Compound and organic light emitting device comprising the same

Abstract

The present specification relates to Formula 1 and an organic light-emitting device comprising the same.

Description

Technology Field

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0148913 filed with the Korean Intellectual Property Office on November 9, 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] R1 to R5 are the same or different from each other and each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group, and

[0015] Ar1 is a substituted or unsubstituted heteroaryl group containing 2 or more Ns, and

[0016] Ar2 is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted condensed ring, and

[0017] a and c are integers from 1 to 4, and

[0018] b is an integer from 1 to 3, and

[0019] d and e are integers from 1 to 5, and

[0020] When a is 2 or greater, R1 are equal to or different from each other, and

[0021] When b is 2 or greater, R2 are equal to or different from each other, and

[0022] When c is 2 or greater, R3 are equal to or different from each other, and

[0023] When d is 2 or greater, R4 are the same or different, and

[0024] When e is 2 or greater, R5 are equal to or different from each other.

[0025] 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

[0026] 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 transport layer of an organic light-emitting device, the high intramolecular polarization results in a high electron transfer effect, thereby enabling the manufacture of an organic light-emitting device having long lifespan characteristics.

[0027] The compound of the present invention exhibits high efficiency characteristics by maximizing electron mobility through appropriately breaking conjugation within the molecule by limiting the substitution position of the linker to the ortho direction instead of narrowing the distance between electron transport groups, and also maintains long life characteristics by attaching a CN group, which is a highly electronegative substituent. Brief explanation of the drawing

[0028] Figures 1 and 2 illustrate examples of organic light-emitting devices according to the present invention. Specific details for implementing the invention

[0029] The present specification will be described in more detail below.

[0030] 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.

[0031] 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.

[0032] Examples of substituents in this specification are described below, but are not limited thereto.

[0033] 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.

[0034] In this specification, the term “substituted or unsubstituted” means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; cyano 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 heterocyclic 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.

[0035] Examples of the above substituents are described below, but are not limited thereto.

[0036] In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] In this specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted on N of the amine group.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] In this specification, the arylene group is as defined in the aryl group, except that it is a divalent group.

[0049] In this specification, the heteroarylene group is as defined in the heteroaryl group, except that it is a divalent group.

[0050] In this specification, a condensed ring refers to a ring formed by the condensation of two or more selected from an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and a heteroring, wherein the definition of a cycloalkyl group applies to the aliphatic hydrocarbon ring except that it is not monovalent, the definition of an aryl group applies to the aromatic hydrocarbon ring except that it is not monovalent, and the definition of a heteroring applies to the heteroaryl group except that it is not monovalent.

[0051] According to one embodiment of the present specification, the formula 1 is the following formula 1-1 or 1-2.

[0052] [Chemical Formula 1-1]

[0053]

[0054] [Chemical Formula 1-2]

[0055]

[0056] In the above chemical formulas 1-1 and 1-2, R1 to R5, Ar1, Ar2 and a to e are as defined in the above chemical formula 1.

[0057] According to one embodiment of the present specification, the formula 1 is any one of the following formulas 1-3 to 1-7.

[0058] [Chemical Formula 1-3]

[0059]

[0060] [Chemical Formula 1-4]

[0061]

[0062] [Chemical Formula 1-5]

[0063]

[0064] [Chemical Formula 1-6]

[0065]

[0066] [Chemical Formula 1-7]

[0067]

[0068] In the above chemical formulas 1-3 to 1-7, R1 to R5, Ar1, Ar2 and a to e are as defined in the above chemical formula 1.

[0069] According to one embodiment of the present specification, the formula 1 is the following formula 1-1-1 or 1-1-2.

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

[0071]

[0072] [Chemical Formula 1-1-2]

[0073]

[0074] In the above chemical formulas 1-1-1 and 1-1-2, R4, R5, Ar1, Ar2, d, and e are as defined in the above chemical formula 1.

[0075] According to one embodiment of the present specification, the formula 1 is any one of the following formulas 1-1-3 to 1-1-7.

[0076] [Chemical Formula 1-1-3]

[0077]

[0078] [Chemical Formula 1-1-4]

[0079]

[0080] [Chemical Formula 1-1-5]

[0081]

[0082] [Chemical Formula 1-1-6]

[0083]

[0084] [Chemical Formula 1-1-7]

[0085]

[0086] In the above chemical formulas 1-1-3 to 1-1-7, R4, R5, Ar1, Ar2, d, and e are as defined in the above chemical formula 1.

[0087] According to one embodiment of the present specification, Ar1 is a heteroaryl group having 3 to 30 carbon atoms comprising 2 or more Ns substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.

[0088] According to one embodiment of the present specification, the Ar1 is a heteroaryl group having 3 to 30 carbon atoms comprising 2 or more Ns substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

[0089] According to one embodiment of the present specification, the Ar1 is a heteroaryl group having 3 to 30 carbon atoms containing 2 or more N, and the heteroaryl group is substituted or unsubstituted with a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or anthracene group.

[0090] According to one embodiment of the present specification, the Ar1 is a heteroaryl group having 3 to 30 carbon atoms containing 2 or more N, and the heteroaryl group is substituted or unsubstituted with a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0091] According to one embodiment of the present specification, the Ar1 is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms containing 2 or more N.

[0092] According to one embodiment of the present specification, the Ar1 is a heteroaryl group having 3 to 30 carbon atoms containing 2 or more N.

[0093] According to one embodiment of the present specification, the Ar1 is a heteroaryl group having 3 to 20 carbon atoms containing 2 or more N.

[0094] According to one embodiment of the present specification, the Ar1 is a heteroaryl group having 3 to 15 carbon atoms containing 2 or more N.

[0095] According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic heteroaryl group having 3 to 30 carbon atoms containing 2 or more N.

[0096] According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic heteroaryl group having 3 to 20 carbon atoms and containing 2 or more N.

[0097] According to one embodiment of the present specification, the Ar1 is a monocyclic or polycyclic heteroaryl group having 3 to 15 carbon atoms and containing 2 or more N.

[0098] According to one embodiment of the present specification, Ar1 is a single-ring heteroaryl group having 3 to 30 carbon atoms and containing 2 or more N.

[0099] According to one embodiment of the present specification, the Ar1 is a single-ring heteroaryl group having 3 to 20 carbon atoms and containing 2 or more N.

[0100] According to one embodiment of the present specification, the Ar1 is a single-ring heteroaryl group having 3 to 15 carbon atoms and containing 2 or more N.

[0101] According to one embodiment of the present specification, the Ar1 is a triazine group or a pyrimidine group, and the triazine group and the pyrimidine group are substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

[0102] According to one embodiment of the present specification, the Ar1 is a triazine group or a pyrimidine group, and the triazine group and the pyrimidine group are substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group.

[0103] According to one embodiment of the present specification, Ar1 is a triazine group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

[0104] According to one embodiment of the present specification, the Ar1 is a pyrimidine group substituted with or unsubstituted by an aryl group having 6 to 20 carbon atoms.

[0105] According to one embodiment of the present specification, Ar1 is a triazine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group.

[0106] According to one embodiment of the present specification, Ar1 is a pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group.

[0107] According to one embodiment of the present specification, Ar1 is a triazine group or a pyrimidine group.

[0108] According to one embodiment of the present specification, Ar1 is a triazine group.

[0109] According to one embodiment of the present specification, Ar1 is a pyrimidine group.

[0110] According to one embodiment of the present specification, the Ar1 is a polycyclic heteroaryl group having 3 to 20 carbon atoms containing 2 or more N.

[0111] According to one embodiment of the present specification, Ar1 is a polycyclic heteroaryl group having 3 to 15 carbon atoms containing 2 or more N.

[0112] According to one embodiment of the present specification, the Ar1 is a quinazolin group.

[0113] According to one embodiment of the present specification, Ar1 is a quinoxaline group.

[0114] According to one embodiment of the present specification, the Ar2 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, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a substituted or unsubstituted condensation group having 3 to 30 carbon atoms.

[0115] According to one embodiment of the present specification, the Ar2 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0116] According to one embodiment of the present specification, the Ar2 is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0117] According to one embodiment of the present specification, the Ar2 is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0118] According to one embodiment of the present specification, the Ar2 is an aryl group having 6 to 30 carbon atoms.

[0119] According to one embodiment of the present specification, the Ar2 is an aryl group having 6 to 20 carbon atoms.

[0120] According to one embodiment of the present specification, the Ar2 is an aryl group having 6 to 15 carbon atoms.

[0121] According to one embodiment of the present specification, the Ar2 is a methyl group, an ethyl group, a terbutyl group, an isopropyl group, a phenyl group, a biphenyl group, a naphthyl group, an anthracene group, or a phenanthrene group.

[0122] According to one embodiment of the present specification, the Ar2 is a methyl group, an ethyl group, a phenyl group, a biphenyl group, or a naphthyl group.

[0123] According to one embodiment of the present specification, R1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group.

[0124] According to one embodiment of the present specification, R1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0125] According to one embodiment of the present specification, R1 to R5 are the same or different from each other and each independently hydrogen, deuterium, nitrile group, halogen group, or substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0126] According to one embodiment of the present specification, R1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, nitrile group, halogen group, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 30 carbon atoms, or heteroaryl group having 3 to 30 carbon atoms.

[0127] According to one embodiment of the present specification, R1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, nitrile group, halogen group, or alkyl group having 1 to 10 carbon atoms.

[0128] According to one embodiment of the present specification, R1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, nitrile group, F, Cl, Br, I, methyl group, ethyl group, propyl group, isopropyl group, butyl group, terbutyl group, phenyl group, naphthyl group, biphenyl group, terphenyl group, pyrrole group, furan group, thiophene group, triazine group, pyrimidine group, pyridine group, carbazole group, dibenzofuran group, or dibenzothiophene group.

[0129] According to one embodiment of the present specification, R1 to R5 are the same or different from each other and each independently hydrogen, deuterium, nitrile group, F, Cl, Br, I, methyl group, ethyl group, propyl group, isopropyl group, butyl group, phenyl group, naphthyl group, or terbutyl group.

[0130] According to one embodiment of the present specification, R1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, nitrile group, halogen group, phenyl group or naphthyl group.

[0131] According to one embodiment of the present specification, R1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, a phenyl group or a naphthyl group.

[0132] According to one embodiment of the present specification, R1 to R5 are hydrogen or deuterium.

[0133] According to one embodiment of the present specification, the chemical formula 1 is any one of the following structural formulas.

[0134]

[0135]

[0136]

[0137]

[0138]

[0139] 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.

[0140] 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.

[0141] 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.

[0142] 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.

[0143] 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.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0151] According to another embodiment, the first electrode is a negative electrode and the second electrode is a positive electrode.

[0152] (1) Anode / hole transport layer / emissive layer / cathode

[0153] (2) Anode / hole injection layer / hole transport layer / emissive layer / cathode

[0154] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / cathode

[0155] (4) Anode / hole transport layer / emissive layer / electron transport layer / cathode

[0156] (5) Anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0157] (6) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / cathode

[0158] (7) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0159] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / cathode

[0160] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0161] (10) Anode / hole transport layer / electron suppression layer / emissive layer / electron transport layer / cathode

[0162] (11) Anode / hole transport layer / electron suppression layer / emissive layer / electron transport layer / electron injection layer / cathode

[0163] (12) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / electron transport layer / cathode

[0164] (13) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / electron transport layer / electron injection layer / cathode

[0165] (14) Anode / hole transport layer / emissive layer / hole suppression layer / electron transport layer / cathode

[0166] (15) Anode / hole transport layer / emissive layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0167] (16) Anode / hole injection layer / hole transport layer / emissive layer / hole suppression layer / electron transport layer / cathode

[0168] (17) Anode / hole injection layer / hole transport layer / emissive layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0169] (18) Anode / hole injection layer / hole transport layer / electron suppression layer / emissive layer / hole blocking layer / electron injection and transport layer / cathode

[0170] The structure of the organic light-emitting device of the present invention may have a structure such as that shown in FIGS. 1 and 2, but is not limited thereto.

[0171] 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).

[0172] 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).

[0173] 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), an electron suppression layer (7), a light-emitting layer (8), a hole blocking layer (9), an electron injection and transport layer (10), and a cathode (4) are sequentially stacked on a substrate (1). A compound represented by the chemical formula 1 may be included in the hole blocking layer (9) or the electron injection and transport layer (10).

[0174] 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.

[0175] 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.

[0176] 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.

[0177] 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.

[0178] 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 in that the hole injection characteristics can be prevented from degrading, and if it is 150 nm or less, there is an advantage in that the driving voltage can be prevented from increasing to improve the movement of holes because the thickness of the hole injection layer is too thick.

[0179] 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.

[0180] [Chemical Formula HI-1]

[0181]

[0182] In the above chemical formula HI-1,

[0183] R400 to R402 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

[0184] L402 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0185] 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.

[0186] 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.

[0187] 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.

[0188] According to one embodiment of the present specification, R400 and R401 are the same or different from each other and are each independently aryl groups substituted or unsubstituted with alkyl groups.

[0189] 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 dimethylfluorene group.

[0190] According to one embodiment of the present specification, the chemical formula HI-1 is the following compound.

[0191]

[0192] 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.

[0193] [Chemical Formula HI-2]

[0194]

[0195] In the above chemical formula HI-1,

[0196] At least one of X'1 to X'6 is N, and the rest are CH, and

[0197] 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.

[0198] According to one embodiment of the present specification, X'1 to X'6 are N.

[0199] According to one embodiment of the present specification, R309 to R314 are nitrile groups.

[0200] According to one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.

[0201]

[0202] 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.

[0203] 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.

[0204] [Chemical Formula HT-2]

[0205]

[0206] In the above chemical formula HT-2,

[0207] R403 to R406 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

[0208] L403 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, and

[0209] l403 is an integer from 1 to 3, and if l403 is 2 or more, L403 are equal to or different from each other.

[0210] According to one embodiment of the present specification, R403 to R406 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.

[0211] According to one embodiment of the present specification, R403 to R406 are the same or different from each other and each is an aryl group having 6 to 30 carbon atoms.

[0212] According to one embodiment of the present specification, R403 to R406 are the same or different from each other, and each is independently a phenyl group, a biphenyl group, or a naphthyl group.

[0213] According to one embodiment of the present specification, R403 to R406 are the same or different from each other, and each is independently a phenyl group.

[0214] According to one embodiment of the present specification, the L403 is an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms substituted with an arylene group.

[0215] According to one embodiment of the present specification, L403 is a divalent carbazole group substituted or unsubstituted with a phenylene group, a divalent biphenyl group, or an aryl group.

[0216] According to one embodiment of the present specification, the chemical formula HT-2 is the following compound.

[0217]

[0218] 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.

[0219] According to one embodiment of the present specification, the electron suppression layer comprises a compound represented by the following chemical formula EB-1, but is not limited thereto.

[0220] [Chemical Formula EB-1]

[0221]

[0222] In the above chemical formula EB-1,

[0223] R407 to R409 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

[0224] L404 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0225] L404 is a phenylene group.

[0226] According to one embodiment of the present specification, R407 to R409 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.

[0227] According to one embodiment of the present specification, the R409 is a carbazole group substituted or unsubstituted with a phenyl group.

[0228] According to one embodiment of the present specification, R407 and R408 are the same or different from each other and are each independently an aryl group substituted or unsubstituted with an alkyl group, or they combine with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0229] According to one embodiment of the present specification, R407 and R408 are the same or different from each other and are each independently a phenyl group, a biphenyl group, or a dimethylfluorene group.

[0230] According to one embodiment of the present specification, the chemical formula EB-1 is the following compound.

[0231]

[0232] 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.

[0233] 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.

[0234] According to one embodiment of the present specification, the host comprises a compound represented by the following chemical formula H-1, but is not limited thereto.

[0235] [Chemical Formula H-1]

[0236]

[0237] In the above chemical formula H-1,

[0238] L20 and L21 are identical or different from each other, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group, and

[0239] Ar20 and Ar21 are identical or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0240] R2O1 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0241] r201 is an integer from 1 to 8, and if r201 is 2 or more, the 2 or more R201s are the same or different from each other.

[0242] In one embodiment of the present specification, L20 and L21 are identical or different from each other and are each independently directly bonded; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0243] In one embodiment of the present specification, L20 and L21 are identical or different from each other and are each independently directly bonded; a phenylene group substituted or unsubstituted with deuterium; a biphenylylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; a dibenzofuran group; or a dibenzothiophene group.

[0244] In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0245] In one embodiment of the present specification, Ar20 and Ar21 are identical or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; or substituted or unsubstituted monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms.

[0246] In one embodiment of the present specification, Ar20 and Ar21 are identical or different from each other and are each independently substituted or unsubstituted aryl groups having 6 to 20 carbon atoms and 4 rings; or substituted or unsubstituted heterocyclic groups having 6 to 20 carbon atoms and 4 rings.

[0247] In one embodiment of the present specification, Ar20 and Ar21 are identical or different from each other and each independently comprises: a phenyl group substituted or unsubstituted with a deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with a deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and a dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. Or it is a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0248] In one embodiment of the present specification, the Ar20 and Ar21 are identical or different from each other and are each independently a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group; a naphthyl group substituted or unsubstituted with deuterium; a thiophene group substituted or unsubstituted with a phenyl group; a phenanthrene group; a dibenzofuran group; a naphthobenzofuran group; a dibenzothiophen group; or a naphthobenzothiophen group.

[0249] In one embodiment of the present specification, Ar20 and Ar21 are identical or different from each other and are each independently a 1-naphthyl group or a 2-naphthyl group.

[0250] According to one embodiment of the present specification, R201 is hydrogen.

[0251] According to one embodiment of the present specification, the formula H-1 is represented by the following compound.

[0252]

[0253] 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.

[0254] According to one embodiment of the present specification, the dopant is represented by a compound of the following chemical formula D-1.

[0255] [Chemical Formula D-1]

[0256]

[0257] In the above chemical formula D-1,

[0258] T1 to T5 are the same or different from each other, and each independently is hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group, and

[0259] t3 and t4 are integers from 1 to 4, respectively, and

[0260] t5 is an integer from 1 to 3, and

[0261] If the above t3 is 2 or more, the above 2 or more T3s are the same or different from each other, and

[0262] If the above t4 is 2 or more, the above 2 or more T4s are the same or different from each other, and

[0263] If the above t5 is 2 or more, the above 2 or more T5s are the same or different from each other.

[0264] According to one embodiment of the present specification, T1 to T5 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 arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0265] According to one embodiment of the present specification, T1 to T5 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 monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

[0266] According to one embodiment of the present specification, T1 to T5 are the same or different from each other and are each independently hydrogen; a methyl group; an isopropyl group; a diphenylamine group; or a phenyl group substituted or unsubstituted with a methyl group or an isopropyl group.

[0267] According to one embodiment of the present specification, T1 to T5 are the same or different from each other and are each independently an isopropyl group; or a phenyl group substituted or unsubstituted with an isopropyl group.

[0268] According to one embodiment of the present specification, the formula D-1 is represented by the following compound.

[0269]

[0270] A hole blocking layer may be provided between the electron transport layer and the light-emitting layer, and materials known in the art may be used.

[0271] According to one embodiment of the present specification, the hole blocking layer comprises a compound of the following formula HB-1.

[0272] [Chemical Formula HB-1]

[0273]

[0274] In the above chemical formula HB-1,

[0275] At least one of Z1 to Z3 is N, and the rest are CH, and

[0276] L601 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0277] Ar601 to Ar603 are the same or different from one another and are each independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups.

[0278] According to one embodiment of the present specification, the L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0279] According to one embodiment of the present specification, the L601 is a phenylene group; a biphenyllylene group; or a naphthylene group.

[0280] According to one embodiment of the present specification, the Ar601 to Ar603 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, or heteroaryl groups having 3 to 30 carbon atoms.

[0281] According to one embodiment of the present specification, Ar601 to Ar603 are phenyl groups or dimethylfluorene groups.

[0282] According to one embodiment of the present specification, the formula HB-1 is represented by the following compound.

[0283]

[0284] 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.

[0285] 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.

[0286] The above electron injection and transport layers can be manufactured by appropriately selecting the materials used in the electron injection layer and electron transport layer.

[0287] The electron injection and transport layer above can be prepared by using the compound of Formula 1 and the metal complex together.

[0288] The electron injection and transport layer comprises the compound of Formula 1 and the metal complex in a weight ratio of 1:10 to 10:1.

[0289] The electron injection and transport layer comprises the compound of Formula 1 and the metal complex in a weight ratio of 1:3 to 3:1.

[0290] 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 thereto.

[0291] 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.

[0292] 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.

[0293] 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.

[0294] 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.

[0295] 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 may be those known in the art.

[0296] 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.

[0297] 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 may be those known in the art.

[0298] Preparation Example 1. Synthesis of Compound E1

[0299]

[0300] After completely dissolving the above compounds 6,6'-(5'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (10.0 g, 15.3 mmol) and (3-cyanophenyl)boronic acid (2.25 g, 15.3 mmol) in tetrahydrofuran (100 ml), potassium carbonate (6.36 g, 46 mmol) dissolved in 20 ml of water was added, and tetracyclotriphenylphosphine palladium (354 mg, 0.3 mmol) dissolved in tetrahydrofuran was slowly added. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and the above white solid was filtered. The filtered white solid was washed twice each with water and ethyl acetate to prepare the above compound E1 (9.7g, yield 88%).

[0301] MS[M+H] + = 717

[0302] Preparation Example 2. Synthesis of Compound E2

[0303]

[0304] Compound E2 was prepared in the same manner as in Preparation Example 1, except that (4-cyanophenyl)boronic acid was used instead of (3-cyanophenyl)boronic acid in Preparation Example 1.

[0305] MS[M+H] + = 717

[0306] Preparation Example 7. Synthesis of Compound E7

[0307]

[0308] Compound E7 was prepared in the same manner as in Preparation Example 1, except that 6,6'-(4'-chloro-[1,1'-biphenylyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of 6,6'-(5'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0309] MS[M+H] + = 717

[0310] Preparation Example 8. Synthesis of Compound E8

[0311]

[0312] Compound E8 was prepared in the same manner as in Preparation Example 7, except that (4-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid in Preparation Example 7.

[0313] MS[M+H] + = 717

[0314] Preparation Example 9. Synthesis of Compound E9

[0315]

[0316] Compound E9 was prepared in the same manner as in Preparation Example 1, except that 6,6'-(6'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of compound 6,6'-(5'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1, and (2-cyanophenyl)boronic acid was used instead of (3-cyanophenyl)boronic acid.

[0317] MS[M+H] + = 717

[0318] Preparation Example 10. Synthesis of Compound E10

[0319]

[0320] Compound E10 was prepared in the same manner as in Preparation Example 9, except that (3-cyanophenyl)boronic acid was used instead of the compound (2-cyanophenyl)boronic acid in Preparation Example 9.

[0321] MS[M+H] + = 717

[0322] Preparation Example 11. Synthesis of Compound E11

[0323]

[0324] Compound E11 was prepared in the same manner as in Preparation Example 9, except that (4-cyanophenyl)boronic acid was used instead of the compound (2-cyanophenyl)boronic acid in Preparation Example 9.

[0325] MS[M+H] + = 717

[0326] Preparation Example 14 Synthesis of Compound E14

[0327]

[0328] Compound E14 was prepared in the same manner as in Preparation Example 1, except that 2',6-bis(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1':4',1''-terphenyl]-3-carbonitrile was used instead of compound 6,6'-(5'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0329] MS[M+H] + = 793

[0330] Preparation Example 15 Synthesis of Compound E15

[0331]

[0332] Compound E15 was prepared in the same manner as in Preparation Example 1, except that 2-([1,1'-biphenyl]-3-yl)-4-(3-chloro-2'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazine) was used instead of compound 6,6'-(5'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0333] MS[M+H] + = 793

[0334] Preparation Example 16 Synthesis of Compound E16

[0335]

[0336] Compound E16 was prepared in the same manner as in Preparation Example 1, except that 2-(4'-chloro-3'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-2-yl)-4-phenylquinazolin was used instead of compound 6,6'-(5'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0337] MS[M+H] + = 690

[0338] 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.

[0339] Example 1-1

[0340] 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.

[0341] A hole injection layer was formed on the prepared ITO transparent electrode by thermal vacuum deposition of compounds HI1 and HI2 in a ratio of 98:2 (molar ratio) to a thickness of 100 Å. A hole transport layer was formed by vacuum deposition of a compound represented by the chemical formula HT1 (1150 Å) on the hole injection layer. Subsequently, an electron suppression layer was formed by vacuum deposition of a compound EB1 with a film thickness of 50 Å on the hole transport layer. Subsequently, an emissive layer was formed by vacuum deposition of a compound represented by the chemical formula BH and a compound represented by the chemical formula BD in a weight ratio of 50:1 on the electron suppression layer to a film thickness of 200 Å. A hole blocking layer was formed by vacuum deposition of a compound represented by the chemical formula HB1 with a film thickness of 50 Å on the emissive layer. Next, a compound of the following chemical formula E-1 and a compound represented by the following chemical formula LiQ were vacuum-deposited in a weight ratio of 1:1 on the hole-blocking layer to form an electron injection and transport layer with a thickness of 30 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 1,000 Å on the electron injection and transport layer.

[0342]

[0343] In the above process, the deposition rate of the organic material was maintained at 0.4–0.7 Å / sec, while the deposition rates for the cathode lithium fluoride and aluminum were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 2 × 10⁻¹⁰ -7 ~ 5 x 10 -6 An organic light-emitting diode was fabricated by maintaining torr.

[0344] Examples 1-2 to 1-16

[0345] An organic light-emitting diode was prepared in the same manner as in Example 1-1, except that the compound listed in Table 1 below was used instead of compound E-1 of Example 1-1.

[0346] Comparative Examples 1-1 to 1-6

[0347] An organic light-emitting diode was prepared in the same manner as in Example 1-1 above, except that a compound listed in Table 1 below was used instead of compound E-1. The compounds ET-1 to ET-6 used in Table 1 below are as follows.

[0348]

[0349] When current was applied to the organic light-emitting diodes fabricated according to Examples 1-1 to 1-16 and Comparative Examples 1-1 to 1-6, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in [Table 1] below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

[0350] Compound (electron injection and transport layer) Voltage (V@20mA / cm²) 2 ) Efficiency (cd / A @ 20mA / cm²) 2 ) Color coordinates (x,y) T95(hr) Experimental Example 1-1 Compound E1 4.32 5.92 (0.138, 0.039) 238 Examples 1-2 Compound E2 4.35 6.12 (0.138, 0.039) 238 Examples 1-7 Compound E7 4.38 6.45 (0.137, 0.038) 241 Examples 1-8 Compound E8 4.31 6.30 (0.138, 0.039) 254 Examples 1-9 Compound E9 4.29 6.29 (0.139, 0.040) 249 Examples 1-10 Compound E10 4.36 6.31 (0.140, 0.040) 251 Example 1-11 Compound E11 4.36 6.17 (0.138, 0.038) 238 Examples 1-14 Compound E14 4.24 6.10 (0.139, 0.039) 246 Examples 1-15 Compound E15 4.42 6.21 (0.138, 0.039) 238 Examples 1-16 Compound E16 4.43 6.37 (0.139, 0.040) 230 Comparative Example 1-1 ET-1 4.64 5.21 (0.139, 0.040) 112 Comparative Example 1-2 ET-2 4.59 4.98 (0.138, 0.039) 131 Comparative Examples 1-3 ET-3 4.84 4.34 (0.140, 0.038) 175 Comparative Examples 1-4 ET-4 4.76 4.56 (0.140, 0.040) 168 Comparative Examples 1-5 ET-5 4.88 4.49 (0.139, 0.040) 191 Comparative Examples 1-6 ET-6 4.83 4.51 (0.140, 0.040) 188

[0351] As shown in Table 1 above, an organic light-emitting diode manufactured using the compound of the present invention as an electron injection and transport layer exhibits excellent characteristics in terms of efficiency, driving voltage, and / or stability. Compared to commonly used electron injection and transport layers, low voltage and high efficiency characteristics were achieved by controlling electron injection and mobility by appropriately adjusting the distance between N-containing ring groups and limiting the linker connection direction between them to ortho to appropriately interrupt conjugation. In addition, long lifespan characteristics were also achieved by introducing highly electronegative CN groups to prevent excessive electron injection.

[0352] Although preferred embodiments of the present invention (electron injection and transport layer) have been described above, the present invention is not limited thereto and may be implemented with various modifications within the scope of the claims and the detailed description of the invention, and such modifications also fall within the scope of the invention. Explanation of the symbols

[0353] 1: Substrate 2: Anode 3: Organic layer 4: Cathode 5: Hole injection layer 6: Precision Transport Layer 7: Electron suppression layer 8: Emissive layer 9: Poison blockade layer 10: Electron injection and transport layer

Claims

Claim 1 Compound of Chemical Formula 1 below: [Chemical Formula 1] In the above Chemical Formula 1, R1 to R5 are the same or different from each other and each independently are hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group; Ar1 ​​is a substituted or unsubstituted heteroaryl group containing 2 or more N; Ar2 is hydrogen, deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, or substituted or unsubstituted condensed ring; a and c are integers from 1 to 4; b is an integer from 1 to 3; d and e are integers from 1 to 5; when a is 2 or more, R1 is the same or different from each other; when b is 2 or more, R2 is the same or different from each other; when c is 2 or more, R3 is the same or different from each other; and d When e is 2 or greater, R4 is equal to or different from each other, and when e is 2 or greater, R5 is equal to or different from each other. Claim 2 The compound of claim 1, wherein the chemical formula 1 is the following chemical formula 1-1 or 1-2: [Chemical formula 1-1] [Chemical Formula 1-2] In the above chemical formulas 1-1 and 1-2, R1 to R5, Ar1, Ar2 and a to e are as defined in the above chemical formula 1. Claim 3 The compound of claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-3 to 1-7: [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] In the above chemical formulas 1-3 to 1-7, R1 to R5, Ar1, Ar2 and a to e are as defined in the above chemical formula 1. Claim 4 The compound of claim 1, wherein the chemical formula 1 is the following chemical formula 1-1-1 or 1-1-2: [Chemical formula 1-1-1] [Chemical Formula 1-1-2] In the above chemical formulas 1-1-1 and 1-1-2, R4, R5, Ar1, Ar2, d, and e are as defined in the above chemical formula 1. Claim 5 The compound of claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-1-3 to 1-1-7: [Chemical Formula 1-1-3] [Chemical Formula 1-1-4] [Chemical Formula 1-1-5] [Chemical Formula 1-1-6] [Chemical Formula 1-1-7] In the above chemical formulas 1-1-3 to 1-1-7, R4, R5, Ar1, Ar2, d, and e are as defined in the above chemical formula 1. Claim 6 A compound according to claim 1, wherein Ar1 is a triazine group. Claim 7 A compound according to claim 1, wherein Ar1 is a pyrimidine group. Claim 8 A compound according to claim 1, wherein Ar2 is an aryl group having 6 to 30 carbon atoms. Claim 9 A compound according to claim 1, wherein R1 to R5 are hydrogen or deuterium. Claim 10 A compound according to claim 1, wherein the chemical formula 1 is any one of the following compounds: Claim 11 An organic light-emitting device 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 comprise a compound according to any one of claims 1 to 10. Claim 12 An organic light-emitting device according to claim 11, wherein the organic layer comprises one or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more of the layers comprises the compound.

Images