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 can be used for a first electrode and a second electrode, one or more organic material layers disposed between the first electrode and the second electrode, an electron transport layer, a hole blocking layer, or a charge generation layer. According to the present invention, a low voltage, high efficiency, and a long lifespan of the organic light emitting device can be realized.

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] X1 to X4 are each independently N or CR2, and at least three are N,

[0010] Y1 to Y4 are each independently N or CR3, and at least three are N,

[0011] Ar1 and Ar2 are each independently deuterium, halogen, 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 C1~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,

[0012] R1 is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano group, nitro group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted heterocycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted sulfide group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted amine group, substituted or unsubstituted arylsilyl group, and substituted or unsubstituted arylphosphine oxide group, wherein the total sum of carbon atoms is 18 or less,

[0013] R2 and R3 are each independently hydrogen, deuterium, halogen, 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 C1~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, wherein adjacent R2s or adjacent R3s may or may not combine with each other to form a ring,

[0014] l is an integer from 0 to 4, and m and n are each independently integers from 0 to 3.

[0015] 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 to realize an organic light-emitting device with high efficiency and long lifespan.

[0016] 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.

[0017] 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.

[0018] In this specification, examples of substituents are described below, but are not limited thereto.

[0019] 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.

[0020] 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 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 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.

[0021] 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.

[0022] 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, etc.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] In the chemical formula or structural formula in this specification, * or indicates the binding position.

[0027] The novel compound of the present invention is described below.

[0028] The novel compound according to the present invention is represented by the following chemical formula 1.

[0029]

[0030] In the above chemical formula 1,

[0031] X1 to X4 are each independently N or CR2, and at least three are N,

[0032] Y1 to Y4 are each independently N or CR3, and at least three are N,

[0033] Ar1 and Ar2 are each independently deuterium, halogen, 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 C1~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,

[0034] R1 is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano group, nitro group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted heterocycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted sulfide group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted amine group, substituted or unsubstituted arylsilyl group, and substituted or unsubstituted arylphosphine oxide group, wherein the total sum of carbon atoms is 18 or less,

[0035] R2 and R3 are each independently hydrogen, deuterium, halogen, 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 C1~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, wherein adjacent R2s or adjacent R3s may or may not combine with each other to form a ring,

[0036] l is an integer from 0 to 4, and m and n are each independently integers from 0 to 3.

[0037] The compound of the present invention has a structural characteristic in which at least three of the four carbon atoms positioned facing each other in each biphenyl are nitrogen (N) based on a structure in which two biphenyls are meta-bonded with phenylene in between, as shown in Chemical Formula 1. The novel compound of the present invention has a characteristic in which electron mobility increases due to the strong nucleophilicity of the nitrogen atom, and has a characteristic in which electron transfer characteristics are improved by aligning the molecules in one direction by varying the orientation of the molecules in which they are stacked, thereby making it suitable for application to an electron transport layer, a hole blocking layer, or a charge generation layer of an organic light-emitting device.

[0038] According to one embodiment of the present invention, the chemical formula 1 may be selected from the following chemical formulas A-1 to A-6.

[0039] In the above chemical formulas A-1 to A-6, Ar1, Ar2, R1 to R3, l, m and n may have the same definitions as in the above chemical formula 1. Among the above chemical formulas, chemical formula A-1 or chemical formula A-4 may be most preferable.

[0040] According to another embodiment of the present invention, the chemical formula 1 may be selected from the following chemical formulas B-1 to B-9. That is, adjacent R2s and adjacent R3s may be bonded to form a benzene ring.

[0041]

[0042]

[0043]

[0044] In the above chemical formulas B-1 to B-9, Ar1, Ar2, R1 and l are the same as defined in the above chemical formula 1,

[0045] R4 and R5 are each independently hydrogen, deuterium, halogen, 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 C1~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, wherein adjacent R4s or adjacent R5s may or may not combine with each other to form a ring,

[0046] o and p can each independently be an integer from 0 to 5.

[0047] Among the above chemical formulas, chemical formula B-3, chemical formula B-4 or chemical formula B-7 may be most preferable.

[0048] According to another embodiment of the present invention, the chemical formula 1 may be selected from among the following chemical formulas C-1 to C-7. That is, adjacent R2s may not bond to each other, and only adjacent R3s may bond to each other to form a benzene ring.

[0049]

[0050]

[0051] In the above chemical formulas C-1 to C-7, Ar1, Ar2, R1, R2, l and m are the same as defined in the above chemical formula 1,

[0052] R5 is each independently hydrogen, deuterium, halogen, 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 C1~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, wherein adjacent R5 groups may or may not combine with each other to form a ring,

[0053] p can be an integer from 0 to 5.

[0054] Among the above chemical formulas, chemical formula C-5 may be the most preferable.

[0055] Meanwhile, specifically, Ar1 and Ar2 may each independently be a substituted or unsubstituted C1~C30 alkyl group, a substituted or unsubstituted C6~C30 aryl group, a substituted or unsubstituted C2~C30 heteroaryl group, or a substituted or unsubstituted C6~C30 amine group. More specifically, they may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, or a substituted or unsubstituted arylamine group. According to one embodiment, it may be formed of one or a combination of two or more of phenyl, naphthyl, pyridine, pyrimidine, and triazine. Ar1 and Ar2 may be the same as or different from each other.

[0056] According to one embodiment, Ar1 and Ar2 can each be independently selected from the structural formulas Ar-1 to Ar-33.

[0057]

[0058]

[0059]

[0060] Meanwhile, l may be 0 or 1, which may be preferable in that it can control the HOMO and LUMO energy levels and lower the operating voltage due to this characteristic. And when l is 1, R1 may be a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group having a total sum of carbon atoms of 18 or less. Specifically, it may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, or a substituted or unsubstituted triazine group having a total sum of carbon atoms of 18 or less and not including a condensed ring. Furthermore, it may be composed of one or a combination of two or more of a phenyl group, a pyridine group, a pyrimidine group, and a triazine group.

[0061] In one embodiment, when l is 1, R1 may be selected from the structural formulas R1-1 to R1-5 below, and R1-1, i.e., a phenyl group, may be most preferable in terms of improving electron transfer properties by having low reorganization energy.

[0062]

[0063] Meanwhile, it may be desirable for the binding position of R1 to be meta, as shown in Chemical Formula 1-1 below. This is because it has the advantage of increasing efficiency by having high triplet energy.

[0064]

[0065] In the above chemical formula 1-1, Ar1, Ar2, R1 to R3, m and n may be the same as defined in the above chemical formula 1.

[0066] According to one embodiment of the present invention, the novel compound of the present invention may be selected from compounds consisting of compounds 1 to 120 below.

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] 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.

[0077] Below, the organic light-emitting device is described in more detail.

[0078] 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.

[0079] The hole injection layer (HIL) is a layer that injects holes from an electrode. As the hole injection material, 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 is preferable.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] 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.

[0085] 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.

[0086] Meanwhile, the composition of the organic light-emitting device can vary. For example, it can be in a tandem form in which two or more light-emitting layers (or light-emitting units) are provided, and 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.

[0087] 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 as a host material of an N-type charge generation layer.

[0088] 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.

[0089] The present invention is described in more detail below through synthetic examples, embodiments, and experimental examples.

[0090] [Synthesis Example 1] Synthesis of Compound 1

[0091]

[0092] 2,6-dibromo-4-phenylpyridine (20 g, 63.90 mmol) and copper(I) cyanide (5.72 g, 63.90 mmol) were added to a 500-ml round-bottom flask. The mixture was stirred under reflux in 200 ml of dimethylformamide for 17 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 1-1 (5.5 g, 33%) was obtained by purification and recrystallization using column chromatography.

[0093]

[0094] Compound 1-1 (10 g, 38.60 mmol), Hydroxylamine hydrochloride (1.34 g, 19.3 mmol), and sodium methoxide (2.09 g, 38.60 mmol) were added to a 250 ml round bottom flask. The mixture was stirred under reflux in 100 ml of MeOH for 24 hours. After the reaction was completed, the mixture was dispersed with ethyl acetate and a 10% aqueous sodium hydroxide solution, and extracted with ethyl acetate. After washing with H2O, the mixture was dried over MgSO4, filtered, concentrated, and dissolved again in ethanol. 1 g of Raney nickel was added, and the mixture was stirred under reflux for 15 hours. After the reaction was completed, the mixture was filtered to remove the catalyst, concentrated, and purified by column chromatography to obtain compound 1-2 (5 g, 47%).

[0095]

[0096] Compound 1-2 (10 g, 36.20 mmol) and 1,2,3-triazine (2.35 g, 29.00 mmol) were added to a 250 ml round-bottom flask. 100 ml of 1,4-dioxane was added, stirred at room temperature, and then refluxed at 60°C for 2 hours. Upon completion of the reaction, the mixture was concentrated, purified by column chromatography, and recrystallized to obtain compound 1-3 (10.3 g, 91%).

[0097] 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (10 g, 30.30 mmol) and compound 1-3 (20.80 g, 66.70 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.05 g, 0.90 mmol) and calcium carbonate (12.56 g, 90.90 mmol) were added, and the mixture was stirred under reflux for 10 hours in a mixed solution of 100 ml of 1,4-dioxane and 30 ml of H2O. After the reaction was completed, the mixture was cooled to room temperature, filtered, and dried. Compound 1 (11.5 g, 70%) was obtained through purification and recrystallization by column chromatography.

[0098] [Synthesis Example 2] Synthesis of Compound 2

[0099]

[0100] Compound 1-2 (10 g, 36.20 mmol) and benzo[d][1,2,3]triazine (3.80 g, 29.00 mmol) were added to a 250 ml round-bottom flask. 100 ml of 1,4-dioxane was added, stirred at room temperature, and then refluxed at 60°C for 2 hours. After the reaction was complete, the mixture was concentrated, purified by column chromatography, and recrystallized to obtain compound 2-3 (11.2 g, 83%).

[0101]

[0102] 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (10 g, 30.30 mmol) and compound 2-3 (24.15 g, 66.70 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.05 g, 0.90 mmol) and calcium carbonate (12.56 g, 90.90 mmol) were added, and the mixture was stirred under reflux for 10 hours in a mixed solution of 100 ml of 1,4-dioxane and 30 ml of H2O. After the reaction was completed, the mixture was cooled to room temperature, filtered, and dried. Compound 2 (14 g, 72%) was obtained through purification and recrystallization by column chromatography.

[0103] [Synthesis Example 3] Synthesis of Compound 11

[0104]

[0105] 4'-(2,6-dibromopyridin-4-yl)-3,2':6',3''-terpyridine (30 g, 64.10 mmol) and copper(I) cyanide (5.72 g, 63.90 mmol) were added to a 500-ml round-bottom flask. The mixture was stirred under reflux in 200 ml of dimethylformamide for 17 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 11-1 (6 g, 22.6%) was obtained through purification and recrystallization by column chromatography.

[0106]

[0107] Compound 11-1 (16 g, 38.60 mmol), Hydroxylamine hydrochloride (1.34 g, 19.3 mmol), and sodium methoxide (2.09 g, 38.60 mmol) were added to a 250 ml round bottom flask. The mixture was stirred under reflux in 100 ml of MeOH for 24 hours. After the reaction was completed, the mixture was dispersed with ethyl acetate and a 10% aqueous sodium hydroxide solution, and extracted with ethyl acetate. After washing with H2O, the mixture was dried over MgSO4, filtered, concentrated, and dissolved again in ethanol. 1 g of Raney nickel was added, and the mixture was stirred under reflux for 15 hours. After the reaction was completed, the mixture was filtered to remove the catalyst, concentrated, and purified by column chromatography to obtain compound 11-2 (8 g, 48%).

[0108]

[0109] Compound 11-2 (10 g, 23.20 mmol) and benzo[d][1,2,3]triazine (2.40 g, 18.50 mmol) were added to a 250 ml round-bottomed flask. 100 ml of 1,4-dioxane was added, stirred at room temperature, and then refluxed at 60°C for 2 hours. After the reaction was complete, the mixture was concentrated, purified by column chromatography, and recrystallized to obtain compound 11-3 (8.5 g, 70.8%).

[0110] 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (10 g, 30.30 mmol) and compound 11-3 (34.49 g, 66.70 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (1.05 g, 0.90 mmol) and calcium carbonate (12.56 g, 90.90 mmol) were added, and the mixture was stirred under reflux for 10 hours in a mixed solution of 100 ml of 1,4-dioxane and 30 ml of H2O. After the reaction was completed, the mixture was cooled to room temperature, filtered, and dried. Compound 11 (15.5 g, 53.8%) was obtained through purification and recrystallization by column chromatography.

[0111] [Synthesis Example 4] Synthesis of Compound 38

[0112]

[0113] 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (10 g, 24.60 mmol) and compound 1-3 (16.91 g, 54.20 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (0.85 g, 0.70 mmol) and calcium carbonate (10.20 g, 73.90 mmol) were added, and the mixture was stirred under reflux for 10 hours in a mixed solution of 100 ml of 1,4-dioxane and 30 ml of H2O. After the reaction was completed, the mixture was cooled to room temperature, filtered, and dried. Compound 38 (13 g, 85%) was obtained through purification and recrystallization by column chromatography.

[0114] [Synthesis Example 5] Synthesis of Compound 42

[0115]

[0116]

[0117] 2-(3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (10 g, 17.80 mmol) and compounds 1-3 (12.24 g, 39.20 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (0.62 g, 0.50 mmol) and calcium carbonate (7.39 g, 53.40 mmol) were added, and the mixture was stirred under reflux for 10 hours in a mixed solution of 100 ml of 1,4-dioxane and 30 ml of H2O. After the reaction was completed, the mixture was cooled to room temperature, filtered, and dried. Compound 42 (8.2 g, 59.63%) was obtained through purification and recrystallization by column chromatography.

[0118] [Synthesis Example 6] Synthesis of Compound 43

[0119]

[0120] 3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl (10 g, 24.60 mmol) and compound 2-3 (19.62 g, 54.20 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (0.85 g, 0.70 mmol) and calcium carbonate (10.20 g, 73.90 mmol) were added, and the mixture was stirred under reflux for 10 hours in a mixed solution of 100 ml of 1,4-dioxane and 30 ml of H2O. After the reaction was completed, the mixture was cooled to room temperature, filtered, and dried. Compound 43 (12 g, 67.98%) was obtained through purification and recrystallization by column chromatography.

[0121] [Synthesis Example 7] Synthesis of Compound 46

[0122]

[0123]

[0124] 2-(3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (10 g, 17.80 mmol) and compound 2-3 (14.2 g, 39.20 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (0.62 g, 0.50 mmol) and calcium carbonate (7.39 g, 53.40 mmol) were added, and the mixture was stirred under reflux for 10 hours in a mixed solution of 100 ml of 1,4-Dioxane and 30 ml of H2O. After the reaction was completed, the mixture was cooled to room temperature, filtered, and dried. Compound 46 (10 g, 64.37%) was obtained through purification and recrystallization by column chromatography.

[0125] [Synthesis Example 8] Synthesis of Compound 53

[0126]

[0127] 2,6-dibromo-4-(naphthalen-2-yl)pyridine (20 g, 55.10 mmol) and copper(I) cyanide (4.94 g, 55.10 mmol) were added to a 500-ml round-bottom flask. The mixture was stirred under reflux in 200 ml of dimethylformamide for 17 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 53-1 (6 g, 35%) was obtained by purification and recrystallization using column chromatography.

[0128]

[0129] Compound 53-1 (10 g, 32.30 mmol), Hydroxylamine hydrochloride (1.1 g, 16.2 mmol), and sodium methoxide (1.75 g, 32.30 mmol) were added to a 250 ml round bottom flask. The mixture was stirred under reflux in 100 ml of MeOH for 24 hours. After the reaction was completed, the mixture was dispersed with ethyl acetate and a 10% aqueous sodium hydroxide solution, and extracted with ethyl acetate. After washing with H2O, the mixture was dried over MgSO4, filtered, concentrated, and dissolved again in ethanol. 1 g of Raney nickel was added, and the mixture was stirred under reflux for 15 hours. After the reaction was completed, the mixture was filtered to remove the catalyst, concentrated, and purified by column chromatography to obtain compound 53-2 (6 g, 56%).

[0130]

[0131] Compound 53-2 (10 g, 36.20 mmol) and benzo[d][1,2,3]triazine (3.20 g, 24.50 mmol) were added to a 250 ml round-bottom flask. 100 ml of 1,4-dioxane was added, stirred at room temperature, and then refluxed at 60°C for 2 hours. After the reaction was complete, the mixture was concentrated, purified by column chromatography, and recrystallized to obtain compound 53-3 (11.5 g, 90%).

[0132]

[0133] 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (10 g, 24.60 mmol) and compound 53-3 (22.33 g, 54.20 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (0.85 g, 0.70 mmol) and calcium carbonate (10.20 g, 73.90 mmol) were added, and the mixture was stirred under reflux for 10 hours in a mixed solution of 100 ml of 1,4-dioxane and 30 ml of H2O. After the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 53 (16.5 g, 82%) was obtained through purification and recrystallization by column chromatography.

[0134] [Synthesis Example 9] Synthesis of Compound 83

[0135]

[0136] 4,6-dibromo-2-(pyridin-2-yl)pyrimidine (20 g, 63.50 mmol) and phenylboronic acid (7.74 g, 63.50 mmol) were added to a 250 ml round-bottomed flask. Pd(PPh3)4 (2.2 g, 1.90 mmol) and calcium carbonate (26.30 g, 190.50 mmol) were added, and the mixture was stirred under reflux for 5 hours in a mixed solution of 200 ml of 1,4-dioxane and 60 ml of H2O. After the reaction was complete, the mixture was cooled to room temperature, filtered, and dried. Compound 83-1 (15 g, 75.6%) was obtained through purification and recrystallization by column chromatography.

[0137]

[0138] 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (10 g, 24.60 mmol) and compound 83-1 (16.90 g, 54.20 mmol) were added to a 250 ml round-bottom flask. Pd(PPh3)4 (0.85 g, 0.70 mmol) and calcium carbonate (10.20 g, 73.90 mmol) were added, and the mixture was stirred under reflux for 10 hours in a mixed solution of 100 ml of 1,4-dioxane and 30 ml of H2O. After the reaction was completed, the mixture was cooled to room temperature, filtered, and dried. Compound 83 (12 g, 79%) was obtained through purification and recrystallization by column chromatography.

[0139] Fabrication of organic light-emitting devices: Application to electron transport layers

[0140] [Comparison Example 1]

[0141] After patterning the ITO substrate to have a light-emitting area of ​​2 mm Х 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 1 Х 10 -7The pressure was set to 10 torr. Afterwards, plasma treatment was performed for 3 minutes under a N2 atmosphere. First, the HAT-CN compound was vacuum-deposited to form a hole injection layer with a thickness of 7 nm. On top of this, the NPB material was formed as a hole transport layer with a thickness of 90 nm. Then, the α,β-ADN material was used as a host and the TPPDA material was used as a dopant at a mass ratio of approximately 4%, and vacuum-deposited to a thickness of 25 nm to form a blue light-emitting layer. On this light-emitting layer, the BCP compound was deposited to a thickness of 5 nm to form a hole blocking layer. On top of this, the Bphen material was formed as an electron transport layer with a thickness of 20 nm. Afterwards, the LiF material was deposited to form an electron injection layer with a thickness of 1 nm. Finally, Al was deposited to a thickness of 100 nm to form a cathode, manufacturing an organic light-emitting device. The HAT-CN, NPB, α,β-AND, TPPDA, BCP, and BPhen used previously are shown in Table 1 below.

[0142] [Table 1]

[0143]

[0144] [Comparative Examples 2 to 5]

[0145] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that each of Comparative Compounds 1 to 4 shown in Table 2 below was used instead of BPhen as the electron transport layer.

[0146] [Table 2]

[0147]

[0148] [Examples 1 to 9]

[0149] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds of the present invention synthesized in Synthesis Examples 1 to 9 were used instead of BPhen as the electron transport layer.

[0150] [Experimental Example 1] Evaluation of Organic Light-Emitting Devices: Application to the Electron Transport Layer

[0151] The driving voltage, current efficiency, and lifespan of the organic light-emitting devices of Comparative Examples 1 to 5 and Examples 1 to 9 previously manufactured were evaluated, respectively. The evaluation results are shown in Table 3 below.

[0152] [Table 3]

[0153]

[0154] As shown in the results of Table 3 above, it was confirmed that examples using the compounds of the present invention as an electron transport layer exhibited lower voltage, higher efficiency, and longer lifespan than comparative examples.

[0155] Fabrication of organic light-emitting devices: Application to hole-blocking layers

[0156] [Comparative Examples 6 to 9]

[0157] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Comparative Compounds 1 to 4 of Table 2 were used instead of BCP as the hole-blocking layer.

[0158] [Examples 10 to 18]

[0159] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds of the present invention synthesized in Synthesis Examples 1 to 9 were used instead of BCP as the hole-blocking layer.

[0160] [Experimental Example 2] Evaluation of Organic Light-Emitting Devices: Application to Hole-Blocking Layers

[0161] The driving voltage, current efficiency, and lifespan of the organic light-emitting devices of Comparative Examples 1, 6 to 9 and Examples 10 to 18 produced previously were evaluated, respectively. The evaluation results are shown in Table 4 below.

[0162] [Table 4]

[0163]

[0164] As shown in the results of Table 4 above, it was confirmed that examples using the compounds of the present invention as a hole-blocking layer exhibited lower voltage, higher efficiency, and longer lifespan than comparative examples.

[0165] The compound of the present invention has a structural characteristic in which two biphenyls are meta-bonded with phenylene in between, and at least three of the four carbons positioned facing each other in each biphenyl are nitrogen (N). The novel compound of the present invention has a characteristic in which electron mobility increases due to the strong nucleophilicity of the nitrogen atom, and has a characteristic in which electron transfer characteristics are improved by aligning the molecules in one direction by varying the stacking orientation of the molecules, thereby making it suitable for application 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, X1 to X4 are each independently N or CR2, and at least three are N, Y1 to Y4 are each independently N or CR3, and at least three are N, Ar1 and Ar2 are each independently deuterium, halogen, 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 C1~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, R1 is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano group, nitro group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted heterocycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted sulfide group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted amine group, substituted or unsubstituted arylsilyl group, and substituted or unsubstituted arylphosphine oxide group, wherein the total sum of carbon atoms is 18 or less, R2 and R3 are each independently hydrogen, deuterium, halogen, 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 C1~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, wherein adjacent R2s or adjacent R3s may or may not combine with each other to form a ring, l is an integer from 0 to 4, m and n are each independently integers from 0 to 3.

2. In paragraph 1, The above chemical formula 1 is a novel compound characterized by being selected from the following chemical formulas A-1 to A-6: In the above chemical formulas A-1 to A-6, Ar1, Ar2, R1 to R3, l, m and n are the same as defined in the above chemical formula 1.

3. In paragraph 1, The above chemical formula 1 is a novel compound characterized by being selected from the following chemical formulas B-1 to B-9: In the above chemical formulas B-1 to B-9, Ar1, Ar2, R1 and l are the same as defined in the above chemical formula 1, R4 and R5 are each independently hydrogen, deuterium, halogen, 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 C1~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, wherein adjacent R4s or adjacent R5s may or may not combine with each other to form a ring, o and p are each independently integers from 0 to 5.

4. In paragraph 1, The above chemical formula 1 is a novel compound characterized by being selected from the following chemical formulas C-1 to C-7: In the above chemical formulas C-1 to C-7, Ar1, Ar2, R1, R2, l and m are the same as defined in the above chemical formula 1, R5 is each independently hydrogen, deuterium, halogen, 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 C1~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, wherein adjacent R5 groups may or may not combine with each other to form a ring, p is an integer from 0 to 5.

5. In paragraph 1, A novel compound, characterized in that the above Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, or a substituted or unsubstituted arylamine group.

6. In paragraph 5, A novel compound characterized in that the above Ar1 and Ar2 are each independently selected from the following structural formulas Ar-1 to Ar-33:

7. In paragraph 1, The above l is 0 or 1, A novel compound, characterized in that when l is 1, R1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, or a substituted or unsubstituted triazine group.

8. In paragraph 7, A novel compound characterized in that the above R1 is selected from the following structural formulas R1-1 to R1-5:

9. In paragraph 1, The above compound is a novel compound characterized in that it is selected from compounds consisting of compounds 1 to 120 below:

10. 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 9.

11. In paragraph 10, An organic light-emitting device, characterized in that the organic layer containing the novel compound is an electron transport layer, a hole blocking layer, or a charge generation layer.

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