Compound and organic light emitting device comprising the same

Abstract

The present specification relates to a compound of Formula 1 and an organic light-emitting device containing the same.

Description

Technology Field

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0150773 filed with the Korean Intellectual Property Office on November 11, 2022, the entire contents of which are incorporated herein.

[0002] This specification relates to a compound and an organic light-emitting device containing the same. Background Technology

[0003] In this specification, an organic light-emitting device refers to a light-emitting device utilizing an organic semiconductor material, which requires the exchange of holes and / or electrons between an electrode and an organic semiconductor material. Organic light-emitting devices can be broadly classified into two types based on their operating principles as follows. The first is a light-emitting device in which excitons are formed in an organic layer by photons introduced into the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are each transferred to different electrodes to be used as current sources (voltage sources). The second is a light-emitting device in which holes and / or electrons are injected into an organic semiconductor material layer forming an interface with the electrodes by applying voltage or current to two or more electrodes, and the device operates based on the injected electrons and holes.

[0004] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) that utilize this phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the OLED; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron suppression layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall back to the ground state. Such OLEDs are known to possess characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, a wide viewing angle, and high contrast.

[0005] Materials used as organic layers in organic light-emitting diodes can be classified according to their function into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, and electron injection materials. Light-emitting materials are classified according to their emission color into blue, green, and red light-emitting materials, as well as yellow and orange light-emitting materials necessary to achieve better natural colors.

[0006] In addition, a host / dopant system can be used as a light-emitting material to increase color purity and luminous efficiency through energy transfer. The principle is that when a small amount of a dopant, which has a smaller energy band gap and superior luminous efficiency than the host that mainly constitutes the light-emitting layer, is mixed into the light-emitting layer, excitons generated from the host are transported to the dopant to emit high-efficiency light. At this time, since the wavelength of the host shifts to the wavelength range of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used.

[0007] In order to fully exhibit the excellent characteristics of the aforementioned organic light-emitting diode, the materials forming the organic layer within the device, such as hole injection materials, hole transport materials, light-emitting materials, electron suppression materials, electron transport materials, and electron injection materials, must be supported by stable and efficient materials, so the development of new materials is continuously required. Prior art literature

[0008] International Patent Publication No. 2017-126443 The problem to be solved

[0009] The present specification describes a compound and an organic light-emitting device containing the same. means of solving the problem

[0010] One embodiment of the present specification provides a compound of the following chemical formula 1.

[0011] [Chemical Formula 1]

[0012]

[0013] In the above chemical formula 1,

[0014] Y1 and Y2 are equal to or different from each other, and each is independently O or S, and

[0015] Q1 and Q2 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and

[0016] At least 2 of X1 to X5 are N, and the remainder that are not N are equal to or different from each other, and each is independently CR, and

[0017] Two or more of X6 to X10 are N, and the remainder that are not N are equal to or different from one another, and each is independently CR, and

[0018] R may be the same or different from one another, and each independently may be hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may combine with an adjacent substituent to form a substituted or unsubstituted ring, and

[0019] L1 and L2 are the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, and

[0020] When a is 1 to 3 and a is 2 or more, Q1 are equal to or different from each other, and

[0021] b is 1 to 7, and when b is 2 or more, Q2 are equal or different.

[0022] In addition, according to one embodiment of the present invention, an organic light-emitting device is provided comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprises the aforementioned compound. Effects of the invention

[0023] The compound of the present invention can be used as a material for the organic layer of an organic light-emitting device. When an organic light-emitting device is manufactured including the compound of the present invention, an organic light-emitting device having high efficiency, low voltage, and long lifespan characteristics can be obtained. Furthermore, when the compound of the present invention is included in the electron injection layer, electron transport layer, and electron injection and transport layer of the organic light-emitting device, an organic light-emitting device having long lifespan characteristics can be manufactured.

[0024] The compound of the present invention is substituted with two or more heterocycles containing an N-containing six-membered ring having electron transport properties, and the substituents are adjacent to each other at ortho positions, so that structural distortion occurs and electron transport ability can be varied. Brief explanation of the drawing

[0025] Figures 1 and 2 illustrate examples of organic light-emitting devices according to the present invention. Specific details for implementing the invention

[0026] The present specification will be described in more detail below.

[0027] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0028] 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.

[0029] Examples of substituents in this specification are described below, but are not limited thereto.

[0030] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0031] In this specification, the term “substituted or unsubstituted” means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group (-CN); silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; and substituted or unsubstituted heteroaryl group, or substituted with a substituent in which two or more of the exemplified substituents are connected, or not having any substituents. For example, “a substituent in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

[0032] Examples of the above substituents are described below, but are not limited thereto.

[0033] In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0034] In the present specification, the silyl group may be substituted or unsubstituted with deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, etc. Specifically, the silyl group includes, but is not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0035] In the present specification, the boron group may be substituted or unsubstituted with deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specifically, the boron group may be a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, etc., but is not limited thereto.

[0036] In the present specification, the alkyl group may be a straight chain or a branched chain, and while the number of carbon atoms is not particularly limited, it is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of alkyl groups include, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto.

[0037] In this specification, the amine group may be selected from the group consisting of -NH2; alkylamine group; N-alkylarylamine group; arylamine group; N-arylheteroarylamine group; N-alkylheteroarylamine group; and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine group; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; naphthylamine group; biphenylamine group; anthracenylamine group; 9-methylanthracenylamine group; diphenylamine group; ditolylamine group; N-phenyltolylamine group; triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, etc., are included, but are not limited thereto.

[0038] In this specification, an N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted on N of the amine group.

[0039] In this specification, the N-aryl heteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted on N of the amine group.

[0040] In this specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted on N of the amine group.

[0041] In this specification, the alkyl groups among the alkylamine groups, N-arylalkylamine groups, alkylthioxy groups, alkyl sulfoxy groups, and N-alkylheteroarylamine groups are the same as the examples of alkyl groups described above. Specifically, alkylthioxy groups include methylthioxy groups; ethylthioxy groups; tert-butylthioxy groups; hexylthioxy groups; octylthioxy groups, etc., and alkyl sulfoxy groups include methyl sulfoxy groups; ethyl sulfoxy groups; propyl sulfoxy groups; butyl sulfoxy groups, etc., but are not limited thereto.

[0042] In the present specification, the cycloalkyl group is not particularly limited, but it is preferable that it has 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, etc., are included but are not limited thereto.

[0043] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. As a polycyclic aryl group, the aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylene group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

[0044] In the present specification, the heteroaryl group is a ring group comprising one or more heteroatoms N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heteroaryl group is 2 to 30. Examples of heteroaryl groups include, but are not limited to, pyridine groups, pyrrole groups, pyrimidine groups, pyridazinyl groups, furan groups, thiophene groups, imidazole groups, pyrazol groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, etc.

[0045] In the present specification, the above chemical formula 1 is any one of the following chemical formulas 1-1 to 1-4.

[0046] [Chemical Formula 1-1]

[0047]

[0048] [Chemical Formula 1-2]

[0049]

[0050] [Chemical Formula 1-3]

[0051]

[0052] [Chemical Formula 1-4]

[0053]

[0054] In the above chemical formulas 1-1 to 1-4, X1 to X10, Y1, Y2, L1, L2, Q1, Q2, a and b are as defined in the above chemical formula 1.

[0055] In the present specification, the above chemical formula 1 is the following chemical formula 1-1-1 or 1-1-2.

[0056] [Chemical Formula 1-1-1]

[0057]

[0058] [Chemical Formula 1-1-2]

[0059]

[0060] In the above chemical formulas 1-1-1 and 1-1-2, X1 to X10, L1, L2, Q1, Q2, a and b are as defined in the above chemical formula 1.

[0061] In the present specification, the above chemical formula 1 is the following chemical formula 1-1-3 or 1-1-4.

[0062] [Chemical Formula 1-1-3]

[0063]

[0064] [Chemical Formula 1-1-4]

[0065]

[0066] In the above chemical formulas 1-1-3 and 1-1-4, X1 to X10, L1, L2, Q1, Q2, a and b are as defined in the above chemical formula 1.

[0067] In the present specification, the above chemical formula 1 is any one of the following chemical formulas 1-1-5 to 1-1-8.

[0068] [Chemical Formula 1-1-5]

[0069]

[0070] [Chemical Formula 1-1-6]

[0071]

[0072] [Chemical Formula 1-1-7]

[0073]

[0074] [Chemical Formula 1-1-8]

[0075]

[0076] In the above chemical formulas 1-1-5 to 1-1-8, X1 to X10, L1, L2, Q1, Q2, a and b are as defined in the above chemical formula 1.

[0077] In one embodiment of the present invention, Y1 and Y2 are O.

[0078] In one embodiment of the present invention, Y1 and Y2 are S.

[0079] In one embodiment of the present invention, Y1 is O and Y2 is S.

[0080] In one embodiment of the present invention, Y1 is S and Y2 is O.

[0081] In one embodiment of the present invention, any two of X1 to X5 are N, and the remainder is CR.

[0082] In one embodiment of the present invention, any three of X1 to X5 are N, and the remainder are CR.

[0083] In one embodiment of the present invention, any four of X1 to X5 are N, and the remainder are CR.

[0084] In one embodiment of the present invention, X1 to X5 are N.

[0085] In one embodiment of the present invention, among X1 to X5, X1 and X3 are N, and the remainder are CR.

[0086] In one embodiment of the present invention, among X1 to X5, X2 and X4 are N, and the remainder are CR.

[0087] In one embodiment of the present invention, among X1 to X5, X1 and X5 are N, and the remainder is CR.

[0088] In one embodiment of the present invention, among X1 to X5, X1, X3, and X5 are N, and the remainder is CR.

[0089] In one embodiment of the present invention, any two of X6 to X10 are N, and the remainder is CR.

[0090] In one embodiment of the present invention, any three of X6 to X10 are N, and the remainder are CR.

[0091] In one embodiment of the present invention, any four of X6 to X10 are N, and the remainder are CR.

[0092] In one embodiment of the present invention, X6 to X10 are N.

[0093] In one embodiment of the present invention, among X6 to X10, X6 and X8 are N, and the remainder are CR.

[0094] In one embodiment of the present invention, among X6 to X10, X7 and X9 are N, and the remainder are CR.

[0095] In one embodiment of the present invention, among X6 to X10, X6 and X10 are N, and the remainder is CR.

[0096] In one embodiment of the present invention, among X6 to X10, X6, X8, and X10 are N, and the remainder is CR.

[0097] In one embodiment of the present invention, L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0098] In one embodiment of the present invention, L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.

[0099] In one embodiment of the present invention, L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

[0100] In one embodiment of the present invention, L1 and L2 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 15 carbon atoms.

[0101] In one embodiment of the present invention, L1 and L2 are the same or different from each other and are each independently an arylene group having 6 to 30 carbon atoms that is directly bonded, substituted with deuterium, or unsubstituted, or a heteroarylene group having 3 to 30 carbon atoms that is substituted with deuterium or unsubstituted.

[0102] In one embodiment of the present invention, L1 and L2 are the same or different from each other and are each independently an arylene group having 6 to 20 carbon atoms that is directly bonded, substituted with deuterium, or unsubstituted, or a heteroarylene group having 3 to 20 carbon atoms that is substituted with deuterium or unsubstituted.

[0103] In one embodiment of the present invention, L1 and L2 are the same or different from each other and are each independently an arylene group having 6 to 15 carbon atoms that is directly bonded, substituted with deuterium, or unsubstituted, or a heteroarylene group having 3 to 15 carbon atoms that is substituted with deuterium or unsubstituted.

[0104] In one embodiment of the present invention, L1 and L2 are the same or different from each other and are each independently a directly bonded, deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted divalent biphenyl group, a deuterium-substituted or unsubstituted divalent naphthyl group, a deuterium-substituted or unsubstituted divalent anthracene group, or a deuterium-substituted or unsubstituted divalent phenanthrene group.

[0105] In one embodiment of the present invention, L1 and L2 are the same or different from each other and are each independently a directly bonded, deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted divalent biphenyl group, or a deuterium-substituted or unsubstituted divalent naphthyl group.

[0106] In one embodiment of the present invention, L1 and L2 are the same or different from each other and are each independently a directly bonded, deuterium-substituted or unsubstituted phenylene group, or a deuterium-substituted or unsubstituted divalent naphthyl group.

[0107] In one embodiment of the present invention, L1 is a direct connection.

[0108] In one embodiment of the present invention, L1 is a phenylene group substituted or unsubstituted with deuterium.

[0109] In one embodiment of the present invention, L1 is a divalent naphthyl group substituted or unsubstituted with deuterium.

[0110] In one embodiment of the present invention, L2 is a direct connection.

[0111] In one embodiment of the present invention, L2 is a phenylene group substituted or unsubstituted with deuterium.

[0112] In one embodiment of the present invention, L2 is a divalent naphthyl group substituted or unsubstituted with deuterium.

[0113] In one embodiment of the present invention, Q1 and Q2 are the same or different from each other and are each independently hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group.

[0114] In one embodiment of the present invention, Q1 and Q2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0115] In one embodiment of the present invention, Q1 and Q2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0116] In one embodiment of the present invention, Q1 and Q2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms.

[0117] In one embodiment of the present invention, Q1 and Q2 are the same or different from each other and are each independently hydrogen, deuterium, halogen group, nitrile group, methyl group, ethyl group, propyl group, or terbutyl group.

[0118] In one embodiment of the present invention, Q1 and Q2 are the same or different from each other and are each independently hydrogen, deuterium, F, Cl, Br, nitrile group, methyl group, ethyl group, propyl group, or terbutyl group.

[0119] In one embodiment of the present invention, Q1 and Q2 are the same or different from each other and are each independently hydrogen or deuterium.

[0120] In one embodiment of the present invention, Q1 and Q2 are hydrogen.

[0121] In one embodiment of the present invention, Q1 and Q2 are deuterium.

[0122] In one embodiment of the present invention, R is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or may form a substituted or unsubstituted ring by combining with an adjacent substituent.

[0123] In one embodiment of the present invention, R may be hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or may be combined with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring.

[0124] In one embodiment of the present invention, R is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or may combine with an adjacent substituent to form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroring.

[0125] In one embodiment of the present invention, R is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or may be combined with an adjacent substituent to form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroring.

[0126] In one embodiment of the present invention, R is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, or may be combined with an adjacent substituent to form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroring.

[0127] In one embodiment of the present invention, R is a nitrile group; a methyl group; a phenyl group substituted or unsubstituted with a deuterium, nitrile group, or dibenzofuran group; a biphenyl group substituted or unsubstituted with a nitrile group; a naphthyl group; a phenanthrene group; a triphenylene group; a pyridine group; a carbazole group substituted or unsubstituted with a phenyl group; a fluorene group substituted or unsubstituted with a methyl group; a benzimidazole group substituted or unsubstituted with an ethyl group and a phenyl group; or a dibenzofuran group.

[0128] In one embodiment of the present invention, R combines with an adjacent ring to form a benzene ring.

[0129] According to one embodiment of the present specification, the chemical formula 1 is any one of the following structural formulas.

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142] The substituents of the compound of Chemical Formula 1 above may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

[0143] In addition, by introducing various substituents into a core structure having the structure described above, compounds possessing the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents primarily used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the core structure, materials that satisfy the conditions required for each organic layer can be synthesized.

[0144] In addition, the organic light-emitting device according to the present invention comprises a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise the aforementioned compound.

[0145] The organic light-emitting device of the present invention can be manufactured by conventional methods and materials for manufacturing organic light-emitting devices, except that one or more organic layers are formed using the aforementioned compound.

[0146] The above compound can be formed as an organic layer by vacuum deposition as well as by solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0147] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure comprising, as an organic layer, a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport simultaneously, a light-emitting layer, an electron transport layer, an electron injection layer, etc. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers or a larger number of organic layers.

[0148] In the organic light-emitting device of the present invention, the organic layer may include one or more layers among an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more layers among the layers may include a compound represented by the chemical formula 1.

[0149] In another organic light-emitting device, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by the chemical formula 1.

[0150] In the organic light-emitting device of the present invention, the electron injection and transport layer comprises a compound of Formula 1 and a metal complex.

[0151] In the organic light-emitting device of the present invention, the organic layer may include one or more layers among a hole injection layer, a hole transport layer, and a layer that performs hole injection and hole transport simultaneously, and one or more layers among the layers may include a compound represented by the chemical formula 1.

[0152] In another organic light-emitting device, the organic layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include a compound represented by the chemical formula 1.

[0153] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0154] According to another embodiment, the first electrode is a negative electrode and the second electrode is a positive electrode.

[0155] (1) Anode / hole transport layer / emissive layer / cathode

[0156] (2) Anode / hole injection layer / hole transport layer / emissive layer / cathode

[0157] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / cathode

[0158] (4) Anode / hole transport layer / emissive layer / electron transport layer / cathode

[0159] (5) Anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0160] (6) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / cathode

[0161] (7) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0162] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / cathode

[0163] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0164] (10) Anode / hole transport layer / electron suppression layer / emissive layer / electron transport layer / cathode

[0165] (11) Anode / hole transport layer / electron suppression layer / emissive layer / electron transport layer / electron injection layer / cathode

[0166] (12) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / electron transport layer / cathode

[0167] (13) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / electron transport layer / electron injection layer / cathode

[0168] (14) Anode / hole transport layer / emissive layer / hole suppression layer / electron transport layer / cathode

[0169] (15) Anode / hole transport layer / emissive layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0170] (16) Anode / hole injection layer / hole transport layer / emissive layer / hole suppression layer / electron transport layer / cathode

[0171] (17) Anode / hole injection layer / hole transport layer / emissive layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0172] (18) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / hole blocking layer / electron injection and transport layer / cathode

[0173] The structure of the organic light-emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.

[0174] FIG. 1 illustrates the structure of an organic light-emitting device in which an anode (2), an organic layer (3), and a cathode (4) are sequentially stacked on a substrate (1). In such a structure, a compound represented by the chemical formula 1 may be included in the organic layer (3).

[0175] FIG. 2 illustrates the structure of an organic light-emitting device in which an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (7), an electron injection and transport layer (8), and a cathode (4) are sequentially stacked on a substrate (1). In such a structure, the compound represented by Chemical Formula 1 may be included in the electron injection and transport layer (8).

[0176] For example, an organic light-emitting device according to the present invention can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic layer comprising one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a layer that performs hole transport and hole injection simultaneously, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that performs electron transport and electron injection simultaneously, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0177] The above organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the above organic layer may be manufactured with fewer layers by using various polymer materials and a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0178] The above-mentioned anode is an electrode that injects holes, and as the anode material, it is generally preferable to use an organic layer with a high work function to facilitate hole injection. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0179] The above-mentioned cathode is an electrode for injecting electrons, and as the cathode material, it is preferable to have a material with a low work function to facilitate electron injection, typically an organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0180] The hole injection layer described above is a layer that facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is a material capable of receiving holes well from the anode at low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile-hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and conductive polymers of polyaniline and polythiophene series, but are not limited to these. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, there is an advantage of preventing the driving voltage from rising to improve the movement of holes because the thickness of the hole injection layer is too thick.

[0181] According to one embodiment of the present specification, the hole injection layer comprises a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0182] [HI-1]

[0183]

[0184] In the above chemical formula HI-1,

[0185] L 1-h is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, and

[0186] Ar 1-h or Ar 4-h are the same or different from each other, and each independently are a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0187] According to one embodiment of the present specification, the L 1-h is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0188] According to one embodiment of the present specification, the L 1-h is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.

[0189] According to one embodiment of the present specification, the L 1-h is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

[0190] According to one embodiment of the present specification, the L 1-h is an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.

[0191] According to one embodiment of the present specification, the L 1-h is an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

[0192] According to one embodiment of the present specification, the L 1-h is a divalent spiroacridineflurene group substituted with a phenyl group.

[0193] According to one embodiment of the present specification, the Ar 1-h or Ar 4-h The groups are the same or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0194] According to one embodiment of the present specification, the Ar1-h or Ar 4-h The groups are the same or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0195] According to one embodiment of the present specification, the Ar 1-h or Ar 4-h The groups are the same or different from each other and are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.

[0196] According to one embodiment of the present specification, the Ar 1-h or Ar 4-h The groups are the same or different from each other and are each independently an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

[0197] According to one embodiment of the present specification, the Ar 1-h or Ar 4-h is a phenyl group or a carbazole group substituted with a phenyl group, which are the same or different from each other and are independently substituted with a phenyl group.

[0198] According to one embodiment of the present specification, the chemical formula HI-1 may be the following compounds, but is not limited thereto.

[0199]

[0200] The hole transport layer described above can play a role in facilitating the transport of holes. Suitable hole transport materials are those capable of receiving holes from the anode or hole injection layer and transferring them to the emissive layer, provided they possess high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0201] The hole transport layer described above can play a role in facilitating the transport of holes. Suitable hole transport materials are those capable of receiving holes from the anode or hole injection layer and transferring them to the emissive layer, provided they possess high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0202] According to one embodiment of the present specification, the hole transport layer comprises a compound represented by the following chemical formula HT-2, but is not limited thereto.

[0203] [Chemical Formula HT-1]

[0204]

[0205] In the above chemical formula HT-1,

[0206] At least one of X'1 to X'6 is N, and the rest are CH, and

[0207] R309 to R314 are the same or different from each other and are each independently hydrogen; deuterium; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0208] According to one embodiment of the present specification, X'1 to X'6 are N.

[0209] According to one embodiment of the present specification, R309 to R314 are nitrile groups.

[0210] According to one embodiment of the present specification, the chemical formula HT-1 is represented by the following compound.

[0211]

[0212] According to one embodiment of the present specification, the hole transport layer comprises a compound represented by the following chemical formula HT-2, but is not limited thereto.

[0213] [Chemical Formula HT-2]

[0214]

[0215] In the above chemical formula HT-1,

[0216] R400 to R403 are the same or different from one another and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring, and

[0217] L402 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0218] According to one embodiment of the present specification, R400 to R402 are the same or different from one another and are each independently selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0219] According to one embodiment of the present specification, the R402 is any one selected from the group consisting of a phenyl group substituted with a carbazole group or an arylamine group; a biphenyl group substituted with a carbazole group or an arylamine group; and combinations thereof.

[0220] According to one embodiment of the present specification, the R400 and R401 are the same or different from each other and are each independently substituted or unsubstituted aryl groups, or they combine with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0221] According to one embodiment of the present specification, R400 and R401 are the same or different from each other and are each independently a phenyl group or a diphenylfluorene group.

[0222] According to one embodiment of the present specification, the chemical formula HT-2 may be the following compounds, but is not limited thereto.

[0223]

[0224] An electron suppression layer may be provided between the hole transport layer and the light-emitting layer. The electron suppression layer may use the aforementioned spiro compound or a material known in the art.

[0225] The above-mentioned light-emitting layer may emit red, green, or blue light and may be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole, and benzimidazole series; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0226] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0227] An organic light-emitting device according to one embodiment of the present specification comprises a light-emitting layer, and the light-emitting layer comprises a compound represented by the following chemical formula H as a host material.

[0228] [Chemical Formula H]

[0229]

[0230] In the above chemical formula H,

[0231] L21 and L22 are identical or different from each other, and each is independently a directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0232] R21 to R28 are identical or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0233] Ar21 and Ar22 are identical or different from each other, and each is an independently substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0234] In one embodiment of the present specification, R21 to R28 are identical or different from one another and are each independently hydrogen or deuterium.

[0235] In one embodiment of the present specification, Ar21 and Ar22 are different from each other.

[0236] In one embodiment of the present specification, Ar21 and Ar22 are the same or different from each other and are each independently substituted or unsubstituted aryl groups.

[0237] In one embodiment of the present specification, Ar21 and Ar22 are naphthyl groups.

[0238] In one embodiment of the present specification, L21 and L22 are identical or different from each other and are each independently directly bonded; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0239] In one embodiment of the present specification, the formula H is represented by the following compound.

[0240]

[0241] When the emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the light-emitting layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distrylarylene (DSA), PFO-based polymers, and PPV-based polymers may be used as light-emitting dopants, but are not limited to these.

[0242] According to one embodiment of the present specification, the dopant comprises a compound represented by the following chemical formula D-1, but is not limited thereto.

[0243] [Chemical Formula D-1]

[0244]

[0245] In the above chemical formula D-1,

[0246] T1 to T6 are the same or different from one another, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0247] t5 and t6 are integers from 1 to 4, respectively, and

[0248] If the above t5 is 2 or more, the above 2 or more T5s are the same or different from each other, and

[0249] If the above t6 is 2 or more, the above 2 or more T6s are the same or different from each other.

[0250] According to one embodiment of the present specification, T1 to T6 are the same or different from each other and are each independently hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0251] According to one embodiment of the present specification, T1 to T6 are the same or different from each other and are each independently hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a nitrile group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched-chain alkylsilyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0252] According to one embodiment of the present specification, T1 to T6 are the same or different from each other and are each independently a phenyl group; or a terphenyl group substituted with a trimethylsilyl group.

[0253] According to one embodiment of the present specification, the formula D-1 is represented by the following compound.

[0254]

[0255] According to one embodiment of the present specification, the light-emitting layer may be provided with a host and a dopant, and a hole-inhibiting layer may be provided between the electron transport layer and the light-emitting layer, and materials known in the art may be used.

[0256] The electron transport layer described above can facilitate the transport of electrons. As an electron transport material, a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility, is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes, but are not limited to these. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the deterioration of electron transport characteristics, and if it is 50 nm or less, there is an advantage in preventing the driving voltage from rising to improve electron transport due to the electron transport layer being too thick.

[0257] The electron injection layer described above can facilitate the injection of electrons. As an electron injection material, a compound is preferred that has the ability to transport electrons, has an excellent electron injection effect from the cathode, an excellent electron injection effect on the emissive layer or emissive material, prevents the movement of excitons generated in the emissive layer to the hole injection layer, and also has excellent thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0258] The above electron injection and transport layer can play a role in facilitating electron injection and transport. The material of the electron transport layer or the electron injection layer described above can be appropriately selected and configured.

[0259] The electron injection and transport layer comprises the compound of Formula 1 and the metal complex in a mass ratio of 1:10 to 10:1.

[0260] The electron injection and transport layer comprises the compound of Formula 1 and the metal complex in a mass ratio of 1:5 to 5:1.

[0261] The electron injection and transport layer comprises the compound of Formula 1 and the metal complex in a mass ratio of 1:3 to 3:1.

[0262] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, Examples include bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited to these.

[0263] The hole blocking layer described above is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc. are used, but are not limited thereto.

[0264] The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0265] The organic light-emitting device of the present invention can be manufactured by conventional methods and materials for manufacturing organic light-emitting devices, except that one or more organic layers are formed using the aforementioned compound.

[0266] The method for preparing the compound of Chemical Formula 1 above and the preparation of an organic light-emitting device using them will be specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0267] In the following reaction scheme, various types of intermediates can be synthesized by appropriately selecting known starting materials regarding the types and number of substituents. The types and conditions of the reaction and reaction conditions known in the art may be utilized.

[0268] The method for preparing the compound of Chemical Formula 1 above and the preparation of an organic light-emitting device using them will be specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0269] In the following reaction scheme, various types of intermediates can be synthesized by appropriately selecting known starting materials regarding the types and number of substituents. The types and conditions of the reaction and reaction conditions known in the art may be utilized.

[0270]

[0271] The above X1 to X10, Y1, Y2, L1, L2, Q1, Q2, a and b are as defined in Chemical Formula 1.

[0272] By appropriately combining the manufacturing formulas described in the embodiments of this specification and the intermediates based on common technical knowledge, all of the compounds of Formula 1 described in this specification can be produced.

[0273] [Synthetic Example]

[0274] Synthesis Example 1: Synthesis of Compound 1

[0275]

[0276] Step 1) Synthesis of Compound 1-a

[0277] (2,4-dichlorophenyl)boronic acid (50 g, 262 mmol) and 2-bromodibenzo[b,e][1,4]dioxine (68.9 g, 262 mmol) were added to 1000 ml of tetrahydrofuran under a nitrogen atmosphere and stirred and refluxed. Subsequently, potassium carbonate (83.3 g, 786.1 mmol) was dissolved in 83 ml of water and added, and after sufficient stirring, tetracitriphenyl-phosphinopalladium (9.1 g, 7.9 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was then dissolved in 1725 ml of 20 times the amount of toluene, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered and the filtrate distilled under reduced pressure. A white solid compound 1-a (73.3 g, 85%, MS: [M+H]+ = 330.2) was prepared by recrystallizing the concentrated compound with toluene and ethyl acetate.

[0278] Step 2) Synthesis of Compound 1-b

[0279] Under a nitrogen atmosphere, compound 1-a (50 g, 151.9 mmol) and bis(pinacolato)diborone (38.6 g, 151.9 mmol) were added to 1000 ml of Diox(1,4-dioxane) and stirred and refluxed. Subsequently, potassium acetate (96.7 g, 455.7 mmol) was added and stirred thoroughly, after which palladium dibenzylideneacetone palladium (0.9 g, 1.5 mmol) and 0 (0 g, 0 mmol) were added. After reacting for 7 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was dissolved in 778 mL of chloroform (10 times the amount of chloroform), washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. A white solid compound 1-b (44.3g, 57%, MS: [M+H]+ = 513.2) was prepared by recrystallizing the concentrated compound with chloroform and ethanol.

[0280] Step 3) Synthesis of Compound 1

[0281] Under a nitrogen atmosphere, compound 1-b (50 g, 92.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (49.8 g, 186 mmol) were added to 1000 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (29.5 g, 278.7 mmol) was dissolved in 30 ml of water and added, and after sufficient stirring, tetracitriphenyl-phosphinopalladium (3.2 g, 2.8 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, separated into organic and water layers, and the organic layer was distilled. This was then dissolved in 1343 mL of 20 times the amount of toluene, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. A white solid compound 1 (47g, 70%, MS: [M+H]+ = 723.3) was prepared by recrystallizing the concentrated compound with toluene and ethyl acetate.

[0282] Synthesis Example 2: Synthesis of Compound 2

[0283]

[0284] Compound 2 (MS[M+H]) was prepared using the same method as Compound 1, except that in Synthesis Example 1, 2-bromodibenzo[b,e][1,4]dioxine and 2-chloro-4,6-diphenyl-1,3,5-triazine were replaced with 1-bromodibenzo[b,e][1,4]dioxine and 2-chloro-4,6-dimethylpyrimidine. + = 721.3) was manufactured.

[0285] Synthesis Example 3: Synthesis of Compound 3

[0286]

[0287] Step 1) Synthesis of Compound 3-a

[0288] (4-bromo-2-chlorophenyl)boronic acid (50 g, 212.5 mmol) and 2-iododibenzo[b,e][1,4]dioxine (65.9 g, 212.5 mmol) were added to 1000 ml of toluene and 50 ml of ethanol under a nitrogen atmosphere and stirred at 60°C. Subsequently, potassium carbonate (67.6 g, 637.6 mmol) was dissolved in 68 ml of water and added, followed by sufficient stirring, after which tetracyclotriphenyl-phosphinopalladium (7.4 g, 6.4 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was then dissolved in 1588 mL of 20 times the amount of toluene, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered and the filtrate distilled under reduced pressure. A white solid compound 3-a (45.3g, 57%, MS: [M+H]+ = 374.6) was prepared by recrystallizing the concentrated compound with toluene and ethyl acetate.

[0289] Step 2) Synthesis of Compound 3-b

[0290] Under a nitrogen atmosphere, compound 3-a (50 g, 133.8 mmol) and bis(pinacolato)diborone (34 g, 133.8 mmol) were added to 1000 ml of Diox(1,4-dioxane) and stirred and refluxed. Subsequently, potassium acetate (85.2 g, 401.5 mmol) was added and stirred thoroughly, after which [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (1 g, 1.3 mmol) was added. After reacting for 6 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was dissolved in 563 mL of chloroform at 10 times the volume, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. A white solid compound 3-b (36g, 64%, MS: [M+H]+ = 421.7) was prepared by recrystallizing the concentrated compound with chloroform and ethanol.

[0291] Step 3) Synthesis of Compound 3-c

[0292] Under a nitrogen atmosphere, compound 3-b (50 g, 118.8 mmol) and 4-chloro-2,6-diphenylpyrimidine (31.7 g, 118.8 mmol) were added to 1000 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (37.8 g, 356.5 mmol) was dissolved in 38 ml of water and added, and after sufficient stirring, tetracitriphenyl-phosphinopalladium (4.1 g, 3.6 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was then dissolved in 1248 mL of 20 times the amount of toluene, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered, with the filtrate subjected to vacuum distillation. A white solid compound 3-c (36.8 g, 59%, MS: [M+H]+ = 526) was prepared by recrystallizing the concentrated compound with toluene and ethyl acetate.

[0293] Step 4) Synthesis of Compound 3-d

[0294] Under a nitrogen atmosphere, compound 3-c (50 g, 95.2 mmol) and bis(pinacolato)diborone (24.2 g, 95.2 mmol) were added to 1000 ml of Diox(1,4-dioxane) and stirred and refluxed. Subsequently, potassium acetate (60.6 g, 285.7 mmol) was added and stirred thoroughly, after which palladium dibenzylideneacetone palladium (0.5 g, 1 mmol) and dicyclohexylphosphine (0.4 g, 1.9 mmol) were added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was dissolved in 587 mL of 10 times the amount of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. A white solid compound 3-d (34.6 g, 59%, MS: [M+H]+ = 617.5) was prepared by recrystallizing the concentrated compound with chloroform and ethanol.

[0295] Step 5) Synthesis of Compound 3

[0296] Under a nitrogen atmosphere, compound 3-d (50 g, 81.1 mmol) and 2-chloro-4-(dibenzo[b,d]thiophene-4-yl)-6-phenylpyrimidine (30.2 g, 81.1 mmol) were added to 1000 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (25.8 g, 243.3 mmol) dissolved in 26 ml of water was added and stirred thoroughly, after which tetracitriphenyl-phosphinopalladium (2.8 g, 2.4 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, separated into organic and water layers, and the organic layer was distilled. This was then dissolved in 1341 mL of 20 times the amount of toluene, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. A white solid compound 3 (52.3 g, 78%, MS: [M+H]+ = 828) was prepared by recrystallizing the concentrated compound with toluene and ethyl acetate.

[0297] Synthesis Example 4: Synthesis of Compound 4

[0298]

[0299] Step 1) Synthesis of Compound 4-a

[0300] (4-bromo-2-chlorophenyl)boronic acid (50 g, 212.5 mmol) and 2-bromodibenzo[b,e][1,4]dioxine (65.9 g, 212.5 mmol) were added to 1000 ml of toluene and 50 ml of ethanol under a nitrogen atmosphere and stirred at 60°C. Subsequently, potassium carbonate (67.6 g, 637.6 mmol) was dissolved in 68 ml of water and added, followed by sufficient stirring, after which tetracitriphenyl-phosphinopalladium (7.4 g, 6.4 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was then dissolved in 1588 mL of 20 times the amount of toluene, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered and the filtrate distilled under reduced pressure. A white solid compound 4-a (67.5 g, 85%, MS: [M+H]+ = 374.6) was prepared by recrystallizing the concentrated compound with toluene and ethyl acetate.

[0301] Step 2) Synthesis of Compound 4-b

[0302] Under a nitrogen atmosphere, compound 4-a (50 g, 133.8 mmol) and bis(pinacolato)diborone (34 g, 133.8 mmol) were added to 1000 ml of Diox(1,4-dioxane) and stirred and refluxed. Subsequently, potassium acetate (85.2 g, 401.5 mmol) was added and stirred thoroughly, after which [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (0.8 g, 1.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was dissolved in 563 mL of chloroform (10 times the amount of chloroform), washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. A white solid compound 4-b (43.4g, 77%, MS: [M+H]+ = 421.7) was prepared by recrystallizing the concentrated compound with chloroform and ethanol.

[0303] Step 3) Synthesis of Compound 4-c

[0304] Under a nitrogen atmosphere, compound 4-b (50 g, 118.8 mmol) and 4-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-2-phenylquinazoline (47 g, 118.8 mmol) were added to 1000 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (37.8 g, 356.5 mmol) was dissolved in 38 ml of water and added, and after sufficient stirring, tetracitriphenyl-phosphinopalladium (4.1 g, 3.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was then dissolved in 1555 ml of 20 times the amount of toluene, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered and the filtrate was distilled under reduced pressure. A white solid compound 4-c (57.5 g, 74%, MS: [M+H]+ = 655.1) was prepared by recrystallizing the concentrated compound with toluene and ethyl acetate.

[0305] Step 4) Synthesis of Compound 4-d

[0306] Under a nitrogen atmosphere, compound 4-c (50 g, 76.4 mmol) and bis(pinacolato)diborone (47.2 g, 76.4 mmol) were added to 1000 ml of Diox(1,4-dioxane) and stirred and refluxed. Subsequently, potassium acetate (48.7 g, 229.3 mmol) was added and stirred thoroughly, after which palladium dibenzylideneacetone palladium (0.4 g, 0.8 mmol) and dicyclohexylphosphine (0.3 g, 1.5 mmol) were added. After reacting for 7 hours, the mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was dissolved in 472 mL of 10 times the amount of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. A white solid compound 4-d (35.9 g, 76%, MS: [M+H]+ = 618.5) was prepared by recrystallizing the concentrated compound with chloroform and ethanol.

[0307] Step 5) Synthesis of Compound 4

[0308] Under a nitrogen atmosphere, compound 4-d (50 g, 81 mmol) and 2-chloro-4,6-diphenylpyrimidine (21.6 g, 162 mmol) were added to 1000 ml of tetrahydrofuran and stirred and refluxed. Subsequently, potassium carbonate (25.7 g, 242.9 mmol) was dissolved in 26 ml of water and added, and after sufficient stirring, tetracitriphenyl-phosphinopalladium (2.8 g, 2.4 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was then dissolved in 1376 mL of 20 times the amount of toluene, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and the mixture was filtered, with the filtrate subjected to vacuum distillation. A white solid compound 4 (41.3 g, 60%, MS: [M+H]+ = 851) was prepared by recrystallizing the concentrated compound with toluene and ethyl acetate.

[0309] Synthesis Example 5: Synthesis of Compound 5

[0310]

[0311] Compound 5 (MS[M+H] + Manufactured = 748.3).

[0312] Synthesis Example 6: Synthesis of Compound 6

[0313]

[0314] Compound 6 (MS[M+H]) was prepared using the same method as Compound 1, except that 2-bromodibenzo[b,e][1,4]dioxine was changed to 2-bromo-8-phenyldibenzo[b,e][1,4]dioxine in Synthesis Example 1. + Manufactured = 799.3).

[0315] Synthesis Example 7: Synthesis of Compound 7

[0316]

[0317] Compound 7 (MS[M+H]) was prepared using the same method as Compound 1, except that in Synthesis Example 1, 2-bromodibenzo[b,e][1,4]dioxin and 2-chloro-4,6-diphenyl-1,3,5-triazine were replaced with 9-bromodibenzo[b,e][1,4]dioxin-2-carbonitrile and 4-chloro-2,6-diphenylpyrimidine. + Manufactured = 746.3).

[0318] Synthesis Example 8: Synthesis of Compound 8

[0319]

[0320] Compound 8 (MS[M+H]) was prepared using the same method as Compound 4, except that in Synthesis Example 4, 4-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-2-phenylquinazolin and 2-chloro-4,6-diphenylpyrimidine were replaced with 4-(3-bromophenyl)-2,6-diphenylpyrimidine and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine. + Manufactured = 874.3).

[0321] Synthesis Example 9: Synthesis of Compound 9

[0322]

[0323] Compound 9 (MS[M+H]) was prepared using the same method as Compound 1, except that in Synthesis Example 1, 2-bromodibenzo[b,e][1,4]dioxin was changed to 2-bromodibenzo[b,e][1,4]dioxin-1,3,4,6,7,8,9-d7. + Manufactured = 730.3).

[0324] Synthesis Example 10: Synthesis of Compound 10

[0325]

[0326] Compound 10 (MS[M+H] + Manufactured = 903.3).

[0327] Synthesis Example 11: Synthesis of Compound 11

[0328]

[0329] In Synthesis Example 4, except that (2,4-dichlorophenyl)boronic acid, 4-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-2-phenylquinazolin, and 2-chloro-4,6-diphenylpyrimidine were replaced with (4-bromo-2-chloro-6-cyanophenyl)boronic acid, 2-chloro-4-(naphthalene-1-yl)-6-phenyl-1,3,5-triazine, and 2-chloro-4,6-diphenyl-1,3,5-triazine, compound 11 (MS[M+H]) was prepared using the same method as that of compound 4. + Manufactured = 798.3).

[0330] Synthesis Example 12: Synthesis of Compound 12

[0331]

[0332] Compound 12 (MS[M+H]) was prepared using the same method as Compound 1, except that in Synthesis Example 1, 2-bromodibenzo[b,e][1,4]dioxin and 2-chloro-4,6-diphenyl-1,3,5-triazine were replaced with 1-bromophenoxatin and 2-chloro-4,6-diphenylpyrimidine. + = 737.3) was manufactured.

[0333] Synthesis Example 13: Synthesis of Compound 13

[0334]

[0335] Compound 13 (MS[M+H]) was prepared using the same method as Compound 1, except that 2-bromodibenzo[b,e][1,4]dioxine was replaced with 1-bromothianthrene in Synthesis Example 1. + = 754.2) was manufactured.

[0336] Experimental Example 1

[0337] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,000 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millerpore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0338] A hole injection layer was formed by thermal vacuum deposition of the following compound HI-A to a thickness of 600 Å on the prepared ITO transparent electrode. A hole transport layer was formed by sequentially vacuum depositing hexaazatriphenylene (HAT, 50 Å) and the following compound HT-A (600 Å) of the following chemical formula onto the hole injection layer.

[0339] Next, a light-emitting layer was formed by vacuum depositing the following compounds BH and BD in a weight ratio of 25:1 on the hole transport layer with a film thickness of 200 Å.

[0340] Compound 1 prepared in Synthesis Example 1 and the following compound [LiQ] (Lithium quinolate) were vacuum-deposited in a 1:1 weight ratio on the above-mentioned light-emitting layer to form an electron transport and injection layer with a thickness of 360 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 1,000 Å on the above-mentioned electron transport and injection layer.

[0341]

[0342] In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, while the deposition rates of lithium fluoride and aluminum for the cathode were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 1 × 10⁻⁶ -7 Up to 5 × 10 -8 An organic light-emitting diode was fabricated by maintaining torr.

[0343] Experimental Examples 2 to 13

[0344] An organic light-emitting diode was prepared in the same manner as in Experimental Example 1, except that the compound of Table 1 below was used instead of the compound 1 of Experimental Example 1.

[0345] Comparative Experiment Examples 1 to 8

[0346] An organic light-emitting diode was prepared in the same manner as in Experimental Example 1, except that the compounds in Table 1 below were used instead of Compound 1 of Experimental Example 1. The compounds ET-1 to ET-8 used in Table 1 below are as follows.

[0347]

[0348] For the organic light-emitting diodes prepared in the above experimental and comparative experimental examples, 10 mA / cm 2 The driving voltage, luminous efficiency, and color coordinates were measured at a current density of 20 mA / cm². 2 The time (T) when the brightness reaches 90% of the initial brightness at the current density 90 ) was measured. The results are shown in Table 1 below.

[0349] Compound (electron transport and injection layer) (V@10mA / cm 2 ) Efficiency (cd / A @ 10mA / cm²) 2 ) Color coordinates (x,y) T 90 (hr@20mA / cm 2 ) Experimental Example 1 Compound 1 4.15 4.25 (0.136, 0.112) 180 Experimental Example 2 Compound 2 4.11 4.38 (0.136, 0.111) 177 Experimental Example 3 Compound 3 4.07 4.44 (0.136, 0.112) 188 Experimental Example 4 Compound 4 4.20 4.19 (0.136, 0.111) 190 Experimental Example 5 Compound 5 4.22 4.21 (0.136, 0.111) 172 Experimental Example 6 Compound 6 4.17 4.39 (0.136, 0.111) 159 Experimental Example 7 Compound 7 4.20 4.25 (0.136, 0.112) 161 Experimental Example 8 Compound 8 4.22 4.36 (0.136, 0.111) 191 Experimental Example 9 Compound 9 4.15 4.27 (0.136, 0.112) 241 Experimental Example 10 Compound 10 4.27 4.18 (0.136, 0.111) 200 Experimental Example 11 Compound 11 4.23 4.30 (0.136, 0.111) 170 Experimental Example 12 Compound 12 3.99 4.78 (0.136, 0.111) 158 Experimental Example 13 Compound 13 3.89 4.80 (0.136, 0.111) 101 Comparative Experiment Example 1 ET-1 5.13 2.99 (0.136, 0.111) 30 Comparative Experiment Example 2 ET-2 4.88 3.02 (0.136, 0.111) 99 Comparative Experiment Example 3 ET-3 4.75 3.10 (0.136, 0.112) 100 Comparative Experiment Example 4 ET-4 4.92 3.19 (0.136, 0.111) 54 Comparative Experiment Example 5 ET-5 4.81 3.42 (0.136, 0.112) 59 Comparative Experiment Example 6 ET-6 4.74 3.25 (0.136, 0.112) 36 Comparative Experiment Example 7 ET-7 4.78 3.50 (0.136, 0.112) 54 Comparative Experiment Example 8 ET-8 4.71 2.85 (0.136, 0.112) 65

[0350] As described in Table 1 above, for an organic light-emitting diode using a compound represented by Formula 1 of the present invention, voltage, efficiency, and / or lifetime (T 90It was confirmed that it exhibits excellent characteristics. When comparing Experimental Examples 1 to 13 of Table 1 with Comparative Experimental Example 1, the organic light-emitting device containing the compound of Formula 1 of the present invention is substituted only with N-containing rings having electron transport characteristics, so the electron transport capability can be varied. Therefore, it was confirmed that it exhibits significantly superior characteristics in terms of efficiency and lifespan compared to an organic light-emitting device substituted only with three carbazole groups having excellent hole characteristics.

[0351] When comparing Experimental Examples 1 to 13 and Comparative Experimental Examples 2 to 5 in Table 1 above, the organic light-emitting device containing the compound of Formula 1 of the present invention has two or more N-containing rings with electron transport characteristics substituted therein, and the N-containing rings with electron transport characteristics are adjacent to each other in ortho and para positions with the dioxin, phenoxazine, and thianthrene core structures, which is advantageous for controlling electron transport capabilities in various ways. Therefore, it was confirmed that it exhibits significantly superior characteristics in terms of efficiency and lifespan compared to an organic light-emitting device using a compound substituted with one N-containing ring.

[0352] In Comparative Experimental Examples 6 to 8, substituents are substituted at positions 1, 3, and 5 of the benzene ring, respectively. Although the benzene ring is substituted with the same substituents as in Formula 1 of the present invention, the substitution positions are different. As can be seen from the experimental results, the compounds of the examples in which substituents are substituted at positions 1, 3, and 4 of the benzene ring exhibit characteristics of low voltage, high efficiency, and long lifespan compared to the compounds of Comparative Experimental Examples 6 to 8. Explanation of the symbols

[0353] 1: Substrate 2: Anode 3: Organic layer 4: Cathode 5: Hole injection layer 6: Precision Transport Layer 7: Emissive layer 8: Electron injection and transport layer

Claims

Claim 1 Compound of Chemical Formula 1 below: [Chemical Formula 1] In the above Chemical Formula 1, Y1 and Y2 are the same or different from each other and are each independently O or S; Q1 and Q2 are the same or different from each other and are each independently hydrogen, deuterium, a nitrile group, or an aryl group having 6 to 15 carbon atoms; at least 2 of X1 to X5 are N, and the remainder that is not N are the same or different from each other and are each independently CR; at least 2 of X6 to X10 are N, and the remainder that is not N are the same or different from each other and are each independently CR; R is hydrogen, an aryl group having 6 to 15 carbon atoms substituted or unsubstituted with a nitrile group, or a heteroaryl group having 3 to 15 carbon atoms substituted or unsubstituted with a phenyl group; L1 and L2 are the same or different from each other and are each independently a direct bond or an arylene group having 6 to 15 carbon atoms; when a is 1 to 3 and a is 2 or more, Q1 is the same or different from each other; and b is 1 to When 7 and b is 2 or greater, Q2 are equal to or different from each other. Claim 2 A compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, X1 to X10, Y1, Y2, L1, L2, Q1, Q2, a and b are as defined in the above chemical formula 1. Claim 3 A compound according to claim 1, wherein Y1 is O and Y2 is S. Claim 4 A compound according to claim 1, wherein Y1 and Y2 are S. Claim 5 A compound according to claim 1, wherein Y1 and Y2 are O. Claim 6 delete Claim 7 delete Claim 8 A compound according to claim 1, wherein any two of X1 to X5 are N and the remainder is CR. Claim 9 A compound according to claim 1, wherein any two of X6 to X10 are N and the remainder are CR. Claim 10 A compound according to claim 1, wherein X1, X3, and X5 among X1 to X5 are N, and the remainder are CR. Claim 11 A compound according to claim 1, wherein among X6 to X10, X6, X8, and X10 are N, and the remainder are CR. Claim 12 A compound according to claim 1, wherein the chemical formula 1 is any one of the following compounds: Claim 13 An organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound according to any one of claims 1 to 5 and 8 to 12. Claim 14 An organic light-emitting device according to claim 13, wherein the organic layer comprises one or more of an electron injection layer, an electron transport layer, and an electron injection and transport layer, and one or more of the layers comprises the compound. Claim 15 An organic light-emitting device according to claim 14, wherein the electron injection and transport layer comprises the compound and the metal complex in a mass ratio of 1:10 to 10:1.

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