Compound and organic light-emitting device comprising same

Abstract

The present specification provides a compound of chemical formula 1 and an organic light-emitting device comprising same. Specifically, the organic light-emitting device comprises: a first electrode; a second electrode provided to face 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 compound of chemical formula 1.

Description

Compound and organic light-emitting device containing the same

[0001] This application claims the benefit of Korean Patent Application No. 10-2023-0174543, filed with the Korean Intellectual Property Office on December 5, 2023, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to a compound and an organic light-emitting device comprising the same.

[0003] In this specification, an organic light-emitting device is a light-emitting device using an organic semiconductor material, and requires the exchange of holes and / or electrons between an electrode and the organic semiconductor material. Organic light-emitting devices can be broadly divided into two types according to their operating principles. First, a light-emitting device is a type in which excitons are formed in an organic layer by photons that enter the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as a current source (voltage source). Second, a light-emitting device is a type 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 is operated by the injected electrons and holes.

[0004] In general, organic light emitting diodes (OLEDs) are devices that utilize the organic light emitting phenomenon, typically comprising an anode and a cathode, with an organic layer between them. These organic layers are often multilayered, composed of different materials, to enhance the efficiency and stability of the device. For example, they may include a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in this device, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. Excitons form when the injected holes and electrons meet, and light is emitted when these excitons fall back to their ground state. These devices are known to exhibit characteristics such as self-luminescence, high brightness, high efficiency, low operating voltage, wide viewing angle, and high contrast.

[0005] In order to fully demonstrate the excellent characteristics of the aforementioned organic light-emitting device, the materials forming the organic layer within the device, such as hole injection materials, hole transport materials, luminescent materials, electron blocking materials, electron transport materials, and electron injection materials, must be supported by stable and efficient materials, and therefore, the development of new materials is continuously required.

[0006] The present specification describes a novel compound and an organic light-emitting device comprising the same.

[0007] One embodiment of the present disclosure provides a compound of the following chemical formula 1.

[0008] [Chemical Formula 1]

[0009]

[0010] In the above chemical formula 1,

[0011] L1 is a direct bond or a substituted or unsubstituted monocyclic or bicyclic arylene group,

[0012] Ar1 is a heteroaryl group containing N substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group,

[0013] R1 to R4 are the same or different and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group,

[0014] a is 1 or 2,

[0015] b and c are integers from 1 to 4, respectively,

[0016] d is an integer from 1 to 3,

[0017] When a is 2, the substituents in parentheses are the same or different,

[0018] When b to d are 2 or more, the substituents in parentheses are the same or different.

[0019] In addition, according to one embodiment of the present invention, an organic light-emitting device is provided, including a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes the above-described compound.

[0020] The compound of the present invention can be used as a material for an organic layer of an organic light-emitting device, and can improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light-emitting device. In particular, the compound of the above-described chemical formula 1 can be used as a material for an electron injection layer, an electron transport layer, or an electron injection and transport layer.

[0021] Figures 1 and 2 illustrate examples of organic light-emitting devices according to the present invention.

[0022] [Explanation of symbols]

[0023] 1: Substrate

[0024] 2: First electrode

[0025] 3: Organic layer

[0026] 4: Second electrode

[0027] 5: Hole injection layer

[0028] 6: Hole transport layer

[0029] 7: Emissive layer

[0030] 8: Electron injection and transport layer

[0031] The following describes this specification in more detail.

[0032] In this specification, when a part is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0033] In this specification, when it is said that a member is located “on” another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

[0034] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., a position where the substituent can be replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0035] The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group (-CN); a silyl group; a boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; and a substituted or unsubstituted heterocyclic group, or substituted with a substituent in which two or more substituents among the above-mentioned substituents are connected, or has no substituents. For example, "a substituent connected with two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are connected.

[0036] Examples of the above substituents are described below, but are not limited thereto.

[0037] In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0038] In the present specification, a silyl group may be represented by the chemical formula -SiY1Y2Y3, wherein Y1, Y2, and Y3 may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0039] In the present specification, the boron group may be represented by the chemical formula -BY4Y5, wherein Y4 and Y5 may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, a diphenyl boron group, a phenyl boron group, etc.

[0040] In the present specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and the like.

[0041] In this specification, the arylalkyl group refers to an alkyl group substituted with an aryl group. The number of carbon atoms is not particularly limited, but according to one embodiment, the alkyl group has 1 to 30 carbon atoms, and the aryl group substituted with the alkyl group has 6 to 30 carbon atoms.

[0042] In the present specification, the amine group may be selected from the group consisting of -NH2; an alkylamine group; an N-alkylarylamine group; an arylamine group; an N-arylheteroarylamine group; an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group; a dimethylamine group; an ethylamine group; a diethylamine group; a phenylamine group; a naphthylamine group; a biphenylamine group; anthracenylamine group; a 9-methylanthracenylamine group; a diphenylamine group; a ditolylamine group; an N-phenyltolylamine group; a triphenylamine group; an N-phenylbiphenylamine group; an N-phenylnaphthylamine group; an N-biphenylnaphthylamine group; an N-naphthylfluorenylamine group; an N-phenylphenanthrenylamine group; an N-biphenylphenanthrenylamine group; an N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, etc., but are not limited thereto.

[0043] In this specification, an N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.

[0044] In this specification, an N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N of the amine group.

[0045] In this specification, an N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted for N of the amine group.

[0046] In the present specification, the alkyl group among the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the examples of the alkyl group described above. Specifically, the alkylthioxy group includes a methylthioxy group; an ethylthioxy group; a tert-butylthioxy group; a hexylthioxy group; an octylthioxy group, etc., and the alkylsulfoxy group includes, but is not limited to, a mesyl group; an ethylsulfoxy group; a propylsulfoxy group; a butylsulfoxy group, etc.

[0047] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0048] 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 aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenylene group, a chrysenyl group, a fluorenyl group, etc.

[0049] In the present specification, a heteroaryl group is a ring group containing at least one of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, and the like.

[0050] In this specification, the meaning of “adjacent” in “forming a ring by bonding with adjacent groups” is the same as described above, and the “ring” means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0051] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, this specification, including definitions, will control unless a specific passage is cited. Furthermore, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0052] In this specification, the arylene group is as defined in the above aryl group, except that it is a divalent group.

[0053] In this specification, the heteroarylene group is as defined in the heteroaryl group above, except that it is divalent.

[0054] In this specification, the chemical formula 1 is any one of the chemical formulas 1-1 to 1-4 below.

[0055] [Chemical Formula 1-1]

[0056]

[0057] [Chemical Formula 1-2]

[0058]

[0059] [Chemical Formula 1-3]

[0060]

[0061] [Chemical Formula 1-4]

[0062]

[0063] In the above chemical formulas 1-1 to 1-4, R1 to R4, L1, Ar1, and a to d are as defined in the above chemical formula 1.

[0064] In this specification, the chemical formula 1 is any one of the chemical formulas 2-1 to 2-4 below.

[0065] [Chemical Formula 2-1]

[0066]

[0067] [Chemical Formula 2-2]

[0068]

[0069] [Chemical Formula 2-3]

[0070]

[0071] [Chemical Formula 2-4]

[0072]

[0073] In the above chemical formulas 2-1 to 2-4, R1 to R3, L1, Ar1, and a to c are as defined in the above chemical formula 1.

[0074] In this specification, the chemical formula 1 is any one of the chemical formulas 2-5 to 2-10 below.

[0075] [Chemical Formula 2-5]

[0076]

[0077] [Chemical Formula 2-6]

[0078]

[0079] [Chemical Formula 2-7]

[0080]

[0081] [Chemical Formula 2-8]

[0082]

[0083] [Chemical Formula 2-9]

[0084]

[0085] [Chemical Formula 2-10]

[0086]

[0087] In the above chemical formulas 2-5 to 2-10, R1 to R4, L1, Ar1, and a to c are as defined in the above chemical formula 1.

[0088] In this specification, the chemical formula 1 is any one of the chemical formulas 2-11 to 2-16 below.

[0089] [Chemical Formula 2-11]

[0090]

[0091] [Chemical Formula 2-12]

[0092]

[0093] [Chemical Formula 2-13]

[0094]

[0095] [Chemical Formula 2-14]

[0096]

[0097] [Chemical Formula 2-15]

[0098]

[0099] [Chemical Formula 2-16]

[0100]

[0101] In the above chemical formulas 2-11 to 2-16, R1 to R4, L1, Ar1, and a to c are as defined in the above chemical formula 1.

[0102] In the present specification, R1 to R3 are the same as or different from each other, and each independently represents 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, a substituted or unsubstituted amine group, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a substituted or unsubstituted silyl group.

[0103] In the present specification, R1 to R3 are the same as or different from each other, and each independently represents 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.

[0104] In the present specification, R1 to R3 are the same as or different from each other, and each independently represents 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 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0105] In the present specification, R1 to R3 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a nitrile group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0106] In the present specification, R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium, F, Cl, Br, I, a nitrile group, a methyl group, an ethyl group, an isopropyl group, a propyl group, or a terbutyl group.

[0107] In this specification, R1 to R3 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0108] In this specification, R1 to R3 are hydrogen.

[0109] In this specification, R1 to R3 are deuterium.

[0110] In the present specification, R4 is hydrogen, deuterium, or a substituted or unsubstituted heteroaryl group.

[0111] In the present specification, R4 is a heteroaryl group containing hydrogen, deuterium, or substituted or unsubstituted N.

[0112] In the present specification, R4 is a heteroaryl group having 3 to 30 carbon atoms and containing hydrogen, deuterium, or substituted or unsubstituted N.

[0113] In the present specification, R4 is a heteroaryl group having 3 to 20 carbon atoms and containing hydrogen, deuterium, or substituted or unsubstituted N.

[0114] In the present specification, R4 is a heteroaryl group having 3 to 15 carbon atoms and containing hydrogen, deuterium, or substituted or unsubstituted N.

[0115] In the present specification, R4 is a monocyclic or bicyclic heteroaryl group containing hydrogen, deuterium, or substituted or unsubstituted N.

[0116] In this specification, R4 is hydrogen or deuterium.

[0117] In this specification, R4 is hydrogen.

[0118] In this specification, R4 is deuterium.

[0119] In the present specification, R4 is a substituted or unsubstituted heteroaryl group.

[0120] In the present specification, R4 is a monocyclic or bicyclic heterocyclic group containing substituted or unsubstituted N.

[0121] In the present specification, R4 is a monocyclic or bicyclic heterocyclic group containing N, and the heterocyclic group is substituted or unsubstituted with an aryl group substituted or unsubstituted with a nitrile group.

[0122] In the present specification, R4 is a pyridine group, a pyrimidine group, a triazine group, a pyridazine group, a quinoline group, a quinazoline group, or a quinoxaline group, and the pyridine group, pyrimidine group, triazine group, pyridazine group, quinoline group, quinazoline group, or quinoxaline group is substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0123] In the present specification, R4 is a pyridine group, a pyrimidine group, a triazine group, or a pyridazine group, and the pyridine group, pyrimidine group, triazine group, or pyridazine group is substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0124] In the present specification, R4 is a quinoline group, a quinazoline group, or a quinoxaline group, and the quinoline group, quinazoline group, or quinoxaline group is substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0125] In the present specification, R4 is a pyridine group, a pyrimidine group, a triazine group, a pyridazine group, a quinoline group, a quinazoline group, or a quinoxaline group, and the pyridine group, pyrimidine group, triazine group, pyridazine group, quinoline group, quinazoline group, or quinoxaline group is substituted or unsubstituted with a phenyl group substituted or unsubstituted with a nitrile group, a naphthyl group substituted or unsubstituted with a nitrile group, or a biphenyl group substituted or unsubstituted with a naphthyl group.

[0126] In this specification, L1 is a direct bond or a substituted or unsubstituted phenylene group.

[0127] In this specification, L1 is a direct bond or a substituted or unsubstituted naphthalene group.

[0128] In this specification, L1 is a direct bond or a substituted or unsubstituted divalent biphenyl group.

[0129] In this specification, L1 is a direct bond or a phenylene group substituted or unsubstituted with a nitrile group.

[0130] In this specification, L1 is a direct bond or a naphthalene group substituted or unsubstituted with a nitrile group.

[0131] In this specification, L1 is a direct bond or a divalent biphenyl group substituted or unsubstituted with a nitrile group.

[0132] In this specification, the L1 is a direct bond.

[0133] In this specification, L1 is a direct bond or a phenylene group.

[0134] In this specification, L1 is a direct bond or a divalent naphthalene group.

[0135] In this specification, L1 is a direct bond, a phenylene group, or a divalent naphthalene group.

[0136] In this specification, L1 is a substituted or unsubstituted phenylene group.

[0137] In this specification, L1 is a substituted or unsubstituted divalent naphthylene group.

[0138] In this specification, L1 is a substituted or unsubstituted divalent biphenyl group.

[0139] In this specification, L1 is a phenylene group substituted or unsubstituted with a nitrile group.

[0140] In the present specification, L1 is a divalent naphthylene group substituted or unsubstituted with a nitrile group.

[0141] In this specification, L1 is a divalent biphenyl group substituted or unsubstituted with a nitrile group.

[0142] In this specification, L1 is a phenylene group.

[0143] In this specification, L1 is a divalent naphthylene group.

[0144] In this specification, L1 is a phenylene group or a divalent naphthylene group.

[0145] In the present specification, Ar1 is a heteroaryl group including N substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0146] In the present specification, Ar1 is a monocyclic or bicyclic heteroaryl group containing N substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0147] In the present specification, Ar1 is a heteroaryl group having 3 to 30 carbon atoms, including N, which is substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0148] In the present specification, Ar1 is a heteroaryl group having 3 to 20 carbon atoms, including N, which is substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0149] In the present specification, Ar1 is a heteroaryl group having 3 to 15 carbon atoms, including N, which is substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0150] In the present specification, Ar1 is a monocyclic heteroaryl group including N substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0151] In the present specification, Ar1 is a bicyclic heteroaryl group containing N substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0152] In the present specification, the Ar1 is a pyridine group, a pyrimidine group, a triazine group, a pyridazine group, a quinoline group, a quinazoline group, or a quinoxaline group, and the Ar is substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0153] In the present specification, the Ar1 is a pyridine group, a pyrimidine group, a triazine group, or a pyridazine group, and the Ar is substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0154] In the present specification, the Ar1 is a quinoline group, a quinazoline group, or a quinoxaline group, and the Ar is substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

[0155] In the present specification, the Ar1 is a pyridine group, a pyrimidine group, a triazine group, a pyridazine group, a quinoline group, a quinazoline group, or a quinoxaline group, and the Ar is substituted or unsubstituted with a phenyl group substituted or unsubstituted with a nitrile group, a naphthyl group substituted or unsubstituted with a nitrile group, or a biphenyl group substituted or unsubstituted with a naphthyl group.

[0156] In this specification, a is 1.

[0157] In this specification, a is 2.

[0158] In this specification, b and c are each an integer from 1 to 4.

[0159] In this specification, b is 1.

[0160] In this specification, b is 2.

[0161] In this specification, b is 3.

[0162] In this specification, b is 4.

[0163] In this specification, c is 1.

[0164] In this specification, c is 2.

[0165] In this specification, c is 3.

[0166] In this specification, c is 4.

[0167] In this specification, d is 1.

[0168] In this specification, d is 2.

[0169] In this specification, d is 3.

[0170] According to one embodiment of the present specification, at least 10% of the substitutable positions of the chemical formula 1 are substituted with deuterium.

[0171] According to one embodiment of the present specification, at least 25% of the substitutable positions of the chemical formula 1 are substituted with deuterium.

[0172] According to one embodiment of the present specification, at least 30% of the substitutable positions of the chemical formula 1 are substituted with deuterium.

[0173] According to one embodiment of the present specification, at least 45% of the substitutable positions of the chemical formula 1 are substituted with deuterium.

[0174] According to one embodiment of the present specification, more than 50% of the substitutable positions of the chemical formula 1 are substituted with deuterium.

[0175] According to one embodiment of the present specification, more than 60% of the substitutable positions of the chemical formula 1 are substituted with deuterium.

[0176] According to one embodiment of the present specification, more than 80% of the substitutable positions of the chemical formula 1 are substituted with deuterium.

[0177] According to one embodiment of the present specification, more than 90% of the substitutable positions of the chemical formula 1 are substituted with deuterium.

[0178] An organic light-emitting device according to one embodiment of the present specification has a deuterium substitution rate of independently 1% or more and 100% or less for the compound represented by the chemical formula 1.

[0179] In one embodiment of the present specification, the deuterium substitution rate for the compound represented by the chemical formula 1 may independently be 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more.

[0180] In one embodiment of the present specification, the deuterium substitution rate for the compound represented by the chemical formula 1 may independently be 100% or less, 99% or less, 98% or less, 97% or less, 96% or less, or 95% or less.

[0181] In one embodiment of the present specification, the deuterium substitution rate for the compound represented by the chemical formula 1 is 100%.

[0182] The above deuterium substitution rate can be calculated by the method described above. According to an additional example, at least one deuterium is directly substituted in anthracene of the above chemical formula 2. The light-emitting layer of the organic light-emitting device is a region that emits light and is a region where the loss of molecules due to energy is large. The carbon-deuterium bond is stronger than the carbon-hydrogen bond, and deuterium has a higher mass value than hydrogen, so it lowers the zero point energy with carbon and the bond energy is high. Therefore, by replacing the carbon-hydrogen bond included in the molecule of the compound of the above chemical formula 2 with a carbon-deuterium bond, the bond energy of the molecule is increased, and a device having an excellent lifespan can be obtained.

[0183] Zero point energy =

[0184] An organic light-emitting device comprising a compound of chemical formula 1 and / or chemical formula 2 having a deuterium substitution rate according to an embodiment of the present specification has improved heat resistance and an improved lifespan.

[0185] As used herein, “deuterated” or “deuterated” means that a hydrogen at a substitutable position of a compound is replaced with deuterium.

[0186] In this specification, “perdeuterated” means a compound or group in which all hydrogens in the molecule are substituted or unsubstituted with deuterium, and has the same meaning as “100% deuterated.”

[0187] In the present specification, “X% deuterated”, “degree of deuteration X%”, or “deuterium substitution rate X%” means that X% of the hydrogens at substitutable positions in the structure are replaced with deuterium. For example, when the structure is dibenzofuran, “25% deuterated” of the dibenzofuran, “degree of deuteration 25%” of the dibenzofuran, or “deuterium substitution rate 25%” of the dibenzofuran means that 2 of the 8 hydrogens at substitutable positions of the dibenzofuran are substituted or unsubstituted with deuterium.

[0188] In this specification, “degree of deuteration” or “deuterium substitution rate” can be confirmed by a known method such as nuclear magnetic resonance spectroscopy (1H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0189] Specifically, when analyzing the "degree of deuteration" or "deuterium substitution rate" by nuclear magnetic resonance spectroscopy (1H NMR), by adding DMF (dimethylformamide) as an internal standard, the degree of deuteration or deuterium substitution rate can be calculated from the total peak integration amount through the integration ratio on 1H NMR.

[0190] In addition, when analyzing the "degree of deuteration" or "deuterium substitution rate" through TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), the substitution rate can be calculated based on the maximum value (median value) of the distribution of molecular weights at the end of the reaction. For example, when analyzing the degree of deuteration of the following compound A, when the molecular weight of the following starting material is 506 and the maximum value (median value) of the molecular weight of the following compound A in the MS graph is 527, since 21 of the hydrogens (26) at the substitutable positions of the following starting material were substituted with deuterium, it can be calculated that approximately 81% of the hydrogens were deuterated.

[0191] In this specification, D means deuterium.

[0192] In this specification, "or" means an inclusive "or" and not an exclusive "or." For example, a condition A or B is satisfied by either: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), or both A and B are true (or exist).

[0193] In this specification, "mixture thereof" or "mixture" means that two or more substances are included. The "mixture" or "mixture" may include, but is not limited to, a uniformly and / or non-uniformly mixed state, a dissolved state, a uniformly and / or non-uniformly dispersed state, etc.

[0194] In this specification, "energy level" or "energy level" refers to the magnitude of energy. Therefore, "energy level" is interpreted as referring to the absolute value of the corresponding energy value. For example, a lower or deeper energy level means that the absolute value increases in a negative direction from the vacuum level.

[0195] In this specification, the chemical formula 1 is one of the following structural formulas.

[0196]

[0197]

[0198] The substituent of the compound of the above chemical formula 1 can be combined by a method known in the art, and the type, position or number of the substituent can be changed according to a technique known in the art.

[0199] In addition, by introducing various substituents into the core structure as described above, compounds having the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly 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, a material satisfying the conditions required for each organic layer can be synthesized.

[0200] In addition, an organic light-emitting device according to the present invention is an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, characterized in that one or more of the organic layers includes the compound described above.

[0201] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

[0202] The above compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0203] 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 laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously injects holes and transports holes, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. 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.

[0204] In the organic light-emitting device of the present invention, the organic layer may include at least one layer among an electron transport layer, an electron injection layer, and a layer that simultaneously injects electrons and transports electrons, and at least one layer among the layers includes the compound of the chemical formula 1.

[0205] In the organic light-emitting device of the present invention, the organic layer includes an electron injection and transport layer, and the electron injection and transport layer includes a compound of the chemical formula 1.

[0206] In the organic light-emitting device of the present invention, the electron injection and transport layer includes a metal complex together with the compound of the chemical formula 1.

[0207] In the organic light-emitting device of the present invention, the electron injection and transport layer contains the compound of the chemical formula 1 and the metal complex in a mass ratio of 10:1 to 1:10.

[0208] In the organic light-emitting device of the present invention, the electron injection and transport layer contains the compound of the chemical formula 1 and the metal complex in a mass ratio of 7:1 to 1:7.

[0209] In the organic light-emitting device of the present invention, the electron injection and transport layer contains the compound of the chemical formula 1 and the metal complex in a mass ratio of 5:1 to 1:5.

[0210] In the organic light-emitting device of the present invention, the electron injection and transport layer contains the compound of the chemical formula 1 and the metal complex in a mass ratio of 3:1 to 1:3.

[0211] In the organic light-emitting device of the present invention, the electron injection and transport layer contains the compound of the chemical formula 1 and the metal complex in a mass ratio of 2:1 to 1:2.

[0212] In the organic light-emitting device of the present invention, the electron injection and transport layer contains the compound of the chemical formula 1 and the metal complex in a mass ratio of 1.5:1 to 1:1.5.

[0213] 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 includes the compound of the above chemical formula 1.

[0214] In the organic light-emitting device of the present invention, the organic layer containing the compound is an electron transport layer, an electron injection layer, or an electron injection and transport layer.

[0215] In the organic light-emitting device of the present invention, the organic layer may include at least one layer among a hole injection layer, a hole transport layer, and a layer that simultaneously injects holes and transports holes, and at least one layer among the layers includes the compound of the chemical formula 1.

[0216] 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 includes the compound of the above chemical formula 1.

[0217] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0218] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0219] (1) Anode / hole transport layer / light emitting layer / cathode

[0220] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0221] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0222] (4) Anode / hole transport layer / light emitting layer / electron transport layer / cathode

[0223] (5) Anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0224] (6) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0225] (7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0226] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0227] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0228] (10) Anode / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / cathode

[0229] (11) Anode / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0230] (12) Anode / hole injection layer / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / cathode

[0231] (13) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0232] (14) Anode / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / cathode

[0233] (15) Anode / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0234] (16) Anode / hole injection layer / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / cathode

[0235] (17) Anode / hole injection layer / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0236] (18) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0237] The structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

[0238] Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode (2), an organic layer (3), and a second electrode (4) are sequentially laminated on a substrate (1). In such a structure, the compound of the chemical formula 1 may be included in the organic layer (3).

[0239] FIG. 2 illustrates the structure of an organic light-emitting device in which a first electrode (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 second electrode (4) are sequentially laminated on a substrate (1). In this structure, the compound of the chemical formula 1 may be included in the electron injection and transport layer (8).

[0240] For example, the 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 PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and then forming an organic layer including at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons, 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.

[0241] 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 a smaller number of layers using various polymer materials by a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0242] The above anode is an electrode that injects holes, and as the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are not limited to, 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.

[0243] The above cathode is an electrode that injects electrons, and the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0244] The above hole injection layer is a layer that facilitates the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can well inject holes from the anode at a 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 the hole injection material include, but are not limited to, metal porphyrine, oligothiophene, arylamine-based organic compounds, hexanitrilehexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and conductive polymers such as polyaniline and polythiophene. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the above hole injection layer is 1 nm or more, there is an advantage of being able to prevent the hole injection characteristics from being deteriorated, and if it is 150 nm or less, there is an advantage of being able to prevent the driving voltage from being increased to improve the movement of holes due to the thickness of the hole injection layer being too thick.

[0245] According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-1.

[0246] [Chemical formula HI-1]

[0247]

[0248] In the above chemical formula HI-1,

[0249] R300 to R308 are the same or different, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are bonded to adjacent groups to form a substituted or unsubstituted ring,

[0250] r301 and r302 are integers from 1 to 4, respectively,

[0251] r303 and r304 are integers from 1 to 3, respectively.

[0252] If the above r301 is 2 or more, the above R301 are the same or different from each other,

[0253] If the above r302 is 2 or more, the above R302 are the same or different from each other,

[0254] If the above r303 is 2 or more, the above R303 are the same or different from each other,

[0255] When the above r304 is 2 or more, the above R304 are the same or different from each other.

[0256] According to the temporary state of this specification, the above R301 to R304 are hydrogen.

[0257] According to the temporary state of this specification, the R300 is a substituted or unsubstituted aryl group.

[0258] According to the temporary state of this specification, the R300 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0259] According to the temporary state of this specification, the R300 is a phenyl group.

[0260] According to one embodiment of the present specification, R305 to R308 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0261] According to one embodiment of the present specification, R305 to R308 are the same as or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, which is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0262] According to one embodiment of the present specification, R305 to R308 are the same as or different from each other, and each independently represents a phenyl group; or a carbazole group substituted or unsubstituted with a phenyl group.

[0263] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

[0264]

[0265] The above-mentioned hole transport layer can play a role in facilitating hole transport. A hole transport material capable of transporting holes from the anode or hole injection layer and transferring them to the light-emitting layer, and having high hole mobility, is suitable. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.

[0266] According to one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound represented by the following chemical formula HT-1.

[0267] [Chemical formula HT-1]

[0268]

[0269] In the above chemical formula HT-1,

[0270] At least one of X'1 to X'6 is N, and the rest are CH,

[0271] R309 to R314 are the same or different, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring.

[0272] According to one embodiment of the present specification, X'1 to X'6 are N.

[0273] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0274] According to one embodiment of the present specification, the chemical formula HT-1 is represented by the following compound.

[0275]

[0276] According to one embodiment of the present specification, the hole transport layer further includes, but is not limited to, a compound represented by the following chemical formula HT-2.

[0277] [Chemical formula HT-2]

[0278]

[0279] In the above chemical formula HT-2,

[0280] R315 to R317 are the same or different, and each independently represent one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0281] r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same as or different from each other,

[0282] r316 is an integer from 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

[0283] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

[0284] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; and combinations thereof.

[0285] According to one embodiment of the present specification, R317 is a phenyl group substituted with an N-phenylcarbazole group.

[0286] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or are combined with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0287] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a phenyl group or combine with an adjacent group to form a spirobifluorene ring.

[0288] According to one embodiment of the present specification, the chemical formula HT-2 is represented by the following compound.

[0289]

[0290] An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and includes a hole injection or transport material known in the art.

[0291] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be formed using the aforementioned spiro compound or a material known in the art.

[0292] The above-mentioned light-emitting layer can emit red, green, or blue light, and can be made of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0293] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compound-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthylene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic ring-containing compounds include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

[0294] According to one embodiment of the present specification, the host includes, but is not limited to, a compound represented by the following chemical formula H-1.

[0295] [Chemical Formula H-1]

[0296]

[0297] In the above chemical formula H-1,

[0298] L20 and L21 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0299] Ar20 and Ar21 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0300] R201 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,

[0301] r201 is an integer from 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same as or different from each other.

[0302] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represents a direct bond; 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.

[0303] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represent a direct bond; 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 divalent dibenzofuran group; or a divalent dibenzothiophene group.

[0304] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0305] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0306] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted 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.

[0307] In one embodiment of the present specification, Ar20 and Ar21 are the same as 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 dibenzothiophene group; or a naphthobenzothiophene group.

[0308] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.

[0309] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a 1-naphthyl group or a 2-naphthyl group.

[0310] According to one embodiment of the present specification, R201 is hydrogen or a phenyl group.

[0311] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0312]

[0313] When the light-emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-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) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymer, or PPV polymer can be used as a light-emitting dopant, but is not limited thereto.

[0314] According to one embodiment of the present specification, the dopant includes, but is not limited to, a compound represented by the following chemical formula D-1.

[0315] [Chemical Formula D-1]

[0316]

[0317] In the above chemical formula D-1,

[0318] T1 to T6 are the same or different and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0319] t5 and t6 are integers from 1 to 4, respectively.

[0320] If the above t5 is 2 or more, the two or more T5 are the same or different from each other,

[0321] When the above t6 is 2 or more, the two or more T6 are the same or different from each other.

[0322] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently represents 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.

[0323] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently represents hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a cyano group, a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, or a silyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0324] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently hydrogen; an isopropyl group; a phenyl group substituted with a trimethylsilyl group; or a phenyl group substituted with a methyl group.

[0325] According to one embodiment of the present specification, T1 to T4 are the same as or different from each other, and each independently represents a phenyl group; or a terphenyl group substituted with a methyl or trimethylsilyl group.

[0326] According to one embodiment of the present specification, T5 and T6 are hydrogen.

[0327] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

[0328]

[0329] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.

[0330] The above electron transport layer can play a role in facilitating electron transport. As the electron transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, there is an advantage in that the electron transport characteristics can be prevented from being deteriorated, and when the thickness of the electron transport layer is 50 nm or less, there is an advantage in that the driving voltage can be prevented from increasing to improve electron movement due to the electron transport layer being too thick.

[0331] The above electron injection layer can play a role in facilitating electron injection. As the electron injection material, a compound having the ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect for the light-emitting layer or light-emitting material, a compound that prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and an excellent thin film forming ability is preferable. Specifically, examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0332] 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-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

[0333] The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0334] The organic light-emitting device according to the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0335] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

[0336] The method for preparing the compound of the above chemical formula 1 and the preparation of an organic light-emitting device using the compound are 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.

[0337] In the following reaction scheme, the type and number of substituents can be appropriately selected by those skilled in the art from known starting materials, enabling the synthesis of various types of intermediates. The reaction types and reaction conditions known in the art can be utilized.

[0338] By appropriately combining the manufacturing formula and the intermediates described in the examples of this specification based on common technical knowledge, all of the compounds of the above chemical formula 1 described in this specification can be manufactured.

[0339]

[0340] In a nitrogen atmosphere, E1-A (20 g, 50.3 mmol) and E1-B (24.11 g, 55.4 mmol) were added to 400 ml of 1,4-dioxane, stirred, and refluxed. Then, potassium triphosphate (32.06 g, 151.0 mmol) dissolved in 150 ml of water was added, stirred sufficiently, and tetrakistriphenyl-phosphinopalladium (0.37 g, 0.5 mmol) was added. After 6 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 1900 ml of chloroform and dissolved, washed twice with water, separated, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a yellow solid compound E1 (14.7 g, 46.6%).

[0341] MS: [M+H]+ = 626

[0342]

[0343] Compound E2 was prepared in the same manner as the method for preparing compound E1, except that E2-A and E2-B were used as the starting materials.

[0344] MS: [M+H]+ = 550

[0345]

[0346] Compound E3 was prepared in the same manner as the preparation method of compound E1, except that E3-A and E3-B were used as the starting materials.

[0347] MS: [M+H]+ = 675

[0348]

[0349] Compound E4 was prepared in the same manner as the method for preparing compound E1, except that E4-A and E4-B were used as the starting materials.

[0350] MS: [M+H]+ = 676

[0351]

[0352] Compound E5 was prepared in the same manner as the preparation method of compound E1, except that E5-A and E5-B were used as the starting materials.

[0353] MS: [M+H]+ = 726

[0354]

[0355] Compound E6 was prepared in the same manner as the preparation method of compound E1, except that E6-A and E6-B were used as the starting materials.

[0356] MS: [M+H]+ = 778

[0357]

[0358] Compound E7 was prepared in the same manner as in Manufacturing Example 1, except that E7-A and E7-B were used as the starting materials.

[0359] MS: [M+H]+ = 626

[0360]

[0361] Compound E8 was prepared in the same manner as in Manufacturing Example 1, except that E8-A and E8-B were used as the starting materials.

[0362] MS: [M+H]+ = 651

[0363] Hereinafter, examples will be provided to specifically explain the present specification. However, the embodiments described herein may be modified in various ways, and the scope of the present application is not limited to the embodiments described below. The embodiments of the present application are provided to more fully explain the present specification to those of ordinary skill in the art.

[0364] Example 1

[0365] A glass substrate coated with a 1,000 Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was filtered twice through a Millipore Co. filter. The ITO was washed for 30 minutes, then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water wash was complete, the substrate was ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition device. On the ITO transparent electrode thus prepared, the following compound HI-A was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, hexanitrile hexaazatriphenylene (HAT, 50 Å) of the following chemical formula and the compound HT-A (600 Å) below were sequentially vacuum-deposited to form a hole transport layer. Subsequently, on the hole transport layer, the compounds BH and BD below were vacuum-deposited at a weight ratio of 25:1 to a film thickness of 200 Å to form a light-emitting layer. On the light-emitting layer, the compound E1 prepared in Example 1 and the compound LiQ (Lithium quinolate) below were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 360 Å. On the electron injection and transport layer, lithium fluoride (LiF) was sequentially deposited at a thickness of 10 Å and aluminum was sequentially deposited at a thickness of 1,000 Å to form a cathode.

[0366] In the above process, the deposition rate of organic materials was maintained at 0.4 to 0.9 Å / sec, the lithium fluoride of the cathode was maintained at 0.3 Å / sec, and the aluminum was maintained at 2 Å / sec, and the vacuum during deposition was 1 x 10 -7 5 x 10 -8Torr was maintained, and an organic light-emitting device was fabricated.

[0367]

[0368] Examples 2 to 8

[0369] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound in Table 1 below was used instead of compound E1 in Example 1.

[0370] Comparative Examples 1 to 9

[0371] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds in Table 1 below were used instead of Compound E1 in Example 1. The compounds ET1 to ET9 used in Table 1 below are as follows.

[0372]

[0373]

[0374] Experimental example

[0375] For the organic light-emitting devices manufactured in Examples 1 to 8 and Comparative Examples 1 to 9, 10 mA / cm 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20 mA / cm 2 The time (T90) for the initial luminance to reach 90% of the current density was measured. The results are shown in Table 1 below.

[0376] Compound (electron injection and transport layer) voltage (V) (@10 mA / cm) 2 )Efficiency (cd / A)(@10mA / cm 2 )Color coordinates (x,y)T90 (hr)(@20mA / cm 2) Example 1 E13.89 5.26 (0.138, 0.111) 244 Example 2 E23.62 4.51 (0.138, 0.110 207 Example 3 E33.73 5.08 (0.138, 0.112) 216 Example 4 E43.58 4.98 (0.138, 0.110) 223 Example 5 E53.66 5.31 (0.138, 0.111) 248 Example 6 E64.01 4.89 (0.138, 0.111) 265 Example 7 E73.81 5.02 (0.138, 0.110) 225 Example 8E83.644.88(0.138, 0.111)270Comparative Example 1ET14.681.95(0.138, 0.112)99Comparative Example 2ET24.532.42(0.138, 0.111)104Comparative Example 3ET34.482.51(0.138, 0.110)105Comparative Example 4ET44.712.38(0.138, 0.110)91Comparative Example 5ET54.462.16(0.138, 0.111)110Comparative Example 6ET64.801.99(0.138, 0.110)97Comparative Example 7ET74.322.46(0.138, 0.111)100Comparative example 8ET84.553.10(0.138, 0.112)85Comparative example 9ET94.692.98(0.138, 0.110)104

[0377] Comparative Examples 1 to 5 used compounds ET1 to ET5. Compounds ET1 to ET5 have the same core structure as the present invention (a structure in which benzofuran is condensed at the same position of triphenylene), but the positions at which substituents are substituted on the core are different from those of the present invention. In the case of the compounds of the present invention, the substituent is substituted on the benzene ring on the benzofuran side, but in the case of the compounds used in Comparative Examples 1 to 5, the substituent is substituted on the benzene ring on the triphenylene side. Comparative Examples 6 to 9 used compounds ET6 to ET9.

[0378] Compounds ET6 to ET8 have the same substitution positions as those of the present invention, but differ in the types of substituents. Specifically, compound ET6 differs from the present invention in that L1 is a heteroarylene group, and compound ET8 differs from the present invention in that L1 is a tricyclic arylene group, and L1 is a direct bond or a monocyclic or bicyclic arylene group.

[0379] Compound ET7 is a pyridine in which Ar1 is substituted with a deuterated alkyl group, and is different in that Ar1 of the present invention is an N-containing heteroaryl group substituted or unsubstituted with an aryl group substituted or unsubstituted with a nitrile group.

[0380] Compound ET9 is different from the chemical formula 1 of the present invention in that it is a condensed form of triphenylene and benzofuran.

[0381] As described in Table 1 above, it was confirmed that the organic light-emitting device of the example manufactured using the compound of chemical formula 1 of the present invention had a lower driving voltage and exhibited superior characteristics in efficiency and lifespan compared to the organic light-emitting device of the comparative example.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, L1 is a direct bond, or a substituted or unsubstituted monocyclic or bicyclic arylene group, Ar1 is a heteroaryl group containing N substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group, R1 to R4 are the same or different and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group, a is 1 or 2, b and c are each integers from 1 to 4, d is an integer from 1 to 3, When a is 2, the substituents in parentheses are the same or different, When b to d are 2 or more, the substituents in parentheses are the same or different.

2. A compound according to claim 1, wherein R4 is hydrogen or deuterium.

3. A compound according to claim 1, wherein R4 is a substituted or unsubstituted heteroaryl group.

4. In claim 1, the chemical formula 1 is a compound which is any one of the chemical formulas 1-1 to 1-4 below: [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, R1 to R4, L1, Ar1, and a to d are as defined in the above chemical formula 1.

5. In claim 1, the compound wherein the chemical formula 1 is any one of the chemical formulas 2-1 to 2-4 below: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] In the above chemical formulas 2-1 to 2-4, R1 to R3, L1, Ar1, and a to c are as defined in the above chemical formula 1.

6. In claim 1, the compound wherein the chemical formula 1 is any one of the chemical formulas 2-5 to 2-10 below: [Chemical Formula 2-5] [Chemical Formula 2-6] [Chemical Formula 2-7] [Chemical Formula 2-8] [Chemical Formula 2-9] [Chemical Formula 2-10] In the above chemical formulas 2-5 to 2-10, R1 to R4, L1, Ar1, and a to c are as defined in the above chemical formula 1.

7. In claim 1, the compound wherein the chemical formula 1 is any one of the chemical formulas 2-11 to 2-16 below: [Chemical Formula 2-11] [Chemical Formula 2-12] [Chemical Formula 2-13] [Chemical Formula 2-14] [Chemical Formula 2-15] [Chemical Formula 2-16] In the chemical formulas 2-11 to 2-16, R1 to R4, L1, Ar1, and a to c are as defined in the chemical formula 1.

8. A compound according to claim 1, wherein R1 to R3 are the same as or different from each other and are each independently hydrogen or deuterium.

9. A compound according to claim 1, wherein R4 is a monocyclic or bicyclic heteroaryl group containing substituted or unsubstituted N.

10. A compound according to claim 1, wherein L1 is a phenylene group substituted or unsubstituted with a nitrile group, or a divalent naphthylene group substituted or unsubstituted with a nitrile group.

11. A compound according to claim 1, wherein Ar1 is a pyridine group, a pyrimidine group, a triazine group, a pyridazine group, a quinoline group, a quinazoline group, or a quinoxaline group, and Ar1 is substituted or unsubstituted with a monocyclic or bicyclic aryl group substituted or unsubstituted with a nitrile group.

12. In claim 1, the chemical formula 1 is a compound having one of the following structural formulas: .

13. An organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 12.

14. An organic light-emitting device according to claim 13, wherein the organic layer containing the compound is an electron transport layer, an electron injection layer, or an electron injection and transport layer.

15. An organic light-emitting device according to claim 14, wherein the electron transport layer, electron injection layer, or electron injection and transport layer comprises the compound and metal complex.

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