Compound and organic light-emitting device including same
The introduction of a compound in the organic layer of an organic light emitting device addresses the need for improved efficiency and stability by reducing driving voltage and enhancing light efficiency and thermal stability.
Patent Information
- Application Number
- JP2024540740
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2022-06-29
- Filing Date
- 2023-06-20
- Publication Date
- 2025-01-24
- Estimated Expiration
- 2043-06-20
AI Technical Summary
There is a need for new materials in organic light emitting devices to improve efficiency and stability.
A compound of Formula 1 is introduced, which can be incorporated into the organic layer of an organic light emitting device, enhancing hole mobility and molecular stability, thereby reducing driving voltage and improving light efficiency and lifetime.
The compound lowers the driving voltage and enhances the light efficiency and thermal stability of the organic light emitting device, leading to improved performance.
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Figure 2025502034000001_ABST
Abstract
Description
[Technical field]
[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0079953, filed with the Korean Intellectual Property Office on June 29, 2022, the entire contents of which are incorporated herein by reference.
[0002] The present specification relates to a compound and an organic light-emitting device including the same. [Background technology]
[0003] Generally, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon usually has a structure including a positive electrode, a negative electrode, and an organic material layer between them. Here, the organic material layer is often a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic light emitting device structure, when a voltage is applied between two electrodes, holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic material layer, and when the injected holes and electrons combine, excitons are formed, and when the excitons fall back to the ground state, light is emitted.
[0004] There is a continuing need to develop new materials for such organic light emitting devices. Summary of the Invention [Problem to be solved by the invention]
[0005] The present specification provides a compound and an organic light-emitting device including the same. [Means for solving the problem]
[0006] The present specification provides a compound of Formula 1: [Chemical formula 1] [ka] In the above Chemical Formula 1, at least one of R1 to R3 is -L-Ar1, and the rest of R1 to R3 other than -L-Ar1 and R11 are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; r11 is an integer of 1 to 7, and when r11 is 2 or more, the 2 or more R11's are the same or different from each other, L is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; Ar1 is any 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 above chemical formulas A-1 and A-2, Y1 or Y2 is a site that binds to L, and the remaining Y1 and Y2 that are not bound to L, Y3 to Y5, and Y7 to Y10 are the same or different from each other and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heteroaryl group, or any one or more adjacent pairs of Y3, Y5, and Y7 to Y10 are bonded to each other to form a substituted or unsubstituted ring, In the above chemical formula A-3, Y1 or Y2 is a site that binds to L, and the remaining Y1 and Y2 that are not bound to L, and Y7 to Y10 are the same or different and each independently represent: hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heteroaryl group, or any one or more pairs of adjacent Y7 to Y10 are bonded to each other to form a substituted or unsubstituted ring, Y5 and Y6 are the same or different and each independently is hydrogen; or deuterium.
[0007] Furthermore, one embodiment of the present specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound described above. Effect of the Invention
[0008] The compound according to an embodiment of the present specification can be used in an organic layer of an organic light-emitting device to reduce the driving voltage of the organic light-emitting device and improve the light efficiency. In addition, the thermal stability of the compound can improve the life characteristics of the device. [Brief description of the drawings]
[0009] [Figure 1] 1 illustrates an example of an organic light-emitting device according to an embodiment of the present specification. [Diagram 2] 1 illustrates an example of an organic light-emitting device according to an embodiment of the present specification. [Explanation of symbols]
[0010] 1. Circuit Board 2...1st electrode 3...Second electrode 4. Emitting layer 5. Hole injection layer 6. Hole transport layer 7. Hole control layer 8...electronic adjustment layer 9...electron transport layer 10...electron injection layer 11 Capping layer DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0011] This specification will be explained in more detail below.
[0012] One embodiment of the present specification provides a compound of formula 1.
[0013] According to one embodiment of the present specification, Formula 1 includes a compound that is bonded to the 2- or 3-position of electron-rich naphthofuran via L at at least one of the 2-, 9-, and 10-positions of anthracene, and thus has structural characteristics that improve the electron and hole mobility and the molecular stability. Therefore, an organic light emitting device including the same has excellent driving voltage, efficiency, and lifespan.
[0014] Throughout this specification, the term "combinations thereof" in a Markush form expression means a mixture or combination of one or more selected from the group of elements set forth in the Markush form expression, and is meant to include one or more selected from the group of elements.
[0015] In this specification, examples of the substituents are described below, but are not limited to these.
[0016] In this specification, [ka] means the site to be linked.
[0017] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different.
[0018] As used herein, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkenyl group; a haloalkyl group; a haloalkoxy group; an arylalkyl group; a silyl group; a boron group; an amine group; an aryl group; a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; and a heterocyclic group, or substituted with a substituent in which two or more of the substituents exemplified above are linked, or has no substituents.
[0019] In the present specification, the term "two or more substituents are linked" refers to a case where a hydrogen atom of any one of the substituents is linked to another substituent. For example, the term "two substituents are linked" refers to a case where a phenyl group is linked to a naphthyl group, [ka] or [ka] In addition, the linking of three substituents includes not only the linking of (substituent 1)-(substituent 2)-(substituent 3) successively, but also the linking of (substituent 1) to (substituent 2) and (substituent 3). For example, a phenyl group, a naphthyl group, and an isopropyl group are linked to form [ka] , [ka] ,or [ka] The above definitions also apply to the case where four or more substituents are linked together.
[0020] As used herein, examples of halogen groups include fluorine, chlorine, bromine, or iodine.
[0021] In this specification, the alkyl group may be a straight chain or a branched chain, 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, 5-methylhexyl, and the like.
[0022] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specific examples thereof include 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, and norbornyl group, but are not limited thereto.
[0023] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferable that the number of carbon atoms is 1 to 30. Specific 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.
[0024] In this specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include 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, a stilbenyl group, and a styrenyl group, but are not limited thereto.
[0025] In this specification, the term "haloalkyl group" refers to an alkyl group defined above in which at least one halogen group is substituted for a hydrogen atom.
[0026] In this specification, the term "haloalkoxy group" refers to an alkoxy group defined above in which at least one halogen group is substituted for a hydrogen atom of the alkoxy group.
[0027] 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.
[0028] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably is 6 to 30. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group.
[0029] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but preferably is 10 to 30. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, and a fluorene group.
[0030] As used herein, fluorene groups may be substituted and adjacent groups may be linked to each other to form a ring.
[0031] Examples of the fluorene group include [ka] These include, but are not limited to:
[0032] In this specification, the term "adjacent" groups may refer to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically 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 positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as "adjacent" groups to each other.
[0033] In this specification, the arylalkyl group means that the alkyl group is substituted with an aryl group, and the aryl group and the alkyl group of the arylalkyl group may be the same as the examples of the aryl group and the alkyl group described above.
[0034] In this specification, the term "aryloxy group" refers to an alkoxy group defined above, where the alkyl group of the alkoxy group is replaced with an aryl group. Examples of the aryloxy group include, but are not limited to, a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, and a 9-phenanthryloxy group.
[0035] In this specification, the alkyl group of the alkylthioxy group is the same as the above-mentioned alkyl group.Specific examples of the alkylthioxy group include, but are not limited to, a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, and an octylthioxy group.
[0036] In the present specification, the aryl group in the arylthioxy group is the same as the above-mentioned examples of the aryl group.Specific examples of the arylthioxy group include, but are not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, and a 4-tert-butylphenylthioxy group.
[0037] In the present specification, a heterocyclic group includes one or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and includes an aromatic heterocyclic group or an aliphatic heterocyclic group. 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 the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group, a pyridazine group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phthalazine group, a pyridopyrimidine group, a pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuran group, a phenanthridine group, and a phenanthridine group. Examples of the alkyl group include, but are not limited to, a phenanthroline group, an isoxazole group, a thiadiazole group, a dibenzofuran group, a dibenzosilole group, a phenoxathiine group, a phenoxazine group, a phenothiazine group, a decahydrobenzocarbazole group, a hexahydrocarbazole group, a dihydrobenzoazasiline group, a dihydroindenocarbazole group, a spirofluorenexanthene group, a spirofluorenethioxanthene group, a tetrahydronaphthothiophene group, a tetrahydronaphthofuran group, a tetrahydrobenzothiophene group, and a tetrahydrobenzofuran group.
[0038] In this specification, the silyl group may be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, a heteroarylsilyl group, etc. The alkyl group in the alkylsilyl group may be the above-mentioned examples of the alkyl group, the aryl group in the arylsilyl group may be the above-mentioned examples of the aryl group, the alkyl group and the aryl group in the alkylarylsilyl group may be the above-mentioned examples of the alkyl group and the aryl group, and the heteroaryl group in the heteroarylsilyl group may be the above-mentioned examples of the heterocyclic group.
[0039] As used herein, a boron group is represented by -BY 100 Y 101 and Y may be 100 and Y 101 may be the same or different and each independently selected from the group consisting of hydrogen, deuterium, halogen, a nitrile group, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms. Specific examples of the boron group include, but are not limited to, a dimethyl boron group, a diethyl boron group, a t-butyl methyl boron group, and a diphenyl boron group.
[0040] In this specification, the amine group may be selected from the group consisting of -NH2, an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a ditolylamine group, an N-phenyltolylamine group, an N-phenylbiphenylamine group, an N-phenylnaphthylamine group, an N-biphenylnaphthylamine group, an N-naphthylfluorenylamine group, an N-phenylphenanthrenylamine group, an N-biphenylphenanthrenylamine group, an N-phenylfluorenylamine group, an N-phenylterphenylamine group, an N-phenanthrenylfluorenylamine group, and an N-biphenylfluorenylamine group.
[0041] In this specification, the term "N-alkylarylamine group" refers to an amine group in which an alkyl group and an aryl group are substituted at the N of the amine group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.
[0042] In the present specification, the term "N-arylheteroarylamine group" refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and the heterocyclic group described above.
[0043] In the present specification, the term "N-alkylheteroarylamine group" refers to an amine group in which an alkyl group and a heteroaryl group are substituted at the N of the amine group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the alkyl group and the heterocyclic group exemplified above.
[0044] In this specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a straight-chain or branched-chain alkyl group. The alkylamine group containing two or more alkyl groups may contain a straight-chain alkyl group, a branched-chain alkyl group, or both a straight-chain alkyl group and a branched-chain alkyl group. For example, the alkyl group in the alkylamine group may be selected from the alkyl group examples given above.
[0045] In this specification, examples of the heteroarylamine group include substituted or unsubstituted monoheteroarylamine groups, or substituted or unsubstituted diheteroarylamine groups.The 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 at the same time.For example, the heteroaryl group in the heteroarylamine group may be selected from the above-mentioned examples of heterocyclic groups.
[0046] In this specification, the alkyl group in the N-alkylarylamine group, the alkylthio group, and the N-alkylheteroarylamine group is the same as the above-mentioned alkyl group.Specific examples of the alkylthio group include, but are not limited to, a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, and an octylthio group.
[0047] In this specification, the aryl group in the aryloxy group, the arylthioxy group, the N-arylalkylamine group, and the N-arylheteroarylamine group is the same as the above-mentioned aryl group.Specifically, the aryloxy group includes phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy 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, 9-phenanthryloxy group, etc., and the arylthioxy group includes, but is not limited to, phenylthioxy group, 2-methylphenylthioxy group, 4-tert-butylphenylthioxy group, etc.
[0048] In this specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from the above-mentioned exemplified cycloalkyl group, aryl group, 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.
[0049] In this specification, the meaning of "adjacent" in "bonding to adjacent groups to form a ring" is as defined above, and the "ring" means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.
[0050] In the present 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 exemplified cycloalkyl group, aryl group, 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.
[0051] In the present specification, a heterocycle includes one or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be a monocycle or polycycle, and may be an aromatic, aliphatic, or aromatic-aliphatic condensed ring, and the aromatic heterocycle may be selected from the examples of the heteroaryl group in the heterocycle group, except that it is not monovalent.
[0052] In this specification, the term "aliphatic heterocycle" refers to an aliphatic ring containing one or more heteroatoms. It also refers to a heterocycle excluding aromatic heterocycles, and 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, oxepane, azocane, thiocane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran.
[0053] In this specification, an aliphatic heterocycle (group) refers to an aliphatic ring (group) containing one or more heteroatoms. It also refers to a heterocycle (group) excluding aromatic heterocycles (groups), and a heterocycle (group) containing a double bond but not aromatic is an aliphatic heterocycle (group).
[0054] As used herein, examples of the aliphatic or aromatic and aliphatic fused heterocycle include, but are not limited to, tetrahydrobenzonaphthothiophene, tetrahydrobenzonaphthofuran, and the like.
[0055] In the present specification, an arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The above description of the aryl group may be applied, except that each of these is a divalent group.
[0056] In the present specification, the heteroarylene group refers to a heteroaryl group having two bonding positions, i.e., a divalent group. The above description of the heteroaryl group in the heterocyclic group may be applied, except that each of these is a divalent group.
[0057] In this specification, unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the present invention belongs. Methods and materials similar or equivalent to those described herein may be used in the practice or testing of embodiments of the present invention, and suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in the event of a conflict, the present specification, including definitions, shall prevail unless a specific passage is mentioned. It should be noted that the materials, methods, and examples are merely illustrative and not limiting.
[0058] The compound of Formula 1 will now be described in detail.
[0059] According to one embodiment of the present specification, in the chemical formula A-1, the Y1 is a site that binds to the L.
[0060] According to one embodiment of the present specification, in the chemical formula A-1, the Y2 is a site that binds to the L.
[0061] According to one embodiment of the present specification, in the chemical formula A-2, the Y1 is a site that binds to the L.
[0062] According to one embodiment of the present specification, in the chemical formula A-2, the Y2 is a site that binds to the L.
[0063] According to one embodiment of the present specification, in the chemical formula A-3, Y1 is a site that binds to L.
[0064] According to one embodiment of the present specification, in the chemical formula A-3, the Y2 is a site that binds to the L.
[0065] According to one embodiment of the present specification, the chemical formula 1 is any one of the chemical formulas 1-1 to 1-6 below. [Chemical formula 1-1] [ka] [Chemical formula 1-2] [ka] [Chemical formula 1-3] [ka] [Chemical formula 1-4] [ka] [Chemical formula 1-5] [ka] [Chemical formula 1-6] [ka] In the above Chemical Formulas 1-1 to 1-6, The definitions of R1 to R3, R11, r11, and L are the same as those in Chemical Formula 1. The definitions of Y1 to Y4 and Y7 to Y10 are the same as those in the above-mentioned chemical formula A-1.
[0066] According to one embodiment of the present specification, the chemical formula 1 is any one of the chemical formulas 1-7 to 1-12 below. [Chemical formula 1-7] [ka] [Chemical formula 1-8] [ka] [Chemical formula 1-9] [ka] [Chemical formula 1-10] [ka] [Chemical formula 1-11] [ka] [Chemical formula 1-12] [ka] In the above Chemical Formulas 1-7 to 1-12, The definitions of R1 to R3, R11, r11, and L are the same as those in Chemical Formula 1. The definitions of Y1 to Y3, Y5, and Y7 to Y10 are the same as those in the above-mentioned chemical formula A-2.
[0067] According to one embodiment of the present specification, the chemical formula 1 is any one of the chemical formulas 1-13 to 1-18 below. [Chemical formula 1-13] [ka] [Chemical formula 1-14] [ka] [Chemical formula 1-15] [ka] [Chemical formula 1-16] [ka] [Chemical formula 1-17] [ka] [Chemical formula 1-18] [ka] In the above Chemical Formulas 1-13 to 1-18, The definitions of R1 to R3, R11, r11, and L are the same as those in Chemical Formula 1. The definitions of Y1 to Y2 and Y5 to Y10 are the same as those in the above-mentioned chemical formula A-3.
[0068] According to one embodiment of the present specification, at least one of R1 to R3 is -L-Ar1, and the remaining groups among R1 to R3 other than -L-Ar1 and R11 are the same or different and each independently represents hydrogen; deuterium; an alkenyl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; or deuterium, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
[0069] According to one embodiment of the present specification, at least one of R1 to R3 is -L-Ar1, and the remaining groups among R1 to R3 other than -L-Ar1 and R11 are the same or different and each independently represents hydrogen; deuterium; an alkenyl group having 2 to 20 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms; or deuterium, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
[0070] According to one embodiment of the present specification, at least one of R1 to R3 is -L-Ar1, and the remaining R1 to R3 other than -L-Ar1 and R11 are selected from the group consisting of hydrogen, deuterium, a vinyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a phenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a biphenyl group substituted or unsubstituted with deuterium, a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted with deuterium. a fluorene group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a phenanthrene group; a spirobifluorene group; a dibenzofuran group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a naphthobenzofuran group; a benzobisbenzofuran group; a benzoxazole group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a naphthofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzothiophene group substituted or unsubstituted with deuterium; or a naphthobenzothiophene group.
[0071] According to one embodiment of the present specification, at least one of R1 to R3 is -L-Ar1, and the remaining R1 to R3 other than -L-Ar1 and R11 are selected from the group consisting of hydrogen, deuterium, a vinyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a phenyl group substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, a biphenyl group substituted or unsubstituted with deuterium, a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted with deuterium. a fluorene group substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; a phenanthrene group; a spirobifluorene group; a dibenzofuran group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group; a benzobisbenzofuran group; a benzoxazole group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group substituted or unsubstituted with deuterium; or a naphthobenzothiophene group.
[0072] According to one embodiment of the present specification, at least one of R1 to R3 is -L-Ar1, and the remaining of R1 to R3 other than -L-Ar1 and R11 are hydrogen; deuterium; a vinyl group substituted or unsubstituted with a phenyl group; a phenyl group substituted or unsubstituted with deuterium, a phenyl group, a naphthyl group, a benzoxazole group, or a dibenzofuran group; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with a phenyl group or a naphthyl group; a fluorene group substituted or unsubstituted with a methyl group substituted or unsubstituted with deuterium; a phenanthrene group; a spirobifluorene group; a dibenzofuran group substituted or unsubstituted with a phenyl group or a naphthyl group; a naphthobenzofuran group; a benzobisbenzofuran group; a benzoxazole group substituted or unsubstituted with a phenyl group; a naphthofuran group substituted or unsubstituted with a phenyl group; a dibenzothiophene group substituted or unsubstituted with deuterium; or a naphthobenzothiophene group.
[0073] According to one embodiment of the present specification, L is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
[0074] According to one embodiment of the present specification, L is a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
[0075] According to one embodiment of the present specification, L is a direct bond; a phenylene group; a divalent naphthyl group; or a divalent dibenzofuran group.
[0076] According to one embodiment of the present specification, in the chemical formulas A-1 and A-2, the Y1 or Y2 is a site that is bonded to the L, and the remaining of the Y1 and Y2 that is not bonded to the L is hydrogen; deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched alkyl group having 1 to 30 carbon atoms, deuterium, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms 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,
[0077] The Y3 to Y5 and Y7 to Y10 may be the same or different and each independently represent hydrogen; 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 which is unsubstituted or substituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
[0078] According to one embodiment of the present specification, in the chemical formulas A-1 and A-2, the Y1 or Y2 is a site that is bonded to the L, and the remaining of the Y1 and Y2 that is not bonded to the L is hydrogen; deuterium; a linear or branched alkyl group having 1 to 20 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted with deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms,
[0079] The Y3 to Y5 and Y7 to Y10 may be the same or different and each independently represent hydrogen; 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 which is unsubstituted or substituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
[0080] According to one embodiment of the present specification, in the chemical formulas A-1 and A-2, the Y1 or Y2 is a site that is bonded to the L, and the remaining Y1 and Y2 that are not bonded to the L are hydrogen, deuterium, an isopropyl group, a cyclopentyl group, a phenyl group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a biphenyl group substituted or unsubstituted with deuterium, a naphthyl group, a fluorene group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, a benzofuran group, a dibenzofuran group, a dibenzothiophene group, or a tetrahydronaphthyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms,
[0081] The Y3 to Y5 and Y7 to Y10 are the same or different and each independently represents hydrogen; deuterium; an isopropyl group; a tert-butyl group; a phenyl group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group; or a dibenzofuran group.
[0082] According to one embodiment of the present specification, in the chemical formulas A-1 and A-2, the Y1 or Y2 is a site that is bonded to the L, and the remaining Y1 and Y2 that are not bonded to the L are hydrogen, deuterium, an isopropyl group, a cyclopentyl group, a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a biphenyl group substituted or unsubstituted with deuterium, a naphthyl group, a fluorene group substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms, a benzofuran group, a dibenzofuran group, a dibenzothiophene group, or a tetrahydronaphthyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms,
[0083] The Y3 to Y5 and Y7 to Y10 are the same or different and each independently represents hydrogen; deuterium; an isopropyl group; a tert-butyl group; 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; a naphthyl group; or a dibenzofuran group.
[0084] According to one embodiment of the present specification, in the chemical formulas A-1 and A-2, Y1 or Y2 is a site that is bonded to L, and the remaining of Y1 and Y2 that is not bonded to L is hydrogen; deuterium; an isopropyl group; a cyclopentyl group; a phenyl group substituted or unsubstituted with deuterium or a phenyl group; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group; a fluorene group substituted or unsubstituted with a methyl group; a benzofuran group; a dibenzofuran group; a dibenzothiophene group; or a tetrahydronaphthyl group substituted or unsubstituted with a methyl group;
[0085] The Y3 to Y5 and Y7 to Y10 are the same or different and each independently represents hydrogen; deuterium; an isopropyl group; a tert-butyl group; a phenyl group substituted or unsubstituted with deuterium or a phenyl group; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group; or a dibenzofuran group.
[0086] According to one embodiment of the present specification, in the chemical formula A-3, Y1 or Y2 is a site that is bonded to L, and the remaining of Y1 and Y2 that is not bonded to L is hydrogen; deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched alkyl group having 1 to 30 carbon atoms, deuterium, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms 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,
[0087] the Y7 to Y10 are the same or different and each independently represents hydrogen; 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 which is unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms;
[0088] Said Y5 and Y6 are the same or different and each independently represents hydrogen or deuterium.
[0089] According to one embodiment of the present specification, in the chemical formula A-3, Y1 or Y2 is a site that is bonded to L, and the remaining of Y1 and Y2 that is not bonded to L is hydrogen; deuterium; a linear or branched alkyl group having 1 to 20 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted with deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms,
[0090] the Y7 to Y10 are the same or different and each independently represents hydrogen; 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 which is unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms;
[0091] Said Y5 and Y6 are the same or different and each independently represents hydrogen or deuterium.
[0092] According to one embodiment of the present specification, in the chemical formula A-3, Y1 or Y2 is a site that is bonded to L, and the remaining of Y1 and Y2 that is not bonded to L is hydrogen; deuterium; an isopropyl group; a cyclopentyl group; a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group; a fluorene group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a benzofuran group; a dibenzofuran group; a dibenzothiophene group; or a tetrahydronaphthyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms,
[0093] the Y3 to Y5 and the Y7 to Y10 are the same or different and each independently represents hydrogen; deuterium; an isopropyl group; a tert-butyl group; a phenyl group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group; or a dibenzofuran group;
[0094] Said Y5 and Y6 are the same or different and each independently represents hydrogen or deuterium.
[0095] According to one embodiment of the present specification, in the chemical formula A-3, Y1 or Y2 is a site that is bonded to L, and the remaining of Y1 and Y2 that is not bonded to L is hydrogen; deuterium; an isopropyl group; a cyclopentyl group; a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group; a fluorene group substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; a benzofuran group; a dibenzofuran group; a dibenzothiophene group; or a tetrahydronaphthyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms,
[0096] the Y3 to Y5 and the Y7 to Y10 are the same or different and each independently represents hydrogen; deuterium; an isopropyl group; a tert-butyl group; 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; a naphthyl group; or a dibenzofuran group;
[0097] Said Y5 and Y6 are the same or different and each independently represents hydrogen or deuterium.
[0098] According to one embodiment of the present specification, in the chemical formula A-3, Y1 or Y2 is a site that is bonded to the L, and the remaining of the Y1 and Y2 that are not bonded to the L is hydrogen; deuterium; an isopropyl group; a cyclopentyl group; a phenyl group substituted or unsubstituted with deuterium or a phenyl group; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group; a fluorene group substituted or unsubstituted with a methyl group; a benzofuran group; a dibenzofuran group; a dibenzothiophene group; or a tetrahydronaphthyl group substituted or unsubstituted with a methyl group;
[0099] the Y to Y and the Y to Y are the same or different and each independently represents hydrogen; deuterium; an isopropyl group; a tert-butyl group; a phenyl group which is unsubstituted or substituted with deuterium or a phenyl group; a biphenyl group which is unsubstituted or substituted with deuterium; a naphthyl group; or a dibenzofuran group;
[0100] Said Y5 and Y6 are the same or different and each independently represents hydrogen or deuterium.
[0101] According to one embodiment of the present specification, the compound represented by Chemical Formula 1 is any one selected from the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0102] The present specification provides an organic light emitting device comprising the compound described above.
[0103] In this specification, when a member is said to be located "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member is present between the two members.
[0104] In this specification, when a part "comprises" a certain component, this does not mean excluding other components, but means that the part may further include other components, unless otherwise specified to the contrary.
[0105] In this specification, the term "layer" is interchangeable with the term "film" used primarily in this technical field, and refers to a coating that covers a desired area. The size of the "layer" is not limited, and each "layer" may be the same or different in size. According to one embodiment, the size of the "layer" may be the same as the entire device, may correspond to the size of a specific functional area, or may be smaller by a single sub-pixel.
[0106] In this specification, the inclusion of a specific substance A in layer B includes both i) one or more types of substance A being contained in one layer B, and ii) layer B being composed of one or more layers and substance A being contained in one or more of the multiple layer Bs.
[0107] In this specification, when a specific substance A is contained in layer C or layer D, it means that i) it is contained in one or more of one or more C layers, ii) it is contained in one or more of one or more D layers, or iii) it is contained in one or more C layers and one or more D layers, respectively.
[0108] The present specification provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers contains a compound represented by Chemical Formula 1.
[0109] The organic layer of the organic light-emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. For example, it may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.
[0110] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.
[0111] According to one embodiment of the present specification, the organic layer includes an emitting layer, and the emitting layer includes the compound as a host of the emitting layer.
[0112] According to one embodiment of the present specification, the light-emitting layer includes a dopant, and the dopant includes a fluorescent dopant.
[0113] According to one embodiment of the present specification, the fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound.
[0114] According to one embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.
[0115] According to one embodiment of the present specification, the light emitting layer further includes one or more hosts different from the compound of Chemical Formula 1.
[0116] The host other than the compound of Chemical Formula 1 may be any anthracene-based host used in the art, as long as it is different from the compound of Chemical Formula 1, but is not limited thereto.
[0117] According to one embodiment of the present specification, the light emitting layer includes a host and a dopant.
[0118] According to one embodiment of the present specification, the light emitting layer includes a host and a dopant, and the host includes a compound represented by Chemical Formula 1.
[0119] According to one embodiment of the present specification, the dopant is a blue dopant.
[0120] According to one embodiment of the present specification, the organic light-emitting element is a blue organic light-emitting element.
[0121] According to one embodiment of the present specification, the light emitting layer includes two or more mixed hosts, and at least one of the two or more mixed hosts includes the compound represented by Chemical Formula 1.
[0122] According to one embodiment of the present specification, the light-emitting layer includes two or more mixed hosts, at least one of which includes a compound represented by Chemical Formula 1, and the remaining of which includes an anthracene-based compound different from Chemical Formula 1.
[0123] At least one of the two or more mixed hosts includes a compound represented by Chemical Formula 1, and the remaining hosts are different from Chemical Formula 1, and may be any anthracene-based host used in the art without limitation, but are not limited thereto.
[0124] An organic light-emitting device using a mixed host of two or more types according to an embodiment of the present specification aims to improve the performance of the device by combining the advantages of each host. For example, when two types of hosts are mixed, one host having the effects of high efficiency and low voltage and one host having the effects of long life can be mixed to prepare an organic light-emitting device having the effects of high efficiency, low voltage, and long life.
[0125] According to one embodiment of the present specification, the organic light-emitting element has a maximum emission wavelength (λ max ) is 400nm~470nm.
[0126] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the dopant is a fluorescent dopant.
[0127] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the dopant includes one or more selected from a pyrene-based compound and a non-pyrene-based compound.
[0128] The pyrene-based compound and the non-pyrene-based compound may be any compound known in the art, and are not limited thereto.
[0129] According to one embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.
[0130] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes a compound represented by Chemical Formula 1, and the dopant includes one or more selected from a pyrene-based compound and a non-pyrene-based compound.
[0131] According to one embodiment of the present specification, the light emitting layer contains a host and a dopant, and the light emitting layer contains the host:dopant in a weight ratio of 0.1:99.9 to 20:80.
[0132] According to another embodiment of the present specification, the device further includes a capping layer provided on a surface of at least one of the first electrode and the second electrode opposite to the surface facing the organic layer.
[0133] The capping layer is formed in an organic light emitting device to prevent a significant amount of light from being lost due to total reflection. The capping layer has a function of sufficiently protecting the lower anode and light emitting layer from external moisture penetration or contamination, and has a high refractive index to prevent light loss due to total reflection.
[0134] According to another embodiment of the present specification, the capping layer may be provided on each of the opposite surface of the first electrode facing the organic layer and the opposite surface of the second electrode facing the organic layer.
[0135] According to another embodiment of the present specification, the capping layer may be provided on a surface of the first electrode opposite to a surface facing the organic layer.
[0136] According to another embodiment of the present specification, the capping layer may be provided on each of the surfaces of the second electrode opposite to the surface facing the organic layer.
[0137] According to one embodiment of the present specification, the organic light-emitting device further includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
[0138] According to one embodiment of the present 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.
[0139] According to one embodiment of the present specification, the 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 two or more 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 blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.
[0140] According to one embodiment of the present specification, the device includes two or more hole transport layers between the light emitting layer and the first electrode. The two or more hole transport layers may contain the same or different materials.
[0141] According to one embodiment of the present specification, the first electrode is an anode or a cathode.
[0142] According to one embodiment of the present specification, the second electrode is a cathode or an anode.
[0143] According to one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate.
[0144] According to one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.
[0145] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is illustrated in Figures 1 and 2. Figures 1 and 2 are illustrative of, but not limiting, organic light-emitting devices.
[0146] 1 illustrates the structure of an organic light-emitting device in which a first electrode 2, an organic layer 4, and a second electrode 3 are sequentially laminated on a substrate 1. The compound is contained in the organic layer.
[0147] 2 illustrates a 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 control layer 7, an emission layer 4, an electron control layer 8, an electron transport layer 9, an electron injection layer 10, a second electrode 3, and a capping layer 11 are sequentially laminated on a substrate 1. The compound is contained in the emission layer.
[0148] The organic light emitting device of the present specification may be manufactured by materials and methods well known in the art, except that the light emitting layer contains the above compound, ie, the compound represented by Chemical Formula 1 above.
[0149] When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
[0150] For example, the organic light emitting device of the present invention may be fabricated 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 may be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode, and an organic layer including a hole injection layer, a hole transport layer, an emitting layer, and an electron transport layer may be formed thereon, and a material usable as a cathode may be deposited thereon. In addition to this method, an organic light emitting device may be fabricated by sequentially depositing a second electrode material, an organic layer, and a first electrode material on a substrate.
[0151] In addition, the compound represented by Formula 1 may be formed in an organic layer by a solution coating method as well as a vacuum deposition method during the preparation of an organic light emitting device, where the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blade, inkjet printing, screen printing, spraying, roll coating, etc.
[0152] In addition to the above method, the organic light emitting device can be fabricated by sequentially depositing the second electrode material, the organic material layer, and the first electrode material on the substrate, but the fabrication method is not limited thereto.
[0153] The first electrode material is preferably a material having a large work function so that holes can be easily injected into the organic layer, and examples of the material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof, metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO), combinations of metals and oxides such as ZnO:Al or SnO2:Sb, and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.
[0154] The second electrode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer, such as, but not limited to, metals or alloys thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; and materials having a multilayer structure, such as LiF / Al or LiO2 / Al.
[0155] The light-emitting layer may include a host material and a dopant material. When an additional light-emitting layer is included in addition to the light-emitting layer including the compound of Chemical Formula 1 according to one embodiment of the present specification, the host material may include fused and / or non-fused aromatic ring derivatives or heterocycle-containing compounds. Specifically, the fused aromatic ring derivatives may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocycle-containing compounds may include, but are not limited to, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.
[0156] According to one embodiment of the present specification, the host includes, but is not limited to, a compound represented by the following chemical formula H-1: [Chemical formula H-1] [ka] In the above chemical formula H-1, L20 and L21 are the same or different and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group; Ar20 and Ar21 are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; R201 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; r201 is an integer of 1 to 8, and when r201 is 2 or more, the 2 or more R201's are the same or different from each other.
[0157] In one embodiment of the present specification, L20 and L21 are the same or different and each independently represent a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.
[0158] In one embodiment of the present specification, L20 and L21 are the same or different and each independently represent a direct bond; 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.
[0159] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and each independently represent a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
[0160] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and each independently represent a substituted or unsubstituted monocyclic to 4-ring aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.
[0161] In one embodiment of the present specification, Ar20 and Ar21 are the same or different, and each independently represents 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.
[0162] In one embodiment of the present specification, Ar20 and Ar21 are the same or different, and each independently represents 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.
[0163] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and each independently a substituted or unsubstituted aryl group.
[0164] In one embodiment of the present specification, Ar20 and Ar21 are the same or different, and each independently represents 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.
[0165] According to one embodiment of the present specification, R201 is hydrogen.
[0166] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound. [ka]
[0167] The dopant material includes aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative includes fused aromatic ring derivatives having a substituted or unsubstituted arylamine group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamine group. The styrylamine compound includes a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. The metal complex includes, but are not limited to, an iridium complex, a platinum complex, etc.
[0168] According to one embodiment of the present specification, the dopant material includes, but is not limited to, compounds of the following formula D-1 or D-2: [Chemical formula D-1] [ka] In the above chemical formula D-1, L101 and L102 are the same or different and each independently represents a direct bond; or a substituted or unsubstituted arylene group; Ar101 to Ar104 are the same or different and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; [Chemical formula D-2] [ka] In the above chemical formula D-2, T1 to T5 are the same or different and each independently represents hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group; t3 and t4 are each an integer from 1 to 4, t5 is an integer from 1 to 3, When the t3 is 2 or more, the two or more T3 are the same or different, When t4 is 2 or more, the two or more T4 are the same or different, When the t5 is 2 or more, the two or more T5's may be the same or different.
[0169] According to one embodiment of the present specification, L101 and L102 are direct bonds.
[0170] According to one embodiment of the present specification, Ar101 to Ar104 are the same or different and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
[0171] According to one embodiment of the present specification, Ar101 to Ar104 are the same or different and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which 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.
[0172] According to one embodiment of the present specification, Ar101 to Ar104 are the same or different and each independently represents a phenyl group substituted with a methyl group; or a dibenzofuran group.
[0173] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound. [ka]
[0174] According to one embodiment of the present specification, T1 to T5 are the same or different and each independently represent a hydrogen atom; 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.
[0175] According to one embodiment of the present specification, T1 to T5 are the same or different and each independently represent a hydrogen atom; 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, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.
[0176] According to one embodiment of the present specification, T1 to T5 are the same or different and each independently represent a hydrogen atom; a methyl group; a tert-butyl group; a diphenylamine group; or a phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group.
[0177] According to one embodiment of the present specification, the chemical formula D-2 is represented by the following compound. [ka]
[0178] 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 effect of receiving holes from the anode and injecting holes into the light emitting layer or light emitting material. In addition, a material that is excellent in the ability to prevent excitons generated from the light emitting layer from moving to the electron injection layer or electron injection material is preferable. In addition, a material that is excellent in the ability to form a thin film is preferable. 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 material layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrin, oligothiophene, and arylamine-based organic materials; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; anthraquinone, polythiophene-based conductive polymers such as polyaniline, etc.
[0179] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following formula HI-1, but is not limited thereto. [Chemical formula HI-1] [ka] In the above chemical formula HI-1, At least one of X'1 to X'6 is N, and the rest are CH; R309 to R314 are the same or different and each independently represent a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are bonded to adjacent groups to form a substituted or unsubstituted ring.
[0180] According to one embodiment of the present specification, X′1 to X′6 are N.
[0181] According to one embodiment of the present specification, R309 to R314 are cyano groups.
[0182] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound. [ka]
[0183] 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 the hole injection layer and transfer them to the light emitting layer, and is preferably a material that has high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.
[0184] According to one embodiment of the present specification, the hole transport layer or the hole modulating layer includes, but is not limited to, a compound of the following formula HT-1: [Chemical formula HT-1] [ka] In the formula HT-1, R315 to R317 are the same or different, and each independently represents one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or are bonded to adjacent groups to form a substituted or unsubstituted ring; r315 is an integer of 1 to 5, and when r315 is 2 or more, the two or more R315's are the same or different from each other, r316 is an integer of 1 to 5, and when said r316 is 2 or more, said 2 or more R316's are the same or different from each other.
[0185] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof.
[0186] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; and combinations thereof.
[0187] According to one embodiment of the present specification, R315 and R316 are the same or different from each other, and each independently represent a substituted or unsubstituted aryl group, or are bonded to adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.
[0188] According to one embodiment of the present specification, R315 and R316 are the same or different from each other, and each independently represent a phenyl group or a phenanthrene group, or are bonded to adjacent groups to form an indene substituted with a methyl group.
[0189] According to one embodiment of the present specification, the chemical formula HT-1 is represented by any one of the following compounds: [ka]
[0190] The electron control layer is a layer that controls the electrons transferred from the electron transport layer so that they can be smoothly injected into the light emitting layer, and may be made of any known material without limitation.
[0191] According to one embodiment of the present specification, the electron modulating layer includes, but is not limited to, a compound of the following formula EG-1: [Chemical formula EG-1] [ka] In the above 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 direct bond; or a substituted or unsubstituted arylene group; Ar5 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; L51 is O; or S.
[0192] According to one embodiment of the present specification, L51 is O.
[0193] According to one embodiment of the present specification, L51 is S.
[0194] According to one embodiment of the present specification, G1 and G18 are linked by -L51- to form a substituted or unsubstituted heterocycle.
[0195] According to one embodiment of the present specification, G1 and G18 are linked by -L51- to form a substituted or unsubstituted xanthene ring; or a substituted or unsubstituted thioxanthene ring.
[0196] According to one embodiment of the present specification, G1 and G18 are linked by -O- to form a substituted or unsubstituted xanthene ring.
[0197] According to one embodiment of the present specification, G1 and G18 are linked via -S- to form a substituted or unsubstituted thioxanthene ring.
[0198] According to one embodiment of the present specification, G1 and G18 are linked via -O- to form a xanthene ring.
[0199] According to one embodiment of the present specification, G1 and G18 are linked via -S- to form a thioxanthene ring.
[0200] According to one embodiment of the present specification, L5 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
[0201] 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.
[0202] According to one embodiment of the present specification, L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
[0203] According to one embodiment of the present specification, L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
[0204] According to one embodiment of the present specification, L5 is a direct bond; or a phenylene group.
[0205] According to one embodiment of the present specification, Ar5 is a substituted or unsubstituted triazine group.
[0206] According to one embodiment of the present specification, Ar5 is a triazine group which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
[0207] According to one embodiment of the present specification, Ar5 is a triazine group substituted with a phenyl group.
[0208] According to one embodiment of the present specification, the EG-1 is represented by the following compound. [ka]
[0209] 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 electrons injected from the cathode and transfer them to the light-emitting layer, and is preferably a material with high mobility for electrons. Specific examples include, but are not limited to, Al complex of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the prior art. In particular, suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, and in each case, are followed by an aluminum or silver layer.
[0210] According to one embodiment of the present specification, the electron transport layer includes a compound of the following formula ET-1, but is not limited thereto. [Chemical formula ET-1] [ka] In the above formula ET-1, At least one of Z11 to Z13 is N, and the rest are CH; L601 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; Ar601 and Ar602 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; l601 is an integer of 1 to 5, and when said l601 is 2 or more, said 2 or more L601's may be the same or different from each other.
[0211] According to one embodiment of the present specification, L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
[0212] According to one embodiment of the present specification, L601 is a phenylene group; a biphenylylene group; or a naphthylene group.
[0213] According to one embodiment of the present specification, Ar601 and Ar602 are the same or different and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
[0214] According to one embodiment of the present specification, Ar601 and Ar602 are phenyl groups.
[0215] According to one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound: [ka]
[0216] The electron injection layer is a layer that receives electrons from an electrode. The electron injection material is preferably excellent in the ability to transport electrons, has an effect of receiving electrons from the second electrode, and has an excellent effect of injecting electrons into the light-emitting layer or light-emitting material. In addition, a material that prevents excitons generated from the light-emitting layer from moving to the hole injection layer and has excellent thin-film forming ability is preferable. Specific examples of the electron injection material include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.
[0217] Examples of the metal complex compound include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolate) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato) aluminum, and bis(2-methyl-8-quinolinato) (2-naphtholato) gallium.
[0218] 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 materials exemplified for the electron transport layer and the electron injection layer, but is not limited thereto.
[0219] According to one embodiment of the present specification, the electron injection and transport layer may further include a metal complex compound. The metal complex compound is as described above.
[0220] The electron blocking layer is a layer that prevents electrons injected from the electron injection layer from passing through the light emitting layer to the hole injection layer, thereby improving the life and efficiency of the device. Any known material can be used for the electron blocking layer, and the electron blocking layer 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 a layer that simultaneously injects and transports holes.
[0221] The material of the electron blocking layer may be, but is not limited to, the examples of the formula HI-I.
[0222] The hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer, and may be made of, but is not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc.
[0223] The capping layer is formed to prevent a significant amount of light from being lost due to total reflection in an organic light emitting device. The capping layer has the ability to sufficiently protect the lower anode and light emitting layer from external moisture penetration and contamination, has a high refractive index, and can prevent light loss due to total reflection. Conventional materials can be used for the capping layer without any restrictions.
[0224] According to one embodiment of the present specification, the capping layer includes a compound represented by the following chemical formula CP-1, but is not limited thereto. [Chemical formula CP-1] [ka] In the above formula CP-1, L501 and L502 are the same or different and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; R501 and Ar501 to Ar504 are the same or different and each independently represent a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
[0225] According to one embodiment of the present specification, L501 and L502 are the same or different and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
[0226] According to one embodiment of the present specification, L501 and L502 are phenylene groups.
[0227] According to one embodiment of the present specification, R501 and Ar501 to Ar504 are the same or different and each independently represent a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or bond with adjacent groups to each other to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
[0228] According to one embodiment of the present specification, R501 and Ar501 to Ar504 are phenyl groups or are bonded to adjacent groups to form a carbazole substituted or unsubstituted with a phenyl group.
[0229] According to one embodiment of the present specification, Ar501 is bonded to L501 to form a carbazole substituted with a phenyl group.
[0230] According to one embodiment of the present specification, Ar503 is bonded to L503 to form a carbazole substituted with a phenyl group.
[0231] According to one embodiment of the present specification, the chemical formula CP-1 is represented by the following compound: [ka]
[0232] The organic light emitting devices according to the present specification may be top-emitting, bottom-emitting or double-sided emitting depending on the materials used.
[0233] The organic light emitting device according to the present specification may be included in various electronic devices, such as, but not limited to, a display panel, a touch panel, a solar module, a lighting device, etc. EXAMPLES
[0234] Hereinafter, the present specification will be described in detail with reference to examples and comparative examples in order to specifically explain the present specification. However, the examples and comparative examples according to the present specification may be modified in various different forms, and the scope of the present specification is not to be construed as being limited to the examples and comparative examples described below. The examples and comparative examples of the present specification are provided to more completely explain the present specification to those having average knowledge in the art.
[0235] Preparation Example 1. Synthesis of Chemical Formula A1-1 and A2-1 [ka] SM1 (1eq) and SM2 (1.1eq) were added to acetone (excess), potassium carbonate (2eq) was added, and the mixture was refluxed and stirred for 24 hours. The temperature was lowered to room temperature to terminate the reaction, and water and ethanol were added and filtered to produce the compounds A1-1 and A2-1 (Chemical Formulas A1-1-1 to A1-1-3 and A2-1-1 to A2-1-5), respectively.
[0236] The definition of R in the above reaction formula is the same as the definition of Y3 to Y10 described above.
[0237] In the synthesis method of the chemical formulae A1-1 and A2-1, except that SM1 and SM2 were changed to SM1 and SM2 in Table 1 below, the chemical formulae A1-1-1 to A1-1-3 and A2-1-1 to A2-1-5 in Table 1 below were synthesized in the same manner, respectively.
[0238] [Table 1] [Table 1] [Table 2]
[0239] Preparation Example 2. Synthesis of Chemical Formulas A1-2, A2-2, and A3-2 1) Synthesis of Chemical Formulas A1-2 and A2-2 [ka] SM1 (1eq, formula A1-1 or A2-1) was added to chloroform (excess), heated to reflux and dissolved, and then Eaton's reagent (1eq, phosphorus pentoxide, 7.7wt.% 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 the layers were separated. The organic layer was extracted with aq. saturated aqueous sodium bicarbonate (NaHCO3) solution until the pH became neutral. The organic layer was then columned with hexane and ethyl acetate to produce formulas A1-2 and A2-2 (formulas A1-2-1 to A1-2-3 and A2-2-1 to A2-2-5), respectively.
[0240] The definition of R in the above reaction formula is the same as the definition of Y3 to Y10 described above.
[0241] In the synthesis method of the chemical formulae A1-2 and A2-2, except that SM1 and SM2 were changed to SM1 and SM2 in Table 2 below, the chemical formulae A1-2-1 to A1-2-3 and A2-2-1 to A2-2-5 in Table 2 below were synthesized in the same manner, respectively.
[0242] 2) Synthesis of Chemical Formula A3-2 [ka] SM1 (1eq, formula A3-1) was added to benzene (excess) and stirred, and 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, then the layers were separated, and the organic layer was extracted with aq. saturated aqueous sodium bicarbonate (NaHCO3) solution until the pH became neutral. The organic layer was then columned with hexane and ethyl acetate to produce formula A3-2 (A3-2-1 and A3-2-2), respectively. The definition of R in the above reaction formula is the same as the definition of Y3 to Y10 described above. In the synthesis method of the above-mentioned chemical formula A3-2, except that SM1 and SM2 were changed to SM1 and SM2 in Table 2 below, A3-2-1 and A3-2-2 in Table 2 below were synthesized in the same manner.
[0243] [Table 2] [Table 3] [Table 4]
[0244] Preparation Example 3. Synthesis of compounds of formula A1-3(a), A2-3(a), A3-3(a), A1-3(b), A2-3(b), and A3-3(b) 1) Synthesis of Compounds of Formulae A1-3(a), A2-3(a), and A3-3(a) [ka] SM1 (1eq, chemical formula A1-2, A2-2, or A3-2) was dissolved in tetrahydrofuran (excess), the temperature was lowered to -78°C, 2.5M n-BuLi (1eq) was added dropwise, and the mixture was stirred for 1 hour, after which N-bromosuccinimide (1eq) was added. The reaction mixture was then warmed to room temperature and stirred for 4 hours, and 1N HCl (excess) was added to terminate the reaction. After the reaction was completed, the layers were separated and the solvent was removed, and the residue was subjected to silica column chromatography (ethyl acetate / hexane 1:15) to produce A1-3(a), A2-3(a), and A3-3(a) (chemical formula A1-3(a)-1, A1-3(a)-2, A2-3(a)-1 to A2-3(a)-3, and A3-3(a)-1), respectively.
[0245] In the synthesis method of the chemical formulae A1-3(a), A2-3(a), and A3-3(a), except that SM1 and SM2 were changed to SM1 and SM2 in Table 3 below, the chemical formulae A1-3(a)-1, A1-3(a)-2, A2-3(a)-1 to A2-3(a)-3, and A3-3(a)-1 in Table 3 below were synthesized in the same manner.
[0246] 2) Synthesis of Formulae A1-3(b), A2-3(b), and A3-3(b) [ka] SM1 (1eq, chemical formula A1-2, A2-2, or A3-2) was dissolved in chloroform (excess), N-bromosuccinimide (1eq) was added, and the mixture was heated to 40°C and stirred for 3 hours. After cooling to room temperature, 1N HCl (excess) was added to terminate the reaction. After the reaction was completed, the layers were separated and the solvent was removed, and the residue was subjected to silica column chromatography (ethyl acetate / hexane 1:15) to produce A1-3(b), A2-3(b), and A3-3(b) (chemical formula A1-3(b)-1, A1-3(b)-2, A2-3(b)-1 to A2-3(b)-3, A3-3(b)-1, and A3-3(b)-2), respectively.
[0247] In the synthesis method of the chemical formulae A1-3(b), A2-3(b), and A3-3(b), except that SM1 and SM2 were changed to SM1 and SM2 in Table 3 below, the chemical formulae A1-3(b)-1, A1-3(b)-2, A2-3(b)-1 to A2-3(b)-3, A3-3(b)-1, and A3-3(b)-2 in Table 3 below were synthesized in the same manner.
[0248] [Table 3] [Table 5] [Table 6] [Table 7]
[0249] Preparation Example 4. Synthesis of compounds of formula A1-4(a), A2-4(a), A3-4(a), A1-4(b), A2-4(b), and A3-4(b) [ka] [ka] SM1 (1eq, chemical formula A1-3(a), A2-3(a), A3-3(a), A1-3(b), A2-3(b), or A3-3(b)) and SM2 (1.02eq) were added to tetrahydrofuran (excess), and then 2M potassium carbonate aqueous solution (30 times the volume ratio of THF) was added, and tetrakistriphenyl-phosphinopalladium (2mol%) was added, followed by heating and stirring for 10 hours. The temperature was lowered to room temperature, the reaction was terminated, and the potassium carbonate aqueous solution was removed and the layers were separated. After removal of the solvent, the mixture was vacuum distilled and recrystallized with ethyl acetate and hexane to produce compounds of formula A1-4(a), A2-4(a), A3-4(a), A1-4(b), A2-4(b), and A3-4(b) (formula A1-4(a)-1 to A1-4(a)-4, A1-4(b)-1 to A1-4(b)-3, A2-4(a)-1 to A2-4(a)-6, A2-4(b)-1, A2-4(b)-2, A3-4(a)-1, A3-4(a)-2, and A3-4(b)-1), respectively.
[0250] In the above reaction scheme, R'' is defined as Y1 and Y2 above.
[0251] In the synthesis method of the above-mentioned chemical formulae A1-4(a), A2-4(a), A3-4(a), A1-4(b), A2-4(b), and A3-4(b), except that SM1 and SM2 were changed to SM1 and SM2 in Table 4 below, the chemical formulae A1-4(a)-1 to A1-4(a)-4, A1-4(b)-1 to A1-4(b)-3, A2-4(a)-1 to A2-4(a)-6, A2-4(b)-1, A2-4(b)-2, A3-4(a)-1, A3-4(a)-2, and A3-4(b)-1 in Table 4 below were synthesized in the same manner.
[0252] [Table 4] [Table 8] [Table 9] [Table 10] [Table 11]
[0253] Preparation Example 5. Synthesis of compounds of formula A1-5(a), A2-5(a), A3-5(a), A1-5(b), A2-5(b), and A3-5(b) [ka] [ka] In the synthesis method of the chemical formulae A1-3(b), A2-3(b), and A3-3(b), except that SM1 and SM2 were changed to SM1 and SM2 in Table 5 below, the chemical formulae A1-5(a)-1 to A1-5(a)-4, A1-5(b)-1 to A1-5(b)-3, A2-5(a)-1 to A2-5(a)-6, A2-5(b)-1, A2-5(b)-2, A3-5(a)-1, A3-5(a)-2, and A3-5(b)-1 in Table 5 below were synthesized in the same manner.
[0254] In the above reaction scheme, R'' is defined as Y1 and Y2 above.
[0255] [Table 5] [Table 12] [Table 13] [Table 14] [Table 15]
[0256] Preparation Example 6. Synthesis of compounds of formula A1-6(a), A2-6(a), A3-6(a), A1-6(b), A2-6(b), and A3-6(b) [ka] [ka] Add SM1 (1 eq, chemical formulas A1-6(a), A2-6(a), A3-6(a), A1-6(b), A2-6(b), and A3-6(b)) and SM2 (1.3 eq) to 1,4-dioxane (12 times the mass ratio of SM1), add potassium acetate (3 eq), and stir and reflux. Add palladium acetate (0.02 eq) and tricyclohexylphosphine (0.04 eq) after stirring in 1,4-dioxane for 5 minutes, and cool to room temperature after confirming the completion of the reaction after 10 hours. After adding ethanol and water, the mixture was filtered and purified by recrystallization with ethyl acetate and ethanol to produce the above-mentioned compounds A1-6(a), A2-6(a), A3-6(a), A1-6(b), A2-6(b), and A3-6(b) (chemical formulas A1-6(a)-1 to A1-6(a)-5, A1-6(b)-1 to A1-6(b)-6, A2-6(a)-1 to A2-6(a)-5, A2-6(b)-1 to A2-6(b)-7, A3-6(a)-1, A3-6(a)-2, and A3-6(b)-1 to A3-6(b)-4).
[0257] In the above reaction scheme, R'' is defined as Y1 and Y2 above.
[0258] In the synthesis method of the above-mentioned chemical formulae A1-6(a), A2-6(a), A3-6(a), A1-6(b), A2-6(b), and A3-6(b), except that SM1 and SM2 were changed to SM1 and SM2 in Table 6 below, the chemical formulae A1-6(a)-1 to A1-6(a)-5, A1-6(b)-1 to A1-6(b)-6, A2-6(a)-1 to A2-6(a)-5, A2-6(b)-1 to A2-6(b)-7, A3-6(a)-1, A3-6(a)-2, and A3-6(b)-1 to A3-6(b)-4 in Table 6 below were synthesized in the same manner.
[0259] [Table 6] [Table 16] [Table 17] [Table 18] [Table 19] [Table 20] [Table 21]
[0260] Preparation Example 7. Synthesis of Compounds 1 to 30 [ka] The SM1 (1.05 eq, chemical formula A1-6(a), A2-6(a), A3-6(a), A1-6(b), A2-6(b), or A3-6(b)) and SM2 ((1 eq) in Table 7 below were added to tetrahydrofuran (excess), and then a 2M aqueous potassium carbonate solution (30 times the volume ratio of THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added, followed by heating and stirring for 10 hours. The temperature was lowered to room temperature to terminate the reaction, and the aqueous potassium carbonate 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 the following compounds 1 to 30, respectively.
[0261] Compounds 1 to 30 in Table 7 below were synthesized in the same manner, except that SM1 and SM2 were changed to SM1 and SM2 in Table 7 below.
[0262] SM2 in Table 7 below was prepared according to the following scheme. SM2 scheme [ka] Example 1 of SM2> [ka] Example 2 of SM2> [ka]
[0263] SM2 of compounds 1 to 30 were prepared according to the synthesis examples described above.
[0264] In addition, the Suzuki reaction is the same as in the synthesis of compounds of formulae A1-4(a), A2-4(a), A3-4(a), A1-4(b), A2-4(b), and A3-4(b), and the bromination is the same as in the synthesis of compounds of formulae A1-3(a), A2-3(a), A3-3(a), A1-3(b), A2-3(b), and A3-3(b), except that SM1 and SM2 are changed.
[0265] [Table 7] [Table 22] [Table 23] [Table 24] [Table 25] [Table 26] [Table 27] [Table 28] [Table 29]
[0266] Production Example 8 (Synthesis of Compounds 31 to 33) [ka] The reactant (1eq) and trifluoromethanesulfonic acid (cat.) were added to C6D6 (10-50 times the mass ratio of the reactant) and stirred at 70°C for 10-100 minutes. After the reaction was completed, D2O (excess) was added and stirred for 30 minutes, and then trimethylamine (excess) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried with MgSO4, and then heated with toluene for recrystallization to obtain compounds 31 to 33 in Table 8 below.
[0267] The definition of the substituent in the reaction formula is as described above, and Dx means the number of deuterium substituted in the compound.
[0268] Compounds 31 to 33 in Table 8 below were synthesized in the same manner as above, except that SM1 and SM2 were changed to the reactants in Table 8 below and C6D6.
[0269] The reactants in Table 8 below were prepared in a similar manner to Preparation 7 above, except for changing SM1 and SM2 (non-deuterated compounds). [Each product has 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 for the above product was carried out in accordance with the prior art document Korean Patent No. 1538534.
[0270] [Table 8] [Table 30] [Table 31]
[0271] <Example 1> OLED manufacturing The substrate on which ITO / Ag / ITO was deposited at 70 / 1000 / 70 Å as the positive electrode was cut to a size of 50 mm x 50 mm x 0.5 mm, placed in distilled water with a dispersant dissolved therein, and ultrasonically cleaned. The detergent used was from Fischer Co., and the distilled water used was distilled water that had been filtered a second time with a Millipore Co. filter. After cleaning the ITO for 30 minutes, it was ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was completed, it was ultrasonically cleaned with isopropyl alcohol, acetone, and methanol solvents in that order, and then dried.
[0272] On the cathode thus prepared, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and T1, a material for transporting holes, was vacuum deposited to a thickness of 1150 Å to form a hole transport layer. Next, a hole control layer was formed using EB1 (150 Å), and then the compound 1 (host) and dopant BD1 (2 wt%) were vacuum deposited to a thickness of 360 Å to form an emission layer. Then, ET1 was deposited to a thickness of 50 Å to form an electron control 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. Magnesium and lithium fluoride (LiF) were sequentially deposited to a thickness of 50 Å as an electron injection layer (EIL), and magnesium and silver (weight ratio of 1:4) were formed to a thickness of 200 Å as an anode, and CP1 was deposited to a thickness of 600 Å as a capping layer to complete the device. The deposition rate of the organic material in the above process was maintained at 1 Å / sec. [ka]
[0273] Examples 2 to 38 and Comparative Examples 1 to 8 Organic light emitting devices of Examples 2 to 38 and Comparative Examples 1 to 8 were manufactured in the same manner as in Example 1, except that compounds in Table 9 below were used instead of Compound 1 and BD1, respectively. [ka]
[0274] Element evaluation The organic light-emitting devices manufactured in Examples 1 to 38 and Comparative Examples 1 to 8 were supplied with an electric current of 20 mA / cm 2 The voltage, efficiency, color coordinates, and life (T95) were measured by applying a current of 20 mA / cm. The results are shown in Table 9 below. T95 is defined as 20 mA / cm. 2 This refers to the time it takes for the initial luminance to decrease to 95% at a current density of
[0275] [Table 9] [Table 32] [Table 33] [Table 34]
[0276] According to one embodiment of the present specification, Chemical Formula 1 is intended to improve the properties of an anthracene blue fluorescent host by introducing an oxygen-containing naphthofuran unit, thereby improving a blue light emitting device.
[0277] By comparing various conventionally known derivatives shown in Comparative Examples 1 to 8, a clear improvement in device performance of blue devices can be observed compared to the conventional prior art.
[0278] In an organic electroluminescent device combined with the compound derivative of Chemical Formula 1 according to an embodiment of the present specification, the compound of Preparation Examples 7 and 8 can be used as a host for a blue organic electroluminescent device to control the role of smooth hole injection into the light-emitting layer, and due to the balance of holes and electrons in the organic electroluminescent device due to the chemical structure, the device according to the present specification exhibits excellent characteristics in terms of efficiency, driving voltage, and stability.
Claims
1. A compound of the following formula 1: [Chemical formula 1] 【Chemistry 80】 In the above Chemical Formula 1, At least one of R1 to R3 is -L-Ar1, and the rest of R1 to R3 other than -L-Ar1 and R11 are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; r11 is an integer of 1 to 7, and when r11 is 2 or more, the two or more R11's are the same or different from each other, L is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; Ar1 is any one of the following chemical formulas A-1 to A-3: [Chemical formula A-1] 【Chemistry 81】 [Chemical formula A-2] 【Chemistry 82】 [Chemical formula A-3] 【Chemistry 83】 In the above chemical formulas A-1 and A-2, Y1 or Y2 is a site that bonds to L, and the remaining Y1 and Y2 that are not bonded to L, Y3 to Y5, and Y7 to Y10 are the same or different from each other and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heteroaryl group, or any one or more adjacent pairs of Y3, Y5, and Y7 to Y10 are bonded to each other to form a substituted or unsubstituted ring, In the above Chemical Formula A-3, Y1 or Y2 is a site that bonds to L, and the remaining Y1 and Y2 that are not bonded to L, and Y7 to Y10 are the same or different and each independently represent: hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heteroaryl group; or any one or more adjacent pairs of Y7 to Y10 bond to each other to form a substituted or unsubstituted ring, Y5 and Y6 are the same or different and each independently is hydrogen; or deuterium.
2. The compound according to claim 1, wherein the formula 1 is any one of the following formulas 1-1 to 1-6: [Chemical formula 1-1] 【Chemistry 84】 [Chemical formula 1-2] 【Chemistry 85】 [Chemical formula 1-3] 【Chemistry 86】 [Chemical formula 1-4] 【Chemistry 87】 [Chemical formula 1-5] 【Chemistry 88】 [Chemical formula 1-6] 【Chemistry 89】 In the above Chemical Formulas 1-1 to 1-6, The definitions of R1 to R3, R11, r11, and L are the same as those in Chemical Formula 1. The definitions of Y1 to Y4 and Y7 to Y10 are the same as those in the above-mentioned chemical formula A-1.
3. The compound according to claim 1, wherein the formula 1 is any one of the following formulas 1-7 to 1-12: [Chemical formula 1-7] 【Chemistry 90】 [Chemical formula 1-8] 【Chemistry 91】 [Chemical formula 1-9] 【Chemistry 92】 [Chemical formula 1-10] 【Chemistry 93】 [Chemical formula 1-11] 【Chemistry 94】 [Chemical formula 1-12] 【Chemistry 95】 In the above Chemical Formulas 1-7 to 1-12, The definitions of R1 to R3, R11, r11, and L are the same as those in Chemical Formula 1. The definitions of Y1 to Y3, Y5, and Y7 to Y10 are the same as those in Chemical Formula A-2.
4. The compound according to claim 1, wherein the formula 1 is any one of the following formulas 1-13 to 1-18: [Chemical formula 1-13] 【Chemistry 96】 [Chemical formula 1-14] 【Chemistry 97】 [Chemical formula 1-15] 【Chemistry 98】 [Chemical formula 1-16] 【Chemistry 99】 [Chemical formula 1-17] 【Chemistry 100】 [Chemical formula 1-18] 【Chemistry 101】 In the above Chemical Formulas 1-13 to 1-18, The definitions of R1 to R3, R11, r11, and L are the same as those in Chemical Formula 1. The definitions of Y1 to Y2 and Y5 to Y10 are the same as those in the above-mentioned Chemical Formula A-3.
5. The compound according to claim 1, wherein at least one of R1 to R3 is -L-Ar1, and the remaining groups among R1 to R3 other than -L-Ar1 and R11 are the same or different and each independently represents hydrogen; deuterium; an alkenyl group having 2 to 30 carbon atoms and substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms and substituted or unsubstituted with deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; or deuterium, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms and substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
6. The compound according to claim 1, wherein L is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
7. In the chemical formulas A-1 and A-2, Y1 or Y2 is a site that bonds to L, and the remaining Y1 and Y2 that are not bonded to L are hydrogen; deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 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, The compound according to claim 1, wherein Y3 to Y5 and Y7 to Y10 are the same or different and each independently represents hydrogen; 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 which is unsubstituted or substituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
8. In the chemical formula A-3, Y1 or Y2 is a site that bonds to L, and the remaining one of Y1 and Y2 that is not bonded to L is hydrogen; deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 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, Y7 to Y10 are the same or different and each independently represents hydrogen; 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 which is unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; The compound according to claim 1, wherein Y5 and Y6 are the same or different and each independently is hydrogen or deuterium.
9. The compound according to claim 1 , wherein the formula 1 is any one selected from the following compounds: 【Chemistry 102】 【Chemistry 103】 【Chemistry 104】 【Chemistry 105】 【Chemistry 106】 【Chemistry 107】 【Chemistry 108】 【Chemistry 109】 【Chemistry 110】 【Chemistry 111】 【Chemistry 112】 【Chemistry 113】 【Chemistry 114】 【Chemistry 115】 【Chemistry 116】 【Chemistry 117】 。
10. An organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 9.
11. The organic light-emitting device according to claim 10 , wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host for the light-emitting layer.
12. The organic light emitting device of claim 11 , wherein the light emitting layer comprises a dopant, the dopant comprising a fluorescent dopant.
13. The organic light-emitting device according to claim 12 , wherein the fluorescent dopant comprises at least one selected from the group consisting of a pyrene-based compound and a non-pyrene-based compound.
14. The organic light-emitting device according to claim 13 , wherein the non-pyrene-based compound comprises a boron-based compound.
15. The organic light-emitting device according to claim 11 , wherein the light-emitting layer further comprises one or more hosts different from the compound.
Citation Information
Patent Citations
Compound containing naphthofuran and anthracene and organic light-emitting device using compound
CN116199656A
Anthracene compound and organic electroluminescent element containing the anthracene compound
JP2005047868A
Anthracene derivative and use thereof
JP2009203203A
Fused polycyclic aromatic compound
JP2023122010A
Electroactive materials
US20110042652A1