Organic compound and organic light-emitting device including same
By using specific organic compounds [Chemical Formula 1] and multi-layer structure design in organic light emitting devices, the problem of insufficient efficiency and stability of organic light emitting devices in the prior art is solved, and higher efficiency, lower driving voltage and longer life are achieved.
Patent Information
- Application Number
- CN202411242274.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-06-24
- Filing Date
- 2024-09-05
- Publication Date
- 2025-03-11
AI Technical Summary
There are shortcomings in existing organic light emitting devices in terms of efficiency and stability, especially in terms of driving voltage and life characteristics.
A specific organic compound is used, and the chemical formula is [Chemical Formula 1], as the material of the organic matter layer of the organic light emitting device, and the performance of the device is improved by the design of a multi-layer structure.
The efficiency improvement of organic light emitting devices is achieved, the driving voltage is reduced, and the life characteristics of the device are improved.
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Figure CN119591626A_ABST
Abstract
Description
Technical Field
[0001] This application claims the priority of Korean Patent Application No. 10-2023-0119454 filed with the Korean Patent Office on September 8, 2023 and Korean Patent Application No. 10-2024-0081830 filed with the Korean Patent Office on June 24, 2024, the entire contents of which are incorporated into this specification.
[0002] The present specification relates to an organic compound and an organic light-emitting device including the same. Background Art
[0003] Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting device using the phenomenon of organic light emitting generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.
[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above.
[0005] Prior art literature
[0006] Patent Literature
[0007] (Patent Document 1) Korean Patent Publication No. 2022-0153759 Summary of the invention
[0008] Technical issues
[0009] This specification provides an organic compound and an organic light-emitting device including the same.
[0010] Solution to the problem
[0011] One embodiment of the present specification provides an organic compound of the following Chemical Formula 1.
[0012] [Chemical formula 1]
[0013]
[0014] In the above chemical formula 1,
[0015] R1 to R 16At least one of the following chemical formula 2,
[0016] The above R1 to R 16 The groups not in the above chemical formula 2 are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heterocyclic group, or selectively combine with adjacent groups to form a substituted or unsubstituted ring,
[0017] When the above R4 and R5 are combined with each other, they are connected by a -(X)a- linking group.
[0018] The above R9 and R 10 When combined with each other, they are connected by a -(Y)b- linking group,
[0019] The above X and Y are the same or different from each other, and are each independently a direct bond, O, S, CR'R", NR' or SiR'R",
[0020] R' and R" are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,
[0021] a and b are 0 or 1 respectively,
[0022] [Chemical formula 2]
[0023]
[0024] In the above chemical formula 2,
[0025] * is the site that binds to the above chemical formula 1,
[0026] At least one of X1 to X3 is N, and the others are CH,
[0027] L1 and L2 are the same or different from each other, and are each independently a directly bonded, substituted or unsubstituted arylene group having 6 to 30 carbon atoms,
[0028] A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms,
[0029] R 17 To R 24 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 heterocyclic group.
[0030] 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 disposed between the anode and the cathode, wherein one or more of the organic layers includes the organic compound.
[0031] Effects of the Invention
[0032] The organic compound described in this specification can be used as a material for an organic layer of an organic light-emitting device. The organic compound according to at least one embodiment of this specification can achieve improved efficiency, lower driving voltage and / or improved lifespan characteristics in an organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS
[0033] Figure 1 An example of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 9 are stacked in this order is shown.
[0034] Figure 2 The diagram shows an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 9 are stacked in this order.
[0035] Explanation of symbols
[0036] 1: Substrate
[0037] 2: Anode
[0038] 3: Hole injection layer
[0039] 4: Hole transport layer
[0040] 5: Electron blocking layer
[0041] 6: Luminous layer
[0042] 7: Hole blocking layer
[0043] 8: Electron injection and transport layer
[0044] 9: Cathode DETAILED DESCRIPTION
[0045] Next, this specification is described in more detail.
[0046] In the present specification, when a part is indicated to “include / comprise” a certain component, unless there is a particular description to the contrary, it means that other components may be further included, rather than excluding other components.
[0047] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.
[0048] In the present specification, "*" indicates a position bonded to a chemical formula or a compound.
[0049] In the present specification, examples of substituents are described below, but are not limited thereto.
[0050] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.
[0051] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium, a halogen group, a nitrile group (-CN), a silyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, Arylthio Alkylsulfonyl Arylsulfonyl The alkylene group may be substituted with one or more substituents selected from the group consisting of alkenyl, amine, aryl and heterocyclic groups, or may be substituted with a substituent formed by connecting two or more substituents selected from the group consisting of the above-mentioned substituents, or may not have any substituent. For example, a "substituent formed by connecting 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 formed by connecting two phenyl groups.
[0052] In the present specification, the term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, a silyl group, a nitro group, a hydroxyl group, an amino group, an alkoxy group, an aryloxy group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group and a heterocyclic group, or is substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or has no substituent.
[0053] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a silyl group, a nitrile group, an alkyl group, an aryl group and a heterocyclic group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.
[0054] Examples of the above substituents are described below, but are not limited thereto.
[0055] In the present specification, as examples of the halogen group, there are fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).
[0056] In the present specification, the silyl group can be represented by the chemical formula -SiYaYbYc, wherein Ya, Yb and Yc can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.
[0057] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group 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 thereto.
[0058] In this specification, the alkoxy group may be straight chain, branched chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 20. Specifically, it may be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, etc., but is not limited thereto.
[0059] The alkyl group, alkoxy group, and other substituents containing an alkyl portion described in the present specification include all linear or branched forms.
[0060] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.
[0061] In the present specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, and may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkynyl group is 2 to 10.
[0062] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 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 another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.
[0063] In the present specification, the amino group is -NH2, and the above-mentioned alkyl, aryl, heterocyclic group, alkenyl, cycloalkyl and combinations thereof may be substituted in the above-mentioned amino group. The number of carbon atoms of the above-mentioned substituted amino group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 20. According to one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 10. As specific examples of substituted amino groups, there are methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthracenylamino, dibenzofuranylphenylamino, 9-methylanthrylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, diphenylamino, etc., but are not limited thereto.
[0064] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, quaterphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, triphenylene, phenylene, fluorenyl, triphenylene, etc., but are not limited to these.
[0065] In the present specification, the above description on the aryl group can be applied to the aryl group in the aryloxy group and the arylamine group.
[0066] In the present specification, the above description about the alkyl group can be applied to the alkyl group in the above alkylthio group and alkylsulfonyl group.
[0067] In the present specification, the above description about the aryl group can be applied to the aryl group in the arylthio group and the arylsulfonyl group.
[0068] In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarbazolyl, triazinyl and the like, but are not limited thereto.
[0069] In the present specification, a heteroaryl group is aromatic, and other than this, the above description about the heterocyclic group is applicable.
[0070] In the present specification, the above-mentioned arylene group is divalent, and the above-mentioned description of the aryl group is applicable except for this.
[0071] In the present specification, the heteroarylene group is divalent, and the same explanation as for the above-mentioned heteroaryl group is applicable except for this.
[0072] In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" means a hydrocarbon ring or a heterocyclic ring.
[0073] For example, when the adjacent groups are combined to form a ring, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle, or a condensed ring thereof may be formed. The above hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms. The above heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si and Se. In this specification, the above aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle and aromatic heterocycle may be monocyclic or polycyclic.
[0074] In this specification, an aliphatic hydrocarbon ring refers to a ring that is not an aromatic ring and is composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.
[0075] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenanthene, pyrene, tetracene, In the present specification, the aromatic hydrocarbon ring can be interpreted as having the same meaning as the aryl group.
[0076] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane Azoctane Thioctane etc., but not limited thereto.
[0077] In the present 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, Azoles, Isopropylamine Azoles, thiazoles, isothiazoles, triazoles, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazines, Azine, thiazine, di Olefins, triazines, tetrazines, isoquinolines, quinolines, quinones, quinazolines, quinoxalines, naphthyridines, acridines, phenanthridines, naphthyridines, triazaindene, indoles, indolizines, benzothiazoles, benzo azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phen Oxazine, indolecarbazole, indenocarbazole, etc., but are not limited to these.
[0078] Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention can be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.
[0079] Next, the organic compound of the following Chemical Formula 1 will be described in detail.
[0080] [Chemical formula 1]
[0081]
[0082] In the above chemical formula 1,
[0083] R1 to R 16 At least one of the following chemical formula 2,
[0084] The above R1 to R 16 The groups not in the above chemical formula 2 are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heterocyclic group, or selectively combine with adjacent groups to form a substituted or unsubstituted ring,
[0085] When the above R4 and R5 are combined with each other, they are connected by a -(X)a- linking group.
[0086] The above R9 and R 10 When combined with each other, they are connected by a -(Y)b- linking group,
[0087] The above X and Y are the same or different from each other, and are each independently a direct bond, O, S, CR'R", NR' or SiR'R",
[0088] R' and R" are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,
[0089] a and b are 0 or 1 respectively,
[0090] [Chemical formula 2]
[0091]
[0092] In the above chemical formula 2,
[0093] * is the site that binds to the above chemical formula 1,
[0094] At least one of X1 to X3 is N, and the others are CH,
[0095] L1 and L2 are the same or different from each other, and are each independently a directly bonded, substituted or unsubstituted arylene group having 6 to 30 carbon atoms,
[0096] A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms,
[0097] R 17 To R 24 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 heterocyclic group.
[0098] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently any one of the following structures.
[0099]
[0100] In the above structure,
[0101] The dotted line indicates the binding position.
[0102] R 25 It is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group.
[0103] In one embodiment of the present specification, the above-mentioned A is an aryl group having 6 to 30 carbon atoms which may be substituted by deuterium or a triphenylsilyl group, or a heterocyclic group having 2 to 30 carbon atoms which may be substituted by deuterium or an unsubstituted triphenylsilyl group.
[0104] In one embodiment of the present specification, the above Chemical Formula 1 is any one of the organic compounds of Chemical Formulas 1-1 to 1-6.
[0105] [Chemical formula 1-1]
[0106]
[0107] [Chemical formula 1-2]
[0108]
[0109] [Chemical formula 1-3]
[0110]
[0111] [Chemical formula 1-4]
[0112]
[0113] [Chemical formula 1-5]
[0114]
[0115] [Chemical formula 1-6]
[0116]
[0117] In the above Chemical Formulas 1-1 to 1-6, R1 to R3, R6 to R 16 The definitions of R, R' and R" are the same as those in the above Chemical Formula 1.
[0118] In one embodiment of the present specification, A is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group.
[0119] In one embodiment of the present specification, the above Chemical Formula 1 is any one of the organic compounds of Chemical Formulas 1-A to 1-L.
[0120]
[0121]
[0122] In the above Chemical Formulas 1-A to 1-L,
[0123] R1 to R 16 , X1 to X3, L1, L2, A, and R 17 To R 24 The definition of is the same as that in the above Chemical Formulas 1 and 2.
[0124] In one embodiment of the present specification, R1 to R 16 At least one of them is the above chemical formula 2, and the above R1 to R 16 The groups other than those in the above Chemical Formula 2 are the same as or different from each other, and are each independently hydrogen or deuterium.
[0125] In one embodiment of the present specification, R1 to R 16 At least one of them is the above chemical formula 2, and the above R1 to R 16 The group not in the above chemical formula 2 is hydrogen.
[0126] In one embodiment of the present specification, R1 to R 16 At least one of them is the above chemical formula 2, and the above R1 to R 16 The group not in the above chemical formula 2 is deuterium.
[0127] In one embodiment of the present specification, the organic compound of the above Chemical Formula 1 has a deuterium substitution rate of 30% or more.
[0128] In one embodiment of the present specification, the organic compound of the above Chemical Formula 1 has a deuterium substitution rate of 40% or more.
[0129] In one embodiment of the present specification, the organic compound of the above Chemical Formula 1 has a deuterium substitution rate of 50% or more.
[0130] In one embodiment of the present specification, the organic compound of the above Chemical Formula 1 has a deuterium substitution rate of 70% or more.
[0131] In one embodiment of the present specification, the organic compound of the above Chemical Formula 1 has a deuterium substitution rate of 100%.
[0132] In one embodiment of the present specification, the above-mentioned a is 0 or 1.
[0133] In one embodiment of the present specification, the above b is 0 or 1.
[0134] In one embodiment of the present specification, a is 0 and b is 0.
[0135] In one embodiment of the present specification, a is 1 and b is 0.
[0136] In one embodiment of the present specification, a is 0 and b is 1.
[0137] In one embodiment of the present specification, a is 1 and b is 1.
[0138] In one embodiment of the present specification, at least one of X1 to X3 is N, and the rest are CH.
[0139] In one embodiment of the present specification, X1 is N, and X2 and X3 are CH.
[0140] In one embodiment of the present specification, X2 is N, and X1 and X3 are CH.
[0141] In one embodiment of the present specification, X3 is N, and X1 and X2 are CH.
[0142] In one embodiment of the present specification, at least two of the above X1 to X3 are N, and the rest are CH.
[0143] In one embodiment of the present specification, X1 and X2 are N, and X3 is CH.
[0144] In one embodiment of the present specification, X1 and X3 are N, and X2 is CH.
[0145] In one embodiment of the present specification, X2 and X3 are N, and X1 is CH.
[0146] In one embodiment of the present specification, all of X1 to X3 are N.
[0147] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a directly bonded or substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
[0148] In one embodiment of the present specification, L1 and L2 are each independently a direct bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
[0149] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently an arylene group having 6 to 30 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.
[0150] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently an arylene group having 6 to 20 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.
[0151] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
[0152] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a deuterium-substituted or unsubstituted phenylene group, or a deuterium-substituted or unsubstituted biphenylene group.
[0153] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond, a phenylene group, or a biphenylene group.
[0154] In one embodiment of the present specification, L1 and L2 are directly bonded.
[0155] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenylene group.
[0156] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a substituted or unsubstituted biphenylene group.
[0157] In one embodiment of the present specification, L1 is a direct bond.
[0158] In one embodiment of the present specification, L1 is a substituted or unsubstituted phenylene group.
[0159] In one embodiment of the present specification, L1 is a substituted or unsubstituted biphenylene group.
[0160] In one embodiment of the present specification, L1 is a phenylene group which may be substituted with deuterium.
[0161] In one embodiment of the present specification, L1 is a deuterium-substituted or unsubstituted biphenylene group.
[0162] In one embodiment of the present specification, L2 is a direct bond.
[0163] In one embodiment of the present specification, L2 is a substituted or unsubstituted phenylene group.
[0164] In one embodiment of the present specification, L2 is a substituted or unsubstituted biphenylene group.
[0165] In one embodiment of the present specification, L2 is a phenylene group which may be substituted with deuterium.
[0166] In one embodiment of the present specification, L2 is a deuterium-substituted or unsubstituted biphenylene group.
[0167] In one embodiment of the present specification, the above R 17 To R 24 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
[0168] In one embodiment of the present specification, the above R 17 To R 24 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
[0169] In one embodiment of the present specification, the above R 17 To R 24 are the same as or different from each other and 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 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
[0170] In one embodiment of the present specification, the above R 17 To R 24 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
[0171] In one embodiment of the present specification, the above R 17 To R 24 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
[0172] In one embodiment of the present specification, the above R 17 To R 24 They are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.
[0173] In one embodiment of the present specification, the above R 17 To R 24 They are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms.
[0174] In one embodiment of the present specification, the above R 17 To R 24 They are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0175] In one embodiment of the present specification, the above R 17 To R 24 They are the same as or different from each other and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
[0176] In one embodiment of the present specification, the above R 17 To R 24 are the same as or different from each other, and are each independently hydrogen or deuterium.
[0177] In one embodiment of the present specification, the above R 17 To R 24 are the same as or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms and containing O, S or N.
[0178] In one embodiment of the present specification, the above R 17 To R 24are the same as or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms and containing O, S or N.
[0179] In one embodiment of the present specification, the above R 17 To R 24 are the same as or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms and containing O, S or N.
[0180] In one embodiment of the present specification, the above R 17 To R 24 The same as or different from each other, and each independently represents hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted naphthobenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl.
[0181] In one embodiment of the present specification, the above R 17 To R 24 The same as or different from each other, and each independently represents hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl.
[0182] In one embodiment of the present specification, the above R 17 To R 24 The same as or different from each other, and each independently represents hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thienyl, or substituted or unsubstituted dibenzothienyl.
[0183] In one embodiment of the present specification, the above R 17 To R 24 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted dibenzofuranyl.
[0184] In one embodiment of the present specification, the above R 17 To R 24 are the same as or different from each other and are each independently hydrogen, deuterium, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, or dibenzofuranyl substituted or unsubstituted by deuterium.
[0185] In one embodiment of the present specification, the above-mentioned A is an aryl group having 6 to 30 carbon atoms which may be substituted by deuterium or an arylsilyl group, or a heterocyclic group having 2 to 30 carbon atoms which may be substituted by deuterium.
[0186] In one embodiment of the present specification, A is a phenyl group which may be substituted by deuterium or an arylsilyl group, a biphenyl group which may be substituted by deuterium, a dibenzofuranyl group which may be substituted by deuterium, a dibenzothienyl group which may be substituted by deuterium, or a carbazolyl group which may be substituted by deuterium.
[0187] In one embodiment of the present specification, the above-mentioned A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
[0188] In one embodiment of the present specification, the above-mentioned A is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
[0189] In one embodiment of the present specification, the above-mentioned A is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
[0190] In one embodiment of the present specification, the above-mentioned A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.
[0191] In one embodiment of the present specification, the above-mentioned A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms.
[0192] In one embodiment of the present specification, the above-mentioned A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0193] In one embodiment of the present specification, the above-mentioned A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms containing O, S or N.
[0194] In one embodiment of the present specification, the above-mentioned A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms containing O, S or N.
[0195] In one embodiment of the present specification, the above-mentioned A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms containing O, S or N.
[0196] In one embodiment of the present specification, A is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted naphthobenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted pyrimidinyl group.
[0197] In one embodiment of the present specification, the above-mentioned A is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted pyrimidinyl group.
[0198] In one embodiment of the present specification, A is a phenyl group which is substituted or unsubstituted by hydrogen, deuterium, a nitrile group, an alkylsilyl group, an arylsilyl group, or an alkyl group having 1 to 10 carbon atoms; a biphenyl group which is substituted or unsubstituted by hydrogen, deuterium, a nitrile group, an alkylsilyl group, an arylsilyl group, or an alkyl group having 1 to 10 carbon atoms; a terphenyl group which is substituted or unsubstituted by hydrogen, deuterium, a nitrile group, an alkylsilyl group, an arylsilyl group, or an alkyl group having 1 to 10 carbon atoms; a terphenyl group which is substituted or unsubstituted by hydrogen, deuterium, a nitrile group, an alkylsilyl group, an arylsilyl group, or an alkyl group having 1 to 10 carbon atoms; substituted naphthyl; dibenzofuranyl substituted or unsubstituted by hydrogen, deuterium, nitrile, alkylsilyl, arylsilyl or alkyl having 1 to 10 carbon atoms; thienyl substituted or unsubstituted by hydrogen, deuterium, nitrile, alkylsilyl, arylsilyl or alkyl having 1 to 10 carbon atoms; dibenzothienyl substituted or unsubstituted by hydrogen, deuterium, nitrile, alkylsilyl, arylsilyl or alkyl having 1 to 10 carbon atoms; or carbazolyl substituted or unsubstituted by hydrogen, deuterium, nitrile, alkylsilyl, arylsilyl or alkyl having 1 to 10 carbon atoms.
[0199] In one embodiment of the present specification, R' and R" are the same or different and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
[0200] In one embodiment of the present specification, R' and R" are the same or different and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
[0201] In one embodiment of the present specification, R' and R" are the same or different and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.
[0202] In one embodiment of the present specification, the above R' and R" are the same as or different from each other, and are each independently hydrogen, deuterium or methyl.
[0203] In one embodiment of the present specification, the above Chemical Formula 1 is any one of the following compounds.
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211]
[0212]
[0213]
[0214]
[0215]
[0216]
[0217]
[0218]
[0219]
[0220] The organic compound of Chemical Formula 1 according to one embodiment of the present specification can produce a core structure as described in the following production examples. The substituents can be bonded by methods known in the art, and the type, position or number of the substituents can be changed according to techniques known in the art.
[0221] In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the organic compound of the above Chemical Formula 1. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can also be adjusted by introducing various substituents into the core structure of the structure as described above.
[0222] In addition, the present specification provides an organic light-emitting device including the above-mentioned organic compound.
[0223] The organic light-emitting device according to the present specification is characterized in that it includes: an anode, a cathode, and one or more organic layers arranged between the anode and the cathode, and one or more of the organic layers contain an organic compound represented by the above-mentioned chemical formula 1.
[0224] The organic layer of the organic light-emitting device of the present specification may be formed by a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including 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 one or more of the electron transport and injection layers as organic layers. However, the structure of the organic light-emitting device of the present specification is not limited thereto and may include a smaller number or a larger number of organic layers.
[0225] In the organic light-emitting device of the present specification, the organic light-emitting device includes a light-emitting layer, and the light-emitting layer may include the organic compound.
[0226] For example, the organic compound of the above Chemical Formula 1 may be included as a host of the light emitting layer.
[0227] In the organic light-emitting device of the present specification, the light-emitting layer contains the organic compound as a host and may further contain a dopant.
[0228] In one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and a hole blocking layer. The electron injection layer, the electron transport layer, or the electron injection and transport layer may contain the organic compound represented by the above Chemical Formula 1.
[0229] In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes the organic compound represented by Chemical Formula 1.
[0230] The organic light-emitting device of the present specification may further include a hole transport layer, a hole injection layer, an electron blocking layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and one or more organic layers among the hole injection and transport layer.
[0231] In one embodiment of the present specification, the organic light-emitting device may be a (normal type) organic light-emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
[0232] In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.
[0233] The structure of the organic light-emitting device of the present specification may have the following Figure 1 and Figure 2 The structure shown is not limited thereto.
[0234] Figure 1 The structure of the organic light-emitting device is exemplified in which a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 9 are sequentially stacked. In the above structure, the organic compound may be contained in the light-emitting layer 6.
[0235] Figure 2 The structure of an organic light-emitting device is illustrated, which is sequentially stacked with a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 9. In the structure described above, the compound may be contained in any one of the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the hole blocking layer 7, and the electron injection and transport layer 8, for example, in the light-emitting layer 6 or the hole blocking layer 7.
[0236] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the technical field, except that at least one layer of the organic material layer contains the above compound, that is, the compound represented by the above Chemical Formula 1.
[0237] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
[0238] For example, the organic light-emitting device according to the present specification can be manufactured by evaporating 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 to form an anode, then forming an organic layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer and an electron injection layer on the anode, and then evaporating a substance that can be used as a cathode on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by evaporating a cathode substance, an organic layer, and an anode substance on a substrate in sequence.
[0239] The organic layer may further include one or more of 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.
[0240] The anode is an electrode for injecting holes. As the anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of anode materials that can be used in the present 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, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
[0241] The cathode is an electrode for injecting electrons. In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.
[0242] The hole injection layer is a layer that plays a role in facilitating the injection of holes from the anode to the light-emitting layer. The hole injection material is a material that can well receive holes from the anode at a low voltage. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine compounds, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, perylene derivatives, anthraquinone, and polyaniline and polythiophene conductive polymers, but are not limited thereto.
[0243] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but is not limited thereto.
[0244] [Chemical formula HI-1]
[0245]
[0246] In the above chemical formula HI-1,
[0247] R315 to R317 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,
[0248] r315 is an integer from 1 to 5. When the above r315 is 2 or more, the two or more R315 are the same or different from each other.
[0249] r316 is an integer of 1 to 5. When the number of r316 is 2 or more, two or more R316 are the same as or different from each other.
[0250] 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.
[0251] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazolyl group, a phenyl group, a biphenyl group, a triphenylene group, and a combination thereof.
[0252] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently substituted or unsubstituted aryl groups, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.
[0253] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently phenyl or biphenyl, or are combined with adjacent groups to form an indene substituted with a methyl group.
[0254] According to one embodiment of the present specification, the chemical formula HI-1 is represented by any one of the following compounds.
[0255]
[0256] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-2, but the present invention is not limited thereto.
[0257] [Chemical formula HI-2]
[0258]
[0259] In the above chemical formula HI-2,
[0260] R401 to R403 are the same as or different from each other and are each independently a halogen group,
[0261] R401 to R403 are 4.
[0262] According to one embodiment of the present specification, R401 to R403 are F.
[0263] According to one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.
[0264]
[0265] According to one embodiment of the present specification, the hole injection layer includes the chemical formulas HI-1 and HI-2.
[0266] According to one embodiment of the present specification, the hole injection layer includes the chemical formulas HI-1 and HI-2 at a weight ratio of 1:99 to 99:1.
[0267] The hole transport layer can play a role in smoothing the transport of holes. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material with a large hole mobility is suitable. As specific examples, there are arylamine organic substances, conductive polymers, and block copolymers with both conjugated parts and non-conjugated parts, but are not limited to these.
[0268] According to one embodiment of the present specification, the hole transport layer may include the chemical formula HI-1.
[0269] An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
[0270] According to one embodiment of the present specification, the electron blocking layer includes a compound represented by the following chemical formula EP, but is not limited thereto.
[0271] The light-emitting layer can emit red, green or blue light and can be formed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo Compounds of the oxazole, benzothiazole and benzimidazole series; polymers of the poly(p-phenylene vinylene) (PPV) series; spiro compounds; polyfluorene, rubrene, etc., but are not limited thereto.
[0272] The host material of the above-mentioned light-emitting layer includes aromatic fused ring derivatives or heterocyclic compounds. Specifically, as aromatic fused ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.
[0273] In one embodiment of the present specification, the light-emitting layer includes the compound of Chemical Formula 1 as a main component.
[0274] In one embodiment of the present specification, the light-emitting layer includes the compound of Chemical Formula 1 as a host, and further includes one or more hosts different from those of Chemical Formula 1.
[0275] In one embodiment of the present specification, a host different from the compound of the above Chemical Formula 1 is represented by the following Chemical Formula EP.
[0276] [Chemical formula EP]
[0277]
[0278] In the above chemical formula EP,
[0279] Ra and Rb are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
[0280] Rc is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
[0281] In one embodiment of the present specification, Ra and Rb are the same as or different from each other, and are each independently hydrogen or deuterium.
[0282] In one embodiment of the present specification, the above-mentioned Ra and Rb are hydrogen.
[0283] In one embodiment of the present specification, Rc is a substituted or unsubstituted aryl group.
[0284] In one embodiment of the present specification, Rc is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
[0285] In one embodiment of the present specification, Rc is a substituted or unsubstituted phenyl group.
[0286] In one embodiment of the present specification, Rc is a phenyl group.
[0287] In one embodiment of the present specification, the chemical formula EP is the following structure.
[0288]
[0289] In the organic light-emitting device of the present specification, the light-emitting layer contains the organic compound as a host and may further contain a dopant.
[0290] According to one embodiment of the present specification, the light emitting layer includes a host and a dopant in a weight ratio of 99:1 to 1:99, specifically, in a weight ratio of 99:1 to 50:50, and more specifically, in a weight ratio of 99:1 to 95:5.
[0291] When the above-mentioned light-emitting layer emits red light, as a light-emitting dopant, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium, bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium, bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium, tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the light-emitting layer emits green light, as a light-emitting dopant, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium, face-tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinoline)aluminum) can be used, but it is not limited to these. When the light-emitting layer emits blue light, as a light-emitting dopant, phosphorescent materials such as platinum coordination compounds, (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers can be used, but it is not limited to these.
[0292] According to one embodiment of the present specification, the dopant is a metal coordination compound.
[0293] According to one embodiment of the present specification, the dopant is a platinum coordination compound.
[0294] According to one embodiment of the present specification, the dopant is an iridium complex.
[0295] According to one embodiment of the present specification, the dopant is represented by the following chemical formula D-1 or D-2, but is not limited thereto.
[0296] [Chemical formula D-1]
[0297]
[0298] [Chemical formula D-2]
[0299]
[0300] In the above chemical formulas D-1 and D-2,
[0301] M is a transition metal,
[0302] A1, A3, A5, A6, K1, K2 and K3 are the same as or different from each other, and are each independently a direct bond, O, S, a divalent ester group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted divalent alkenyl group, a substituted or unsubstituted divalent aryl group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
[0303] A2 and A4 are the same as or different from each other, and are each independently a direct bond, N, a substituted or unsubstituted trivalent alkylene group, a substituted or unsubstituted trivalent aryl group, or a substituted or unsubstituted trivalent heteroaryl group,
[0304] n is 1 or 2. When n is 2, the structures in the brackets are the same as or different from each other.
[0305] According to one embodiment of the present specification, the above-mentioned M is iridium or platinum.
[0306] According to one embodiment of the present specification, the dopant may be selected from the following structural formulas, but is not limited thereto.
[0307]
[0308]
[0309]
[0310]
[0311] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
[0312] The hole blocking layer is a layer that prevents holes from reaching the cathode and can usually be formed using the same conditions as the hole injection layer. Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.
[0313] In one embodiment of the present specification, the hole blocking layer may include the compound of Chemical Formula 1.
[0314] The above-mentioned electron transport layer or electron injection and transport layer can play a role in smoothing the transmission of electrons. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, and a material with a large electron mobility is suitable. As specific examples, there are the above-mentioned compounds or Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to these.
[0315] The electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, the following compounds are preferred: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.
[0316] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, 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.
[0317] According to one embodiment of the present specification, the electron injection and transport layer includes a compound represented by the following chemical formula ET, but is not limited thereto.
[0318] [Chemical formula ET-1]
[0319]
[0320] In the above chemical formula ET-1,
[0321] At least one of Z11 to Z13 is N, and the rest are CH,
[0322] At least one of Z21 to Z23 is N, and the others are CH,
[0323] L601 and L602 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
[0324] Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
[0325] In one embodiment of the present specification, all of Z11 to Z13 are N.
[0326] In one embodiment of the present specification, all of Z21 to Z23 are N.
[0327] In one embodiment of the present specification, L601 and L602 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms. In one embodiment of the present specification, L601 and L602 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 12 carbon atoms.
[0328] In one embodiment of the present specification, L601 and L602 are substituted or unsubstituted phenylene groups.
[0329] In one embodiment of the present specification, L601 and L602 are phenylene groups.
[0330] In one embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.
[0331] In one embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 12 carbon atoms.
[0332] In one embodiment of the present specification, Ar601 to Ar604 are substituted or unsubstituted phenyl groups.
[0333] In one embodiment of the present specification, Ar601 to Ar604 are phenyl groups.
[0334] In one embodiment of the present specification, the chemical formula ET-1 is the following structure.
[0335]
[0336] In one embodiment of the present specification, the electron injection and transport layer may further include a metal coordination compound. The metal coordination compound is as described above.
[0337] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.
[0338] Below, in order to specifically describe this specification, an embodiment will be cited to describe in detail. However, the embodiments according to this specification can be deformed into various different forms, and it is not interpreted that the scope of this application is limited to the embodiments described in detail below. The embodiments of this application are provided to more completely describe this specification to those skilled in the art.
[0339] [Manufacturing example]
[0340] <Production Example 1> Synthesis of Compound 1
[0341]
[0342] In a 500 ml round-bottom flask under nitrogen atmosphere, compound 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carba zole) (3.50 g, 7.85 mmol) and a-1 (4.07 g, 8.63 mmol) were completely dissolved in 240 ml of tetrahydrofuran (THF), and then 2M potassium carbonate aqueous solution (120 ml) was added. After adding tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.54 g, 0.47 mmol), the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The mixture was recrystallized from 310 ml of ethyl acetate to produce compound 1 (3.66 g, 62%).
[0343] MS[M+H] + =755
[0344] <Production Example 2> Synthesis of Compound 2
[0345]
[0346] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) (3.50 g, 7.85 mmol) and compound a-2 (4.20 g, 8.63 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.54 g, 0.47 mmol) was added, and then heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, and recrystallized with 280 mL of ethyl acetate to produce compound 2 (3.44 g, 57%).
[0347] MS[M+H] + =769
[0348] <Production Example 3> Synthesis of Compound 3
[0349]
[0350] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(2-(4-(9H-carbazol-9-yl)-6-chloro-1,3,5-triazin-2-yl)phenyl)-9H-carbazole (3.50 g, 6.70 mmol) and compound a-3 (3.70 g, 7.38 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.46 g, 0.40 mmol) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 300 mL of ethyl acetate to produce Compound 3 (3.79 g, 66%).
[0351] MS[M+H] + =861
[0352] <Production Example 4> Synthesis of Compound 4
[0353]
[0354] Under a nitrogen atmosphere, in a 500-mL round-bottom flask, compound 9-(4-chloro-6-(dibenzo[b,d]furan-2-yl)-1,3,5-triazin-2-yl)-9H-carbazole (3.50 g, 7.83 mmol) and compound a-1 (4.06 g, 8.61 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2 M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.54 g, 0.47 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 290 mL of ethyl acetate to produce Compound 4 (3.34 g, 56%).
[0355] MS[M+H] + =756
[0356] <Production Example 5> Synthesis of Compound 5
[0357]
[0358] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4-chloro-6-(dibenzo[b,d]thiophe n-1-yl)-1,3,5-triazin-2-yl)-9H-carbazole (3.50 g, 7.56 mmol) and compound a-1 (3.92 g, 8.32 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.52 g, 0.45 mmol), the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 330 mL of ethyl acetate to produce Compound 5 (3.12 g, 53%).
[0359] MS[M+H] + =772
[0360] <Production Example 6> Synthesis of Compound 6
[0361]
[0362] In a 500 mL round-bottom flask under a nitrogen atmosphere, compound 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole (3.50 g, 9.81 mmol) and compound a-4 (5.51 g, 10.79 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then a 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.68 g, 0.59 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The mixture was recrystallized from 310 ml of ethyl acetate to produce compound 6 (4.15 g, 60%).
[0363] MS[M+H] + =706
[0364] <Production Example 7> Synthesis of Compound 7
[0365]
[0366] Under nitrogen atmosphere, in a 500 ml round-bottom flask, compounds 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (3.50 g, 7.58 mmol) and a-1 (3.93 g, 8.33 mmol) were completely dissolved in 240 ml of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 ml) was added, followed by addition of tetrakis(triphenylphosphine)palladium (0.53 g, 0.45 mmol) and heated with stirring for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and the mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 300 ml of ethyl acetate to produce Compound 7 (3.89 g, 67%).
[0367] MS[M+H] + =771
[0368] <Production Example 8> Synthesis of Compound 8
[0369]
[0370] Under nitrogen atmosphere, in a 500 ml round-bottom flask, compound 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (3.50 g, 7.58 mmol) and a-5 (4.05 g, 8.33 mmol) were completely dissolved in 240 ml of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 ml) was added, and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.53 g, 0.45 mmol) was added, and then heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, and recrystallized from 310 ml of ethyl acetate to produce compound 8 (3.73 g, 63%).
[0371] MS[M+H] + =786
[0372] Example 1-1
[0373] ITO (indium tin oxide) The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
[0374] On the ITO transparent electrode prepared as the anode, the following compound HT1 and the following compound HI1 were mixed in a ratio of 98:2 (molar ratio). A hole injection layer is formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, a compound represented by the following chemical formula HT1 is deposited Then, a film with a thickness of 1000 nm was deposited on the hole transport layer. The electron blocking layer was formed by vacuum evaporation of a compound of BH (p-type) as a p-type host of the light-emitting layer and the compound 1 synthesized in the above-mentioned manufacturing example 1 as a (n-type) host of the light-emitting layer in a weight ratio of 1:1 and a compound represented by the following chemical formula BD in a weight ratio of 88:12 to form a light-emitting layer. On the above-mentioned light-emitting layer, a film thickness of 1000 nm was formed. The compound 1 synthesized in the above-mentioned manufacturing example 1 was vacuum-deposited to form a hole blocking layer. Next, on the above-mentioned hole blocking layer, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-deposited at a weight ratio of 1:1, thereby forming a hole blocking layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A thickness of is evaporated to form a cathode.
[0375]
[0376] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2×10 -7 ~5×10 -6 A support is provided to produce an organic light-emitting device.
[0377] Example 1-2 to Example 1-8
[0378] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that Compounds 2 to 8 described in Table 1 below were used instead of the compound of Preparation Example 1.
[0379] [Comparative Example]
[0380] Comparative Examples 1-1 to 1-6
[0381] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds described in Table 1 below were used instead of the compounds in Preparation Example 1. The compounds BH1 (n-type) to BH6 (n-type) used in Table 1 below are as follows.
[0382]
[0383] [Experimental example]
[0384] Experimental Example 1
[0385] When current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in the following Table 1. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.
[0386]
Table 1
[0387]
[0388] As shown in Table 1 above, the organic light-emitting devices of Examples 1-1 to 1-8, in which the compound containing a six-membered N ring substituted with a carbazole group represented by Chemical Formula 2 of the present application is combined with the core structure represented by Chemical Formula 1 of the present application as an n-type host of the hole blocking layer and the light-emitting layer, show excellent characteristics in terms of efficiency, driving voltage and stability of the organic light-emitting device. In contrast, the compounds of Comparative Examples 1-1 to 1-4 are organic light-emitting devices in which the structure containing a six-membered N ring is not combined with the core structure represented by Chemical Formula 1, and the organic light-emitting devices using the above compounds show results of increased voltage, decreased efficiency and stability (lifetime) compared to the organic light-emitting devices of Examples 1-1 to 1-8 using the compounds according to Chemical Formula 1 of the present application.
[0389] In addition, the compounds of Comparative Examples 1-5 have a core structure different from the core structure represented by Chemical Formula 1, and the compounds of Comparative Examples 1-6 are structures substituted with only a pyridine group but no carbazole group. In the case of organic light-emitting devices using the above compounds, compared with the organic light-emitting devices of Examples 1-1 to 1-8 using the compounds according to Chemical Formula 1 of the present application, the voltage is increased and the efficiency and stability (lifespan) are reduced.
[0390] The above content describes the preferred embodiments of the present invention (the hole blocking layer and the n-type main body of the light-emitting layer), but the present invention is not limited thereto. It can be transformed into various forms and implemented within the scope of protection claimed by the present invention and the scope of the detailed description of the invention, which also falls within the scope of the present invention.
Claims
1. An organic compound of the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, R1 to R 16 At least one of the following chemical formula 2, The R1 to R 16 The groups not in the chemical formula 2 are the same or different from each other, and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group, or selectively combine with adjacent groups to form a substituted or unsubstituted ring, When R4 and R5 are combined with each other, they are connected by a -(X)a- linking group. The R9 and R 10 When combined with each other, they are connected by a -(Y)b- linking group, The X and Y are the same or different from each other, and are each independently a direct bond, O, S, CR'R", NR' or SiR'R", R' and R" are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, a and b are 0 or 1 respectively, [Chemical formula 2] In the chemical formula 2, * is the site that binds to the chemical formula 1, At least one of X1 to X3 is N, and the others are CH, L1 and L2 are the same or different from each other, and are each independently a directly bonded, substituted or unsubstituted arylene group having 6 to 30 carbon atoms, A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, R 17 To R 24 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 heterocyclic group.
2. The organic compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical formula 1-5] [Chemical formula 1-6] In the chemical formulas 1-1 to 1-6, R1 to R3, R6 to R 16 The definitions of R, R' and R" are the same as those in the chemical formula 1.
3. The organic compound according to claim 1, wherein The L1 and L2 are the same or different from each other, and are each independently any one of the following structures: In the structure, The dotted line indicates the binding position. R 25 It is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group.
4. The organic compound according to claim 1, wherein A is an aryl group having 6 to 30 carbon atoms which may be substituted by deuterium or an unsubstituted heterocyclic group having 2 to 30 carbon atoms which may be substituted by deuterium or an unsubstituted heterocyclic group having 2 to 30 carbon atoms.
5. The organic compound according to claim 1, wherein The A is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group.
6. The organic compound according to claim 1, wherein The L1 and L2 are the same as or different from each other, and are each independently an arylene group having 6 to 30 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.
7. The organic compound according to claim 1, wherein The chemical formula 1 is any one of the chemical formulas 1-A to 1-L, In the chemical formula 1-A to the chemical formula 1-L, R1 to R 16 , X1 to X3, L1, L2, A, and R 17 To R 24 The definition of is the same as that in the chemical formulas 1 and 2.
8. The organic compound according to claim 1, wherein The deuterium substitution rate of the chemical formula 1 is greater than 30%.
9. The organic compound according to claim 1, wherein The organic compound of Chemical Formula 1 is any one of the following organic compounds:
10. An organic light emitting device, wherein: include: An anode, a cathode, and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprises the organic compound according to any one of claims 1 to 9.
11. The organic light emitting device according to claim 10, wherein: The organic layer includes a light-emitting layer, and the light-emitting layer contains the organic compound.
12. The organic light emitting device according to claim 11, wherein: The organic compound is included as a host of the light-emitting layer.
13. The organic light emitting device according to claim 11, wherein: The light-emitting layer includes the organic compound as a host of the light-emitting layer and further includes a dopant of the light-emitting layer.
14. The organic light emitting device according to claim 10, wherein: The organic layer includes a hole blocking layer, and the hole blocking layer contains the organic compound.
Citation Information
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