, 38.47 mmol), potassium carbonate (14.5 g, 104.91 mmol), and tetrakis(triphenylphophine)palladium (2.0 g, 1.75 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 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 (10.5 g, 73.0%).

[0212] Synthesis of intermediate-29

[0213]

[0214] Intermediate-28 (10.5 g, 25.53 mmol), bis(pinacolato)diboron (7.8 g, 30.63 mmol), potassium acetate (7.5 g, 76.59 mmol), and [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.6 g, 0.77 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 160 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 (11.0 g, 94.0%).

[0215] Synthetic Example 15. Synthesis of Compound 121

[0216]

[0217] In a round-bottomed flask were added 2-chloro-4,6-diphenyl-1,3,5-triazine (6.0 g, 22.41 mmol), intermediate-29 (11.3 g, 24.65 mmol), potassium carbonate (9.3 g, 67.23 mmol), and tetrakis(triphenylphophine)palladium (1.3 g, 1.12 mmol), and the mixture was 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 dissolved in dichlorobenzene, and the filtrate was filtered under reduced pressure through silica gel and Celite to obtain a filtrate. The filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 122 (6.3 g, 49.9%).

[0218] Synthesis Example 16. Synthesis of Compound 122

[0219]

[0220] 2-Bromo-4,6-diphenylpyrimidine (6.0 g, 19.28 mmol), intermediate-29 (9.7 g, 21.21 mmol), potassium carbonate (8.0 g, 57.84 mmol), and tetrakis(triphenylphophine)palladium (1.1 g, 0.96 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 dissolved in dichlorobenzene, and the filtrate was filtered under reduced pressure through silica gel and Celite to obtain a filtrate. The filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 122 (6.3 g, 58.1%).

[0221] Synthesis of intermediate-30

[0222]

[0223] 2-Bromonaphthalene (15.0 g, 72.44 mmol), bis(pinacolato)diboron (22.1 g, 86.93 mmol), potassium acetate (21.3 g, 217.32 mmol), [1,1'-phenylphosphino)ferrocene]dichloropalladium(II) (1.8 g, 2.17 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 225 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-30 (16.8 g, 91.3%).

[0224] Synthesis of intermediate-31

[0225]

[0226] 3,7-dibromo-1,5-naphthyridine (15.0 g, 52.09 mmol), intermediate-30 (14.6 g, 57.30 mmol), potassium carbonate (21.6 g, 156.28 mmol), and tetrakis(triphenylphophine)palladium (3.0 g, 2.60 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 (11.2 g, 64.1%).

[0227] Synthetic Example 17. Synthesis of Compound 123

[0228]

[0229] Intermediate-31 (11.2 g, 33.41 mmol) and intermediate-5 (16.0 g, 36.75 mmol), potassium carbonate (13.9 g, 100.24 mmol), and tetrakis(triphenylphophine)palladium (1.9 g, 1.67 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 120.0 mL of 1,4-dioxane and 60 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 under reduced pressure through silica gel and Celite to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 123 (9.3 g, 47.2%).

[0230] Synthesis of intermediate-32

[0231]

[0232] 1,3-dibromo-5-chlorobenzene (10.0 g, 36.99 mmol), intermediate-26 (20.8 g, 81.38 mmol), potassium carbonate (20.4 g, 147.96 mmol), and tetrakis(triphenylphophine)palladium (3.0 g, 2.59 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 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-32 (10.2 g, 74.8%).

[0233] Synthesis of intermediate-33

[0234]

[0235] Intermediate-32 (10.2 g, 27.66 mmol), bis(pinacolato)diboron (8.4 g, 33.19 mmol), potassium acetate (8.1 g, 82.97 mmol), [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.7 g, 0.83 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 160 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-33 (11.9 g, 93.5%).

[0236] Synthetic Example 18. Synthesis of Compound 124

[0237]

[0238] 2-Bromo-4,6-diphenylpyrimidine (7.0 g, 22.50 mmol), intermediate-33 (11.4 g, 24.74 mmol), potassium carbonate (9.3 g, 67.49 mmol), and tetrakis(triphenylphophine)palladium (1.3 g, 1.12 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 under reduced pressure through silica gel and Celite to obtain a filtrate. The filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 124 (7.2 g, 54.3%).

[0239] Synthetic Example 19. Synthesis of Compound 125

[0240]

[0241] In a round-bottomed flask were added 2-chloro-4,6-diphenyl-1,3,5-triazine (10.0 g, 37.35 mmol), intermediate-33 (18.9 g, 41.09 mmol), potassium carbonate (15.5 g, 112.06 mmol), and tetrakis(triphenylphophine)palladium (2.2 g, 1.87 mmol), and the mixture was stirred overnight under reflux in 100 mL of 1,4-dioxane and 50 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 under reduced pressure through silica gel and Celite to obtain a filtrate. The filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 124 (9.2 g, 41.8%).

[0242] Synthesis of intermediate-34

[0243]

[0244] In a round-bottomed flask were added 1,3-dibromo-5-chlorobenzene (15.0 g, 55.48 mmol), intermediate-27 (40.6 g, 122.06 mmol), potassium carbonate (30.7 g, 221.93 mmol), and tetrakis(triphenylphophine)palladium (4.5 g, 3.88 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 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-34 (14.3 g, 49.5%).

[0245] Synthesis of intermediate-35

[0246]

[0247] Intermediate-34 (14.3 g, 27.45 mmol), bis(pinacolato)diboron (8.4 g, 32.94 mmol), potassium acetate (8.1 g, 82.34 mmol), [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II)(0.7 g, 0.82 mmol) were added to a round-bottomed flask and stirred overnight under reflux in 160 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-35 (13.8 g, 82.1%).

[0248] Synthetic Example 20. Synthesis of Compound 157

[0249]

[0250] 2-Bromo-4,6-diphenylpyrimidine (5.0 g, 16.07 mmol), intermediate-35 (10.8 g, 17.67 mmol), potassium carbonate (6.7 g, 48.20 mmol), and tetrakis(triphenylphophine)palladium (0.9 g, 0.80 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 under reduced pressure through silica gel and Celite to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 157 (6.8 g, 59.0%).

[0251] Synthetic Example 21. Synthesis of Compound 158

[0252]

[0253] In a round-bottomed flask were added 2-chloro-4,6-diphenyl-1,3,5-triazine (5.0 g, 18.68 mmol), intermediate-35 (12.6 g, 20.54 mmol), potassium carbonate (7.7 g, 56.03 mmol), and tetrakis(triphenylphophine)palladium (1.1 g, 0.93 mmol), and the mixture was stirred overnight while refluxing 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 under reduced pressure through silica gel and Celite to obtain a filtrate. The obtained filtrate was concentrated under reduced pressure, dissolved in dichlorobenzene, and recrystallized with acetone to obtain compound 157 (6.8 g, 50.7%).

[0254] Fabrication of organic light-emitting devices: Application to hole-blocking layers

[0255] Comparative Example 1

[0256] After patterning the ITO substrate to have a 2 mm × 2 mm emission area, 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 pressure was adjusted to 1 × 10-7 torr. Afterwards, plasma treatment was performed for 3 minutes under a N2 atmosphere. First, HAT-CN was vacuum-deposited to form a 7 nm thickness. This material served as a hole injection layer. On top of this, NPB material was formed to a 90 nm thickness as a hole transport layer. Then, α,β-AND material was vacuum-deposited to a thickness of 25 nm at a mass ratio of approximately 4% as a host and TPPDA material as a dopant to form a blue emission layer. A BCP compound was formed to a 5 nm thickness as a hole blocking layer on this emission layer, and a Bphen material was formed to a 20 nm thickness as an electron transport layer on this. Afterwards, LiF material was deposited to form an electron injection layer with a thickness of 1 nm. Afterwards, Al was deposited with a thickness of 100 nm to form a cathode, and an organic EL device was manufactured. The HAT-CN, NPB, α,β-ADN, TPPDA, BCP, and Bphen used previously are respectively shown in Table 1 below.

[0257] [Table 1]

[0258]

[0259] Comparative Examples 2 and 3

[0260] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Comparative Compounds 1 and 2 shown in Table 2 below were used instead of BCP as a hole-blocking layer.

[0261] [Table 2]

[0262]

[0263] Examples 1 to 21

[0264] 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 21 were used instead of BCP as the hole-blocking layer.

[0265] Experimental Example 1. Evaluation of Organic Light-Emitting Diodes: Application to Hole-Blocking Layers

[0266] The operating voltage, current efficiency, and lifespan of the previously fabricated organic light-emitting device were evaluated. The evaluation results are shown in Table 3 below.

[0267] [Table 3]

[0268]

[0269] As can be seen from the results in Table 3 above, examples using the compounds of the present invention as a hole blocking layer showed lower driving voltage and improved current efficiency and lifespan than comparative examples using comparative compounds as a hole blocking layer.

[0270] Fabrication of organic light-emitting devices: Application to electron transport layers

[0271] Comparative Examples 4 and 5

[0272] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Comparative Compounds 1 and 2 shown in Table 2 were used instead of Bphen as the electron transport layer.

[0273] Examples 22 to 42

[0274] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds synthesized in Synthetic Examples 1 to 21 were used instead of Bphen as the electron transport layer.

[0275] Experimental Example 2. Evaluation of Organic Light-Emitting Devices: Application to the Electron Transport Layer

[0276] The operating voltage, current efficiency, and lifespan of the previously fabricated organic light-emitting device were evaluated. The evaluation results are shown in Table 4 below.

[0277] [Table 4]

[0278]

[0279] As shown in Table 4 above, examples in which the compounds of the present invention were applied to the electron transport layer showed lower operating voltage and improved current efficiency and lifespan compared to the comparative examples.

[0280] As can be seen from Tables 3 and 4, in the case of the compounds of the present invention in which a heterocyclic ring containing N is introduced compared to Comparative Compound 1, electron mobility increases, thereby increasing electron transport capability. Accordingly, when applied as a hole blocking layer or electron transport layer of an organic light-emitting device, low voltage, efficiency, and lifespan can be improved. In addition, it can be seen that, compared to Comparative Compound 2, the heterocyclic ring containing N is bonded to the 3-position of 1,5-naphthyridine, which is preferable for the performance of the organic light-emitting device.

[0281] The novel compound of the present invention is characterized by having a structure in which an N-containing heterocyclic ring is bonded to the 3-position of 1,5-naphthyridine. The N-containing heterocyclic ring containing at least one nitrogen atom N has the characteristic of increasing electron mobility due to the strong nucleophilicity of the nitrogen atom, 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 has excellent electron transport capability, and also has excellent durability due to its rigid structure. Therefore, the compound of the present invention combining these has the advantage of easy electron transport due to characteristics such as excellent electron mobility and strong nucleophilicity, and can be applied to an electron transport layer, a hole blocking layer, or a charge generation 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 N-containing heterocyclic ring, 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, 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 Selected from the group consisting of an 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.

2. In paragraph 1, A novel compound characterized in that the chemical formula 1 above is the following chemical formula 2 or chemical formula 3: In the above chemical formulas 2 and 3, Ar1, Ar2, L1 and L2 have the same definitions as in the above chemical formula 1.

3. In paragraph 2, The above chemical formula 3 is a novel compound characterized by the following chemical formula 4: In the above chemical formula 4, Ar1, Ar2 and L2 are the same as defined in the above chemical formula 1, X1 to X3 are each independently N or CH, L3 is a direct bond, a substituted or unsubstituted C6~C30 arylene group, or a substituted or unsubstituted C2~C30 heteroarylene group.

4. In paragraph 1, A novel compound characterized in that the above Ar1 is one selected from the following structural formulas A-1 to A-5: In the above structural formulas A-1 to A-5, R1 is independently any one substituent selected from the group consisting of hydrogen, deuterium, halogen, 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, n is an integer from 0 to 4, each independently.

5. In paragraph 4, A novel compound characterized in that the above n is 1 or 2, and at this time, R1 is each independently any one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyrazine group, a substituted or unsubstituted pyridazine group, and a substituted or unsubstituted triazine group.

6. In paragraph 1, A novel compound characterized in that the above Ar2 is hydrogen or one selected from the following structural formulas B-1 to B-50:

7. In paragraph 1, The above compound is a novel compound characterized in that it is selected from compounds consisting of compounds 1 to 159 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 is an electron transport layer, a hole blocking layer, or a charge generation layer.

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