Compounds and organic light-emitting devices containing the same
Deuterium-substituted compounds in the organic layer of organic light-emitting devices enhance electron and hole mobility, improving efficiency and stability by reducing steric hindrance and breaking down under high energy states, thus extending device lifetime.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- LG CHEM LTD
- Filing Date
- 2023-06-20
- Publication Date
- 2026-07-22
AI Technical Summary
Existing organic light-emitting devices face challenges in achieving high efficiency and stability due to the degradation of luminescent compounds, particularly those containing alkyl groups that break down under high energy states, leading to reduced device lifetime.
The introduction of deuterium-substituted compounds with stronger CD bonds in the organic layer, which enhances electron and hole mobility, molecular stability, and reduces steric hindrance, thereby improving the driving voltage, efficiency, and lifetime of the devices.
The use of deuterium-substituted compounds in the organic layer reduces the driving voltage and improves the light efficiency and thermal stability of organic light-emitting devices, extending their lifetime.
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Abstract
Description
Technical Field
[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0079962, filed with the Korean Intellectual Property Office on June 29, 2022, and all of its content is incorporated herein.
[0002] This specification relates to a compound and an organic light-emitting device including the same.
Background Art
[0003] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light-emitting device using the organic light-emitting phenomenon usually has a structure including an anode, a cathode, and an organic layer therebetween. Here, the organic layer often has a multilayer structure composed of different substances in order to enhance the efficiency and stability of the organic light-emitting device. For example, it can be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. In such a structure of an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons combine, an exciton is formed, and light is emitted when this exciton falls back to the ground state again.
[0004] The development of new materials for the organic light-emitting devices as described above has been continuously demanded.
Summary of the Invention
Problems to be Solved by the Invention
[0005] This specification provides a compound and an organic light-emitting device including the same.
Means for Solving the Problems
[0006] This specification provides a compound of Chemical Formula 1 below. [Chemical Formula 1]
Chem.
[0007] Furthermore, one embodiment of this specification provides an organic light-emitting element comprising a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound described above. [Effect of the Invention]
[0008] The compound according to one embodiment of the present specification can be used in the organic layer of an organic light-emitting device, thereby reducing the driving voltage of the organic light-emitting device and improving the light efficiency. In addition, the lifetime characteristics of the device can be improved due to the thermal stability of the compound. [Brief Description of the Drawings]
[0009] [Figure 1] This shows an example of an organic light-emitting device according to one embodiment of the present specification. [Figure 2] This shows an example of an organic light-emitting device according to one embodiment of the present specification. [Description of Reference Numerals]
[0010] 1 ··· Substrate 2 ··· First electrode 3 ··· Second electrode 4 ··· Light-emitting layer 5 ··· Hole injection layer 6 ··· Hole transport layer 7 ··· Hole modulation layer 8 ··· Electron modulation layer 9 ··· Electron transport layer 10 ··· Electron injection layer 11 ··· Capping layer [Embodiments for Carrying Out the Invention]
[0011] Hereinafter, the present specification will be described in more detail.
[0012] One embodiment of the present specification provides the compound of Chemical Formula 1.
[0013] Chemical formula 1 according to one embodiment of this specification has a substituted or unsubstituted aryl group bonded to the 9-position of anthracene, and naphthofuran bonded to the 10-position via L. Because chemical formula 1 contains at least one deuterium atom, it has structural properties that improve electron and hole mobility and molecular stability. Therefore, organic light-emitting devices containing this are superior in terms of drive voltage, efficiency, and lifetime.
[0014] Furthermore, this specification provides compounds in which at least one hydrogen atom of chemical formula 1 is substituted with deuterium, and organic light-emitting devices containing the same. Since the CD bond of the compounds of the present invention is stronger than the CH bond, the stability of the compounds can be improved. When the chemical decomposition of a luminescent compound involves the breakdown of relatively weak C(sp3)-H bonds, using a CD bond, which is stronger than a CH bond, can further improve the stability of the compound.
[0015] In this case, when alkyl groups are used as electron-donating substituents, the luminescence properties can be effectively tuned. However, the CH bond of the alkyl group introduced at high energy states is broken, accelerating the decomposition of the compound and causing problems with the overall device lifetime. Therefore, when deuterium-substituted alkyl groups are used, the stability of the blue device can be ensured and the luminescence properties can be effectively tuned. Furthermore, when using deuterium with a smaller van der Waals radius, the steric hindrance is reduced compared to conventional alkyl groups, thus improving conjugation.
[0016] Throughout this specification, the term “these combinations” as used in any Markush expression means one or more mixtures or combinations selected from the group of components described in the Markush expression, and includes one or more selected from the group of components.
[0017] Examples of substituents described herein are, but are not limited to, those described below.
[0018] In this specification, [ka] This refers to the parts that are connected.
[0019] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The position of substitution is not limited to any position where a hydrogen atom can be substituted, i.e., any position where a substituent can be substituted. If two or more substituents are substituted, the two or more substituents may be the same or different from each other.
[0020] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium; halogen groups; cyano groups; alkyl groups; cycloalkyl groups; alkoxy groups; aryloxy groups; alkylthiooxy groups; arylthiooxy groups; alkenyl groups; haloalkyl groups; haloalkoxy groups; arylalkyl groups; silyl groups; boron groups; amine groups; aryl groups; and heterocyclic groups; substituted with substituents in which two or more substituents from the exemplified substituents are linked; or having no substituents at all.
[0021] In this specification, the linking of two or more substituents means that a hydrogen atom of any one substituent is linked to another substituent. For example, the linking of two substituents means that a phenyl group and a naphthyl group are linked, [ka] or [ka] It can be a substituent. Furthermore, the linking of three substituents includes not only the sequential linking of (substituent 1)-(substituent 2)-(substituent 3), but also the linking of (substituent 2) and (substituent 3) to (substituent 1). For example, a phenyl group, a naphthyl group, and an isopropyl group can be linked. [ka] , [ka] ,or [ka] It can be a substituent. The definition mentioned above also applies to cases where four or more substituents are linked together.
[0022] Examples of halogen groups used herein include fluorine, chlorine, bromine, or iodine.
[0023] In this specification, alkyl groups may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.
[0024] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms. Specifically, examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.1]octyl group, norbornyl group.
[0025] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferably 1 to 30. Specifically, examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, and p-methylbenzyloxy.
[0026] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include, but are not limited to, 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-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc.
[0027] In this specification, a haloalkyl group means, in the definition of an alkyl group, that at least one halogen group is substituted for a hydrogen atom in the alkyl group.
[0028] In this specification, a haloalkoxy group means, in the definition of an alkoxy group, that at least one halogen group is substituted for a hydrogen atom in the alkoxy group.
[0029] In this specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
[0030] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. Specifically, examples of monocyclic aryl groups include, but are not limited to, phenyl groups, biphenyl groups, and terphenyl groups.
[0031] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 10 to 30 carbon atoms. Specifically, examples of polycyclic aryl groups include, but are not limited to, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, phenalene, perylene, chrysene, and fluorene groups.
[0032] In this specification, the fluorene group may be substituted, or adjacent groups may bond to each other to form a ring.
[0033] Examples of the aforementioned fluorene group include: [ka] These are some examples, but they are not limited to these.
[0034] In this specification, “adjacent” groups may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent that is stereostructically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring, and two substituents substituted on the same carbon in an aliphatic ring, can be interpreted as “adjacent” groups.
[0035] In this specification, arylalkyl groups mean that the alkyl group is substituted with an aryl group, and the aryl group and alkyl group of the arylalkyl group may be those exemplified above.
[0036] In this specification, an aryloxy group means, in the definition of an alkoxy group, that an aryl group is substituted for the alkyl group of the alkoxy group. Examples of aryloxy groups include, but are not limited to, phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethylphenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, and 9-phenanthryloxy group.
[0037] In this specification, the alkyl group of the alkyl thioxy group is the same as the examples of alkyl groups described above. Specifically, examples of alkyl thioxy groups include, but are not limited to, methyl thioxy group, ethyl thioxy group, tert-butyl thioxy group, hexyl thioxy group, and octyl thioxy group.
[0038] In this specification, the aryl group in the aryl thioxy group is the same as the examples of aryl groups described above. Specifically, examples of aryl thioxy groups include, but are not limited to, the phenyl thioxy group, the 2-methylphenyl thioxy group, and the 4-tert-butylphenyl thioxy group.
[0039] In this specification, a heterocyclic group comprises one or more non-carbon atoms and heteroatoms. Specifically, the heteroatoms may comprise one or more atoms selected from the group consisting of O, N, Se, and S, and may include aromatic heterocyclic groups or aliphatic heterocyclic groups. The aromatic heterocyclic group may be represented by a heteroaryl group. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably 2 to 30, and the heterocyclic group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthridine Examples of such groups include, but are not limited to, phenanthroline, isoxazole, thiadiazole, dibenzofuran, dibenzosilol, phenoxathiine, phenoxazine, phenothiazine, decahydrobenzocarbazole, hexahydrocarbazole, dihydrobenzoazacillin, dihydroindenocarbazole, spirofluorenexanthen, spirofluorenthoxanthen, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran.
[0040] In this specification, the silyl group may be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, a heteroarylsilyl group, and the like. The alkyl group in the alkylsilyl group may be the example of alkyl groups described above, the aryl group in the arylsilyl group may be the example of aryl groups described above, the alkyl group and aryl group in the alkylarylsilyl group may be the example of alkyl and aryl groups described above, and the heteroaryl group in the heteroarylsilyl group may be the example of heterocyclic groups described above.
[0041] In this specification, the boron group is defined as -BY 100 Y 101 It may be the case that Y 100 and Y 101 These may be identical or different, and each may be independently selected from the group consisting of hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms; substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms. Specific examples of the boron group include, but are not limited to, dimethylboron group, diethylboron group, t-butylmethylboron group, and diphenylboron group.
[0042] In this specification, the amine group may be selected from the group consisting of -NH2, alkylamine group, N-alkylarylamine group, arylamine group, N-arylheteroarylamine group, N-alkylheteroarylamine group, and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include, but are not limited to, methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, ditolylamine group, N-phenyltolylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenantrenylamine group, N-biphenylphenantrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenantrenylfluorenylamine group, and N-biphenylfluorenylamine group.
[0043] In this specification, an N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for the nitrogen atom of the amine group. The alkyl group and aryl group in the N-alkylarylamine group are the same as the examples of alkyl and aryl groups described above.
[0044] In this specification, an N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for the nitrogen atom of the amine group. The aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of aryl groups and heterocyclic groups described above.
[0045] In this specification, an N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted for the nitrogen atom of the amine group. The alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of alkyl and heterocyclic groups described above.
[0046] In this specification, examples of alkylamine groups include substituted or unsubstituted monoalkylamine groups, or substituted or unsubstituted dialkylamine groups. The alkyl group in the alkylamine group may be a linear or branched alkyl group. An alkylamine group containing two or more alkyl groups may contain a linear alkyl group, a branched alkyl group, or both a linear and a branched alkyl group. For example, the alkyl group in the alkylamine group may be selected from the examples of alkyl groups described above.
[0047] In this specification, examples of heteroarylamine groups include substituted or unsubstituted monoheteroarylamine groups, or substituted or unsubstituted diheteroarylamine groups. A heteroarylamine group containing two or more heteroaryl groups may contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group simultaneously. For example, the heteroaryl groups in the heteroarylamine group may be selected from the examples of heterocyclic groups described above.
[0048] In this specification, the alkyl groups in the N-alkylarylamine group, alkyl thioxy group, and N-alkyl heteroarylamine group are the same as the examples of alkyl groups described above. Specifically, examples of alkyl thioxy groups include, but are not limited to, methyl thioxy group, ethyl thioxy group, tert-butyl thioxy group, hexyl thioxy group, and octyl thioxy group.
[0049] In this specification, the aryl groups in aryloxy groups, arylthiooxy groups, N-arylalkylamine groups, and N-arylheteroarylamine groups are the same as the examples of aryl groups described above. Specifically, examples of aryloxy groups include phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethylphenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, and 9-phenanthryloxy group, and examples of arylthiooxy groups include phenylthiooxy group, 2-methylphenylthiooxy group, and 4-tert-butylphenylthiooxy group, but are not limited to these.
[0050] In this specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from the examples of cycloalkyl groups, aryl groups, and combinations thereof. Examples of the hydrocarbon ring group include, but are not limited to, a phenyl group, a cyclohexyl group, an adamantyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.1]octyl group, a tetrahydronaphthalene group, a tetrahydroanthracene group, a 1,2,3,4-tetrahydro-1,4-methanonaphthalene group, a 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group, a spirocyclopentanefluorene group, a spiroadamantanefluorene group, and a spirocyclohexanefluorene group.
[0051] In this specification, the meaning of "adjacent" in "bonding with adjacent groups to form a ring" is as described above, and the "ring" means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heteroring.
[0052] In this specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from the examples of cycloalkyl groups, aryl groups, and combinations thereof, except that it is not monovalent. Examples of the hydrocarbon ring include, but are not limited to, benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2,3,4-tetrahydro-1,4-methanonaphthalene, 1,2,3,4-tetrahydro-1,4-ethanonaphthalene, spirocyclopentanefluorene, spiroadamantanefluorene, and spirocyclohexanefluorene.
[0053] In this specification, a heterocycle comprises one or more non-carbon atoms and heteroatoms, and specifically, the heteroatoms may comprise one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic groups, and the aromatic heterocycle may be selected from examples of heteroaryl groups in the heterocyclic group, except that it is not monovalent.
[0054] In this specification, an aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. It also means a heterocycle excluding aromatic heterocycles; a heterocycle containing a double bond but not aromatic is an aliphatic heterocycle. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepan, azocan, thiocan, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran.
[0055] In this specification, an aliphatic heterocycle (group) means an aliphatic ring (group) containing one or more heteroatoms. It also means a heterocycle (group) excluding aromatic heterocycles (groups), and a heterocycle (group) containing a double bond but not aromatic is an aliphatic heterocycle (group).
[0056] Examples of aliphatic or aromatic-aliphatic condensed heterocycles used herein include, but are not limited to, tetrahydrobenzonaphthothiophene and tetrahydrobenzonaphthofuran.
[0057] In this specification, an arylene group refers to a group in which an aryl group has two bonding positions, i.e., a divalent group. The description of the aryl group described above may apply, except that each of these groups is divalent.
[0058] In this specification, a heteroarylene group refers to a group in which a heteroaryl group has two bonding positions, i.e., a divalent group. The description of heteroaryl groups in heterocyclic groups described above may also apply, except that these are each divalent groups.
[0059] In this specification, unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art in which the present invention pertains. Similar or equivalent methods and materials to those described herein may be used in carrying out or testing embodiments of the present invention, but suitable methods and materials will be described later. All publications, patent applications, patents, and other references referenced herein are included herein by reference in whole, and in the event of any conflict, unless a specific passage is mentioned, the definitions and other information in this specification shall prevail. The materials, methods, and examples are illustrative and not limiting.
[0060] The compound of chemical formula 1 will be described in detail below.
[0061] According to one embodiment of this specification, the chemical formula A is one of the following chemical formulas A-1 to A-3. [Chemical formula A-1] [ka] [Chemical formula A-2] [ka] [Chemical formula A-3] [ka] In the aforementioned chemical formula A-1, Any one of Y1-Y4 and Y7-Y10 is a site that bonds to L, and the remaining substituents of Y1-Y4 and Y7-Y10 that do not bond to L are either identical or different to each other and independently consist of hydrogen, deuterium, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthiooxy group, substituted or unsubstituted arylthiooxy group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group, or any one or more adjacent pairs bond to each other to form a substituted or unsubstituted ring. In the aforementioned chemical formula A-2, Any one of Y1-Y3, Y5, and Y7-Y10 is a site that bonds to L, and the remaining substituents of Y1-Y3, Y5, and Y7-Y10 that do not bond to L are either identical or different to each other and independently consist of hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryloxy group; substituted or unsubstituted alkylthiooxy group; substituted or unsubstituted arylthiooxy group; substituted or unsubstituted silyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group, or any one or more adjacent pairs bond to each other to form a substituted or unsubstituted ring. In the aforementioned chemical formula A-3, Any one of Y1, Y2, and Y5-Y10 is a site that bonds to L, and the remaining substituents of Y1, Y2, and Y5-Y10 that do not bond to L are either identical or different to each other and are independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryloxy group; substituted or unsubstituted alkylthiooxy group; substituted or unsubstituted arylthiooxy group; substituted or unsubstituted silyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group, or any one or more adjacent pairs bond to each other to form a substituted or unsubstituted ring.
[0062] According to one embodiment of this specification, in the chemical formula A-1, Y1 is a site that binds to L.
[0063] According to one embodiment of this specification, in the chemical formula A-1, Y2 is a site that binds to L.
[0064] According to one embodiment of this specification, in the chemical formula A-1, Y3 is a site that binds to L.
[0065] According to one embodiment of this specification, in the chemical formula A-1, Y4 is a site that binds to L.
[0066] According to one embodiment of this specification, in the chemical formula A-1, Y7 is a site that binds to L.
[0067] According to one embodiment of this specification, in the chemical formula A-1, Y8 is a site that binds to L.
[0068] According to one embodiment of this specification, in the chemical formula A-1, Y9 is a site that binds to L.
[0069] According to one embodiment of this specification, in the chemical formula A-1, Y10 is a site that binds to L.
[0070] According to one embodiment of this specification, in the chemical formula A-2, Y1 is a site that binds to L.
[0071] According to one embodiment of this specification, in the chemical formula A-2, Y2 is a site that binds to L.
[0072] According to one embodiment of this specification, in the chemical formula A-2, Y3 is a site that binds to L.
[0073] According to one embodiment of this specification, in the chemical formula A-2, Y5 is a site that binds to L.
[0074] According to one embodiment of this specification, in the chemical formula A-2, Y7 is a site that binds to L.
[0075] According to one embodiment of this specification, in the chemical formula A-2, Y8 is a site that binds to L.
[0076] According to one embodiment of this specification, in the chemical formula A-2, Y9 is a site that binds to L.
[0077] According to one embodiment of this specification, in the chemical formula A-2, Y10 is a site that binds to L.
[0078] According to one embodiment of this specification, in the chemical formula A-3, Y1 is a site that binds to L.
[0079] According to one embodiment of this specification, in the chemical formula A-3, Y2 is a site that binds to L.
[0080] According to one embodiment of this specification, in the chemical formula A-3, Y5 is a site that binds to L.
[0081] According to one embodiment of this specification, in the chemical formula A-3, Y6 is a site that binds to L.
[0082] According to one embodiment of this specification, in the chemical formula A-3, Y7 is a site that binds to L.
[0083] According to one embodiment of this specification, in the chemical formula A-3, Y8 is a site that binds to L.
[0084] According to one embodiment of this specification, in the chemical formula A-3, Y9 is a site that binds to L.
[0085] According to one embodiment of this specification, in the chemical formula A-3, Y10 is a site that binds to L.
[0086] According to one embodiment of this specification, the chemical formula 1 is the following chemical formula 1-1. [Chemical formula 1-1] [ka] In the above chemical formula 1-1, The definitions of R1, R3-R10, and L are the same as those in Chemical Formula 1 above. Any one of Y11 to Y13 is a site that bonds to L, and the remaining substituents of Y11 to Y13 that do not bond to L are either identical or different to each other, and each independently is a hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryloxy group; substituted or unsubstituted alkylthiooxy group; substituted or unsubstituted arylthiooxy group; substituted or unsubstituted silyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group, or any one or more adjacent pairs bond to each other to form a substituted or unsubstituted ring. y11 and y13 are either 1 or 2, y12 is an integer between 1 and 4. y11+y12+y13≦7, If y11 is 2, then the two Y11s are either the same or different from each other. If y13 is 2, then the two Y13s are either the same or different from each other. If the aforementioned y12 is 2 or more, then the 2 or more Y12s are either the same or different from each other.
[0087] According to one embodiment of this specification, the chemical formula 1 is one of the following chemical formulas 1-2 to 1-4. [Chemical formula 1-2] [ka] [Chemical formula 1-3] [ka] [Chemical formula 1-4] [ka] In the above chemical formulas 1-2 to 1-4, The definitions of R1, R3-R10, and L are the same as those in Chemical Formula 1 above. Any one of Y11 to Y13 is a site that bonds to L, and the remaining substituents of Y11 to Y13 that do not bond to L are either identical or different to each other, and each independently is a hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryloxy group; substituted or unsubstituted alkylthiooxy group; substituted or unsubstituted arylthiooxy group; substituted or unsubstituted silyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group, or any one or more adjacent pairs bond to each other to form a substituted or unsubstituted ring. y11 and y13 are either 1 or 2, y12 is an integer between 1 and 4. y11+y12+y13≦7, If y11 is 2, then the two Y11s are either the same or different from each other. If y13 is 2, then the two Y13s are either the same or different from each other. If the aforementioned y12 is 2 or more, then the 2 or more Y12s are either the same or different from each other.
[0088] According to one embodiment of this specification, R1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
[0089] According to one embodiment of this specification, R1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
[0090] According to one embodiment of this specification, R1 is a deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with one or more of these combinations.
[0091] According to one embodiment of this specification, R1 is a deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with one or more of these combinations.
[0092] According to one embodiment of this specification, R1 is a phenyl group substituted or unsubstituted with one or more of the following: deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, and a phenyl group substituted or unsubstituted with one or more of the following: deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, and a naphthyl group substituted or unsubstituted with one or more of the following: a biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a phenanthrene group substituted or unsubstituted with deuterium; a triphenylene group substituted or unsubstituted with deuterium; or a linear or branched alkyl group having 1 to 20 carbon atoms, or a fluorene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
[0093] According to one embodiment of this specification, R1 is a phenyl group substituted or unsubstituted with one or more of the following: deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, and a phenyl group substituted or unsubstituted with one or more of the following: deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, and a naphthyl group substituted or unsubstituted with one or more of the following: a biphenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a phenanthrene group substituted or unsubstituted with deuterium; a triphenylene group substituted or unsubstituted with deuterium; or a linear or branched alkyl group having 1 to 20 carbon atoms, or a fluorene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
[0094] According to one embodiment of this specification, R1 is a phenyl group substituted or unsubstituted with one or more of the following: deuterium, a deuterium-substituted or unsubstituted naphthyl group, and a phenyl group substituted or unsubstituted with one or more of the following: deuterium, a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted naphthyl group, and a naphthyl group substituted or unsubstituted with one or more of the following: a biphenyl group substituted or unsubstituted with a phenyl group; a phenanthrene group substituted or unsubstituted with a deuterium; a triphenylene group substituted or unsubstituted with a deuterium; or a methyl group, or a fluorene group substituted or unsubstituted with a phenyl group.
[0095] According to one embodiment of this specification, R3 to R10 are identical or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
[0096] According to one embodiment of this specification, R3 to R10 are identical or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
[0097] According to one embodiment of this specification, R3 to R10 are identical or different from each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a deuterium-substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
[0098] According to one embodiment of this specification, R3 to R10 are identical or different from each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a deuterium-substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
[0099] According to one embodiment of this specification, R3 to R10 are identical or different from each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted naphthyl group; or a deuterium-substituted or unsubstituted dibenzofuran group.
[0100] According to one embodiment of this specification, R3 to R10 are identical or different from each other and are independently hydrogen; deuterium; a phenyl group; a deuterium-substituted or unsubstituted naphthyl group; or a dibenzofuran group.
[0101] According to one embodiment of this specification, L is a directly bonded; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
[0102] According to one embodiment of this specification, L is a directly bonded; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
[0103] According to one embodiment of this specification, L is a directly bonded; a deuterium-substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a deuterium-substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
[0104] According to one embodiment of this specification, L is a directly bonded; a deuterium-substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a deuterium-substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
[0105] According to one embodiment of this specification, L is directly bonded; a deuterium-substituted or unsubstituted phenylene group; a deuterium-substituted or unsubstituted biphenylylene group; a deuterium-substituted or unsubstituted divalent naphthyl group; or a deuterium-substituted or unsubstituted divalent dibenzofuran group.
[0106] According to one embodiment of this specification, L is a direct bond; a phenylene group; a biphenylylene group; a divalent naphthyl group; or a divalent dibenzofuran group.
[0107] According to one embodiment of this specification, any one of Y1, Y2, and Y7-Y11 is a site that bonds to L, and the remaining substituents of Y1, Y2, and Y7-Y11 that do not bond to L are identical or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 2 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms.
[0108] According to one embodiment of this specification, any one of Y1, Y2, and Y7-Y11 is a site that bonds to L, and the remaining substituents of Y1, Y2, and Y7-Y11 that do not bond to L are identical or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 2 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 3 to 20 carbon atoms.
[0109] According to one embodiment of this specification, any one of Y1, Y2, and Y7-Y11 is a site that bonds to L, and the remaining substituents of Y1, Y2, and Y7-Y11 that do not bond to L are identical or different from each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a deuterium-substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 2 to 30 carbon atoms; or one or more adjacent pairs bond to each other to form a deuterium-substituted or unsubstituted linear or branched alkyl group having 3 to 30 carbon atoms.
[0110] According to one embodiment of this specification, any one of Y1, Y2, and Y7-Y11 is a site that bonds to L, and the remaining substituents of Y1, Y2, and Y7-Y11 that do not bond to L are identical or different from each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; a deuterium-substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 2 to 20 carbon atoms; or a deuterium-substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or one or more adjacent pairs bond to each other to form a deuterium-substituted or unsubstituted linear or branched alkyl group having 3 to 20 carbon atoms.
[0111] According to one embodiment of this specification, any one of Y1, Y2, and Y7-Y11 is a site that bonds to L, and the remaining substituents of Y1, Y2, and Y7-Y11 that do not bond to L are identical or different to each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted methyl group; a deuterium-substituted or unsubstituted isopropyl group; a deuterium-substituted or unsubstituted tert-butyl group; a deuterium-substituted or unsubstituted cyclopentyl group; a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted naphthyl group; or a deuterium-substituted or unsubstituted biphenyl group; or one or more adjacent pairs bond to each other to form a deuterium-substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cyclohexane.
[0112] According to one embodiment of this specification, any one of Y1, Y2, and Y7-Y11 is a site that bonds to L, and the remaining substituents of Y1, Y2, and Y7-Y11 that do not bond to L are identical or different from each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted methyl group; a deuterium-substituted or unsubstituted isopropyl group; a deuterium-substituted or unsubstituted tert-butyl group; a deuterium-substituted or unsubstituted cyclopentyl group; a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted naphthyl group; or a deuterium-substituted or unsubstituted biphenyl group, or one or more adjacent pairs bond to each other to form a deuterium-substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cyclohexane.
[0113] According to one embodiment of this specification, any one of Y1, Y2, and Y7-Y11 is a site that bonds to L, and the remaining substituents of Y1, Y2, and Y7-Y11 that do not bond to L are identical or different from each other, and each independently is hydrogen; deuterium; methyl group; isopropyl group; tert-butyl group; cyclopentyl group; deuterium-substituted or unsubstituted phenyl group; naphthyl group; or any one or more adjacent pairs bond to each other to form a deuterium-substituted or unsubstituted methyl-substituted or unsubstituted cyclohexane.
[0114] According to one embodiment of this specification, the chemical formula 1 is one selected from the following compounds. [ka] [ka] [ka]
[0115] This specification provides an organic light-emitting device containing the aforementioned compound.
[0116] In this specification, when one member is said to be "on top of" another member, this includes not only cases where one member is in contact with another member, but also cases where another member exists between the two members.
[0117] In this specification, when a part is described as "including" a component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise stated.
[0118] In this specification, the term "layer" is interchangeable with "film" as it is commonly used in the art, and refers to a coating that covers a target area. The size of the "layer" is not limited, and each "layer" may be the same size or different in size. In one embodiment, the size of the "layer" may be the same as the entire element, may correspond to the size of a specific functional area, or may be smaller by a single sub-pixel.
[0119] In this specification, the inclusion of a specific substance A in a layer B includes both i) the inclusion of one or more substances A in a single layer B, and ii) the inclusion of one or more layers B, with substance A being present in one or more of the multilayered layers B.
[0120] In this specification, "a particular substance A is contained in the C layer or D layer" means that i) it is contained in one or more of the one or more C layers, ii) it is contained in one or more of the one or more D layers, or iii) it is contained in one or more C layers and one or more D layers, respectively.
[0121] This specification provides an organic light-emitting element comprising a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain a compound represented by the chemical formula 1.
[0122] The organic layers of the organic light-emitting element described herein may consist of a single layer, or they may consist of a multilayer structure in which two or more organic layers are stacked. For example, they may have a structure that includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron barrier layer, a hole barrier layer, and so on. However, the structure of the organic light-emitting element is not limited thereto and may include even fewer organic layers.
[0123] According to one embodiment of this specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.
[0124] According to one embodiment of this specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host for the light-emitting layer.
[0125] According to one embodiment of this specification, the light-emitting layer comprises a dopant, and the dopant comprises a fluorescent dopant.
[0126] According to one embodiment of this specification, the fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound.
[0127] According to one embodiment of this specification, the nonpyrene compound includes a boron compound.
[0128] According to one embodiment of this specification, the light-emitting layer further comprises one or more hosts different from the compound of chemical formula 1.
[0129] A host other than the compound of chemical formula 1 can be any anthracene-based host used in the art, as long as it is different from the compound of chemical formula 1, and is not limited thereto.
[0130] According to one embodiment of this specification, the light-emitting layer includes a host and a dopant.
[0131] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, wherein the host comprises a compound represented by the chemical formula 1.
[0132] According to one embodiment of this specification, the dopant is a blue dopant.
[0133] According to one embodiment of this specification, the organic light-emitting element is a blue organic light-emitting element.
[0134] According to one embodiment of this specification, the light-emitting layer comprises two or more mixed hosts, one or more of which comprises a compound represented by the chemical formula 1.
[0135] According to one embodiment of this specification, the light-emitting layer comprises two or more mixed hosts, at least one of which comprises a compound represented by chemical formula 1, and the remainder comprises an anthracene-based compound different from chemical formula 1.
[0136] Any anthracene-based host used in the art may be used without limitation, provided that at least one of the two or more mixed hosts includes a compound represented by chemical formula 1, and the remainder is different from chemical formula 1.
[0137] An organic light-emitting element using a mixture of two or more hosts according to one embodiment of this specification aims to improve the performance of the element by combining the advantages of each host. For example, when mixing two types of hosts, one host having the effect of high efficiency and low voltage and another host having the effect of long life can be mixed to create an organic light-emitting element that has the effects of high efficiency, low voltage, and long life.
[0138] According to one embodiment of this specification, the organic light-emitting element has a maximum emission wavelength (λ) of the emission spectrum. max The wavelength range is 400nm to 470nm.
[0139] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, wherein the dopant is a fluorescent dopant.
[0140] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, the dopant comprising one or more compounds selected from pyrene compounds and non-pyrene compounds.
[0141] The pyrene-based and non-pyrene-based compounds mentioned above can be any compound used in this industry, and are not limited thereto.
[0142] According to one embodiment of this specification, the nonpyrene compound includes a boron compound.
[0143] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, the host comprising a compound represented by the chemical formula 1, and the dopant comprising one or more compounds selected from pyrene compounds and non-pyrene compounds.
[0144] According to one embodiment of this specification, the light-emitting layer comprises a host and a dopant, wherein the light-emitting layer comprises the host and dopant in a weight ratio of 0.1:99.9 to 20:80.
[0145] According to yet another embodiment of this specification, the capping layer is further provided on the opposite side of at least one of the first electrode and the second electrode from the side facing the organic layer.
[0146] The capping layer is formed in the organic light-emitting element to prevent a considerable amount of light from being lost due to total internal reflection. The capping layer has the ability to adequately protect the lower negative electrode and light-emitting layer from external moisture penetration and contamination, and has a high refractive index, which can prevent light loss due to total internal reflection.
[0147] According to yet another embodiment of this specification, the capping layer may be provided on the opposite surface of the first electrode to the surface facing the organic layer, and on the opposite surface of the second electrode to the surface facing the organic layer.
[0148] According to yet another embodiment of this specification, the capping layer may be provided on the opposite side of the first electrode from the side facing the organic layer.
[0149] According to yet another embodiment of this specification, the capping layer may be provided on each of the surfaces of the second electrode opposite to the surface facing the organic layer.
[0150] According to one embodiment of this specification, the organic light-emitting element further comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
[0151] According to one embodiment of this specification, the organic light-emitting element includes a first electrode; a second electrode provided opposite the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and two or more organic layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.
[0152] According to one embodiment of this specification, two or more organic layers between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, may be selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, an electron barrier layer, a hole barrier layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.
[0153] According to one embodiment of this specification, two or more hole transport layers are included between the light-emitting layer and the first electrode. The two or more hole transport layers may contain the same or different materials.
[0154] According to one embodiment of this specification, the first electrode is an anode or a cathode.
[0155] According to one embodiment of this specification, the second electrode is a cathode or an anode.
[0156] According to one embodiment of this specification, the organic light-emitting element may be an organic light-emitting element of the normal type in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.
[0157] According to one embodiment of this specification, the organic light-emitting element may be an inverted type organic light-emitting element in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.
[0158] For example, the structure of an organic light-emitting element according to one embodiment of this specification is illustrated in Figures 1 and 2. Figures 1 and 2 illustrate organic light-emitting elements, but are not limited to these.
[0159] Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode 2, an organic material layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The compound is contained in the organic material layer.
[0160] Figure 2 illustrates the structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, a hole adjustment layer 7, a light-emitting layer 4, an electron adjustment layer 8, an electron transport layer 9, an electron injection layer 10, a second electrode 3, and a capping layer 11 are sequentially stacked on a substrate 1. The compound is contained in the light-emitting layer.
[0161] The organic light-emitting devices described herein may be manufactured by materials and methods well known in the art, except that the light-emitting layer contains the compound, i.e., the compound represented by chemical formula 1.
[0162] If the organic light-emitting element includes multiple organic layers, the organic layers may be formed from the same substance or different substances.
[0163] For example, the organic light-emitting element described herein can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, a metal or a conductive metal oxide or an alloy thereof can be deposited on the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, an emissive layer, and an electron transport layer can be formed on top of that, and finally a material that can be used as a cathode can be deposited on top of that. In addition to such methods, an organic light-emitting element can also be manufactured by sequentially depositing a second electrode material, an organic layer, and a first electrode material on a substrate.
[0164] Furthermore, the compound represented by chemical formula 1 may be formed in the organic layer not only by vacuum deposition but also by solution coating during the manufacture of the organic light-emitting element. Here, solution coating means, but is not limited to, spin coating, dip coating, doctor blade, inkjet printing, screen printing, spray method, roll coating, etc.
[0165] In addition to this method, organic light-emitting devices can also be fabricated by sequentially depositing a second electrode material, an organic layer, and a first electrode material onto a substrate. However, the manufacturing method is not limited to this.
[0166] As the first electrode material, a material with a large work function is generally preferred to facilitate hole injection into the organic layer. Examples include, but are not limited to, metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.
[0167] The second electrode material is usually preferably a material with a small work function to facilitate electron injection into the organic layer. Examples include, but are not limited to, metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; and multilayer materials such as LiF / Al or LiO2 / Al.
[0168] The light-emitting layer may include a host material and a dopant material. In cases where an additional light-emitting layer is included in addition to the light-emitting layer containing the compound of chemical formula 1 according to one embodiment of this specification, the host material may be a condensed and / or non-condensed aromatic ring derivative or a heterocycle-containing compound. Specifically, examples of condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluorantene compounds, while examples of heterocycle-containing compounds include, but are not limited to, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.
[0169] According to one embodiment of this specification, the host includes, but is not limited to, a compound represented by the following chemical formula H-1. [Chemical formula H-1] [ka] In the aforementioned chemical formula H-1, L20 and L21 are identical or different from each other, and independently, they are directly bonded; substituted or unsubstituted arylene groups; or substituted or unsubstituted divalent heterocyclic groups. Ar20 and Ar21 are either identical or different from each other, and independently of each other, are hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group. R201 is hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group. r201 is an integer from 1 to 8, and if r201 is 2 or greater, then r201 values of 2 or greater are either the same or different from each other.
[0170] In one embodiment of this specification, L20 and L21 are identical or different from each other and independently directly bonded; monocyclic or polycyclic arylene groups having 6 to 30 carbon atoms; or monocyclic or polycyclic divalent heterocyclic groups having 2 to 30 carbon atoms.
[0171] In one embodiment of this specification, L20 and L21 are identical or different from each other and independently of each other: directly bonded; a deuterium-substituted or unsubstituted phenylene group; a deuterium-substituted or unsubstituted biphenylylene group; a deuterium-substituted or unsubstituted naphthylene group; a divalent dibenzofuran group; or a divalent dibenzothiophene group.
[0172] In one embodiment of this specification, Ar20 and Ar21 are identical or different from each other, and are independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; or substituted or unsubstituted monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms.
[0173] In one embodiment of this specification, Ar20 and Ar21 are identical or different from each other and are independently substituted or unsubstituted monocyclic to tetracyclic aryl groups having 6 to 20 carbon atoms; or substituted or unsubstituted monocyclic to tetracyclic heterocyclic groups having 6 to 20 carbon atoms.
[0174] In one embodiment of this specification, Ar20 and Ar21 are identical or different from each other and are independently a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
[0175] In one embodiment of this specification, Ar20 and Ar21 are identical or different from each other and are independently a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; a terphenyl group; a deuterium-substituted or unsubstituted naphthyl group; a phenyl-substituted or unsubstituted thiophene group; a phenanthrene group; a dibenzofuran group; a naphthobenzofuran group; a dibenzothiophene group; or a naphthobenzothiophene group.
[0176] In one embodiment of this specification, Ar20 and Ar21 are identical or different from each other, and are independently substituted or unsubstituted aryl groups.
[0177] In one embodiment of this specification, Ar20 and Ar21 are identical or different from each other and are independently a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; a terphenyl group; or a deuterium-substituted or unsubstituted naphthyl group.
[0178] According to one embodiment of this specification, R201 is hydrogen.
[0179] According to one embodiment of this specification, the chemical formula H-1 is represented by the following compound. [ka]
[0180] Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluorantene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and perifurantene, which have arylamine groups. Styrylamine compounds are compounds in which at least one aryl vinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups (one or more). Specifically, examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. Examples of metal complexes include, but are not limited to, iridium complexes and platinum complexes.
[0181] According to one embodiment of this specification, the dopant material includes, but is not limited to, a compound of the following chemical formula D-1 or D-2. [Chemical formula D-1] [ka] In the aforementioned chemical formula D-1, L101 and L102 are identical or different from each other, and independently, directly bonded; or substituted or unsubstituted arylene groups. Ar101 to Ar104 are identical or different from each other, and each is independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. [Chemical formula D-2] [ka] In the aforementioned chemical formula D-2, T1 to T5 are either identical or different from each other, and each is independently a hydrogen atom; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group. t3 and t4 are integers from 1 to 4, t5 is an integer between 1 and 3. If the aforementioned t3 is 2 or more, the 2 or more T3s are either the same or different from each other. If the t4 is 2 or more, the 2 or more T4s are either the same or different from each other. If the aforementioned t5 is 2 or more, then the 2 or more T5s are either the same or different from each other.
[0182] According to one embodiment of this specification, L101 and L102 are directly coupled.
[0183] According to one embodiment of this specification, Ar101 to Ar104 are identical or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
[0184] According to one embodiment of this specification, Ar101 to Ar104 are identical or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
[0185] According to one embodiment of this specification, Ar101 to Ar104 are identical or different from each other and are independently methyl-substituted phenyl groups; or dibenzofuran groups.
[0186] According to one embodiment of this specification, the chemical formula D-1 is represented by the following compound. [ka]
[0187] According to one embodiment of this specification, T1 to T5 are identical or different from each other and are independently hydrogen; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
[0188] According to one embodiment of this specification, T1 to T5 are identical or different from each other and are independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.
[0189] According to one embodiment of this specification, T1 to T5 are identical or different from each other and are independently hydrogen; a methyl group; a tert-butyl group; a diphenylamine group; or a phenyl group substituted or unsubstituted with a methyl group or a tert-butyl group.
[0190] According to one embodiment of this specification, the chemical formula D-2 is represented by the following compound. [ka]
[0191] The hole injection layer is a layer that receives holes from the electrode. The hole injection material preferably has the ability to transport holes and has an excellent hole injection effect on the anode and on the light-emitting layer or light-emitting material. It is also preferable that the material has an excellent ability to prevent the movement of excitons generated from the light-emitting layer to the electron injection layer or electron injection material. Furthermore, it is preferable that the material has an excellent thin-film formation ability. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic compounds; hexanitrile hexaazatriphenylene-based organic compounds; quinacridone-based organic compounds; perylene-based organic compounds; and polythiophene-based conductive polymers such as anthraquinone and polyaniline.
[0192] According to one embodiment of this specification, the hole injection layer comprises, but is not limited to, a compound of the following chemical formula HI-1. [Chemical formula HI-1] [ka] In the aforementioned chemical formula HI-1, At least one of X'1 to X'6 is N, and the rest are CH. R309 to R314 are either identical or different from each other, and each is independently a hydrogen; deuterium; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group, or bonded to adjacent groups to form a substituted or unsubstituted ring.
[0193] According to one embodiment of this specification, X'1 to X'6 are N.
[0194] According to one embodiment of this specification, R309 to R314 are cyano groups.
[0195] According to one embodiment of this specification, the chemical formula HI-1 is represented by the following compound. [ka]
[0196] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and a material with high mobility for holes is preferred. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which both conjugated and unconjugated parts exist.
[0197] According to one embodiment of this specification, the hole transport layer or hole regulating layer comprises, but is not limited to, a compound of the following chemical formula HT-1. [Chemical formula HT-1] [ka] In the aforementioned chemical formula HT-1, R315~R317 are either identical or different from each other, and each is independently one of the group consisting of hydrogen; deuterium; substituted or unsubstituted alkyl groups; substituted or unsubstituted aryl groups; substituted or unsubstituted heteroaryl groups; and combinations thereof, or bonded to adjacent groups to form a substituted or unsubstituted ring. r315 is an integer from 1 to 5, and if r315 is 2 or greater, then the 2 or greater R315s are either identical or different from each other. r316 is an integer from 1 to 5, and if r316 is 2 or greater, then 2 or greater R316s are either the same or different from each other.
[0198] According to one embodiment of this specification, R317 is selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof.
[0199] According to one embodiment of this specification, R317 is selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; and combinations thereof.
[0200] According to one embodiment of this specification, R315 and R316 are identical or different from each other, and independently are substituted or unsubstituted aryl groups, or bonded to adjacent groups to form an alkyl-substituted aromatic hydrocarbon ring.
[0201] According to one embodiment of this specification, R315 and R316 are identical or different from each other, and independently are either a phenyl group or a phenanthrene group, or bonded to each other with adjacent groups to form an indene substituted with a methyl group.
[0202] According to one embodiment of this specification, the chemical formula HT-1 is represented by any one of the following compounds. [ka]
[0203] The electron adjustment layer is a layer that adjusts electrons transmitted from the electron transport layer so that they are smoothly injected into the light-emitting layer, and any known material can be used without limitation.
[0204] According to one embodiment of this specification, the electronically regulated layer comprises, but is not limited to, a compound of the following chemical formula EG-1. [Chemical formula EG-1] [ka] In the aforementioned chemical formula EG-1, At least one of G1 to G18 is -L5-Ar5 and the rest are hydrogen, or G1 and G18 are linked by -L51- to form a substituted or unsubstituted ring. L5 is a directly bonded; or a substituted or unsubstituted arylene group. Ar5 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. L51 is either O or S.
[0205] According to one embodiment of this specification, L51 is O.
[0206] According to one embodiment of this specification, L51 is S.
[0207] According to one embodiment of this specification, G1 and G18 are linked by -L51- to form a substituted or unsubstituted heterocycle.
[0208] According to one embodiment of this specification, G1 and G18 are linked by -L51- to form a substituted or unsubstituted xanthene ring; or a substituted or unsubstituted thioxanthene ring.
[0209] According to one embodiment of this specification, G1 and G18 are linked by -O- to form a substituted or unsubstituted xanthene ring.
[0210] According to one embodiment of this specification, G1 and G18 are linked by -S- to form a substituted or unsubstituted thioxanthene ring.
[0211] According to one embodiment of this specification, G1 and G18 are connected by -O- to form a xanthene ring.
[0212] According to one embodiment of this specification, G1 and G18 are linked by -S- to form a thioxanthene ring.
[0213] According to one embodiment of this specification, L5 is a directly bonded, or substituted or unsubstituted, monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
[0214] According to one embodiment of the present specification, the L5 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
[0215] According to one embodiment of the present specification, the L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
[0216] According to one embodiment of the present specification, the L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
[0217] According to one embodiment of the present specification, the L5 is a direct bond; or a phenylene group.
[0218] According to one embodiment of the present specification, the Ar5 is a substituted or unsubstituted triazine group.
[0219] According to one embodiment of the present specification, the Ar5 is a substituted or unsubstituted triazine group substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
[0220] According to one embodiment of the present specification, the Ar5 is a triazine group substituted with a phenyl group.
[0221] According to one embodiment of the present specification, the EG-1 is represented by the following compound.
Chemical formula
[0222] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material that can smoothly receive electron injections from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is preferred. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer may be used with any desired cathode material, as used in the prior art. Particularly preferred cathode materials are ordinary materials with a low work function followed by an aluminum layer or a silver layer. Specifically, examples include cesium, barium, calcium, ytterbium, and samarium, in which case an aluminum layer or a silver layer follows.
[0223] According to one embodiment of this specification, the electron transport layer comprises, but is not limited to, a compound of the following chemical formula ET-1. [Chemical formula ET-1] [ka] In the aforementioned chemical formula ET-1, At least one of Z11-Z13 is N, and the rest are CH. L601 is a directly bonded; substituted or unsubstituted arylene group; or substituted or unsubstituted heteroarylene group. Ar601 and Ar602 are identical or different from each other, and are independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups. l601 is an integer from 1 to 5, and if l601 is 2 or greater, then the l601s that are 2 or greater are either the same or different from each other.
[0224] According to one embodiment of this specification, L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
[0225] According to one embodiment of this specification, L601 is a phenylene group; a biphenylylene group; or a naphthylene group.
[0226] According to one embodiment of this specification, Ar601 and Ar602 are identical or different from each other, and are independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms.
[0227] According to one embodiment of this specification, Ar601 and Ar602 are phenyl groups.
[0228] According to one embodiment of this specification, the chemical formula ET-1 is represented by the following compound. [ka]
[0229] The electron injection layer is a layer that receives electrons from the electrode. The electron injection material preferably has excellent electron transport ability and has an excellent electron receiving effect from the second electrode and an excellent electron injection effect on the light-emitting layer or light-emitting material. Furthermore, it is preferable that the material prevents excitons generated from the light-emitting layer from moving to the hole injection layer and has excellent thin-film formation ability. Specifically, examples include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone and its derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.
[0230] Examples of the metal complex compound include, but are not limited to, lithium 8-hydroxyquinolinate, zinc bis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganese bis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminum tris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate), beryllium bis(10-hydroxybenzo[h]quinolinate), zinc bis(10-hydroxybenzo[h]quinolinate), gallium bis(2-methyl-8-quinolinate) chloride, gallium bis(2-methyl-8-quinolinate)(o-cresolate), aluminum bis(2-methyl-8-quinolinate)(1-naphtholate), and gallium bis(2-methyl-8-quinolinate)(2-naphtholate).
[0231] According to one embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The electron injection and transport layer may use the substances exemplified in the electron transport layer and the electron injection layer, but is not limited thereto.
[0232] According to one embodiment of the present specification, the electron injection and transport layer may further contain a metal complex compound. The metal complex compound is as described above.
[0233] The electron blocking layer is a layer that prevents electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer, and can improve the lifetime and efficiency of the device. Known materials can be used without limitation, and it may be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and the layer that simultaneously performs hole injection and hole transport.
[0234] [[ID=十六]]The examples of the material of the electron blocking layer may be applicable to the exemplified chemical formula HI-I, but are not limited thereto.
[0235] The hole-blocking layer is a layer that prevents holes from reaching the cathode, and may generally be formed under the same conditions as the electron injection layer. Specifically, examples include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.
[0236] The capping layer is formed in the organic light-emitting element to prevent a considerable amount of light from being lost due to total internal reflection. The capping layer has the ability to adequately protect the lower negative electrode and light-emitting layer from external moisture penetration and contamination, has a high refractive index, can prevent light loss due to total internal reflection, and can use conventional materials without limitation.
[0237] According to one embodiment of this specification, the capping layer contains, but is not limited to, a compound represented by the following chemical formula CP-1. [Chemical formula CP-1] [ka] In the aforementioned chemical formula CP-1, L501 and L502 are identical or different from each other, and independently of each other, are directly bonded; substituted or unsubstituted arylene groups; or substituted or unsubstituted heteroarylene groups. R501 and Ar501~Ar504 are either identical or different from each other, and each is independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; or bonded to adjacent groups to form a substituted or unsubstituted ring.
[0238] According to one embodiment of this specification, L501 and L502 are identical or different from each other, and are independently substituted or unsubstituted monocyclic or polycyclic arylene groups having 6 to 30 carbon atoms.
[0239] According to one embodiment of this specification, L501 and L502 are phenylene groups.
[0240] According to one embodiment of this specification, R501 and Ar501 to Ar504 are identical or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
[0241] According to one embodiment of this specification, R501 and Ar501 to Ar504 are phenyl groups, or they are bonded to adjacent groups to form phenyl-substituted or unsubstituted carbazoles.
[0242] According to one embodiment of this specification, Ar501 combines with L501 to form a phenyl-substituted carbazole.
[0243] According to one embodiment of this specification, Ar503 combines with L503 to form a phenyl-substituted carbazole.
[0244] According to one embodiment of this specification, the chemical formula CP-1 is represented by the following compound. [ka]
[0245] The organic light-emitting element according to this specification may be of the top-emission type, bottom-emission type, or double-sided emission type, depending on the material used.
[0246] The organic light-emitting elements described herein may be used in various electronic devices. For example, such electronic devices may be, but are not limited to, display panels, touch panels, solar modules, and lighting devices. [Examples]
[0247] The following provides a detailed explanation of this specification using examples and comparative examples. However, the examples and comparative examples described herein may be modified in various different forms, and the scope of this specification is not limited to the examples and comparative examples described below. The examples and comparative examples described herein are provided to give a more complete explanation of this specification to a person of average knowledge in the industry.
[0248] Manufacturing Example 1. Synthesis of Chemical Formulas A1 and B1 [ka] SM1 (1 eq) and SM2 (1.1 eq) were added to acetone (excess), then potassium carbonate (2 eq) was added and the mixture was refluxed and stirred for 24 hours. After the temperature was lowered to room temperature and the reaction was terminated, water and ethanol were added and the mixture was filtered to produce chemical formulas A1 and B1 (chemical formulas A1-1 to A1-6 and B1-1 to B1-7), respectively.
[0249] In the above reaction equation, X is a halogen group, n is an integer from 1 to 7, and the definition of R is the same as the definition of Y7 to Y11 mentioned above.
[0250] Chemical formulas A1-1 to A1-6 and B1-1 to B1-7 in Table 1 below were synthesized using the same method as described above, except that SM1 and SM2 were replaced with SM1 and SM2 as shown in Table 1 below.
[0251] [Table 1] [Table 1] [Table 2] [Table 3]
[0252] Manufacturing Example 2. Synthesis of Chemical Formulas A2, B2, and C2 1) Synthesis of chemical formulas A2 and B2 [ka] SM1 (1 eq, chemical formula A1 or B1) was added to chloroform (excess), heated and refluxed to dissolve, then Eaton's reagent (1 eq, phosphorus pentoxide, 7.7 wt.% in methanesulfonic acid, Sigma-Aldrich) was added and stirred for 1 hour. The temperature was lowered to room temperature, water was added and stirred for 30 minutes, and then the layers were separated. The organic layer was extracted with aq. saturated aqueous sodium bicarbonate (NaHCO3) until the pH was neutral. Subsequently, the organic layer was column-mounted on hexane and ethyl acetate to produce chemical formulas A2 and B2 (chemical formulas A2-1 to A2-6 and B2-1 to B2-8), respectively.
[0253] In the above reaction equation, X is a halogen group and n is an integer from 1 to 6.
[0254] Chemical formulas A2-1 to A2-6 and B2-1 to B2-7 in Table 2 below were synthesized using the same method as described above, except that SM1 and SM2 were replaced with SM1 and SM2 as shown in Table 2 below.
[0255] 2) Synthesis of chemical formula C2 [ka] SM1 (1 eq) was added to benzene (excess) and stirred, then PPA (Polyphosphoric acid, excess) was added and stirred for 4 hours. The temperature was lowered to room temperature, water was added and stirred for 30 minutes, and then the layers were separated. The organic layer was extracted with a saturated aqueous solution of sodium bicarbonate (NaHCO3) until the pH became neutral. Subsequently, the organic layer was column-driven using hexane and ethyl acetate to produce the aforementioned chemical formula C2 (chemical formulas C2-1 and C2-8).
[0256] In the above reaction equation, X is a halogen group and n is an integer from 1 to 6.
[0257] Chemical formulas C2-1 and C2-8, shown in Table 2 below, were synthesized using the same method as described above for the synthesis of chemical formula C2, except that SM1 and SM2 were replaced with SM1 and SM2 as shown in Table 2 below.
[0258] [Table 2] [Table 4] [Table 5] [Table 6] [Table 7] [Table 8]
[0259] Manufacturing Example 2-1. Synthesis of Chemical Formulas A2'' and B2'' [ka] SM1 (1 eq) and trifluoromethanesulfonic acid (cat.) were placed in a C6D6 mixture (10 to 50 times the mass of the reactants) and stirred at 70°C for 10 to 100 minutes. After the reaction was complete, D2O (excess) was added and stirred for 30 minutes, then trimethylamine (excess) was added dropwise. The reaction mixture was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried over MgSO4 and then column-followed with ethyl acetate and hexane to obtain the chemical formulas A2'' and B2'', respectively.
[0260] In the above reaction equation, X is a halogen group and n is an integer from 1 to 6.
[0261] The chemical formulas in Table 3 below were synthesized using the same method as in the synthesis of chemical formulas A2'' and B2'', except that SM1 and SM2 were replaced with SM1 and SM2 as shown in Table 3 below.
[0262] [Table 3] [Table 9]
[0263] Manufacturing Example 3. Synthesis of chemical formulas A3-1 to A3-3, B3-1 to B3-3, and C3-1 to C3-3. [ka] [ka] [ka] 1) Synthesis of chemical formulas A3-1, B3-1, and C3-1 SM1 (1 eq, chemical formula A2, B2, or C2) was dissolved in THF (excess), the temperature was lowered to -78°C, 2.5 M n-BuLi (1 eq) was added dropwise, and the mixture was stirred for 1 hour. Then, N-bromosuccinimide (1 eq) was added. The reaction mixture was then heated to room temperature and stirred for 4 hours, and the reaction was terminated by adding 1N HCl (excess). After the reaction was complete, the solvent was removed by layer separation, and the residue was subjected to silica column chromatography (ethyl acetate / hexane 1:15) to produce chemical formulas A3-1, B3-1, and C3-1, respectively.
[0264] In the above reaction equation, X is a halogen group and n is an integer from 1 to 6.
[0265] The chemical formulas in Table 4 below were synthesized using the same method as in the synthesis methods for chemical formulas A3-1, B3-1, and C3-1, except that SM1 and SM2 were replaced with SM1 and SM2 as shown in Table 4 below.
[0266] 2) Synthesis of chemical formulas A3-2, B3-2, and C3-2 SM1 (1 eq, chemical formula A2, B2, or C2) was dissolved in chloroform (excess), then N-bromosuccinimide (1 eq) was added, and the mixture was heated and stirred at 40°C for 3 hours. After cooling to room temperature, 1N HCl (excess) was added to terminate the reaction. After the reaction was complete, the solvent was removed by layer separation, and the residue was subjected to silica column chromatography (ethyl acetate / hexane 1:15) to produce chemical formulas A3-2, B3-2, and C3-2, respectively.
[0267] In the above reaction equation, X is a halogen group and n is an integer from 1 to 6.
[0268] The chemical formulas in Table 4 below were synthesized using the same method as in the synthesis methods for chemical formulas A3-2, B3-2, and C3-2, except that SM1 and SM2 were replaced with SM1 and SM2 as shown in Table 4 below.
[0269] 3) Synthesis of chemical formulas A3-3, B3-3, and C3-3 SM1 (1 eq, chemical formula A2, B2, or C2) was dissolved in THF (excess), the temperature was lowered to -78°C, 2.5 M n-BuLi (1 eq) was added dropwise, and the mixture was stirred for 1 hour. Then, N-bromosuccinimide (1 eq) was added. The reaction mixture was then heated to room temperature and stirred for 4 hours, and the reaction was terminated by adding 1N HCl (excess). After the reaction was complete, the solvent was removed by layer separation, and the mixture was dissolved in chloroform (excess). N-bromosuccinimide (1 eq) was added, and the temperature was raised to 40°C and heated and stirred for 3 hours. After cooling to room temperature, the reaction was terminated by adding 1N HCl (excess). After the reaction was complete, the solvent was removed by layer separation, and the residue was subjected to silica column chromatography (ethyl acetate / hexane 1:15) to produce chemical formulas A3-3, B3-3, and C3-3, respectively.
[0270] In the above reaction equation, X is a halogen group and n is an integer from 1 to 6.
[0271] The chemical formulas in Table 4 below were synthesized using the same method as in the synthesis methods for chemical formulas A3-3, B3-3, and C3-3, except that SM1 and SM2 were replaced with SM1 and SM2 as shown in Table 4 below.
[0272] [Table 4] [Table 10] [Table 11] [Table 12] [Table 13]
[0273] Manufacturing Example 4. Synthesis of Chemical Formulas A4, B4, and C4 [ka] [ka] [ka] SM1 (1 eq, chemical formulas A3-1~A3-3, B3-1~B3-3, C3-1, C3-2, or C3-3) and SM2 (1.02 eq) were added to tetrahydrofuran (excess), then a 2M potassium carbonate aqueous solution (30 times the volume relative to THF) was added, followed by tetrakistriphenyl-phosphinopalladium (2 mol%), and the mixture was heated and stirred for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate aqueous solution was removed and the layers were separated. After solvent removal, the mixture was vacuum distilled and recrystallized with ethyl acetate and hexane to produce chemical formulas A4, B4, and C4, respectively.
[0274] In the above reaction equation, X is a halogen group, n is an integer from 1 to 5, and the definition of R'' is the same as the definition of Y7 to Y11 mentioned above.
[0275] The chemical formulas in Table 5 below were synthesized using the same method as in the synthesis of chemical formulas A4, B4, and C4, except that SM1 and SM2 were replaced with SM1 and SM2 as shown in Table 5 below.
[0276] [Table 5] [Table 14] [Table 15] [Table 16]
[0277] Manufacturing Example 5. Synthesis of Chemical Formulas A5, B5, and C5 [ka] SM1 (1 eq, chemical formula A4, B4, or C4) and SM2 (1.3 eq) were added to 1,4-dioxane (12 times the mass of SM1), potassium acetate (3 eq) was added, and the mixture was stirred and refluxed. Palladium acetate (0.02 eq) and tricyclohexylphosphine (0.04 eq) were added to 1,4-dioxane after stirring for 5 minutes, and after confirming the completion of the reaction after 10 hours, the mixture was allowed to cool to room temperature. Ethanol and water were added, the mixture was filtered, and the product was purified by recrystallization with ethyl acetate and ethanol to produce chemical formulas A5, B5, and C5, respectively.
[0278] In the above reaction equation, the definition of R'' is the same as the definition of Y7 to Y11 mentioned above, and m is an integer from 1 to 7.
[0279] The chemical formulas in Table 6 below were synthesized using the same method as in the synthesis of chemical formulas A5, B5, and C5, except that SM1 and SM2 were replaced with SM1 and SM2 as shown in Table 6 below.
[0280] [Table 6] [Table 17] [Table 18] [Table 19] [Table 20] [Table 21] [Table 22]
[0281] Manufacturing Example 6. Synthesis of Chemical Formulas A6, B6, and C6 [ka] In the above reaction equation, the definition of R'' is the same as the definition of Y7 to Y11 mentioned above, and m is an integer from 1 to 7.
[0282] The chemical formulas in Table 7 below were synthesized using the same method as in the synthesis of chemical formulas A4, B4, and C4, except that SM1 and SM2 were replaced with SM1 and SM2 as shown in Table 7 below.
[0283] [Table 7] [Table 23] [Table 24]
[0284] Manufacturing Example 7. Synthesis of Chemical Formulas A7, B7, and C7 [ka] In the above reaction equation, the definition of R'' is the same as the definition of Y7 to Y11 mentioned above, and m is an integer from 1 to 7.
[0285] The chemical formulas in Table 8 below were synthesized using the same method as in the synthesis of chemical formulas A5, B5, and C5, except that SM1 and SM2 were replaced with SM1 and SM2 as shown in Table 8 below.
[0286] [Table 8] [Table 25] [Table 26]
[0287] Manufacturing Example 8. Synthesis of Compounds 1-25 [ka] After adding SM1 (1.05 eq, chemical formulas A5, B5, C5, A7, B7, or C7) and SM2 (1 eq) to tetrahydrofuran (excess), a 2M potassium carbonate aqueous solution (30 times the volume relative to THF) was added, followed by tetrakistriphenyl-phosphinopalladium (2 mol%), and the mixture was heated and stirred for 10 hours. The temperature was lowered to room temperature to complete the reaction, and the potassium carbonate aqueous solution was removed and the layers were separated. After confirming the completion of the reaction, the solvent was removed by extraction at room temperature, and the mixture was purified by recrystallization using toluene to produce compounds 1 to 25 below.
[0288] In the above reaction equation, the definition of R'' is the same as the definition of Y7 to Y11 mentioned above, and m is an integer from 1 to 7.
[0289] The compounds 1 to 25 in Table 9 below were synthesized using the same method, except that SM1 and SM2 were replaced with the SM1 and SM2 shown in Table 9 below.
[0290] SM2 in Table 9 below was prepared using the following scheme. SM2 scheme [ka] Example 1 of SM2> [ka] Example 2 of SM2> [ka] SM2 of compounds 1 to 25 was prepared using the aforementioned example synthesis.
[0291] Furthermore, the Suzuki reaction is similar to the synthesis of chemical formulas A4, B4, and C4, and the bromination is similar to the synthesis of chemical formulas A3-1 to A3-3, B3-1 to B3-3, and C3-1 to C3-3, except that SM1 and SM2 are modified.
[0292] [Table 9] [Table 27] [Table 28] [Table 29] [Table 30] [Table 31] [Table 32] [Table 33] [Table 34]
[0293] Manufacturing Example 9. Synthesis of Compounds 26-28 [ka] The reactants (1 eq) and trifluoromethanesulfonic acid (cat.) were placed in a C6D6 mixture (10 to 50 times the mass of the reactants) and stirred at 70°C for 10 to 100 minutes. After the reaction was complete, D2O (excess) was added and stirred for 30 minutes, then trimethylamine (excess) was added dropwise. The reaction mixture was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried over MgSO4, then heated with toluene and recrystallized to obtain compounds 26 to 28 shown in Table 10 below.
[0294] The definition of substituents in the above reaction equation is as described above, and Dx represents the number of deuterium atoms substituted in the compound.
[0295] The compounds 26 to 28 in Table 10 below were synthesized in the same manner as described above, except that SM1 and SM2 were replaced with the reactants and C6D6 shown in Table 10 below.
[0296] The reaction products in Table 10 below were prepared by changing SM1 and SM2 in the same manner as in Production Example 8 (compounds that were not deuterated). [Each product exhibits a different degree of deuterium substitution depending on the reaction time, and the substitution rate is determined according to the maximum m / z(M+) value.] The deuterium substitution of the aforementioned product was based on prior art, specifically Korean Patent Publication No. 1538534.
[0297] [Table 10] [Table 35] [Table 36]
[0298] <Example 1> OLED manufacturing A substrate with ITO / Ag / ITO deposited at 70 / 1000 / 70 Å was cut to a size of 50 mm × 50 mm × 0.5 mm and placed in distilled water with a dispersant dissolved in it, then washed ultrasonically. A detergent from Fischer Co. was used as the detergent, and distilled water that had been secondarily filtered using a filter from Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes each time. After the distilled water washing was complete, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, and then the substrate was dried.
[0299] On the prepared positive electrode, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and then T1, a material that transports holes, was vacuum deposited on top of that to a thickness of 1150 Å to form a hole transport layer. Next, a hole adjustment layer was formed using EB1 (150 Å), and then a light-emitting layer was formed by vacuum depositing compound 1 (host) and dopant BD1 (2 wt%) to a thickness of 360 Å. After that, ET1 was deposited to a thickness of 50 Å to form an electron adjustment layer, and compound ET2 and Liq were mixed in a weight ratio of 7:3 to form an electron transport layer with a thickness of 250 Å. After sequentially depositing magnesium and lithium fluoride (LiF) with a thickness of 50 Å as electron injection layers (EILs), a 200 Å layer was formed using magnesium and silver (weight ratio of 1:4) as a negative electrode, and then CP1 was deposited as a capping layer with a thickness of 600 Å to complete the device. The deposition rate of organic materials was maintained at 1 Å / sec during the above process. [ka]
[0300] Examples 2-33 and Comparative Examples 1-4 Organic light-emitting devices of Examples 2-33 and Comparative Examples 1-4 were manufactured in the same manner as in Example 1, except that the compounds in Table 11 below were used instead of Compound 1 and BD1, respectively. [ka]
[0301] This evaluation The organic light-emitting elements manufactured in Examples 1-33 and Comparative Examples 1-4 were supplied with a 20 mA / cm² load. 2 The voltage, efficiency, color coordinates, and lifetime (T95) were measured by applying the specified current, and the results are shown in Table 11 below. In this case, T95 is defined as 20 mA / cm². 2 This refers to the time it takes for the initial brightness to decrease to 95% at a given current density.
[0302] [Table 11] [Table 37] [Table 38]
[0303] Chemical Formula 1 in one embodiment of this specification aims to improve blue light-emitting devices by improving the properties of an oxygen-containing naphthofuran unit and a deuterium-introduced anthracene blue fluorescent host. By showing various conventionally known derivatives in Comparative Examples 1 to 4, a clear improvement in the device performance of the blue device can be observed compared to conventional prior examples.
[0304] An organic electroluminescent element combined with a compound derivative of chemical formula 1 according to one embodiment of this specification can adjust the role of smooth hole injection into the light-emitting layer by using the compounds of manufacturing examples 8 and 9 as the host for the blue organic electroluminescent element. Due to the balance of holes and electrons in the organic electroluminescent element by its chemical structure, the device according to this specification exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.
Claims
1. The compound represented by the following chemical formula 1: [Chemical formula 1] 【Transformation 56】 In the aforementioned chemical formula 1, R1 is a deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with one or more of these combinations. R2 is -L-Ar1, R3 to R10 are deuterium. L is a direct bond; a deuterium-substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a deuterium-substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms. Ar1 has the following chemical formula A: [Chemical formula A] 【Chemistry 57】 In the aforementioned chemical formula A, Any one of Y1, Y2, and Y7-Y11 is a site that bonds to L, and the remaining substituents of Y1, Y2, and Y7-Y11 that do not bond to L are either identical or different to each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a deuterium-substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 2 to 30 carbon atoms; or a deuterium-substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. y11 is 1 or 2, and if y11 is 2, the two Y11s are either the same or different from each other. The aforementioned chemical formula 1 contains at least one deuterium atom.
2. The compound according to claim 1, wherein the chemical formula A is one of the following chemical formulas A-1 to A-3: [Chemical formula A-1] 【Transformation 58】 [Chemical formula A-2] 【Chemistry 59】 [Chemical formula A-3] 【Transformation 60】 In the aforementioned chemical formula A-1, Any one of Y1 to Y4 and Y7 to Y10 is a site that bonds to L, and the remaining substituents of Y1 to Y4 and Y7 to Y10 that do not bond to L are either identical or different to each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a deuterium-substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 2 to 30 carbon atoms; or a deuterium-substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. In the aforementioned chemical formula A-2, Any one of Y1-Y3, Y5, and Y7-Y10 is a site that bonds to L, and the remaining substituents of Y1-Y3, Y5, and Y7-Y10 that do not bond to L are either identical or different to each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a deuterium-substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 2 to 30 carbon atoms; or a deuterium-substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. In the aforementioned chemical formula A-3, Any one of Y1, Y2, and Y5-Y10 is a site that bonds to L, and the remaining substituents of Y1, Y2, and Y5-Y10 that do not bond to L are either the same or different from each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a deuterium-substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 2 to 30 carbon atoms; or a deuterium-substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
3. The compound according to claim 1, wherein the aforementioned chemical formula 1 is the following chemical formula 1-1: [Chemical formula 1-1] 【Chemistry 61】 In the above chemical formula 1-1, The definitions of R1, R3 to R10, and L are the same as those in Chemical Formula 1 above. Any one of Y11 to Y13 is a site that bonds to L, and the remaining substituents of Y11 to Y13 that do not bond to L are either identical or different to each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a deuterium-substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 2 to 30 carbon atoms; or a deuterium-substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. y11 and y13 are either 1 or 2, y12 is an integer between 1 and 4. y11 + y12 + y13 ≤ 7, When y11 is 2, the two Y11s are either the same or different from each other. When y13 is 2, the two Y13s are either the same or different from each other. If the aforementioned y12 is 2 or more, then the 2 or more Y12s are either the same or different from each other.
4. The compound according to claim 1, wherein the chemical formula 1 is one of the following chemical formulas 1-2 to 1-4: [Chemical formula 1-2] 【Transformation 62】 [Chemical formula 1-3] 【Transformation 63】 [Chemical formula 1-4] 【Chemistry 64】 In the aforementioned chemical formulas 1-2 to 1-4, The definitions of R1, R3 to R10, and L are the same as those in Chemical Formula 1 above. Any one of Y11 to Y13 is a site that bonds to L, and the remaining substituents of Y11 to Y13 that do not bond to L are either identical or different to each other and are independently hydrogen; deuterium; a deuterium-substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a deuterium-substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 2 to 30 carbon atoms; or a deuterium-substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. y11 and y13 are either 1 or 2, y12 is an integer between 1 and 4. y11 + y12 + y13 ≤ 7, When y11 is 2, the two Y11s are either the same or different from each other. When y13 is 2, the two Y13s are either the same or different from each other. If the aforementioned y12 is 2 or more, then the 2 or more Y12s are either the same or different from each other.
5. One of the following compounds: 【Transformation 65】 【Chemical Formula 66】 【Transformation 67】 。
6. An organic light-emitting element comprising a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain a compound according to any one of claims 1 to 5.
7. The organic light-emitting element according to claim 6, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host for the light-emitting layer.
8. The organic light-emitting element according to claim 7, wherein the light-emitting layer comprises a dopant, and the dopant comprises a fluorescent dopant.
9. The organic light-emitting element according to claim 8, wherein the fluorescent dopant comprises one or more selected from pyrene compounds and non-pyrene compounds.
10. The organic light-emitting element according to claim 9, wherein the nonpyrene compound includes a boron compound.
11. The organic light-emitting element according to claim 7, wherein the light-emitting layer further comprises one or more hosts different from the compound.