Organic compound and organic light-emitting device including same

Abstract

The present specification provides an organic compound represented by Chemical Formula 1 and an organic light-emitting device comprising the same. The compound described in the specification can be used as a material for an organic layer of an organic light-emitting device. The compound according to at least one embodiment of the present specification can achieve an improvement in efficiency, a lower driving voltage, and / or an improvement in lifespan characteristics in an organic light-emitting device. In particular, the compound described in the specification can be used as a material for a light-emitting layer. Further, the organic light emitting device has the effects of low driving voltage, high efficiency, and / or long lifespan compared to an existing organic light emitting device.

Description

TECHNICAL FIELD

[0001] This application claims priority to Korean Patent Application No. 10-2024-0062870, filed on May 14, 2024, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein.

[0002] The present specification relates to an organic compound and an organic light emitting device including the same. BACKGROUND

[0003] Generally, an organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy by using an organic substance. An organic light emitting device utilizing the organic light emitting phenomenon typically has a structure including an anode and a cathode and an organic layer between them. Here, in order to improve efficiency and stability of the organic light emitting device, the organic layer is mostly formed of a multi-layer structure using different substances respectively, for example, can be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For such a structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and when the excitons re-trip to a ground state, light is emitted.

[0004] There is a continuous demand for development of new materials for an organic light emitting device as described above.

[0005] Prior Art Documents

[0006] Patent Documents

[0007] (Patent Document 1) Korean Patent Laid-Open Publication No. 10-2020-0062465 SUMMARY

[0008] Technical Problem

[0009] The present specification provides an organic compound and an organic light emitting device including the same.

[0010] Solution to Problem

[0011] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In the above Chemical Formula 1,

[0015] Ar is a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl,

[0016] L is a direct bond, or a substituted or unsubstituted arylene group,

[0017] r1 is an integer of 1 to 6, and R1 are the same as or different from each other when r1 is 2 or more,

[0018] r2 is an integer of 1 to 8, and R2 are the same as or different from each other when r2 is 2 or more,

[0019] 7 or more of R1 and R2 are deuterium, and the rest are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0020] R3 to R6 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0021] r3 is an integer of 1 to 5, and R3 are the same as or different from each other when r3 is 2 or more,

[0022] r4 is an integer of 1 to 5, and R4 are the same as or different from each other when r4 is 2 or more,

[0023] r5 is an integer of 1 to 5, and R5 are the same as or different from each other when r5 is 2 or more,

[0024] r6 is an integer of 1 to 4, and R6 are the same as or different from each other when r6 is 2 or more.

[0025] In addition, one embodiment of the present specification provides an organic light emitting device including: an anode, a cathode, and one or more organic layers provided between the anode and the cathode, one or more of the organic layers containing the compound described above.

[0026] Effects of the Invention

[0027] The compound described in the present specification can be used as a material for an organic layer of an organic light emitting device. The compound according to at least one embodiment of the present specification can achieve an improvement in efficiency, a lower driving voltage, and / or an improvement in lifespan characteristics in an organic light emitting device. BRIEF DESCRIPTION OF DRAWINGS

[0028] Figure 1 An example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked is illustrated.

[0029] Figure 2 An example of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4 are sequentially stacked is illustrated.

[0030] SYMBOL EXPLANATION

[0031] 1: Substrate

[0032] 2: Anode

[0033] 3: Emissive layer

[0034] 4: Cathode

[0035] 5: Hole injection layer

[0036] 6: Hole transport layer

[0037] 7: Electron blocking layer

[0038] 8: Hole-blocking layer

[0039] 9: Electron Injection and Transport Layer Detailed Implementation

[0040] The following is a more detailed description of this instruction manual.

[0041] In this specification, when a part is indicated to "include / comprise" a certain element, unless otherwise stated, it means that other elements may be included, rather than excluding other elements.

[0042] In this specification, when it is stated that a component is "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

[0043] In this specification, "*" indicates the position associated with a chemical formula or compound.

[0044] In this specification, the intramolecular deuterium substitution distribution is determined using the two methods described below. TLC-MS, one of these methods, is used to adjust the deuterium substitution ratio during the synthesis of the compound.

[0045] 1. Using TLC-MS (Thin-Layer Chromatography / Mass Spectrometry) (synthetic process verification method)

[0046] The substitution rate can be calculated based on the maximum value (max. value) of the molecular weight distribution at the end of the reaction.

[0047] 2. Quantitative analysis using NMR

[0048] DMF (dimethylformamide) can be added as an internal standard. 1The integration ratio on H-NMR is used to calculate the D-substitution rate from the integration amount of the total peak.

[0049] Examples of substituents in this specification are described below, but are not limited thereto.

[0050] The term "substitution" refers to the replacement of hydrogen atoms on carbon atoms in a compound with other substituents. There is no limitation on the position of substitution, as long as the hydrogen atom can be substituted, that is, the position where the substituent can be substituted. When more than two substituents are substituted, the two or more substituents can be the same or different from each other.

[0051] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, nitrile groups, alkyl groups, cycloalkyl groups, aryl groups, and heterocyclic groups, or substituted by a substituent formed by linking two or more substituents of the substituents exemplified above, or having no substituents.

[0052] Examples of the substituents mentioned above are given below, but are not limited thereto.

[0053] Examples of halogen groups in this specification include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0054] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms 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 yet another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited to these.

[0055] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., are used, but are not limited to these.

[0056] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the aforementioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, tetraphenyl, etc., but is not limited to these. As the aforementioned polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, triphenylene, etc. It includes bases, fluorenes, etc., but is not limited to these.

[0057] In this specification, a heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of heterocyclic groups include pyridyl, pyrroloyl, pyrimidinyl, quinolinyl, pyridazinyl, furanyl, thiopheneyl, imidazoyl, pyrazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocarbazoleyl, naphthobenzofuranyl, benzonaphthothiopheneyl, indenzocarbazoleyl, triazinyl, etc., but are not limited to these.

[0058] In this specification, heteroaryl refers to aromatic compounds; otherwise, the above description of heterocyclic groups applies.

[0059] In this specification, the term arylene can be used to describe aryl groups except that it is divalent.

[0060] In this specification, the term "heteroaryl" can be used to describe the aforementioned heteroaryl groups, except that it is divalent.

[0061] In this specification, "ring" refers to a hydrocarbon ring or heterocycle in the context of a substituted or unsubstituted ring formed by the combination of adjacent groups with each other.

[0062] For example, when combined with adjacent groups to form a ring, substituted or unsubstituted aliphatic hydrocarbon rings, substituted or unsubstituted aromatic hydrocarbon rings, substituted or unsubstituted aliphatic heterocycles, substituted or unsubstituted aromatic heterocycles, or their fused rings can be formed. The aforementioned hydrocarbon rings refer to rings composed only of carbon and hydrogen atoms. The aforementioned heterocycles refer to rings containing one or more elements selected from N, O, P, S, Si, and Se. In this specification, the aforementioned aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles can be monocyclic or polycyclic.

[0063] In this specification, aliphatic hydrocarbon rings refer to non-aromatic rings composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene, but are not limited to these.

[0064] In this specification, aromatic hydrocarbon rings refer to aromatic rings composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenatene, pyrene, and tetraphenylene. The aromatic hydrocarbon rings include, but are not limited to, pentane, fluorene, indene, acenaphthene, benzo[a]fluorene, spirofluorene, etc. In this specification, the aromatic hydrocarbon ring can be interpreted in the same way as the aryl group.

[0065] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, and 1,4-dioxane. Alkane (1,4-dioxane), pyrrolidine, piperidine, morpholine, oxepane Azahexacyclic octane Thioheterocyclic octane etc., but not limited to this.

[0066] In this specification, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, etc. azole, isotonic azole, thiazole, isothiazole, triazole Diazole, thiadiazole, dithiazole, tetraazole, pyran, thiaran, diazine Azine, thiazide, diazine Alkenes, triazines, tetraazines, isoquinoline, quinoline, quinones, quinazoline, quinoxaline, naphthidine, acridine, phenanthridine, diazanaphthalene, triazaindene, indole, indolezine, benzothiazole, benzo[] azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenazine It includes aziridines, indobenzocarbazole, indobenzocarbazole, etc., but is not limited to these.

[0067] The preferred embodiments of the present invention will now be described in detail. However, the embodiments of the present invention can be modified in various ways, and the scope of the present invention is not limited to the embodiments described below.

[0068] The compounds of chemical formula 1 described above will now be explained in detail.

[0069] In one embodiment of this specification, the above-mentioned chemical formula 1 is a compound of chemical formula 1-A or chemical formula 1-B.

[0070] [Chemical Formula 1-A]

[0071]

[0072] [Chemical Formula 1-B]

[0073]

[0074] In the above chemical formulas 1-A and 1-B, R1 to R6, Ar, and r1 to r6 are defined as in chemical formula 1 above.

[0075] L is an arylene group consisting of 6 to 30 carbon atoms, either directly bonded, substituted, or unsubstituted.

[0076] In one embodiment of this specification, the above-mentioned chemical formula 1 is any one of the following chemical formulas 1-1 to 1-5.

[0077] [Chemical Formula 1-1]

[0078]

[0079] [Chemical Formula 1-2]

[0080]

[0081] [Chemical Formulas 1-3]

[0082]

[0083] [Chemical Formulas 1-4]

[0084]

[0085] [Chemical Formulas 1-5]

[0086]

[0087] In the above chemical formulas 1-1 to 1-5, the definitions of R1, R2, L, and r1 to r6 are the same as those in chemical formula 1.

[0088] R3 to R8 are each either hydrogen or deuterium.

[0089] r7 is an integer from 1 to 4. When r7 is 2 or higher, R7 values ​​are either the same or different.

[0090] r8 is an integer from 1 to 5. When r8 is 2 or higher, R8 can be the same or different from each other.

[0091] In this specification, the above chemical formula 1 refers to the above chemical formula 1-1.

[0092] In this specification, the above chemical formula 1 refers to the above chemical formulas 1-2.

[0093] In this specification, the above chemical formula 1 refers to the above chemical formulas 1-3.

[0094] In this specification, the above chemical formula 1 refers to the above chemical formulas 1-4.

[0095] In this specification, the above chemical formula 1 refers to the above chemical formulas 1-5.

[0096] In one embodiment of this specification, the above-mentioned chemical formula 1 is any one of the following chemical formulas 2-1 to 2-4.

[0097] [Chemical Formula 2-1]

[0098]

[0099] [Chemical Formula 2-2]

[0100]

[0101] [Chemical Formula 2-3]

[0102]

[0103] [Chemical Formula 2-4]

[0104]

[0105] In the above chemical formulas 2-1 to 2-4, the definitions of R1, R2, Ar, L, and r1 to r6 are the same as those in chemical formula 1.

[0106] R3 to R6 are each hydrogen or deuterium.

[0107] In one embodiment of this specification, the above-mentioned chemical formula 1 is any one of chemical formulas 3-1 to 3-8.

[0108] [Chemical Formula 3-1]

[0109]

[0110] [Chemical Formula 3-2]

[0111]

[0112] [Chemical Formula 3-3]

[0113]

[0114] [Chemical Formula 3-4]

[0115]

[0116] [Chemical Formula 3-5]

[0117]

[0118] [Chemical Formula 3-6]

[0119]

[0120] [Chemical Formula 3-7]

[0121]

[0122] [Chemical Formula 3-8]

[0123]

[0124] In the above chemical formulas 3-1 to 3-8, the definitions of R1, R2, Ar, L, and r1 to r6 are the same as those in chemical formula 1.

[0125] R3 to R6 are each hydrogen or deuterium.

[0126] In one embodiment of this specification, the above-mentioned chemical formula 1 is represented by the following chemical formula 4-1 or chemical formula 4-2:

[0127] [Chemical Formula 4-1]

[0128]

[0129] [Chemical Formula 4-2]

[0130]

[0131] In chemical formulas 4-1 and 4-2 above, the definitions of R1, R2, Ar, L, and r1 to r6 are the same as those in chemical formula 1 above.

[0132] R3 to R6 are each hydrogen or deuterium.

[0133] In one embodiment of this specification, the L mentioned above is a directly bonded, substituted, or unsubstituted aryl group.

[0134] In one embodiment of this specification, L is a directly bonded, substituted, or unsubstituted aryl group with 6 to 60 carbon atoms.

[0135] In one embodiment of this specification, the L mentioned above is a directly bonded, substituted, or unsubstituted aryl group with 6 to 30 carbon atoms.

[0136] In one embodiment of this specification, the L mentioned above is a directly bonded, substituted, or unsubstituted aryl group with 6 to 20 carbon atoms.

[0137] In one embodiment of this specification, the L mentioned above is a directly bonded, substituted, or unsubstituted aryl group with 6 to 12 carbon atoms.

[0138] In one embodiment of this specification, L is a aryl group consisting of 6 to 12 carbon atoms that is directly bonded, or substituted with deuterium, or unsubstituted.

[0139] In one embodiment of this specification, L is a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted tetraphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted spirodifluorene, or substituted or unsubstituted terphenylene.

[0140] In one embodiment of this specification, L is a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, or substituted or unsubstituted terphenylene.

[0141] In one embodiment of this specification, L is a directly bonded, substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0142] In one embodiment of this specification, L is a directly bonded, deuterated or unsubstituted phenylene, or a deuterated or unsubstituted biphenylene.

[0143] In one embodiment of this specification, L is a direct bond.

[0144] In one embodiment of this specification, the Ar mentioned above is a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl.

[0145] In one embodiment of this specification, the Ar mentioned above is a phenyl group that is either deuterated or unsubstituted, or a biphenyl group that is either deuterated or unsubstituted.

[0146] In this specification, R1 and R2, seven or more of which are deuterium, and the remainder, each independently of which is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, refers to the deuterium substitution rate of bicarbazole of Formula 1 being 50% or more.

[0147] Specifically, when both R1 and R2 are deuterium, that is, when all 14 R1 and R2 are deuterium, it means that the deuterium substitution rate of bicarbazole is 100%.

[0148] For example, in compound B below, there are 8 deuterium atoms in R1 and R2, and the deuterium substitution rate of bicarbazole is approximately 57%. (Approximately 57% = 8 (number of deuterium atoms substituted in bicarbazole) ÷ 14 (the largest number of hydrogen atoms in bicarbazole that can be substituted for deuterium) × 100)

[0149]

[0150] Compound B

[0151] In this specification, at least eight of R1 and R2 are deuterium, and the remainder are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0152] In this specification, at least nine of R1 and R2 are deuterium, and the remainder are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0153] In this specification, at least 10 of R1 and R2 are deuterium, and the remainder are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0154] In this specification, at least 11 of R1 and R2 are deuterium, and the remainder are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0155] In this specification, at least 12 of R1 and R2 are deuterium, and the remainder are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0156] In this specification, at least 13 of R1 and R2 are deuterium, and the remainder are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0157] In this specification, both R1 and R2 are deuterium.

[0158] In this specification, seven or more of R1 and R2 are deuterium, and the remainder are each independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms.

[0159] In this specification, seven or more of R1 and R2 are deuterium, and the remaining ones are each independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 20 carbon atoms.

[0160] In this specification, seven or more of R1 and R2 are deuterium, and the remainder are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0161] In this specification, seven or more of R1 and R2 are deuterium, and the rest are each independently hydrogen, deuterium or phenyl.

[0162] In this specification, R3 to R6 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0163] In this specification, R3 to R6 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 carbon atoms.

[0164] In this specification, R3 to R6 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 20 carbon atoms.

[0165] In this specification, R3 to R6 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 10 carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 10 carbon atoms.

[0166] In this specification, R3 to R6 may be the same as or different from each other, and each is independently hydrogen, deuterium, or a phenyl substituted with or unsubstituted with deuterium.

[0167] In one embodiment of this specification, R1, R2 and R8 are all deuterium.

[0168] In one embodiment of this specification, R1 is hydrogen or deuterium.

[0169] In one embodiment of this specification, R1 is hydrogen.

[0170] In one embodiment of this specification, all of the above R1 are deuterium.

[0171] In one embodiment of this specification, R2 is hydrogen or deuterium.

[0172] In one embodiment of this specification, R2 is hydrogen.

[0173] In one embodiment of this specification, all R2 are deuterium.

[0174] In one embodiment of this specification, R3 is hydrogen or deuterium.

[0175] In one embodiment of this specification, R3 is hydrogen.

[0176] In one embodiment of this specification, all R3 are deuterium.

[0177] In one embodiment of this specification, R4 is hydrogen or deuterium.

[0178] In one embodiment of this specification, R4 is hydrogen.

[0179] In one embodiment of this specification, all R4 are deuterium.

[0180] In one embodiment of this specification, R5 is hydrogen or deuterium.

[0181] In one embodiment of this specification, R5 is hydrogen.

[0182] In one embodiment of this specification, all R5 are deuterium.

[0183] In one embodiment of this specification, R6 is hydrogen or deuterium.

[0184] In one embodiment of this specification, R6 is hydrogen.

[0185] In one embodiment of this specification, all R6 are deuterium.

[0186] In one embodiment of this specification, R7 is hydrogen or deuterium.

[0187] In one embodiment of this specification, R7 is hydrogen.

[0188] In one embodiment of this specification, all R7 are deuterium.

[0189] In one embodiment of this specification, R8 is hydrogen or deuterium.

[0190] In one embodiment of this specification, R8 is hydrogen.

[0191] In one embodiment of this specification, all R8 are deuterium.

[0192] In one embodiment of this specification, r1+r2≥7.

[0193] In one embodiment of this specification, r1 is an integer from 1 to 6.

[0194] In one embodiment of this specification, r1 is 6.

[0195] In one embodiment of this specification, r1 is 5.

[0196] In one embodiment of this specification, r1 is 4.

[0197] In one embodiment of this specification, r1 is 3.

[0198] In one embodiment of this specification, r1 is 2.

[0199] In one embodiment of this specification, r1 is 1.

[0200] In one embodiment of this specification, r2 is an integer from 1 to 8.

[0201] In one embodiment of this specification, r2 is 8.

[0202] In one embodiment of this specification, r2 is 7.

[0203] In one embodiment of this specification, r2 is 6.

[0204] In one embodiment of this specification, r2 is 5.

[0205] In one embodiment of this specification, r2 is 4.

[0206] In one embodiment of this specification, r2 is 3.

[0207] In one embodiment of this specification, r2 is 2.

[0208] In one embodiment of this specification, r3 is an integer from 1 to 5.

[0209] In one embodiment of this specification, r3 is 5.

[0210] In one embodiment of this specification, r3 is 4.

[0211] In one embodiment of this specification, r3 is 3.

[0212] In one embodiment of this specification, r3 is 2.

[0213] In one embodiment of this specification, r3 is 1.

[0214] In one embodiment of this specification, r4 is an integer from 1 to 5.

[0215] In one embodiment of this specification, r4 is 5.

[0216] In one embodiment of this specification, r4 is 4.

[0217] In one embodiment of this specification, r4 is 3.

[0218] In one embodiment of this specification, r4 is 2.

[0219] In one embodiment of this specification, r4 is 1.

[0220] In one embodiment of this specification, r5 is an integer from 1 to 5.

[0221] In one embodiment of this specification, r5 is 5.

[0222] In one embodiment of this specification, r5 is 4.

[0223] In one embodiment of this specification, r5 is 3.

[0224] In one embodiment of this specification, r5 is 2.

[0225] In one embodiment of this specification, r5 is 1.

[0226] In one embodiment of this specification, r6 is an integer from 1 to 4.

[0227] In one embodiment of this specification, r6 is 4.

[0228] In one embodiment of this specification, r6 is 3.

[0229] In one embodiment of this specification, r6 is 2.

[0230] In one embodiment of this specification, r6 is 1.

[0231] In one embodiment of this specification, r7 is an integer from 1 to 4.

[0232] In one embodiment of this specification, r7 is 4.

[0233] In one embodiment of this specification, r7 is 3.

[0234] In one embodiment of this specification, r7 is 2.

[0235] In one embodiment of this specification, r7 is 1.

[0236] In one embodiment of this specification, r8 is an integer from 1 to 5.

[0237] In one embodiment of this specification, r8 is 5.

[0238] In one embodiment of this specification, r8 is 4.

[0239] In one embodiment of this specification, r8 is 3.

[0240] In one embodiment of this specification, r8 is 2.

[0241] In one embodiment of this specification, r8 is 1.

[0242] In one embodiment of this specification, the above chemical formula 1 is represented by any of the following structural formulas.

[0243]

[0244]

[0245]

[0246]

[0247] In the above structural formula,

[0248] n is the number of deuterium substitutions in the structure within the brackets [].

[0249] m is the number of deuterium substitutions in the structure within parentheses ().

[0250] m is 7 or higher and 14 or lower.

[0251] n is greater than m, and the upper limit of n determines the maximum number of hydrogen atoms that can be replaced by deuterium in each structure.

[0252] In one embodiment of this specification, the above chemical formula 1 is represented by any one of the following compounds.

[0253]

[0254] According to one embodiment of this specification, the compound represented by chemical formula 1 can be manufactured with a core structure as described in the manufacturing examples below. Substituents can be combined using methods known in the art, and the type, position, or number of substituents can be varied according to techniques known in the art. Specifically, compounds corresponding to the range of the above-described chemical formula 1 can be synthesized using starting materials, intermediate materials, etc., known in the art, and synthetic methods known in the art.

[0255] In this specification, compounds with various band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above-described chemical formula 1. Furthermore, in this specification, the HOMO and LUMO energy levels of the compound can also be tuned by introducing various substituents into the core structure of the structure described above.

[0256] In addition, this specification provides organic light-emitting devices containing the compounds mentioned above.

[0257] The organic light-emitting device according to this specification is characterized in that it includes: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contains a compound represented by the above-described chemical formula 1.

[0258] The organic light-emitting device described in this specification utilizes the compound of the above-mentioned chemical formula 1 to form an organic layer. Otherwise, it can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0259] The aforementioned compounds can be used to form organic layers not only through vacuum evaporation but also through solution coating in the fabrication of organic light-emitting devices. Here, solution coating refers to methods such as spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating, but is not limited to these.

[0260] The organic layers of the organic light-emitting device described in this specification can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of this invention can have a structure comprising one or more of the following as organic layers: a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer. However, the structure of the organic light-emitting device described in this specification is not limited thereto, and may include fewer or more organic layers.

[0261] In one embodiment of this specification, the organic layer includes a light-emitting layer, which may contain a compound represented by the above-described chemical formula 1.

[0262] In one embodiment of this specification, the organic layer includes a light-emitting layer, which may contain a compound represented by the above-described chemical formula 1 as the main component.

[0263] In one embodiment of this specification, the thickness of the organic layer comprising the compound of Formula 1 can be [missing information]. to or to Preferred to

[0264] In another embodiment, the organic layer may contain other organic compounds, metals, or metal compounds in addition to the compounds represented by the above-described chemical formula 1.

[0265] In one embodiment of this specification, the light-emitting layer may be a blue light-emitting layer, a red light-emitting layer, or a green light-emitting layer.

[0266] In one embodiment of this specification, the light-emitting layer may be a blue light-emitting layer.

[0267] In one embodiment of this specification, the light-emitting layer may comprise a host and a dopant. Specifically, the dopant may be a fluorescent dopant or a phosphorescent dopant.

[0268] In one embodiment of this specification, the light-emitting layer comprises a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, the host and dopant comprise a host and a dopant in a weight ratio of 99:1 to 50:50, 99:1 to 70:30, 99:1 to 80:20, 99:1 to 90:10, or 99:1 to 95:5.

[0269] In one embodiment of this specification, the dopant may include arylamine compounds, heterocyclic compounds containing boron and nitrogen, metal coordination compounds, platinum coordination compounds, or iridium coordination compounds, etc.

[0270] For example, when the aforementioned luminescent layer emits red light, phosphorescent dopants such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum) can be used; or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the luminescent layer emits green light, phosphorescent dopants such as Ir(ppy)3 (facilitated tris(2-phenylpyridine)iridium) or fluorescent dopants such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used, but are not limited to these. When the luminescent layer emits blue light, phosphorescent dopants such as platinum coordination compounds and (4,6-F2ppy)2Irpic can be used; or fluorescent dopants such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbeneylarylene (DSA), PFO-based polymers, PPV-based polymers, etc., can be used, but are not limited to these.

[0271] In one embodiment of this specification, the dopant is a metal coordination compound.

[0272] In one embodiment of this specification, the dopant is a platinum coordination compound.

[0273] In one embodiment of this specification, the dopant is an iridium coordination compound.

[0274] In one embodiment of this specification, the dopant may comprise, but is not limited to, a compound represented by the following chemical formula D-1 or D-2.

[0275] [Chemical Formula D-1]

[0276]

[0277] [Chemical formula D-2]

[0278]

[0279] In the above chemical formulas D-1 and D-2,

[0280] M is a transition metal.

[0281] A1, A3, A5, A6, K1, K2, and K3 may be the same as or different from each other, and each is independently a directly bonded, O, S, divalent ester group, substituted or unsubstituted alkylene group, substituted or unsubstituted divalent alkenyl group, substituted or unsubstituted diallyl group, substituted or unsubstituted arylene group, or substituted or unsubstituted heteroarylene group.

[0282] A2 and A4 may be the same as or different from each other, and each can be independently a directly bonded, N, substituted or unsubstituted trivalent alkylene, substituted or unsubstituted trivalent aryl, or substituted or unsubstituted trivalent heteroaryl.

[0283] n is 1 or 2. When n is 2, the structures inside the parentheses are the same or different from each other.

[0284] In one embodiment of this specification, M is iridium or platinum.

[0285] In one embodiment of this specification, the dopant may be selected from the following structural formulas, but is not limited thereto.

[0286]

[0287]

[0288]

[0289]

[0290] As another example, the aforementioned organic layer includes a light-emitting layer, which contains a compound represented by the aforementioned chemical formula 1 as the main body, and also contains one or more main bodies different from the aforementioned chemical formula 1.

[0291] In one embodiment of this specification, the light-emitting layer may contain a compound represented by the above-described chemical formula 1 as a p-type host, and the light-emitting layer may also contain an n-type host. In this case, the weight ratio of the n-type host to the p-type host may be 2:8 to 8:2, or 4:6 to 6:4, or 5:5.

[0292] The above-described n-type host can be applied to compounds commonly known in the art, for example, it can be a structure containing a carbazole compound.

[0293] In one embodiment of this specification, the light-emitting layer comprises a p-type host and an n-type host, and when it contains a dopant, the weight ratio of the mixture of the p-type host and the n-type host to the dopant can be 99:1 to 70:30, or 95:5 to 80:20, or 90:10 to 85:15.

[0294] In one embodiment of this specification, the light-emitting layer comprises a compound represented by the above-described chemical formula 1 as a p-type host, and may also comprise an n-type host. The above-described n-type host is represented by the following chemical formula EN.

[0295] [Chemical formula EN]

[0296]

[0297] In the above chemical formula EN,

[0298] X1 is either O or S.

[0299] L1 is a directly bonded, substituted, or unsubstituted aryl group.

[0300] Ra to Rc may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0301] In one embodiment of this specification, Ra to Rc may be the same as or different from each other, and each is independently hydrogen or deuterium.

[0302] In one embodiment of this specification, Ra to Rc may be the same as or different from each other, and each is independently hydrogen.

[0303] In one embodiment of this specification, the above chemical formula EN is represented by the following compound.

[0304]

[0305]

[0306] The organic light-emitting device described in this specification may also include one or more organic layers selected from the following: hole transport layer, hole injection layer, electron blocking layer, electron transport and injection layer, electron transport layer, electron injection layer, hole blocking layer, and hole injection and transport layer.

[0307] In one embodiment of this specification, the organic light-emitting device includes: an anode, a cathode, and two or more organic layers disposed between the anode and the cathode, wherein at least one of the two or more organic layers contains a compound represented by the above chemical formula 1.

[0308] In one embodiment of this specification, the two or more organic layers mentioned above may be selected from two or more of the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.

[0309] In one embodiment of this specification, the two or more organic layers mentioned above may be selected from two or more of the group consisting of a light-emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron modulation layer, and a hole blocking layer.

[0310] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with an anode, one or more organic layers and a cathode sequentially stacked on a substrate (normal type).

[0311] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0312] For example, the organic light-emitting device described above can have a stacked structure as shown below, but is not limited to this.

[0313] (1) Anode / hole transport layer / light-emitting layer / cathode

[0314] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0315] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0316] (4) Anode / Hole transport layer / Light emission layer / Electron transport layer / Cathode

[0317] (5) Anode / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0318] (6) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0319] (7) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0320] (8) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0321] (9) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0322] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0323] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0324] (12) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0325] (13) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0326] (14) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0327] (15) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0328] (16) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0329] (17) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0330] (18) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport and Injection Layer / Cathode

[0331] The organic light-emitting device structure described in this specification can have the following characteristics: Figure 1 and Figure 2 The structure shown is not limited to this.

[0332] Figure 1 The illustration shows an example of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 are sequentially stacked. In the structure described above, the aforementioned compound may be contained in the light-emitting layer 3.

[0333] Figure 2 The illustration shows an example of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. In the structure described above, the aforementioned compound may be contained in the light-emitting layer 3 or the electron blocking layer 7.

[0334] In one embodiment of this specification, the hole transport layer and the light-emitting layer may be disposed adjacent to each other. For example, the hole transport layer and the light-emitting layer may be physically connected.

[0335] In one embodiment of this specification, the electron blocking layer and the light-emitting layer may be disposed adjacent to each other. For example, the electron blocking layer and the light-emitting layer may be physically connected.

[0336] In one embodiment of this specification, the hole transport layer and the electron blocking layer may be disposed adjacent to each other. For example, the hole transport layer and the electron blocking layer may be physically connected.

[0337] The organic light-emitting device described in this specification, except that one or more layers of the organic material contain the aforementioned compound, i.e., the compound represented by the aforementioned chemical formula 1, can be manufactured using materials and methods known in the art.

[0338] When the aforementioned organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0339] For example, the organic light-emitting device according to this specification can be manufactured as follows: A metal or a conductive metal oxide or alloy thereof is deposited on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode. Then, an organic layer comprising 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 is formed on the anode. Finally, a material suitable for use as a cathode is deposited on the organic layer. Alternatively, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0340] The aforementioned organic layer may further include one or more of the following: a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer.

[0341] The aforementioned organic layer can be a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer and an electron transport layer, an electron injection layer, and an electron transport and injection layer, but it is not limited to this; it can also be a single-layer structure. Furthermore, the aforementioned organic layer can be manufactured in smaller quantities using various polymer materials and solvent processes other than vapor deposition, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer.

[0342] The anode described above is the electrode for injecting holes. As the anode material, it is generally preferred to be a material with a high work function in order to enable holes to be smoothly injected into the organic layer. Specific examples of anode materials that can be used in this invention include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; 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-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0343] The cathode described above is the electrode into which electrons are injected. As a cathode material, it is generally preferred to be a material with a low work function in order to facilitate the injection of electrons into the 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 their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0344] The aforementioned hole injection layer facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is one that can effectively receive holes from the anode at low voltage. Preferably, 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, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazabenzophenanthrene-based organic compounds, tetrafluorobenzonitrile-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene. The thickness of the hole injection layer can be... to When the thickness of the aforementioned hole injection layer is The above-mentioned features have the advantage of preventing a decrease in hole injection characteristics. The following features the advantage of preventing the driving voltage from rising in order to improve hole migration when the hole injection layer is too thick.

[0345] In one embodiment of this specification, the hole-injecting material may include an aryl amine compound containing a carbazole group and a tetrafluorobenzonitrile compound. According to one example, the amine compound is represented as Het101-L101-N(Ar101)(Ar102), where Het101 is a substituted or unsubstituted carbazole group, L101 is a directly bonded, or substituted or unsubstituted aryl group, and Ar101 and Ar102 may be the same as or different from each other, each independently being a substituted or unsubstituted aryl group. The amine compound and the tetrafluorobenzonitrile compound may be contained in a suitable molar ratio; according to one example, the amine compound and the tetrafluorobenzonitrile compound may be contained in a molar ratio of 99.9:0.1 to 90:10.

[0346] According to one embodiment of this specification, the hole injection layer comprises, but is not limited to, a compound represented by the chemical formula HT-1.

[0347] [Chemical formula HT-1]

[0348]

[0349] In the above chemical formula HT-1,

[0350] L101 is a directly bonded, substituted, or unsubstituted aryl group.

[0351] R101 and R102 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic.

[0352] R103 and R104 may be the same as or different from each other, and each may be independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0353] o is 1 or 2. When o is 2, the structures inside the parentheses are the same or different from each other.

[0354] In one embodiment of this specification, L101 is a directly bonded, substituted or unsubstituted phenylene, or a substituted or unsubstituted naphthylene.

[0355] In one embodiment of this specification, L101 is a directly bonded, substituted, or unsubstituted phenylene oxide.

[0356] In one embodiment of this specification, L101 is a direct bond.

[0357] In one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0358] In one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraceneyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyrene, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted carbazolyl.

[0359] In one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each may be independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazole group.

[0360] In one embodiment of this specification, R101 and R102 may be the same as or different from each other, and each is independently a phenyl group or a carbazole group substituted with biphenyl.

[0361] In one embodiment of this specification, R103 and R104 may be the same as or different from each other, and each may be a substituted or unsubstituted aryl group independently.

[0362] In one embodiment of this specification, R103 and R104 may be the same as or different from each other, and each is independently an aryl group.

[0363] In one embodiment of this specification, R103 and R104 are phenyl groups.

[0364] In one embodiment of this specification, the above chemical formula HT-1 is represented by the following compound.

[0365]

[0366] According to one embodiment of this specification, the hole injection layer comprises a compound with the chemical formula HI-1.

[0367] [Chemical formula HI-1]

[0368]

[0369] In the above chemical formula HI-1,

[0370] R111 to R113 may be the same as or different from each other, and each is independently a hydrogen, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heterocyclic group.

[0371] a111 to a113 are each integers from 1 to 5.

[0372] When a111 is 2 or more, two or more R111 values ​​are either the same or different from each other.

[0373] When a112 is 2 or more, two or more R112 values ​​are either the same or different from each other.

[0374] When a113 is 2 or more, two or more R113s are the same or different from each other.

[0375] According to one embodiment of this specification, R111 to R113 may be the same as or different from each other, and each is a halogen group or a nitrile group.

[0376] According to one embodiment of this specification, R111 to R113 may be the same as or different from each other, and each is a fluorine or nitrile group.

[0377] According to one embodiment of this specification, the above-mentioned chemical formula HI-1 has the following structure.

[0378]

[0379] The aforementioned hole transport layer facilitates hole transport. The hole transport material is capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; materials with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but these are not limited to these.

[0380] In one embodiment of this specification, the hole transport substance may include an aryl amine compound containing a carbazole group.

[0381] According to one embodiment of this specification, the hole transport layer comprises a compound represented by the chemical formula HT-1, but is not limited thereto.

[0382] A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, which may contain materials known in the art for hole injection or transport.

[0383] An electron blocking layer may be disposed between the hole transport layer and the light-emitting layer. Materials known in the art can be used in the electron blocking layer. Specifically, in one embodiment of this specification, the electron blocking layer may contain a carbazole-based compound, but is not limited thereto.

[0384] In one embodiment of this specification, the electron blocking layer may be disposed on the anode side of the light-emitting layer, and the electron blocking material may contain a p-type body represented by the above chemical formula 1.

[0385] The aforementioned hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed using the same conditions as the hole injection layer. Specifically, there are... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0386] In one embodiment of this specification, the hole blocking layer may be disposed on the cathode side of the light-emitting layer, and the n-type body represented by the chemical formula EN of this application may be used as the hole blocking material.

[0387] The aforementioned electron transport layer facilitates electron transport. The electron transport material is one that can effectively receive electrons from the cathode and transfer them to the light-emitting layer; materials with high electron mobility are suitable. Specific examples include the compounds mentioned above, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, and hydroxyflavonoid-metal complexes, but these are not limited to these. The thickness of the electron transport layer can range from 1 nm to 50 nm. When the thickness of the electron transport layer is greater than 1 nm, it has the advantage of preventing a decrease in electron transport properties; when it is less than 50 nm, it has the advantage of preventing the driving voltage from increasing to enhance electron migration when the electron transport layer is too thick.

[0388] The aforementioned electron injection layer facilitates electron injection. Preferred electron injection materials include compounds that possess electron transport capabilities, effectively inject electrons from the cathode, exhibit excellent electron injection performance for the light-emitting layer or material, prevent excitons generated in the light-emitting layer from migrating to the hole injection layer, and demonstrate excellent thin-film formation ability. Specifically, these include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0389] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0390] In one embodiment of this specification, the electron injection and transport material may comprise a triazole compound, and may also comprise an n-type dopant or an organometallic compound. According to one example, the n-type dopant or organometallic compound may be LiQ, and may comprise the triazole compound and the n-type dopant (or organometallic compound) in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

[0391] According to one embodiment of this specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. When the organic light-emitting device includes an electron injection and transport layer other than an electron injection and transport layer comprising a compound of Formula 1, the substances exemplified in the electron transport layer and the electron injection layer may be used, but are not limited thereto.

[0392] According to one embodiment of this specification, the electron injection and transport layer comprises a compound represented by the following chemical formula ET-1, but is not limited thereto.

[0393] [Chemical formula ET-1]

[0394]

[0395] In the above chemical formula ET-1,

[0396] At least one of Z11 to Z13 is N, and the rest are CH.

[0397] At least one of Z21 to Z23 is N, and the rest are CH.

[0398] L601 and L602 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

[0399] Ar601 to Ar604 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0400] According to one embodiment of this specification, L601 and L602 may be the same as or different from each other, and each is independently a monocyclic or polycyclic arylene group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0401] According to one embodiment of this specification, L601 and L602 are phenylene oxides.

[0402] According to one embodiment of this specification, the Ar601 to Ar604 described above may be the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0403] According to one embodiment of this specification, Ar601 to Ar604 are phenyl groups.

[0404] According to one embodiment of this specification, the above-mentioned chemical formula ET-1 is represented by the following compound.

[0405]

[0406] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0407] The organic light-emitting devices according to this specification can be included in and used in various electronic devices. For example, the aforementioned electronic devices can be display panels, touch panels, solar modules, lighting devices, etc., but are not limited thereto.

[0408] The following detailed description, using embodiments, aims to provide a more specific explanation of this specification. However, the embodiments described herein can be modified in various ways and are not intended to limit the scope of this application to the embodiments detailed below. These embodiments are provided to provide a more complete explanation of this specification to those skilled in the art.

[0409] <Manufacturing Example 1: Synthesis of Compound 1>

[0410]

[0411] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, (3-bromophenyl)triphenylsilane (3.50 g, 8.43 mmol) and compound a-1 (3.61 g, 8.43 mmol) were completely dissolved in 240 mL of xylene. NaOtBu (1.62 g, 16.87 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.13 g, 0.25 mmol) were added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was then concentrated under reduced pressure and recrystallized from 260 mL of ethyl acetate to prepare compound 1 (4.51 g, 70%).

[0412] MS[M+H] + =763

[0413] <Manufacturing Example 2: Synthesis of Compound 2>

[0414]

[0415] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, (4-bromophenyl)triphenylsilane (3.50 g, 8.43 mmol) and compound a-2 (3.61 g, 8.43 mmol) were completely dissolved in 230 mL of xylene. NaOtBu (1.62 g, 16.87 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.13 g, 0.25 mmol) were added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure. The resulting solution was recrystallized from 220 mL of ethyl acetate to produce compound 2 (3.96 g, 62%).

[0416] MS[M+H] + =763

[0417] <Manufacturing Example 3: Synthesis of Compound 3>

[0418]

[0419] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound (3-bromophenyl)triphenylsilane (3.50 g, 8.43 mmol) and compound a-3 (3.61 g, 8.43 mmol) were completely dissolved in 240 mL of xylene. NaOtBu (1.62 g, 16.87 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.13 g, 0.25 mmol) were added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The xylene was then concentrated under reduced pressure and recrystallized from 230 mL of ethyl acetate to prepare compound 3 (4.25 g, 66%).

[0420] MS[M+H] + =763

[0421] <Manufacturing Example 4: Synthesis of Compound 4>

[0422]

[0423] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound (3-bromophenyl)triphenylsilane (3.50 g, 8.43 mmol) and compound a-4 (4.21 g, 8.43 mmol) were completely dissolved in 250 mL of xylene. NaOtBu (1.62 g, 16.87 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.13 g, 0.25 mmol) were added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The xylene was then concentrated under reduced pressure and recrystallized from 260 mL of ethyl acetate to prepare compound 4 (4.88 g, 69%).

[0424] MS[M+H] + =834

[0425] <Manufacturing Example 5: Synthesis of Compound 5>

[0426]

[0427] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound (4-bromophenyl)triphenylsilane (3.50 g, 8.43 mmol) and compound a-5 (4.21 g, 8.43 mmol) were completely dissolved in 250 mL of xylene. NaOtBu (1.62 g, 16.87 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.13 g, 0.25 mmol) were added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure. The solution was then recrystallized from 260 mL of ethyl acetate to prepare compound 5 (5.13 g, 73%).

[0428] MS[M+H] + =834

[0429] <Manufacturing Example 6: Synthesis of Compound 6>

[0430]

[0431] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound (4-bromophenyl)triphenylsilane (3.50 g, 8.43 mmol) and compound a-6 (4.21 g, 8.43 mmol) were completely dissolved in 240 mL of xylene. NaOtBu (1.62 g, 16.87 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.13 g, 0.25 mmol) were added, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure. The resulting solution was recrystallized from 240 mL of ethyl acetate to produce compound 6 (4.77 g, 68%).

[0432] MS[M+H] + =834

[0433] <Manufacturing Example 7: Synthesis of Compound 7>

[0434]

[0435] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound (3-bromophenyl-2,4,5,6-d4)tris(phenyl-d5)silane (3.50 g, 8.06 mmol) and compound a-1 (3.44 g, 8.06 mmol) were completely dissolved in 260 mL of xylene. NaOtBu (1.55 g, 16.11 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.12 g, 0.24 mmol) were added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized from 290 mL of ethyl acetate to prepare compound 7 (4.75 g, 75%).

[0436] MS[M+H] + =782

[0437] <Manufacturing Example 8: Synthesis of Compound 8>

[0438]

[0439] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound (4-bromophenyl-2,3,5,6-d4)tris(phenyl-d5)silane (3.50 g, 8.06 mmol) and compound a-8 (3.44 g, 8.06 mmol) were completely dissolved in 230 mL of xylene. NaOtBu (1.55 g, 16.11 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.12 g, 0.24 mmol) were added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 8 (4.88 g, 77%).

[0440] MS[M+H] + =782

[0441] <Example 1-1>

[0442] ITO (indium tin oxide) is used in... A glass substrate coated with a thin film of ITO was immersed in distilled water containing detergent and washed using ultrasound. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0443] On the ITO transparent electrode prepared in this way as the anode, the following compounds HT1 and HI1 are mixed in a ratio of 98:2 (molar ratio). A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. Then, the following compound HT1 is vacuum-deposited onto the hole injection layer. This forms a hole transport layer. Then, on the aforementioned hole transport layer, a film thickness of... An electron blocking layer was formed by vacuum evaporation of BH (p-type) synthesized in Manufacturing Example 1, represented by compound 1. Next, on the electron blocking layer, a mixture of compound BH (n-type) and BH (p-type) synthesized in Manufacturing Example 1 at a weight ratio of 1:1, and compound BD at a weight ratio of 88:12 were vacuum evaporated to form an electron blocking layer. A light-emitting layer is formed with a thickness of [missing information]. On the aforementioned light-emitting layer, a film thickness of [missing information] is [missing information]. A hole-blocking layer was formed by vacuum evaporation of the following compound BH (n-type). Next, compounds ET1 and LiQ were vacuum evaporated onto the hole-blocking layer in a 1:1 weight ratio, thereby achieving... The thickness forms an electron injection and transport layer. On this electron injection and transport layer, lithium fluoride (LiF) is sequentially applied... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness.

[0444]

[0445] During the above process, the evaporation rate of organic matter is maintained. Lithium fluoride maintenance of the cathode The evaporation rate of aluminum maintains The evaporation rate was such that the vacuum level was maintained at 2×10⁻⁶ during evaporation. -7 ~5×10 -6This led to the creation of organic light-emitting devices.

[0446] <Examples 1-2 to Examples 1-8>

[0447] Organic light-emitting devices were manufactured by replacing compound 1 with the compounds described in Examples 1 to 8 above, except that organic light-emitting devices were manufactured by the same method as in Examples 1-1 above.

[0448]

[0449] <Comparative Examples 1-1 to 1-5>

[0450] Organic light-emitting devices were manufactured using the compounds listed in Table 1 below instead of compound 1, except that the method was the same as in Examples 1-1 above. The C1 to C5 compounds used in Table 1 below are shown below.

[0451]

[0452] <Experimental Example>

[0453] When an electric current was applied to the organic light-emitting devices manufactured in the above embodiments and comparative examples, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. 90 This refers to the time required for the brightness to decrease from the initial brightness (1600 nits) to 90%.

[0454] Table 1

[0455]

[0456] As shown in Table 1 above, the organic light-emitting devices of Examples 1-1 to 1-8, in which the compound of the present invention, which binds bicarbazole to TPS (tetraphenylsilane), and in which the carbazole bound to TPS is substituted with phenyl or biphenyl on one side, and the deuterium substitution rate of the bicarbazole is 50% or more, and which are used as the p-type host of the hole transport region (electron blocking layer) and the light-emitting layer, exhibit excellent characteristics in terms of efficiency, driving voltage and stability of the organic light-emitting device.

[0457] Conversely, in Comparative Example 1-1, which used compound C1 with phenyl or biphenyl unsubstituted on bicarbazole; Comparative Example 1-2, which used compound C2 with deuterium unsubstituted on bicarbazole; Comparative Examples 1-3 and 1-4, which used compounds C3 and C4 with phenyl substituted on both sides of the carbazole not bound to TPS; and Comparative Example 1-5, which used compound C5 with a deuterium substitution rate of less than 50% for bicarbazole, compared with the organic light-emitting devices of Examples 1-1 to 1-8 using compounds according to Formula 1 of this application, the results showed increased voltage, decreased efficiency, and decreased stability (lifetime) characteristics.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, Ar represents a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. L represents a directly bonded, substituted, or unsubstituted aryl group. r1 is an integer from 1 to 6. When r1 is 2 or higher, R1 is either the same or different from each other. r2 is an integer from 1 to 8. When r2 is greater than 2, R2 values ​​are either the same or different. Seven or more of R1 and R2 are deuterium, and the remaining ones are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. R3 to R6 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. r3 is an integer from 1 to 5. When r3 is 2 or higher, R3 values ​​are either the same or different. r4 is an integer from 1 to 5. When r4 is 2 or higher, R4 values ​​are either the same or different. r5 is an integer from 1 to 5. When r5 is 2 or higher, R5 values ​​are either the same or different. r6 is an integer from 1 to 4. When r6 is 2 or higher, R6 is either the same or different from each other.

2. The compound according to claim 1, wherein, The chemical formula 1 is either chemical formula 1-A or chemical formula 1-B as follows: [Chemical Formula 1-A] [Chemical Formula 1-B] In chemical formulas 1-A and 1-B, R1 to R6, Ar, and R1 to r6 are defined as in chemical formula 1. L is an arylene group consisting of 6 to 30 carbon atoms, either directly bonded, substituted, or unsubstituted.

3. The compound according to claim 1, wherein, The chemical formula 1 is any one of the following chemical formulas 1-1 to 1-5: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] [Chemical Formulas 1-5] In chemical formulas 1-1 to 1-5, the definitions of R1, R2, L, and r1 to r6 are the same as those in chemical formula 1. R3 to R8 are each hydrogen or deuterium. r7 is an integer from 1 to 4. When r7 is 2 or higher, R7 values ​​are either the same or different. r8 is an integer from 1 to 5. When r8 is 2 or higher, R8 can be the same or different from each other.

4. The compound according to claim 1, wherein, The chemical formula 1 is any one of the following chemical formulas 2-1 to 2-4: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] In chemical formulas 2-1 to 2-4, the definitions of R1, R2, Ar, L, and r1 to r6 are the same as those in chemical formula 1. R3 to R6 are each hydrogen or deuterium.

5. The compound according to claim 1, wherein, The chemical formula 1 is any one of the following chemical formulas 3-1 to 3-8: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] [Chemical Formula 3-5] [Chemical Formula 3-6] [Chemical Formula 3-7] [Chemical Formula 3-8] In chemical formulas 3-1 to 3-8, the definitions of R1, R2, Ar, L, and r1 to r6 are the same as those in chemical formula 1. R3 to R6 are each hydrogen or deuterium.

6. The compound according to claim 1, wherein, The chemical formula 1 is represented by the following chemical formula 4-1 or chemical formula 4-2: [Chemical Formula 4-1] [Chemical Formula 4-2] In chemical formulas 4-1 and 4-2, the definitions of R1, R2, Ar, L, and r1 to r6 are the same as those in chemical formula 1. R3 to R6 are each hydrogen or deuterium.

7. The compound according to claim 1, wherein, The L is a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, or substituted or unsubstituted terphenylene.

8. The compound according to claim 1, wherein, R3 to R6 may be the same as or different from each other, and each is independently hydrogen, deuterium, or a phenyl substituted with or unsubstituted with deuterium.

9. The compound according to claim 1, wherein, R1 and R2 are deuterium.

10. The compound according to claim 1, wherein, The compound represented by chemical formula 1 is represented by any one of the following structural formulas: In the aforementioned structural formula, n is the number of deuterium substitutions in the structure within the brackets []. m is the number of deuterium substitutions in the structure within parentheses (). m is 7 or higher and 14 or lower.

11. The compound according to claim 1, wherein, Chemical Formula 1 is any one of the following compounds:

12. An organic light-emitting device, comprising: An anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers comprise a compound as described in any one of claims 1 to 11.

13. The organic light-emitting device according to claim 12, wherein, The organic layer includes a light-emitting layer, which contains the compound.

14. The organic light-emitting device according to claim 13, wherein, The organic layer includes a light-emitting layer, which contains the compound as the main component.

15. The organic light-emitting device according to claim 14, wherein, The organic layer includes a light-emitting layer, which contains the compound as a p-type host and also contains an n-type host.

16. The organic light-emitting device according to claim 14, wherein, The light-emitting layer comprises the compound as the main component and also contains dopants.

Images