Compound, and organic light-emitting element comprising same

Abstract

The present specification relates to a compound of chemical formula 1, and an organic light-emitting element comprising same.

Description

Compound and organic light-emitting device containing the same

[0001] This application claims the benefit of Korean Patent Application No. 10-2024-0090957, filed with the Korean Intellectual Property Office on July 10, 2024, and Korean Patent Application No. 10-2024-0090964, filed with the Korean Intellectual Property Office on July 10, 2024, the entire contents of which are incorporated herein by reference.

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

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

[0004] In general, organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light emitting devices that utilize the organic light emitting phenomenon typically have a structure that includes an anode and a cathode with an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and can be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted. Such organic light emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low operating voltage, wide viewing angle, and high contrast.

[0005] Materials used as organic layers in organic light-emitting devices can be classified according to their function into light-emitting materials and charge-transport materials, such as hole-injecting materials, hole-transporting materials, electron-blocking materials, electron-transporting materials, and electron-injecting materials. Light-emitting materials include blue, green, and red light-emitting materials according to their emission color, as well as yellow and orange light-emitting materials required to realize better natural colors.

[0006] Furthermore, a host / dopant system can be used as a light-emitting material to enhance color purity and luminescence efficiency through energy transfer. This principle is achieved by mixing a small amount of a dopant with a smaller energy band gap and superior luminescence efficiency than the host, which primarily constitutes the light-emitting layer, into the light-emitting layer. This allows excitons generated in the host to be transported to the dopant, resulting in high-efficiency light emission. Since the wavelength of the host shifts to that of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used.

[0007] In order to fully demonstrate the excellent characteristics of the aforementioned organic light-emitting device, the materials forming the organic layer within the device, such as hole injection materials, hole transport materials, luminescent materials, electron blocking materials, electron transport materials, and electron injection materials, must be supported by stable and efficient materials, and therefore, the development of new materials is continuously required.

[0008] [Prior Art Literature]

[0009] [Patent Document]

[0010] (Patent Document 1) Registered Patent Publication No. 10-2145663

[0011] (Patent Document 2) Registered Patent Publication No. 10-2528855

[0012] The present specification describes compounds and organic light-emitting devices comprising the same.

[0013] One embodiment of the present disclosure provides a compound of the following chemical formula 1.

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] HAr is a group represented by the following chemical formula 2,

[0018] [Chemical Formula 2]

[0019]

[0020] Y is O or S,

[0021] R1 and R2 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted aliphatic ring group; a substituted or unsubstituted aliphatic and aromatic condensed ring group; or a group connected to L1,

[0022] R3 to R6 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted aliphatic ring group; a substituted or unsubstituted aliphatic and aromatic condensed ring group; or a group connected to L1, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted ring,

[0023] At least one of R1 to R6 is a group connected to L1,

[0024] Ar1 is a group represented by the following chemical formula 3,

[0025] [Chemical Formula 3]

[0026]

[0027] X is O, S or It is indicated by one of the following:

[0028] One of R7 and R8 is connected to L1,

[0029] One of R7 and R8 is connected to L2,

[0030] Among R7 and R8, the group not connected to L1 or L2 is deuterium,

[0031] n and m are integers from 0 to 8, respectively, and n+m is an integer greater than or equal to 2.

[0032] L1 and L2 are the same or different and each independently a direct bond; a substituted or unsubstituted divalent to tetravalent arylene group; or a substituted or unsubstituted divalent to tetravalent heteroarylene group,

[0033] a to c are integers from 1 to 3, respectively,

[0034] If a is 2 or more, HAr are equal or different,

[0035] If c is 2 or greater, the structures within the brackets are either the same or different.

[0036] In addition, according to one embodiment of the present invention, an organic light-emitting device is provided, including a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes the above-described compound.

[0037] A compound according to one embodiment of the present specification can be used in an organic light-emitting device, thereby reducing the operating voltage of the organic light-emitting device and improving luminous efficiency. In addition, the lifespan characteristics of the device can be improved due to the thermal stability of the compound.

[0038] Figures 1 and 2 illustrate examples of organic light-emitting devices according to the present invention.

[0039] Hereinafter, the present specification will be described in more detail.

[0040] In this specification, when a part is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0041] In this specification, when it is said that a member is located “on” another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

[0042] In this specification, HOMO (highest occupied molecular orbital) means a molecular orbital (highest occupied molecular orbital) in the region with the highest energy in which electrons can participate in bonding, LUMO (lowest unoccupied molecular orbital) means a molecular orbital (lowest unoccupied molecular orbital) in which electrons have the lowest energy in the antibonding region, and HOMO energy level means the distance from the vacuum level to HOMO. In addition, LUMO energy level means the distance from the vacuum level to LUMO.

[0043] In this specification, bandgap means the difference in energy levels between HOMO and LUMO, i.e., HOMO-LUMO gap.

[0044] In this specification, the HOMO energy level can be measured using an atmospheric photoelectron spectrometer (manufactured by RIKEN KEIKI Co., Ltd.: AC3), and the LUMO energy level can be calculated using a wavelength value measured through photoluminescence (PL).

[0045] In this specification, the term "combination of these" included in the expression in the Makushi format means one or more mixtures or combinations selected from the group consisting of the components described in the expression in the Makushi format, and means including one or more selected from the group consisting of the components.

[0046] Examples of substituents in this specification are described below, but are not limited thereto.

[0047] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., a position where the substituent can be replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0048] In one embodiment of the present specification, 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 (-CN); a nitro group; a hydroxyl group; an alkyl group; a cycloalkyl group; an alkoxy group; a phosphine oxide group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; an alkenyl group; a silyl group; a boron group; an amine group; an aryl group; or a heterocyclic group, or substituted with a substituent in which two or more of the above-exemplified substituents are connected, or having no substituents. For example, "a substituent connected with two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent in which two phenyl groups are connected.

[0049] In one embodiment of the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the group consisting of deuterium; an alkyl group; an aryl group; and a heterocyclic group, or substituted with a substituent in which two or more of the substituents exemplified above are connected, or having no substituents.

[0050] Examples of the above substituents are described below, but are not limited thereto.

[0051] Examples of the above substituents are described below, but are not limited thereto.

[0052] In this specification, examples of halogen groups include a fluoro group (-F), a chloro group (-Cl), a bromo group (-Br), or an iodo group (-I).

[0053] In this specification, the silyl group is -SiY a Y b Y c It can be represented by the chemical formula of Y a , Y b and Y c Each may be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0054] In this specification, the boron group is -BY d Y e It can be represented by the chemical formula of Y d and Y e Each may be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group.

[0055] In the present specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an n-pentyl group, a hexyl group, an n-hexyl group, a heptyl group, an n-heptyl group, an octyl group, an n-octyl group, etc.

[0056] In the present specification, the alkoxy group may be linear, branched, or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto.

[0057] Substituents comprising alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight-chain and branched forms.

[0058] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 6. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, and styrenyl.

[0059] In the present specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkynyl group is 2 to 10.

[0060] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and an adamantyl group.

[0061] In the present specification, the amine group is -NH2, and the amine group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The carbon number of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the carbon number of the amine group is 1 to 20. According to one embodiment, the carbon number of the amine group is 1 to 10. Specific examples of substituted amine groups include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a 9,9-dimethylfluorenylphenylamine group, a pyridylphenylamine group, a diphenylamine group, a phenylpyridylamine group, a naphthylamine group, a biphenylamine group, anthracenylamine group, a dibenzofuranylphenylamine group, a 9-methylanthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like.

[0062] In the present specification, the aryl group is not particularly limited, but is preferably one having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. According to one embodiment, the monocyclic aryl group has 6 to 30 carbon atoms. According to one embodiment, the monocyclic aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, etc., but is not limited thereto. According to one embodiment, the monocyclic aryl group has 10 to 30 carbon atoms. According to one embodiment, the monocyclic aryl group has 10 to 20 carbon atoms. The above polycyclic aryl group may include, but is not limited to, a naphthyl group, anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, and the like.

[0063] In the present specification, the substituted aryl group may include a structure in which an aliphatic hydrocarbon ring is condensed with the aryl group. According to one embodiment, the substituted aryl group may include a tetrahydronaphthalene group, and more specifically, (1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene group), but is not limited thereto.

[0064] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0065] When the above fluorenyl group is substituted, , , Spirofluorenyl group of etc. (9,9-dimethylfluorenyl group) and It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group), but is not limited thereto.

[0066] In this specification, the aryl group among the aryloxy groups may be applied to the description of the aryl group described above.

[0067] In this specification, the description regarding the alkyl group described above may be applied to the alkyl group among the alkylthioxy group and alkylsulfoxy group.

[0068] In this specification, the description regarding the aryl group described above can be applied to the aryl group among the arylthioxy group and arylsulfoxy group.

[0069] In the present specification, a heterocyclic group is a ring group containing at least one of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like.

[0070] In this specification, the description of the heterocyclic group described above may be applied, except that the heteroaryl group is aromatic.

[0071] In this specification, the description of the heterocyclic group described above may be applied, except that the heteroaryl group is aromatic.

[0072] In this specification, the description of the aryl group may be applied to the divalent to tetravalent arylene group, except that the divalent to tetravalent arylene group is divalent to tetravalent.

[0073] In this specification, the description of the above heterocyclic group may be applied to the divalent to tetravalent heterocyclic group, except that the heterocyclic group is divalent to tetravalent.

[0074] In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, “ring” means a hydrocarbon ring; or a heterocycle.

[0075] The above hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group.

[0076] In the present specification, forming a ring by bonding with adjacent groups means forming a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof by bonding with adjacent groups. The hydrocarbon ring means a ring composed only of carbon and hydrogen atoms. The heterocycle means a ring containing one or more elements selected from N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle, and the aromatic heterocycle may be monocyclic or polycyclic.

[0077] In this specification, an aliphatic hydrocarbon ring means a non-aromatic ring composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0078] In this specification, an aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. In this specification, an aromatic hydrocarbon ring can be interpreted to have the same meaning as an aryl group.

[0079] In the present specification, an aliphatic heterocycle means an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocane, and thiocane.

[0080] In this specification, an aromatic heterocycle means an aromatic ring containing at least one heteroatom. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazanaphthalene, dryazaindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, Examples include, but are not limited to, imidazopyridine, phenoxazine, indolocarbazole, and indenocarbazole.

[0081] In this specification, the deuterium substitution rate (Dn) means the ratio of deuterium substitution for hydrogen in a structural formula, and can be expressed as a %.

[0082] Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention may be modified in various ways, and the scope of the present invention is not limited to the embodiments described below.

[0083] In this specification, the chemical formula 1 is any one of the chemical formulas 1-1 to 1-4 below.

[0084] [Chemical Formula 1]

[0085]

[0086] In the above chemical formula 1,

[0087] HAr is a group represented by the following chemical formula 2,

[0088] [Chemical Formula 2]

[0089]

[0090] Y is O or S,

[0091] R1 and R2 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted aliphatic ring group; a substituted or unsubstituted aliphatic and aromatic condensed ring group; or a group connected to L1,

[0092] R3 to R6 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted aliphatic ring group; a substituted or unsubstituted aliphatic and aromatic condensed ring group; or a group connected to L1, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted ring,

[0093] At least one of R1 to R6 is a group connected to L1,

[0094] Ar1 is a group represented by the following chemical formula 3,

[0095] [Chemical Formula 3]

[0096]

[0097] X is O, S or It is indicated by ,

[0098] One of R7 and R8 is connected to L1,

[0099] One of R7 and R8 is connected to L2,

[0100] Among R7 and R8, the group not connected to L1 or L2 is deuterium,

[0101] n and m are integers from 0 to 8, respectively, and n+m is an integer greater than or equal to 2.

[0102] L1 and L2 are the same or different and each independently a direct bond; a substituted or unsubstituted divalent to tetravalent arylene group; or a substituted or unsubstituted divalent to tetravalent heteroarylene group,

[0103] a to c are integers from 1 to 3, respectively,

[0104] If a is 2 or more, HAr are equal or different,

[0105] If c is 2 or greater, the structures within the brackets are either the same or different.

[0106] The compound represented by the above chemical formula contains a nitrile group, which increases the dipole moment of the molecule, thereby controlling the electron transfer rate to the light-emitting layer, thereby imparting long-life characteristics to the organic light-emitting device. In addition, it has a structure in which a substituent represented by chemical formula 2, a substituent represented by chemical formula 3, and a nitrile group are bonded, thereby having an optimal LUMO orbital suitable as a compound used in an electron injection or electron transport layer, and exhibits efficiency-improving characteristics in organic light-emitting devices.

[0107] In one embodiment of the present specification, the chemical formula 2 is one of the following chemical formulas 2-1 and 2-2.

[0108] [Chemical Formula 2-1]

[0109]

[0110] [Chemical Formula 2-2]

[0111]

[0112] In the above chemical formulas 2-1 and 2-2,

[0113] Above represents a portion connected to L1 of the above chemical formula 1.

[0114] In the above chemical formulas 2-1 and 2-2, the definitions of Y and R1 to R6 are as defined in the above chemical formula 2.

[0115] In one embodiment of the present specification, the chemical formula 3 is any one of the following chemical formulas 3-1 to 3-4.

[0116] [Chemical Formula 3-1]

[0117]

[0118] [Chemical Formula 3-2]

[0119]

[0120] [Chemical Formula 3-3]

[0121]

[0122] [Chemical Formula 3-4]

[0123]

[0124] [Chemical Formula 3-5]

[0125]

[0126] [Chemical Formula 3-6]

[0127]

[0128] In the above chemical formulas 3-1 to 3-6,

[0129] The above D stands for deuterium,

[0130] One of the above R7' and R8' is connected to L1, and the other is connected to L2,

[0131] n' and m' are integers from 0 to 6,

[0132] "n" and "m" are integers from 0 to 7,

[0133] X, n and m are as defined in the above chemical formula 3.

[0134] In one embodiment of the present specification, the chemical formula 3 is any one of the following chemical formulas 3A to 3C.

[0135] [Chemical Formula 3A]

[0136]

[0137] [Chemical Formula 3B]

[0138]

[0139] [Chemical Formula 3C]

[0140]

[0141] R7, R8, n and m are as defined in the above chemical formula 3.

[0142] In one embodiment of the present specification, R1 to R6 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms; a substituted or unsubstituted aliphatic and aromatic condensed ring having 6 to 30 carbon atoms; or a group connected to L1.

[0143] In one embodiment of the present specification, R1 to R6 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; a substituted or unsubstituted aliphatic ring having 3 to 20 carbon atoms; a substituted or unsubstituted aliphatic and aromatic condensed ring having 6 to 20 carbon atoms; or a group connected to L1.

[0144] In one embodiment of the present specification, R1 to R6 are the same as or different from each other, and are each independently hydrogen; deuterium; an alkyl group having 1 to 12 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; a heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium; an aliphatic ring having 3 to 20 carbon atoms substituted or unsubstituted with deuterium; a ring in which an aliphatic and an aromatic group are condensed and substituted or unsubstituted with deuterium; or a group connected to L1.

[0145] In one embodiment of the present specification, R1 to R6 are the same as or different from each other, and each independently hydrogen; deuterium; a methyl group substituted or unsubstituted with deuterium; an ethyl group substituted or unsubstituted with deuterium; a propyl group substituted or unsubstituted with deuterium; a butyl group substituted or unsubstituted with deuterium; a pentyl group substituted or unsubstituted with deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a carbazolyl group substituted or unsubstituted with deuterium; a dibenzofuranyl group substituted or unsubstituted with deuterium; a dibenzothiophenyl group substituted or unsubstituted with deuterium; a cyclopropyl group substituted or unsubstituted with deuterium; a cyclobutyl group substituted or unsubstituted with deuterium; A cyclopentyl group substituted or unsubstituted with deuterium; a cyclohexyl group substituted or unsubstituted with deuterium; a tetrahydronaphthyl group substituted or unsubstituted with deuterium; or a group connected to L1.

[0146] In one embodiment of the present specification, R1 to R6 are the same as or different from each other, and are each independently hydrogen; deuterium; a methyl group; an ethyl group; a propyl group; a butyl group; a pentyl group; a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a phenanthrenyl group; a carbazolyl group; a dibenzofuranyl group; a dibenzothiophenyl group; a cyclopropyl group; a cyclobutyl group; a cyclopentyl group; a cyclohexyl group; a tetrahydronaphthyl group; or a group connected to L1.

[0147] In one embodiment of the present specification, at least one of R1 to R6 is a group connected to L1.

[0148] In one embodiment of the present specification, at least two of R1 to R6 are groups connected to L1.

[0149] In one embodiment of the present specification, at least three of R1 to R6 are groups connected to L1.

[0150] In one embodiment of the present specification, at least one of the groups not bonded to L1 among R1 to R6 is a substituted or unsubstituted aryl group.

[0151] In one embodiment of the present specification, at least one of the groups not bonded to L1 among R1 to R6 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0152] In one embodiment of the present specification, at least one of the groups not bonded to L1 among R1 to R6 is a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium.

[0153] In one embodiment of the present specification, at least one of the groups not bonded to L1 among R1 to R6 is a phenyl group; a biphenyl group; or a naphthyl group.

[0154] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond; or a divalent to tetravalent substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent to tetravalent heteroarylene group having 2 to 20 carbon atoms.

[0155] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond; a divalent to tetravalent substituted or unsubstituted arylene group having 6 to 12 carbon atoms; or a divalent to tetravalent substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms.

[0156] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; a divalent to tetravalent substituted or unsubstituted phenylene group; a divalent to tetravalent substituted or unsubstituted biphenylene group; or a divalent to tetravalent substituted or unsubstituted naphthylene group.

[0157] In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represent a direct bond; a phenylene group substituted or unsubstituted with a divalent to tetravalent deuterium; a biphenylene group substituted or unsubstituted with a divalent to tetravalent deuterium; or a naphthylene group substituted or unsubstituted with a divalent to tetravalent deuterium.

[0158] In one embodiment of the present specification, a to c are each an integer of 1 to 3.

[0159] In one embodiment of the present specification, a is 1.

[0160] In one embodiment of the present specification, a is 2.

[0161] In one embodiment of the present specification, a is 3.

[0162] In one embodiment of the present specification, b is 1.

[0163] In one embodiment of the present specification, b is 2.

[0164] In one embodiment of the present specification, b is 3.

[0165] In one embodiment of the present specification, c is 1.

[0166] In one embodiment of the present specification, c is 2.

[0167] In one embodiment of the present specification, c is 3.

[0168] In one embodiment of the present specification, a to c are 1.

[0169] In one embodiment of the present specification, n and m are each integers from 0 to 8.

[0170] In one embodiment of the present specification, n is 0.

[0171] In one embodiment of the present specification, n is 1.

[0172] In one embodiment of the present specification, n is 2.

[0173] In one embodiment of the present specification, n is 3.

[0174] In one embodiment of the present specification, n is 4.

[0175] In one embodiment of the present specification, n is 5.

[0176] In one embodiment of the present specification, n is 6.

[0177] In one embodiment of the present specification, n is 7.

[0178] In one embodiment of the present specification, n is 8.

[0179] In one embodiment of the present specification, m is 0.

[0180] In one embodiment of the present specification, m is 1.

[0181] In one embodiment of the present specification, m is 2.

[0182] In one embodiment of the present specification, m is 3.

[0183] In one embodiment of the present specification, m is 4.

[0184] In one embodiment of the present specification, m is 5.

[0185] In one embodiment of the present specification, m is 6.

[0186] In one embodiment of the present specification, m is 7.

[0187] In one embodiment of the present specification, m is 8.

[0188] In one embodiment of the present specification, n+m is an integer greater than or equal to 2.

[0189] In one embodiment of the present specification, n+m is an integer from 2 to 16.

[0190] In one embodiment of the present specification, n' and m' are integers from 0 to 6.

[0191] In one embodiment of the present specification, n' is 0.

[0192] In one embodiment of the present specification, n' is 1.

[0193] In one embodiment of the present specification, n' is 2.

[0194] In one embodiment of the present specification, n' is 3.

[0195] In one embodiment of the present specification, n' is 4.

[0196] In one embodiment of the present specification, n' is 5.

[0197] In one embodiment of the present specification, n' is 6.

[0198] In one embodiment of the present specification, m' is 0.

[0199] In one embodiment of the present specification, m' is 1.

[0200] In one embodiment of the present specification, m' is 2.

[0201] In one embodiment of the present specification, m' is 3.

[0202] In one embodiment of the present specification, m' is 4.

[0203] In one embodiment of the present specification, m' is 5.

[0204] In one embodiment of the present specification, m' is 6.

[0205] In one embodiment of the present specification, "n" and "m" are integers from 0 to 7.

[0206] In one embodiment of the present specification, the n" is 0.

[0207] In one embodiment of the present specification, the n" is 1.

[0208] In one embodiment of the present specification, the n" is 2.

[0209] In one embodiment of the present specification, n" is 3.

[0210] In one embodiment of the present specification, n" is 4.

[0211] In one embodiment of the present specification, n" is 5.

[0212] In one embodiment of the present specification, n" is 6.

[0213] In one embodiment of the present specification, n" is 7.

[0214] In one embodiment of the present specification, the m" is 0.

[0215] In one embodiment of the present specification, the m" is 1.

[0216] In one embodiment of the present specification, the m" is 2.

[0217] In one embodiment of the present specification, the m" is 3.

[0218] In one embodiment of the present specification, the m" is 4.

[0219] In one embodiment of the present specification, the m" is 5.

[0220] In one embodiment of the present specification, the m" is 6.

[0221] In one embodiment of the present specification, the m" is 7.

[0222] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 0% to 100%.

[0223] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 10% to 100%.

[0224] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 40% to 100%.

[0225] According to one embodiment of the present specification, when the chemical formula 1 contains deuterium, the following effects are provided. Specifically, the physicochemical properties, such as chemical bond lengths, related to deuterium are different from those of hydrogen, and the elongation amplitude of the CD bond is smaller than that of the CH bond, so the van der Waals radius of deuterium is smaller than that of hydrogen, and in general, the CD bond can be shown to be shorter and stronger than the CH bond. Therefore, when hydrogen at a substitutable position in the chemical formula 1 is substituted with deuterium, the energy of the ground state is lowered, and as the bond length of deuterium and carbon is shortened, the molecular hardcore volume is reduced, and accordingly, the electrical polarizability can be reduced, and the intermolecular interaction can be weakened, thereby increasing the thin film volume. In addition, these characteristics can have the effect of lowering the crystallinity of the thin film, that is, creating an amorphous state, and can be generally effective in increasing the lifespan and operating characteristics of organic light-emitting devices, and heat resistance can be improved compared to conventional organic light-emitting devices.

[0226] According to one embodiment of the present specification, the chemical formula 1 is any one of the following compounds.

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239] The substituent of the compound of the above chemical formula 1 can be combined by a method known in the art, and the type, position or number of the substituent can be changed according to a technique known in the art.

[0240] In addition, by introducing various substituents into the core structure as described above, compounds having the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the core structure, a material satisfying the conditions required for each organic layer can be synthesized.

[0241] In addition, an organic light-emitting device according to the present invention is an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, characterized in that one or more of the organic layers includes the compound described above.

[0242] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

[0243] The above compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0244] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously injects holes and transports holes, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers or a larger number of organic layers.

[0245] In the organic light-emitting device of the present invention, the organic layer includes a hole blocking layer, an electron injection layer, an electron transport layer, or an electron injection and transport layer.

[0246] In the organic light-emitting device of the present invention, the hole blocking layer, electron injection layer, electron transport layer, or electron injection and transport layer contains the compound.

[0247] In the organic light-emitting device of the present invention, the electron injection and transport layer may include the compound of the present specification together with a metal complex compound. In this case, a lithium complex or the like may be used as the metal complex, but is not limited thereto.

[0248] In the organic light-emitting device of the present invention, the electron injection and transport layer comprises the compound of the present specification together with a metal complex compound in a weight ratio of 1:5 to 5:1.

[0249] In the organic light-emitting device of the present invention, the electron injection and transport layer comprises the compound of the present specification together with a metal complex compound in a weight ratio of 1:3 to 3:1.

[0250] In the organic light-emitting device of the present invention, the electron injection and transport layer comprises the compound of the present specification together with a metal complex compound in a weight ratio of 1:2 to 2:1.

[0251] In the organic light-emitting device of the present invention, the organic layer may include at least one layer among a hole blocking layer, an electron transport layer, an electron injection layer, and a layer that simultaneously injects and transports electrons, and at least one layer among the layers may include a compound represented by the chemical formula 1.

[0252] In another organic light-emitting device, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by the chemical formula 1.

[0253] In the organic light-emitting device of the present invention, the organic layer may include at least one layer among a hole injection layer, a hole transport layer, and a layer that simultaneously injects holes and transports holes, and at least one layer among the layers may include a compound represented by the chemical formula 1.

[0254] In another organic light-emitting device, the organic layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include a compound represented by the chemical formula 1.

[0255] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0256] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0257] (1) Anode / hole transport layer / light emitting layer / cathode

[0258] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0259] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0260] (4) Anode / hole transport layer / light emitting layer / electron transport layer / cathode

[0261] (5) Anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0262] (6) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0263] (7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0264] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0265] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0266] (10) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0267] (11) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0268] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0269] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0270] (14) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0271] (15) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0272] (16) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0273] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0274] (18) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0275] The structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

[0276] Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode (2), an organic layer (3), and a second electrode (4) are sequentially laminated on a substrate (1). In this structure, the compound represented by the chemical formula 1 may be included in the organic layer (3).

[0277] FIG. 2 illustrates the structure of an organic light-emitting device in which a first electrode (2), a hole injection layer (5), a first hole transport layer (6), a second hole transport layer (7), a light-emitting layer (8), an electron injection and transport layer (9), and a second electrode (4) are sequentially laminated on a substrate (1). In this structure, the compound represented by the chemical formula 1 may be included in the electron injection and transport layer (9).

[0278] For example, the organic light-emitting device according to the present invention can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and then forming an organic layer including at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0279] The above organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the above organic layer may be manufactured with a smaller number of layers using various polymer materials by a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0280] The above anode is an electrode that injects holes, and as the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0281] The above cathode is an electrode that injects electrons, and the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0282] The above hole injection layer is a layer that facilitates the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrine, oligothiophene, arylamine-based organic compounds, hexanitrilehexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and conductive polymers such as polyaniline and polythiophene. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the above hole injection layer is 1 nm or more, there is an advantage of being able to prevent the hole injection characteristics from being deteriorated, and if it is 150 nm or less, there is an advantage of being able to prevent the driving voltage from being increased to improve the movement of holes due to the thickness of the hole injection layer being too thick.

[0283] According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-1.

[0284] [Chemical formula HI-1]

[0285]

[0286] In the above chemical formula HI-1,

[0287] The above R403 to R406 are the same or different from each other, and each independently is 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 amine group; a substituted or unsubstituted heteroaryl group; and a combination thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0288] L403 is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0289] l403 is an integer from 1 to 3, and if l403 is 2 or greater, L403 are equal to or different from each other.

[0290] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and a group consisting of combinations thereof.

[0291] One of the choices is made.

[0292] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms; or a heteroaryl group having 3 to 30 carbon atoms which is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms.

[0293] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents a phenyl group, a biphenyl group, a naphthyl group, or a carbazole group substituted or unsubstituted with a phenyl group.

[0294] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents a phenyl group or a carbazole group substituted or unsubstituted with a phenyl group.

[0295] According to one embodiment of the present specification, the L403 is an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms substituted with an arylene group.

[0296] According to one embodiment of the present specification, the L403 is a divalent carbazole group substituted or unsubstituted with a phenylene group, a divalent biphenyl group, a divalent dimethylfluorene group, or an aryl group.

[0297] According to one embodiment of the present specification, the L403 is a divalent dimethylfluorene group.

[0298] According to one embodiment of the present specification, the chemical formula HI-1 is selected from the following compounds.

[0299]

[0300]

[0301] According to one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound represented by the following chemical formula HT-1.

[0302] [Chemical formula HT-1]

[0303]

[0304] In the above chemical formula HT-1,

[0305] At least one of X'1 to X'6 is N, and the rest are CH,

[0306] R309 to R314 are the same or different, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring.

[0307] According to one embodiment of the present specification, X'1 to X'6 are N.

[0308] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0309] According to one embodiment of the present specification, the chemical formula HT-1 is the following compound.

[0310]

[0311] The above-mentioned hole transport layer can play a role in facilitating hole transport. A hole transport material capable of transporting holes from the anode or hole injection layer and transferring them to the light-emitting layer, and a material with high hole mobility, is suitable. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.

[0312] According to one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound represented by the following chemical formula HT-2.

[0313] [Chemical formula HT-2]

[0314]

[0315] In the above chemical formula HT-2,

[0316] R315 to R317 are the same or different, and each independently represent one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0317] r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same as or different from each other,

[0318] r316 is an integer from 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

[0319] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

[0320] 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.

[0321] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or are combined with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0322] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a phenyl group, or are combined with an adjacent group to form an indene substituted with a methyl group.

[0323] According to one embodiment of the present specification, the chemical formula HT-2 is represented by the following compound.

[0324]

[0325]

[0326] An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

[0327] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be formed using the aforementioned spiro compound or a material known in the art.

[0328] The above-mentioned light-emitting layer can emit red, green, or blue light, and can be made of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0329] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compound-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compound-containing compounds include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

[0330] 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.

[0331] [Chemical Formula H-1]

[0332]

[0333] In the above chemical formula H-1,

[0334] L20 and L21 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0335] Ar20 and Ar21 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0336] 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,

[0337] r201 is an integer from 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same as or different from each other.

[0338] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represents a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0339] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represent a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; a divalent dibenzofuran group; or a divalent dibenzothiophene group.

[0340] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0341] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0342] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or, it is a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0343] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group unsubstituted or substituted with a deuterium or naphthyl group; a biphenyl group unsubstituted or substituted with a deuterium group; a terphenyl group; a naphthyl group unsubstituted or substituted with a deuterium or phenyl group; a thiophene group unsubstituted or substituted with a phenyl group; a phenanthrene group; a dibenzofuran group; a naphthobenzofuran group; a dibenzothiophene group; or a naphthobenzothiophene group.

[0344] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with a deuterium or naphthyl group; or a naphthyl group unsubstituted or substituted with a deuterium or phenyl group.

[0345] According to one embodiment of the present specification, R201 is a phenyl group.

[0346]

[0347]

[0348] When the light-emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymer, or PPV polymer can be used as a light-emitting dopant, but is not limited thereto.

[0349] According to one embodiment of the present specification, the dopant includes, but is not limited to, a compound represented by the following chemical formula D-1.

[0350] [Chemical Formula D-1]

[0351]

[0352] In the above chemical formula D-1,

[0353] T1 to T6 are the same or different and are each independently hydrogen; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0354] t5 and t6 are integers from 1 to 4, respectively.

[0355] If the above t5 is 2 or more, the two or more T5 are the same or different from each other,

[0356] When the above t6 is 2 or more, the two or more T6 are the same or different from each other.

[0357] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a silyl group substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0358] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently represent hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a silyl group substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0359] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently hydrogen; a trimethylsilyl group; an isopropyl group; a phenyl group substituted with a cyano group; or a phenyl group substituted with a methyl group.

[0360] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

[0361]

[0362]

[0363] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.

[0364] The above electron transport layer can play a role in facilitating electron transport. As the electron transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, there is an advantage in that the electron transport characteristics can be prevented from being deteriorated, and when the thickness of the electron transport layer is 50 nm or less, there is an advantage in that the driving voltage can be prevented from increasing to improve electron movement due to the electron transport layer being too thick.

[0365] The above electron injection layer can play a role in facilitating electron injection. As the electron injection material, a compound having the ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect for the light-emitting layer or light-emitting material, a compound that prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and an excellent thin film forming ability is preferable. Specifically, examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0366] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

[0367] In one embodiment of the present specification, the metal complex compound may be selected from among alkali metal compounds and alkaline earth metal compounds, but is not limited thereto.

[0368] According to one embodiment of the present specification, the metal complex is a lithium-based metal complex, but is not limited thereto.

[0369] According to one embodiment of the present specification, the metal complex is represented by the following compound.

[0370]

[0371] The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0372] According to one embodiment of the present specification, the compound used in the hole blocking layer is the same as or different from the compound used in the electron injection layer, the electron transport layer, and the electron injection and transport layer.

[0373] The organic light-emitting device according to the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0374] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

[0375]

[0376] The method for preparing the compound of the above chemical formula 1 and the preparation of an organic light-emitting device using the compound are specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0377]

[0378] [Manufacturing example]

[0379] Manufacturing Example 1-1: Manufacturing of Compound E1

[0380]

[0381] In a nitrogen atmosphere, E1-A (20 g, 41.4 mmol) and E1-B (14.8 g, 41.4 mmol) were added to 400 mL of Diox, stirred, and refluxed. Then, potassium triphosphate (26.3 g, 124.1 mmol) dissolved in 26 mL of water was added, and after sufficient stirring, dibenzylideneacetonepalladium (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.5 mmol) were added. After 6 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 841 mL of chloroform, dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a yellow solid compound E1 (4.2 g, 15%, MS: [M+H]+ = 678).

[0382]

[0383] Manufacturing Example 1-2: Preparation of Compound E2

[0384]

[0385] Compound E2 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0386] MS: [M+H]+ = 754

[0387]

[0388] Manufacturing Example 1-3: Preparation of compound E3

[0389]

[0390] Compound E3 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0391] MS: [M+H]+ = 804

[0392]

[0393] Manufacturing Example 1-4: Preparation of Compound E4

[0394]

[0395] Compound E4 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0396] MS: [M+H]+ = 754

[0397]

[0398] Manufacturing Example 1-5: Preparation of Compound E5

[0399]

[0400] Compound E5 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0401] MS: [M+H]+ = 760

[0402]

[0403] Manufacturing Example 1-6: Preparation of compound E6

[0404]

[0405] Compound E6 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0406] MS: [M+H]+ = 754

[0407]

[0408] Manufacturing Example 1-7: Preparation of compound E7

[0409]

[0410] Compound E7 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0411] MS: [M+H]+ = 678

[0412]

[0413] Manufacturing Example 1-8: Preparation of compound E8

[0414]

[0415] Compound E8 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0416] MS: [M+H]+ = 754

[0417]

[0418] Manufacturing Example 1-9: Preparation of compound E9

[0419]

[0420] Compound E9 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0421] MS: [M+H]+ = 779

[0422]

[0423] Manufacturing Example 1-10: Preparation of compound E10

[0424]

[0425] Compound E10 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0426] MS: [M+H]+ = 754

[0427]

[0428] Manufacturing Example 1-11: Preparation of compound E11

[0429]

[0430] Compound E11 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0431] MS: [M+H]+ = 728

[0432]

[0433] Manufacturing Example 1-12: Preparation of compound E12

[0434]

[0435] Compound E12 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0436] MS: [M+H]+ = 694

[0437]

[0438] Manufacturing Example 1-13: Preparation of compound E13

[0439]

[0440] Compound E13 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0441] MS: [M+H]+ = 745

[0442]

[0443] Manufacturing Example 1-14: Preparation of compound E14

[0444]

[0445] Compound E14 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0446] MS: [M+H]+ = 872

[0447]

[0448] Manufacturing Example 1-15: Preparation of compound E15

[0449]

[0450] Compound E15 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0451] MS: [M+H]+ = 770

[0452]

[0453] Manufacturing Example 1-16: Preparation of compound E16

[0454]

[0455] Compound E16 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0456] MS: [M+H]+ = 848

[0457]

[0458] Manufacturing Example 1-17: Preparation of compound E17

[0459]

[0460] Compound E17 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0461] MS: [M+H]+ = 750

[0462]

[0463] Manufacturing Example 1-18: Preparation of compound E18

[0464]

[0465] Compound E18 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0466] MS: [M+H]+ = 922

[0467]

[0468] Manufacturing Example 1-19: Preparation of compound E19

[0469]

[0470] Compound E19 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0471] MS: [M+H]+ = 683

[0472]

[0473] Manufacturing Example 1-20: Preparation of compound E20

[0474]

[0475] Compound E20 was prepared in the same manner as in Manufacturing Example 1-1, except that each starting material was prepared as in the above reaction formula.

[0476] MS: [M+H]+ = 763

[0477]

[0478] Manufacturing Example 1-21: Preparation of compound E21

[0479]

[0480] In a nitrogen atmosphere, E21-A (20 g, 40 mmol) and E21-B (14.3 g, 40 mmol) were added to 400 mL of Diox, stirred, and refluxed. Then, potassium triphosphate (25.5 g, 120.1 mmol) dissolved in 26 mL of water was added, and after sufficient stirring, dibenzylideneacetonepalladium (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol) were added. After 7 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 834 mL of chloroform, dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a yellow solid compound E21 (4.2 g, 15%, MS: [M+H]+ = 694).

[0481]

[0482] Manufacturing Example 1-22: Manufacturing of compound E22

[0483]

[0484] Compound E22 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0485] MS: [M+H]+ = 754

[0486]

[0487] Manufacturing Example 1-23: Preparation of compound E23

[0488]

[0489] Compound E23 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0490] MS: [M+H]+ = 804

[0491]

[0492] Manufacturing Example 1-24: Preparation of compound E24

[0493]

[0494] Compound E24 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0495] MS: [M+H]+ = 754

[0496]

[0497] Manufacturing Example 1-25: Preparation of compound E25

[0498]

[0499] Compound E25 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0500] MS: [M+H]+ = 760

[0501]

[0502] Manufacturing Example 1-26: Manufacturing of compound E26

[0503]

[0504] Compound E26 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0505] MS: [M+H]+ = 754

[0506]

[0507] Manufacturing Example 1-27: Preparation of compound E27

[0508]

[0509] Compound E7 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0510] MS: [M+H]+ = 678

[0511]

[0512] Manufacturing Example 1-28: Preparation of compound E28

[0513]

[0514] Compound E28 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0515] MS: [M+H]+ = 754

[0516]

[0517] Manufacturing Example 1-29: Preparation of compound E29

[0518]

[0519] Compound E29 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0520] MS: [M+H]+ = 779

[0521]

[0522] Manufacturing Example 1-30: Preparation of compound E30

[0523]

[0524] Compound E30 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0525] MS: [M+H]+ = 754

[0526]

[0527] Manufacturing Example 1-31: Preparation of compound E31

[0528]

[0529] Compound E31 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0530] MS: [M+H]+ = 728

[0531]

[0532] Manufacturing Example 1-32: Preparation of compound E32

[0533]

[0534] Compound E32 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0535] MS: [M+H]+ = 694

[0536]

[0537] Manufacturing Example 1-33: Preparation of compound E33

[0538]

[0539] Compound E33 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0540] MS: [M+H]+ = 745

[0541]

[0542] Manufacturing Example 1-34: Preparation of compound E34

[0543]

[0544] Compound E34 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0545] MS: [M+H]+ = 872

[0546]

[0547] Manufacturing Example 1-35: Preparation of compound E35

[0548]

[0549] Compound E35 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0550] MS: [M+H]+ = 770

[0551]

[0552] Manufacturing Example 1-36: Preparation of compound E36

[0553]

[0554] Compound E36 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0555] MS: [M+H]+ = 848

[0556]

[0557] Manufacturing Example 1-37: Preparation of compound E37

[0558]

[0559] Compound E37 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0560] MS: [M+H]+ = 750

[0561]

[0562] Manufacturing Example 1-38: Preparation of compound E38

[0563]

[0564] Compound E38 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0565] MS: [M+H]+ = 922

[0566]

[0567] Manufacturing Example 1-39: Preparation of compound E39

[0568]

[0569] Compound E39 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0570] MS: [M+H]+ = 683

[0571]

[0572] Manufacturing Example 1-40: Preparation of compound E40

[0573]

[0574] Compound E40 was prepared in the same manner as in Manufacturing Example 1-21, except that each starting material was prepared as in the above reaction formula.

[0575] MS: [M+H]+ = 763

[0576]

[0577] [Example]

[0578] Example 1-1

[0579] A glass substrate coated with a 1000 Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was filtered twice using a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0580] On the ITO transparent electrode thus prepared, the following compound HI-A was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, the following compound HAT at 50 Å and the following compound HT-A at 60 Å were sequentially vacuum deposited to form a first hole transport layer and a second hole transport layer.

[0581] Next, a light-emitting layer was formed by vacuum-depositing the following compounds BH and BD at a weight ratio of 25:1 to a film thickness of 200 Å on the second hole transport layer.

[0582] On the above-mentioned light-emitting layer, the previously prepared compound E1 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 350 Å. On the above-mentioned electron injection and transport layer, lithium fluoride (LiF) was sequentially deposited with a thickness of 10 Å and aluminum was sequentially deposited with a thickness of 1000 Å to form a cathode.

[0583]

[0584] In the above process, the deposition rate of organic materials was maintained at 0.4 Å / sec to 0.9 Å / sec, the lithium fluoride of the cathode was maintained at 0.3 Å / sec, and the aluminum was maintained at 2 Å / sec, and the vacuum during deposition was 1 x 10 -7 torr to 5 x 10 -5 torr, and an organic light-emitting device was manufactured.

[0585] Examples 1-2 to 1-20

[0586] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that compounds E2 to E20 described in Table 1 below were used instead of compound E1 of Example 1-1.

[0587] Comparative Examples 1-1 to 1-6

[0588] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that compounds ET-1 to ET-6 in Table 1 below were used instead of compound E1 in Example 1-1. The structures of compounds ET-1 to ET-6 in Table 1 below are as follows.

[0589]

[0590] Example 1-21

[0591] A glass substrate coated with a 1000 Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was filtered twice using a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0592] On the ITO transparent electrode thus prepared, the following compound HI-A' was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, the following compound HAT 50 Å and the following compound HT-A' 60 Å were sequentially vacuum deposited to form a first hole transport layer and a second hole transport layer.

[0593] Next, the following compounds BH' and BD' were vacuum-deposited at a weight ratio of 25:1 to form a light-emitting layer with a film thickness of 200 Å on the second hole transport layer.

[0594] On the above-mentioned light-emitting layer, the previously prepared compound E21 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 350 Å. On the above-mentioned electron injection and transport layer, lithium fluoride (LiF) was sequentially deposited with a thickness of 10 Å and aluminum was sequentially deposited with a thickness of 1000 Å to form a cathode.

[0595]

[0596] In the above process, the deposition rate of organic materials was maintained at 0.4 Å / sec to 0.9 Å / sec, the lithium fluoride of the cathode was maintained at 0.3 Å / sec, and the aluminum was maintained at 2 Å / sec, and the vacuum during deposition was 1 * 10 -7 torr or 5 * 10 -5 torr, and an organic light-emitting device was manufactured.

[0597]

[0598] Examples 1-21 to 1-40

[0599] An organic light-emitting device was manufactured in the same manner as in Example 1-21, except that compounds E22 to E40 described in Table 1 below were used instead of compound E21 of Example 1-21.

[0600]

[0601] Comparative Examples 1-7 to 1-17

[0602] An organic light-emitting device was manufactured in the same manner as in Example 1-21, except that compounds ET-7 to ET-17 in Table 1 below were used instead of compound E1 in Example 1-21. The structures of compounds ET-7 to ET-17 in Table 1 below are as follows.

[0603]

[0604] [Experimental Example]

[0605] 10 mA / cm for the organic light-emitting devices manufactured in Examples 1-1 to 1-40 and Comparative Examples 1-1 to 1-17 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time (T90) at which the initial luminance reaches 90% of the current density was measured. The results are shown in Table 1 below.

[0606]

[0607] Distinctive compound voltage (V) (@10 mA / cm) 2 )Efficiency (cd / A) (@10 mA / cm 2 )Color coordinates (x, y)Lifespan (hr) (T90 at 20 mA / cm 2) Example 1-1E14.284.43(0.138, 0.111)213 Example 1-2E24.194.56(0.138, 0.111)194 Example 1-3E34.324.34(0.138, 0.111)209 Example 1-4E44.244.47(0.138, 0.110)204 Example 1-5E54.324.38(0.138, 0.111)202 Example 1-6E64.154.65(0.138, 0.111)186 Example 1-7E74.194.70(0.138, 0.111)174 Example 1-8E84.244.63(0.138, 0.110)190Example 1-9E94.454.44(0.138, 0.111)266Example 1-10E104.324.53(0.138, 0.110)209Example 1-11E114.334.50(0.138, 0.111)213Example 1-12E124.294.59(0.138, 0.111)196Example 1-13E134.324.37(0.138, 0.115)222Example 1-14E144.494.35(0.138, 0.111)245 Example 1-15E154.294.60(0.138, 0.111)194 Example 1-16E164.424.44(0.138, 0.115)225 Example 1-17E174.494.26(0.138, 0.111)202 Example 1-18E184.584.39(0.138, 0.115)214 Example 1-19E194.284.43(0.138, 0.111)226 Example 1-20E204.194.56(0.138, 0.115)207 Example 1-21E214.354.29(0.138, 0.111)224 Example 1-22E224.314.33(0.138, 0.111)220 Example 1-23E234.394.20(0.138, 0.111)220 Example 1-24E244.394.25(0.138, 0.110)233 Example 1-25E254.444.16(0.138, 0.111)228 Example 1-26E264.364.33(0.138, 0.111)224 Example 1-27E274.404.38(0.138, 0.111)198 Example 1-28E284.444.31(0.138, 0.110)241 Example 1-29E294.664.13(0.138, 0.111)338 Example 1-30E304.584.14(0.138, 0.110)299 Example 1-31E314.594.11(0.138, 0.111)305 Example 1-32E324.654.20(0.138, 0.111)281 Example 1-33E334.394.23(0.138, 0.115)233 Example 1-34E344.774.03(0.138, 0.111)318 Example 1-35E354.494.28(0.138, 0.111)246Example 1-36E364.674.11(0.138, 0.115)296Example 1-37E374.744.01(0.138, 0.111)266Example 1-38E384.844.13(0.138, 0.115)282Example 1-39E394.354.29(0.138, 0.111)237Example 1-40E404.314.33(0.138, 0.115)235Comparative Example 1-1ET-14.583.62(0.138, 0.111)35Comparative Example 1-2ET-25.032.13(0.138, 0.111)140Comparative Example 1-3ET-34.942.22(0.138, 0.111)143Comparative Example 1-4ET-44.902.26(0.138, 0.111)122Comparative Example 1-5ET-54.713.71(0.138, 0.113)113Comparative Example 1-6ET-64.763.75(0.138, 0.114)124Comparative Example 1-7ET-74.843.41(0.138, 0.111)40Comparative Example 1-8ET-85.322.00(0.138, 0.111)158Comparative example 1-9ET-95.232.08(0.138, 0.111)162Comparative example 1-10ET-105.182.12(0.138, 0.111)138Comparative example 1-11ET-114.983.49(0.138, 0.113)128Comparative example 1-12ET-125.033.53(0.138, 0.114)140Comparative example 1-13ET-134.933.21(0.138, 0.111)47Comparative example 1-14ET-145.471.88(0.138, 0.111)166Comparative example 1-15ET-155.322.00(0.138, 0.111)166Comparative example 1-16ET-165.272.00(0.138, 0.111)142Comparative example 1-17ET-175.133.41(0.138, 0.114)146.

[0608] As described in Table 1 above, the organic light-emitting devices of Examples 1-1 to 1-40, in which the compound represented by Chemical Formula 1 according to the present specification was used in the electron injection and electron transport layers of the organic light-emitting devices, exhibited low driving voltage and excellent characteristics in terms of efficiency and lifespan.

[0609] On the other hand, in the case of organic light-emitting devices using the compounds of Comparative Examples 1-1 to 1-17, the driving voltage was increased and the efficiency and stability were decreased compared to the organic light-emitting devices of Examples 1-1 to 1-40 using the compound according to the chemical formula 1 of the present invention.

[0610] Specifically, in the case of Comparative Examples 1-1, 1-7 and 1-13 using compounds without a nitrile group bond, the dipole moment is small, so electrons cannot be effectively transported to the light-emitting layer, and it can be confirmed that they show inferior effects in terms of efficiency and lifespan compared to Examples 1-1 to 1-40, Comparative Examples 1-2 to 1-6, Comparative Examples 1-8 to 1-12 and 1-14 to 1-17 with a nitrile group bond.

[0611] In addition, the organic light-emitting devices of Comparative Examples 1-2 to 1-4, Comparative Examples 1-8 to 1-10 and 1-14 to 1-16 using compounds having different bonding orders of the heterocycle represented by Chemical Formula 2 of the present invention, the fluorene group represented by Chemical Formula 3 and the nitrile group also showed inferior effects in terms of driving voltage, efficiency and lifespan when used in organic light-emitting devices compared to the compounds of the present invention.

[0612] Comparative Examples 1-5, 1-6, 1-11, 1-12 and 1-17 are organic light-emitting devices that use a compound in which quinazoline is bonded instead of the structure represented by Chemical Formula 3 and a compound in which quinazoline is bonded instead of the structure represented by Chemical Formula 2 in the electron injection and transport layers, respectively. It can also be confirmed that these devices have higher driving voltages and lower efficiency and lifespans than Examples 1-1 to 1-40.

[0613]

[0614] [Explanation of symbols]

[0615] 1: Substrate

[0616] 2: First electrode

[0617] 3: Organic layer

[0618] 4: Second electrode

[0619] 5: Hole injection layer

[0620] 6: First hole transport layer

[0621] 7: Second hole transport layer

[0622] 8: Emissive layer

[0623] 9: Electron injection and transport layer

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, HAr is a group represented by the following chemical formula 2, [Chemical Formula 2] Y is O or S, R1 and R2 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted aliphatic ring group; a substituted or unsubstituted aliphatic and aromatic condensed ring group; or a group connected to L1, R3 to R6 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted aliphatic ring group; a substituted or unsubstituted aliphatic and aromatic condensed ring group; or a group connected to L1, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted ring, At least one of R1 to R6 is a group connected to L1, Ar1 is a group represented by the following chemical formula 3, [Chemical Formula 3] X is O, S or It is indicated by one of the following: One of R7 and R8 is connected to L1, One of R7 and R8 is connected to L2, Among R7 and R8, the group not connected to L1 or L2 is deuterium, n and m are integers from 0 to 8, respectively, and n+m is an integer greater than or equal to 2. L1 and L2 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted divalent to tetravalent arylene group; or a substituted or unsubstituted divalent to tetravalent heteroarylene group, a to c are integers from 1 to 3, respectively, If a is 2 or more, HAr are equal or different, If c is 2 or greater, the structures within the brackets are either the same or different.

2. In claim 1, the compound wherein the chemical formula 2 is one of the following chemical formulas 2-1 and 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] In the above chemical formulas 2-1 and 2-2, Above represents a portion connected to L1 of the above chemical formula 1. In the above chemical formulas 2-1 and 2-2, the definitions of Y and R1 to R6 are as defined in the above chemical formula 2.

3. In claim 1, the compound wherein the chemical formula 3 is any one of the following chemical formulas 3-1 to 3-4: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] [Chemical Formula 3-5] [Chemical Formula 3-6] In the above chemical formulas 3-1 to 3-6, The above D stands for deuterium, One of the above R7' and R8' is connected to L1, and the other is connected to L2, n' and m' are integers from 0 to 6, "n" and "m" are integers from 0 to 7, X, n and m are as defined in the above chemical formula 3.

4. In claim 1, the compound wherein the chemical formula 3 is any one of the following chemical formulas 3A to 3C: [Chemical Formula 3A] [Chemical Formula 3B] [Chemical Formula 3C] R7, R8, n and m are as defined in the above chemical formula 3.

5. A compound according to claim 1, wherein at least one of the groups not bonded to L1 among R1 to R6 is a substituted or unsubstituted aryl group.

6. In claim 1, a compound in which L1 and L2 are the same as or different from each other and each independently represents a direct bond; a divalent to tetravalent substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a divalent to tetravalent substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

7. A compound according to claim 1, wherein each of a to c is 1.

8. In claim 1, the compound having chemical formula 1 is any one of the compounds below: .

9. An organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 8.

10. An organic light-emitting device according to claim 9, wherein the organic layer includes a hole blocking layer, an electron injection layer, an electron transport layer, or an electron injection and transport layer.

11. An organic light-emitting device according to claim 10, wherein the hole blocking layer, electron injection layer, electron transport layer, or electron injection and transport layer comprises the compound.

12. An organic light-emitting device according to claim 10, wherein the electron injection and transport layer comprises the compound together with a metal complex compound.

13. An organic light-emitting device according to claim 12, wherein the metal complex compound is selected from among alkali metal compounds and alkaline earth metal compounds.

14. An organic light-emitting device according to claim 12, wherein the electron injection and transport layer comprises the compound together with a metal complex compound in a weight ratio of 1:5 to 5:1.

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