Compound and organic light-emitting device containing the same

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device including the same.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2019-0171444 filed with the Korean Intellectual Property Office on December 20, 2019, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a compound and an organic light-emitting device including the same. Background Art

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

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above. Summary of the invention

[0005] Technical issues

[0006] The present specification provides a compound and an organic light-emitting device including the same.

[0007] Solution to the problem

[0008] This specification provides a compound represented by the following Compound 1.

[0009] [Chemical formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] A1 is a direct bond, O or S,

[0013] R1 and R2 are the same or different from each other, and are independently substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or may be combined with each other to form a ring substituted or unsubstituted by -L1-Ar1,

[0014] R3 to R10 are the same as or different from each other, and are each independently hydrogen or -L1-Ar1,

[0015] When the above R1 and R2 are combined with each other to form a ring substituted with -L1-Ar1, the above R3 to R10 are hydrogen atoms,

[0016] When the above R1 and R2 are the same or different and are independently substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or are combined with each other to form an unsubstituted ring, any one of the above R3 to R10 is -L1-Ar1, and the rest are hydrogen,

[0017] L1 is a direct bond, or a substituted or unsubstituted arylene group,

[0018] Ar1 is a group represented by any one of the following chemical formulas 2-1 to 2-7,

[0019] [Chemical formula 2-1]

[0020]

[0021] [Chemical formula 2-2]

[0022]

[0023] [Chemical formula 2-3]

[0024]

[0025] [Chemical formula 2-4]

[0026]

[0027] [Chemical formula 2-5]

[0028]

[0029] [Chemical formula 2-6]

[0030]

[0031] [Chemical formula 2-7]

[0032]

[0033] In the above chemical formulas 2-1 to 2-7,

[0034] * is a site that binds to L1 in the above chemical formula 1,

[0035] Y1 is a group represented by the following chemical formula 3,

[0036] At least two of X1 to X3 are N, and the rest are CH,

[0037] At least one of X4 and X5 is N, and the others are CH,

[0038] At least one of X6 and X7 is N, and the others are CH,

[0039] X8 is N, Z1 is N or C, or X8 is CH, Z1 is N,

[0040] X9 is N, Z2 is N or C, or X9 is CH, Z2 is N,

[0041] X10 is N, Z3 is N or C, or X10 is CH, Z3 is N,

[0042] X11 is N, Z4 is N or C, or X11 is CH, Z4 is N,

[0043] Y2 to Y8 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0044] y3 is an integer of 1 to 4. When y3 is 2 or more, two or more Y3 are the same or different from each other.

[0045] y4 is 1 or 2. When y4 is 2, the two Y4 are the same or different from each other.

[0046] y5 is an integer from 1 to 4. When y5 is 2 or more, two or more Y5 are the same or different from each other.

[0047] y6 is an integer of 1 to 4. When y6 is 2 or more, two or more Y6 are the same or different from each other.

[0048] y7 is 1 or 2. When y7 is 2, the two Y7 are the same or different from each other.

[0049] y8 is 1 or 2. When y8 is 2, the two Y8 are the same or different from each other.

[0050] [Chemical formula 3]

[0051]

[0052] In the above chemical formula 3,

[0053] is a site that binds to any one of the above chemical formulae 2-1 to 2-7,

[0054] L2 is a direct bond, or a substituted or unsubstituted arylene group,

[0055] One to four of Q1 to Q5 are N, and the rest are CR.

[0056] At least one of R is a substituted or unsubstituted aryl group, and the others are the same or different from each other and are independently hydrogen or deuterium,

[0057] The above Ar1 is the above Chemical Formula 2-1, and when L2 in the above Chemical Formula 3 is a direct bond, at least two of R are substituted or unsubstituted aryl groups.

[0058] In addition, the present specification provides an organic light-emitting device, which includes: a first electrode, a second electrode arranged opposite to the first electrode, and one or more organic layers arranged between the first electrode and the second electrode, and one or more of the organic layers contains the compound.

[0059] Effects of the Invention

[0060] The compound according to one embodiment of the present specification may be used as a material of an organic layer of an organic light-emitting device, and by using the compound, improved efficiency, low driving voltage, and / or improved lifespan characteristics may be achieved in the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0061] Figures 1 to 3 An example of an organic light-emitting device according to an embodiment of the present specification is illustrated.

[0062] [Explanation of Symbols]

[0063] 101: Substrate

[0064] 102: First electrode

[0065] 103: Hole injection layer

[0066] 104: Hole transport layer

[0067] 105: Electron blocking layer

[0068] 106: Luminous layer

[0069] 107: Hole blocking layer

[0070] 108: Electron transport layer

[0071] 109: Electron injection layer

[0072] 110: Second electrode

[0073] 111: Organic layer

[0074] 112: Electron injection and transport layer

[0075] 104-1: First hole transport layer

[0076] 104-2: Second hole transport layer. DETAILED DESCRIPTION

[0077] Next, this specification is described in more detail.

[0078] The present specification provides a compound represented by the above Chemical Formula 1.

[0079] The compound according to one embodiment of the present specification is a non-linear structure, which can achieve improved efficiency, low driving voltage and improved life characteristics in an organic light-emitting device. In addition, in the structure of the compound represented by the above chemical formula 1, the substituent -L-Ar1 can improve the polarity (dipole moment) of the molecule by having a substituent with an electron depletion structure, so when making an organic light-emitting device containing the compound represented by the above chemical formula 1, the electron mobility is smoothly adjusted, thereby improving the efficiency and life of the organic light-emitting device containing the compound represented by the above chemical formula 1. In addition, when R1 and R2 of the above chemical formula 1 form a ring, the steric hindrance caused by the spiro structure can prevent crystallization from occurring when the film is formed, maintain high thermal stability, and also have a very stable effect at high evaporation temperatures. Therefore, an organic light-emitting device containing a compound according to one embodiment of the present specification can achieve improved efficiency, low driving voltage and improved life characteristics, etc.

[0080] In the present specification, examples of substituents are described below, but are not limited thereto.

[0081] In this manual, Indicates the connected part.

[0082] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0083] In the present specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, a haloalkyl group, a silyl group, a boron group, an amine group, an aryl group and a heteroaryl group, or substituted by a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0084] In this specification, two or more substituents are linked to each other, which means that the hydrogen of any substituent is linked to another substituent. For example, two substituents can be linked to each other to form a phenyl group and a naphthyl group. In addition, the case where three substituents are connected includes not only the case where (substituent 1)-(substituent 2)-(substituent 3) are connected continuously, but also the case where (substituent 2) and (substituent 3) are connected to (substituent 1). For example, phenyl, naphthyl and isopropyl can be connected to form Such substituents. The same definitions as above also apply when 4 or more substituents are linked.

[0085] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0086] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, and 5-methylhexyl.

[0087] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl and the like, but is not limited thereto.

[0088] In this specification, the alkoxy group may be straight chain, branched chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 30. Specifically, it may be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0089] In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0090] In the present specification, the above-mentioned halogenated alkyl group means that at least one halogen group is substituted in place of the hydrogen of the alkyl group in the definition of the above-mentioned alkyl group.

[0091] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0092] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0093] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 10 to 30. Specifically, the polycyclic aryl group may be naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, phenanthrenyl, perylene, yl, fluorenyl, etc., but are not limited to these.

[0094] In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0095] When the fluorenyl group is substituted, it may be

[0096]

[0097] etc., but not limited thereto.

[0098] In this specification, "adjacent" groups may refer to substituents substituted on atoms directly connected to the atom substituted by the substituent, substituents closest to the substituent in stereostructure, or other substituents substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0099] In the present specification, the heteroaryl group contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may contain one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 30. The heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthridine, phenanthroline, isothiophene Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothioyl, phenanthroline Thiazole (phenoxathiine), phen Examples of the present invention include, but are not limited to, phenoxazine, phenothiazine, indenocarbazolyl, spirofluorenylxanthenyl and spirofluorenylthioxanthenyl.

[0100] In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc. The alkyl group in the alkylsilyl group may be the same as the examples given above for the alkyl group, the aryl group in the arylsilyl group may be the same as the examples given above for the aryl group, and the heteroaryl group in the heteroarylsilyl group may be the same as the examples given above for the heteroaryl group.

[0101] In this specification, the boron group can be -BR 100 R 101 , the above R 100 and R 101 The same or different groups may be independently selected from hydrogen, deuterium, halogen, nitrile, substituted or unsubstituted monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted linear or branched alkyl having 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heteroaryl having 2 to 30 carbon atoms. The above-mentioned boryl groups specifically include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but are not limited thereto.

[0102] In the present specification, the amine group can be selected from -NH2, alkylamine, N-alkylarylamine, arylamine, N-arylheteroarylamine, N-alkylheteroarylamine and heteroarylamine, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthrylamino, 9-methyl-anthrylamino, diphenylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, and N-biphenylfluorenylamino.

[0103] In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted on the N of the amine group. The alkyl group and the aryl group in the above-mentioned N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.

[0104] In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group or a heteroaryl group is substituted on the N of the amine group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and the heteroaryl group described above.

[0105] In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted on the N of the amine group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and the heteroaryl group described above.

[0106] In this specification, examples of alkylamino groups include substituted or unsubstituted monoalkylamino groups or substituted or unsubstituted dialkylamino groups. The alkyl group in the above-mentioned alkylamino groups may be a straight-chain or branched alkyl group. The alkylamino group containing two or more of the above-mentioned alkyl groups may contain a straight-chain alkyl group, a branched alkyl group, or may contain a straight-chain alkyl group and a branched alkyl group at the same time. For example, the alkyl group in the above-mentioned alkylamino group may be selected from the examples of the above-mentioned alkyl groups.

[0107] In this specification, examples of heteroarylamine groups include substituted or unsubstituted monoheteroarylamine groups, or substituted or unsubstituted diheteroarylamine groups. The heteroarylamine groups containing two or more of the above heteroaryl groups may contain monocyclic heteroaryl groups, polycyclic heteroaryl groups, or may contain both monocyclic heteroaryl groups and polycyclic heteroaryl groups. For example, the heteroaryl groups in the above heteroarylamine groups may be selected from the examples of the above heteroaryl groups.

[0108] In the present specification, "two adjacent substituents are bonded to form a ring" means that the adjacent substituents are bonded to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0109] In the present specification, in a substituted or unsubstituted ring formed by bonding to each other, "ring" means a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0110] In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from the examples of the cycloalkyl group or aryl group described above except that the ring is not monovalent.

[0111] In the present specification, the heterocyclic ring contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may contain one or more atoms selected from O, N, Se, S, etc. The heterocyclic ring may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic. The aromatic heterocyclic ring may be selected from the examples of the heteroaryl group except that it is not monovalent.

[0112] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane Azoctane Thioctane etc., but not limited thereto.

[0113] In the present specification, an arylene group means an aryl group having two bonding positions, that is, a divalent group. Except that each of them is a divalent group, the above description of the aryl group is applicable.

[0114] In the present specification, a heteroarylene group means a group having two bonding positions in a heteroaryl group, that is, a divalent group. Except that each of them is a divalent group, the above description of the heteroaryl group is applicable.

[0115] Next, the compound represented by the above Chemical Formula 1 will be described in detail.

[0116] According to one embodiment of the present specification, in the above chemical formula 1, the above R1 and R2 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroaromatic group having 6 to 30 carbon atoms, or are combined with each other to form a hydrocarbon ring substituted or unsubstituted by -L1-Ar1.

[0117] According to one embodiment of the present specification, in the above chemical formula 1, the above R1 and R2 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroaromatic group having 6 to 20 carbon atoms, or are combined with each other to form an aromatic hydrocarbon ring which is substituted or unsubstituted by -L1-Ar1.

[0118] According to one embodiment of the present specification, in the above chemical formula 1, the above R1 and R2 are the same or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaromatic group having 6 to 30 carbon atoms, or are combined with each other to form a hydrocarbon ring which is substituted or unsubstituted by -L1-Ar1.

[0119] According to one embodiment of the present specification, in the above Chemical Formula 1, the above R1 and R2 are the same or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, or are combined with each other to form an aromatic hydrocarbon ring which is substituted or unsubstituted by -L1-Ar1.

[0120] According to one embodiment of the present specification, in the above Chemical Formula 1, the above R1 and R2 are the same or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, or are combined with each other to form an aromatic hydrocarbon ring which is substituted or unsubstituted by -L1-Ar1.

[0121] According to one embodiment of the present specification, in the above Chemical Formula 1, the above R1 and R2 are the same or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 10 carbon atoms, or are combined with each other to form an aromatic hydrocarbon ring which is substituted or unsubstituted by -L1-Ar1.

[0122] According to one embodiment of the present specification, in the chemical formula 1, R1 and R2 are phenyl groups, or are combined with each other to form a fluorene ring which is substituted or unsubstituted by -L1-Ar1.

[0123] According to one embodiment of the present specification, in the above Chemical Formula 1, the above R1 and R2 are phenyl groups.

[0124] According to one embodiment of the present specification, in the above Chemical Formula 1, the above R1 and R2 are bonded to each other to form a fluorene ring which may be substituted with -L1-Ar1.

[0125] According to one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.

[0126] [Chemical formula 1-1]

[0127]

[0128] [Chemical formula 1-2]

[0129]

[0130] [Chemical formula 1-3]

[0131]

[0132] [Chemical formula 1-4]

[0133]

[0134] In the above chemical formula 1-1,

[0135] G1 and G2 are the same or different from each other, and each is a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms,

[0136] Any one of R3 to R10 is -L1-Ar1, and the rest are hydrogen,

[0137] L1 and Ar1 are the same as those defined in the above chemical formula 1,

[0138] In the above chemical formulas 1-2 to 1-4,

[0139] Any one of R3 to R10 and R101 to R108 is -L1-Ar1, and the others are hydrogen,

[0140] L1 and Ar1 are the same as defined in the above Chemical Formula 1.

[0141] According to one embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0142] According to one embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.

[0143] According to one embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently a monocyclic or polycyclic aromatic group having 6 to 10 carbon atoms.

[0144] According to one embodiment of the present specification, G1 and G2 are phenyl groups.

[0145] According to one embodiment of the present specification, L1 is a direct bond, or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0146] According to one embodiment of the present specification, L1 is a direct bond, or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 15 carbon atoms.

[0147] According to one embodiment of the present specification, L1 is a direct bond or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0148] According to one embodiment of the present specification, L1 is a direct bond or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0149] According to one embodiment of the present specification, the above-mentioned L1 is a direct bond, or a monocyclic or polycyclic arylene group having 6 to 15 carbon atoms.

[0150] According to one embodiment of the present specification, the above-mentioned L1 is a direct bond, a phenylene group, a biphenylene group, or a naphthylene group.

[0151] According to one embodiment of the present specification, the above-mentioned L1 is a direct bond.

[0152] According to one embodiment of the present specification, the above-mentioned L1 is a phenylene group.

[0153] According to one embodiment of the present specification, the above-mentioned L1 is a biphenylene group.

[0154] According to one embodiment of the present specification, the above-mentioned L1 is a naphthylene group.

[0155] According to one embodiment of the present specification, the above-mentioned Ar1 is a group represented by any one of the following structures.

[0156]

[0157]

[0158] In the above structure,

[0159] * is a site that binds to L1 in the above chemical formula 1,

[0160] Y1 is a group represented by the above chemical formula 3,

[0161] Y2 to Y8 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0162] y3 is an integer of 1 to 4. When y3 is 2 or more, two or more Y3 are the same or different from each other.

[0163] y4 is 1 or 2. When y4 is 2, the two Y4 are the same or different from each other.

[0164] y5 is an integer from 1 to 4. When y5 is 2 or more, two or more Y5 are the same or different from each other.

[0165] y6 is an integer of 1 to 4. When y6 is 2 or more, two or more Y6 are the same or different from each other.

[0166] y7 is 1 or 2. When y7 is 2, the two Y7 are the same or different from each other.

[0167] y8 is 1 or 2. When y8 is 2, two Y8s are the same as or different from each other.

[0168] According to one embodiment of the present specification, the above-mentioned Y2 is a substituted or unsubstituted aryl group.

[0169] According to one embodiment of the present specification, the above Y2 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0170] According to one embodiment of the present specification, the above Y2 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.

[0171] According to one embodiment of the present specification, the above Y2 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 15 carbon atoms.

[0172] According to one embodiment of the present specification, Y2 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

[0173] According to one embodiment of the present specification, Y2 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms.

[0174] According to one embodiment of the present specification, Y2 is a monocyclic or polycyclic aryl group having 6 to 15 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 10 carbon atoms.

[0175] According to one embodiment of the present specification, Y2 is a phenyl group, a biphenyl group, or a naphthyl group which may be substituted with a methyl group.

[0176] According to one embodiment of the present specification, the above-mentioned Y3 is hydrogen.

[0177] According to one embodiment of the present specification, the above-mentioned Y4 is hydrogen.

[0178] According to one embodiment of the present specification, the above-mentioned Y5 is hydrogen.

[0179] According to one embodiment of the present specification, the above-mentioned Y6 is hydrogen.

[0180] According to one embodiment of the present specification, the above-mentioned Y7 is hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0181] According to one embodiment of the present specification, Y7 is hydrogen, a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0182] According to one embodiment of the present specification, Y7 is hydrogen, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0183] According to one embodiment of the present specification, Y7 is hydrogen, a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

[0184] According to one embodiment of the present specification, Y7 is hydrogen, a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0185] According to one embodiment of the present specification, Y7 is hydrogen, a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0186] According to one embodiment of the present specification, Y7 is hydrogen, a linear or branched alkyl group having 1 to 10 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

[0187] According to one embodiment of the present specification, the above Y7 is hydrogen, methyl or phenyl.

[0188] According to one embodiment of the present specification, Y8 is hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0189] According to one embodiment of the present specification, Y8 is hydrogen, a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0190] According to one embodiment of the present specification, Y8 is hydrogen, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0191] According to one embodiment of the present specification, Y8 is hydrogen, a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

[0192] According to one embodiment of the present specification, Y8 is hydrogen, a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0193] According to one embodiment of the present specification, Y8 is hydrogen, a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0194] According to one embodiment of the present specification, Y8 is hydrogen, a linear or branched alkyl group having 1 to 10 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

[0195] According to one embodiment of the present specification, the above Y8 is hydrogen, methyl or phenyl.

[0196] According to one embodiment of the present specification, the above-mentioned Ar1 is a group represented by any one of the following structures.

[0197]

[0198]

[0199]

[0200]

[0201] In the above structure,

[0202] * is a site that binds to L1 in the above chemical formula 1,

[0203] Y1 is a group represented by the above Chemical Formula 3.

[0204] According to one embodiment of the present specification, the above Chemical Formula 3 is a group represented by any one of the following structures.

[0205]

[0206]

[0207] In the above structure,

[0208] The definition of L2 is the same as that in the above chemical formula 3,

[0209] At least one of Ra1 to Ra4 is a substituted or unsubstituted aryl group, and the others are the same or different from each other and are independently hydrogen or deuterium,

[0210] At least one of Rb1 to Rb3 is a substituted or unsubstituted aryl group, and the others are the same or different from each other and are independently hydrogen or deuterium,

[0211] At least one of Rc1 and Rc2 is a substituted or unsubstituted aryl group, and the others are hydrogen or deuterium,

[0212] Rd1 is a substituted or unsubstituted aryl group.

[0213] According to one embodiment of the present specification, the above-mentioned L2 is a direct bond.

[0214] According to one embodiment of the present specification, the above L2 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0215] According to one embodiment of the present specification, L2 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0216] According to one embodiment of the present specification, the above L2 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 15 carbon atoms.

[0217] According to one embodiment of the present specification, L2 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0218] According to one embodiment of the present specification, L2 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0219] According to one embodiment of the present specification, L2 is a monocyclic or polycyclic arylene group having 6 to 15 carbon atoms.

[0220] According to one embodiment of the present specification, the above-mentioned L2 is a phenylene group or a biphenylene group.

[0221] According to one embodiment of the present specification, at least one of the above Ra1 to Ra4 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, and the others are the same or different and are independently hydrogen or deuterium.

[0222] According to one embodiment of the present specification, at least one of the above Ra1 to Ra4 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, and the others are the same or different and are independently hydrogen or deuterium.

[0223] According to one embodiment of the present specification, at least one of the above Ra1 to Ra4 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 15 carbon atoms, and the others are the same or different and are independently hydrogen or deuterium.

[0224] According to one embodiment of the present specification, at least one of the above Ra1 to Ra4 is a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, and the others are the same or different and are independently hydrogen or deuterium.

[0225] According to one embodiment of the present specification, at least one of the above Ra1 to Ra4 is a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, and the others are the same or different and are independently hydrogen or deuterium.

[0226] According to one embodiment of the present specification, at least one of the above Ra1 to Ra4 is a monocyclic or polycyclic aromatic group having 6 to 15 carbon atoms, and the others are the same or different and are independently hydrogen or deuterium.

[0227] According to one embodiment of the present specification, at least one of the above Ra1 to Ra4 is a phenyl group, a biphenyl group or a naphthyl group, and the others are the same as or different from each other and are independently hydrogen or deuterium.

[0228] According to one embodiment of the present specification, at least one of the above Rb1 to Rb3 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, and the others are the same or different and are independently hydrogen or deuterium.

[0229] According to one embodiment of the present specification, at least one of the above Rb1 to Rb3 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, and the others are the same or different and are independently hydrogen or deuterium.

[0230] According to one embodiment of the present specification, at least one of the above Rb1 to Rb3 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 15 carbon atoms, and the others are the same or different and are independently hydrogen or deuterium.

[0231] According to one embodiment of the present specification, at least one of the above Rb1 to Rb3 is a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, and the others are the same or different and are independently hydrogen or deuterium.

[0232] According to one embodiment of the present specification, at least one of the above Rb1 to Rb3 is a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, and the others are the same or different and are independently hydrogen or deuterium.

[0233] According to one embodiment of the present specification, at least one of the above Rb1 to Rb3 is a monocyclic or polycyclic aromatic group having 6 to 15 carbon atoms, and the others are the same or different and are independently hydrogen or deuterium.

[0234] According to one embodiment of the present specification, at least one of the above Rb1 to Rb3 is a phenyl group, a biphenyl group or a naphthyl group, and the others are the same as or different from each other and are independently hydrogen or deuterium.

[0235] According to one embodiment of the present specification, at least one of Rc1 and Rc2 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, and the rest are hydrogen or deuterium.

[0236] According to one embodiment of the present specification, at least one of Rc1 and Rc2 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, and the rest are hydrogen or deuterium.

[0237] According to one embodiment of the present specification, at least one of Rc1 and Rc2 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 15 carbon atoms, and the rest are hydrogen or deuterium.

[0238] According to one embodiment of the present specification, at least one of Rc1 and Rc2 is a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, and the rest are hydrogen or deuterium.

[0239] According to one embodiment of the present specification, at least one of Rc1 and Rc2 is a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, and the rest are hydrogen or deuterium.

[0240] According to one embodiment of the present specification, at least one of Rc1 and Rc2 is a monocyclic or polycyclic aromatic group having 6 to 15 carbon atoms, and the rest are hydrogen or deuterium.

[0241] According to one embodiment of the present specification, at least one of Rc1 and Rc2 is a phenyl group, a biphenyl group or a naphthyl group, and the others are hydrogen or deuterium.

[0242] According to one embodiment of the present specification, the above-mentioned Rd1 is a substituted or unsubstituted aryl group.

[0243] According to one embodiment of the present specification, the above Rd1 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0244] According to one embodiment of the present specification, the above Rd1 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.

[0245] According to one embodiment of the present specification, the above Rd1 is a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 15 carbon atoms.

[0246] According to one embodiment of the present specification, the above Rd1 is a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0247] According to one embodiment of the present specification, the above Rd1 is a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.

[0248] According to one embodiment of the present specification, the above Rd1 is a monocyclic or polycyclic aromatic group having 6 to 15 carbon atoms.

[0249] According to one embodiment of the present specification, the above-mentioned Rd1 is a phenyl group, a biphenyl group or a naphthyl group.

[0250] According to one embodiment of the present specification, the above-mentioned Rd1 is a phenyl group.

[0251] According to one embodiment of the present specification, the above-mentioned Rd1 is a biphenyl group.

[0252] According to one embodiment of the present specification, the above-mentioned Rd1 is a naphthyl group.

[0253] According to one embodiment of the present specification, the chemical formula 1 is selected from the following compounds.

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268] The present specification provides an organic light-emitting device including the compound represented by the above Chemical Formula 1.

[0269] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0270] In the present specification, when it is indicated that a certain part “includes / comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

[0271] In this specification, the above-mentioned "layer" is interchangeable with the "film" mainly used in this technical field, and refers to a coating covering the target area. The size of the above-mentioned "layer" is not limited, and the sizes of each "layer" can be the same or different. According to one embodiment, the size of the "layer" can be equal to the size of the entire device, can be equivalent to the size of a specific functional area, or can be as small as a single sub-pixel.

[0272] In this specification, the meaning of specific substance A contained in layer B includes i) the case where one or more substances A are contained in one layer B, and ii) the case where layer B is composed of one or more layers and substance A is contained in one or more layers of the multiple layers B.

[0273] In this specification, a specific substance A is contained in layer C or layer D, which means that i) it is contained in one or more layers of one or more layers C, or ii) it is contained in one or more layers of one or more layers D, or iii) it is contained in one or more layers C and one or more layers D, respectively.

[0274] The present specification provides an organic light-emitting device, which includes: a first electrode; a second electrode arranged opposite to the first electrode; and one or more organic layers arranged between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound represented by the above chemical formula 1.

[0275] The organic layer of the organic light-emitting device of the present specification may be formed by a single-layer structure, or may be formed by a multi-layer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0276] According to one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.

[0277] According to one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes the compound.

[0278] According to one embodiment of the present specification, the organic layer includes a light-emitting layer.

[0279] According to one embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.

[0280] According to one embodiment of the present specification, the organic layer includes an electron blocking layer.

[0281] According to one embodiment of the present specification, the organic layer includes a hole blocking layer.

[0282] According to one embodiment of the present specification, the above-mentioned organic light-emitting device also includes one or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0283] According to one embodiment of the present specification, the organic light-emitting device includes: a first electrode; a second electrode arranged opposite to the first electrode; a light-emitting layer arranged between the first electrode and the second electrode; and two or more organic layers arranged between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0284] According to one embodiment of the present specification, the above-mentioned two or more organic layers can be selected from two or more of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0285] According to one embodiment of the present specification, two or more hole transport layers are included between the light emitting layer and the first electrode. The two or more hole transport layers may include the same or different substances.

[0286] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0287] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0288] According to one embodiment of the present specification, the organic light emitting device may be a (normal type) organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0289] According to one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0290] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is shown in Figures 1 to 3 . The above Figures 1 to 3 An organic light emitting device is exemplified, but the present invention is not limited thereto.

[0291] Figure 1 The structure of the organic light emitting device is illustrated in which a first electrode 102, an organic layer 111, and a second electrode 110 are sequentially stacked on a substrate 101. The compound represented by the above Chemical Formula 1 is contained in the organic layer.

[0292] Figure 2 The structure of an organic light-emitting device is illustrated in which a first electrode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, and a second electrode 110 are sequentially stacked on a substrate 101. According to one embodiment of the present specification, the compound represented by the above Chemical Formula 1 is included in the electron injection layer, the electron transport layer, or the hole blocking layer.

[0293] Figure 3 The structure of an organic light-emitting device is illustrated in which a first electrode 102, a hole injection layer 103, a first hole transport layer 104-1, a second hole transport layer 104-2, a light-emitting layer 106, an electron injection and transport layer 112, and a second electrode 110 are sequentially stacked on a substrate 101. The compound represented by the above Chemical Formula 1 is contained in the electron injection and transport layer.

[0294] The organic light-emitting device of the present specification can be manufactured by materials and methods known in the art, except that the electron injection layer, the electron transport layer, the electron injection and transport layer, or the hole blocking layer includes the above compound, that is, the compound represented by the above Chemical Formula 1.

[0295] When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0296] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the device can be manufactured as follows: a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0297] In addition, the compound represented by the above chemical formula 1 can be used to form an organic layer by not only vacuum evaporation but also solution coating when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0298] In addition to these methods, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode material, an organic layer, and an anode material on a substrate. However, the manufacturing method is not limited to this.

[0299] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. For example, there are metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited thereto.

[0300] In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function, such as metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but not limited thereto.

[0301] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0302] As the dopant material, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamine. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0303] The hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, thereby having the effect of receiving holes from the anode, and has an excellent hole injection effect for the light-emitting layer or the light-emitting material. In addition, it is preferred that the material has an excellent ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. Moreover, it is preferred that the material has excellent thin film forming ability. In addition, it is preferred 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. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, and arylamine organics; hexanitrile hexaazatriphenylene organics; quinacridone organics; perylene organics; anthraquinone, polyaniline, and polythiophene conductive polymers, etc., but are not limited to these.

[0304] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material with a large hole mobility is suitable. As specific examples, there are arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but it is not limited to these.

[0305] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. When the organic light-emitting device according to one embodiment of the present specification includes an additional electron transport layer in addition to the electron transport layer comprising the above chemical formula 1, the electron transport substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, preferably a substance with a large mobility for electrons. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes comprising Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, a suitable cathode material is a common substance having a low work function and accompanied by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., in each case accompanied by an aluminum layer or a silver layer.

[0306] The electron injection layer is a layer that receives electrons from the electrode. When the organic light-emitting device according to one embodiment of the present specification includes an additional electron injection layer in addition to the electron injection layer comprising the above chemical formula 1, the electron injection material is preferably a material that has excellent ability to transport electrons, has the effect of receiving electrons from the second electrode, and has an excellent electron injection effect for the light-emitting layer or the light-emitting material. In addition, it is preferred to prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer and has excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0307] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0308] The electron blocking layer is a layer that prevents the electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer, thereby improving the life and efficiency of the device. Known materials can be used without restriction, and can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and the layer that simultaneously performs hole injection and hole transport.

[0309] The hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed using the same conditions as the electron injection layer. When the organic light-emitting device according to one embodiment of the present specification includes an additional hole blocking layer in addition to the hole blocking layer comprising the above chemical formula 1, specifically, Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0310] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0311] Modes for Carrying Out the Invention

[0312] Below, in order to specifically describe this specification, examples and comparative examples will be cited for detailed description. However, the examples and comparative examples of this specification can be deformed into various forms, and it is not interpreted that the scope of this specification is limited to the examples and comparative examples described in detail below. The examples and comparative examples of this specification are provided to more completely describe this specification to those skilled in the art.

[0313] Preparation Example 1-1: Preparation of Compound E1

[0314]

[0315] Under a nitrogen atmosphere, E1-A (20 g, 55.2 mmol) and E1-B (27.4 g, 55.2 mmol) were added to 400 ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (22.9 g, 165.6 mmol) was dissolved in 23 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (1.9 g, 1.7 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to 20 times 860 ml of chloroform to dissolve, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound E1 (27.5 g, 64%, MS: [M+H] + =779).

[0316] Preparation Example 1-2: Preparation of Compound E2

[0317]

[0318] The compound E2 was produced by the same method as in Production Example 1-1 except that the starting materials were used as in the above reaction formula.

[0319] MS:[M+H] + =792

[0320] Preparation Example 1-3: Preparation of Compound E3

[0321]

[0322] The compound E3 was produced by the same method as in Production Example 1-1 except that the starting materials were used as in the above reaction formula.

[0323] MS:[M+H] + =792

[0324] Preparation Example 1-4: Preparation of Compound E4

[0325]

[0326] The compound E4 was produced by the same method as in Production Example 1-1 except that the starting materials were used as in the above reaction formula.

[0327] MS:[M+H] + =809

[0328] Preparation Example 1-5: Preparation of Compound E5

[0329]

[0330] The compound E5 was produced by the same method as in Production Example 1-1 except that the starting materials were used as in the above reaction formula.

[0331] MS:[M+H] + =753

[0332] Preparation Example 1-6: Preparation of Compound E6

[0333]

[0334] The compound E6 was produced by the same method as in Production Example 1-1 except that the starting materials were used as in the above reaction formula.

[0335] MS:[M+H] + =717

[0336] Preparation Example 1-7: Preparation of Compound E7

[0337]

[0338] The compound E7 was produced by the same method as in Production Example 1-1 except that the starting materials were used as in the above reaction formula.

[0339] MS:[M+H] + =738

[0340] Preparation Example 1-8: Preparation of Compound E8

[0341]

[0342] The compound E8 was produced by the same method as in Production Example 1-1 except that the starting materials were used as in the above reaction formula.

[0343] MS:[M+H] + =770

[0344] Preparation Example 1-9: Preparation of Compound E9

[0345]

[0346] The compound E9 was produced by the same method as in Production Example 1-1 except that the starting materials were used as in the above reaction formula.

[0347] MS:[M+H] + =810

[0348] Preparation Example 1-10: Preparation of Compound E10

[0349]

[0350] The compound E10 was produced by the same method as in Production Example 1-1 except that the starting materials were used as in the above reaction formula.

[0351] MS:[M+H] + =626

[0352] Preparation Example 1-11: Preparation of Compound E11

[0353]

[0354] The compound E11 was produced by the same method as in Production Example 1-1 except that the starting materials were used as in the above reaction formula.

[0355] MS:[M+H] + =628

[0356] [Experimental Example 1]

[0357] ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0358] On the ITO transparent electrode prepared in this way, the following HI-A compound was applied as The hole injection layer is formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, the following HAT compound is deposited and the following HT-A compound The first hole transport layer and the second hole transport layer were formed by sequentially performing vacuum deposition.

[0359] Next, on the second hole transport layer, the following BH compound and BD compound were vacuum deposited at a weight ratio of 25:1 to form a light-emitting layer with a film thickness of 20 nm.

[0360] On the light-emitting layer, the compound E1 prepared in the above-mentioned preparation example 1-1 and the following LiQ compound were vacuum-deposited at a weight ratio of 1:1, thereby On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A cathode is formed by evaporation with a thickness of .

[0361] In the above process, the evaporation rate of organic matter is maintained at 0.4 to Lithium fluoride at cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 1×10 -7 Up to 5×10 -5 A support is provided to manufacture an organic light-emitting device.

[0362]

[0363] Experimental Examples 2 to 11

[0364] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that Compounds E2 to 11 described in Table 1 below were each used instead of Compound E1 of Experimental Example 1.

[0365] Comparative Examples 1 to 19

[0366] An organic light-emitting device was manufactured by the same method as in Experimental Example 1, except that compounds ET-A to ET-S described in Table 1 below were each used instead of Compound E1 of Experimental Example 1.

[0367]

[0368]

[0369] For the organic light-emitting devices manufactured in the above Experimental Examples 1 to 11 and Comparative Examples 1 to 19, the 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time (T90) until the initial luminance reaches 90% was measured at a current density of . The above results are shown in Table 1 below.

[0370] [Table 1]

[0371]

[0372]

[0373] As described in Table 1, the compound represented by Chemical Formula 1 according to the present specification can be used for an organic layer of an organic light-emitting device that can simultaneously perform electron injection and electron transport. Compared with Experimental Examples 1 to 11 in Table 1 and Comparative Examples 1 to 6, the organic light-emitting device including the compound of Chemical Formula 1 according to the present specification can be confirmed to show significantly superior characteristics in terms of life compared with the organic light-emitting device including the compound not containing the above Y1.

[0374] Compared with Experimental Examples 1 to 11 in Table 1 above and Comparative Examples 7 to 11, the organic light-emitting device comprising Chemical Formula 1 according to the present specification can be confirmed to show significantly superior characteristics in terms of efficiency compared with the organic light-emitting device comprising the compound wherein Y1 is an unsubstituted pyridyl group or an unsubstituted pyrimidine group.

[0375] Compared with Experimental Examples 1 to 11 and Comparative Examples 12 to 14 in Table 1 above, the organic light-emitting device including the compound of Chemical Formula 1 according to the present specification can be confirmed to show significantly superior characteristics in terms of efficiency and lifespan compared with the organic light-emitting device including the compound in which R1 and R2 are alkyl groups.

[0376] Compared with Experimental Example 9 in the above Table 1 and Comparative Example 15, the organic light-emitting device of the present specification comprising an aromatic-substituted fluorene, spirobifluorene, spirofluorenexanthene, or spirofluorenethioxanthene as the core of Chemical Formula 1 can be confirmed to show significantly superior characteristics in terms of efficiency and lifespan compared with the organic light-emitting device comprising a compound that does not contain the core of the above Chemical Formula 1.

[0377] In addition, compared with Experimental Examples 1 to 6 and 9 in Table 1 above and Comparative Examples 16 and 17, the organic light-emitting device according to the present specification comprising a compound in which Ar1 is chemical formula 2-1 and at least two of X1 to X3 are N can be confirmed to show significantly superior characteristics in terms of driving voltage and efficiency compared with the organic light-emitting device comprising a compound in which only any one of X1 to X3 is N.

[0378] Compared with Experimental Examples 5 and 6 in the above Table 1 and Comparative Examples 18 and 19, the organic light-emitting device according to the present specification comprising a compound in which Ar1 is the above Chemical Formula 2-1, L2 in the above Chemical Formula 3 is a direct bond, and at least 2 of R are substituted or unsubstituted aromatic groups, can be confirmed to show significantly superior characteristics in terms of efficiency and lifetime compared with the organic light-emitting device comprising a compound in which Ar1 is the above Chemical Formula 2-1, L2 in the above Chemical Formula 3 is a direct bond, and only any one of R is an aromatic group.

Claims

1. A compound represented by the following chemical formula 1: Chemical formula 1 In the chemical formula 1, A1 is a direct bond, O or S, R1 and R2 are each independently a phenyl group, or optionally combined with each other to form a fluorene ring which may be substituted with -L1-Ar1, R3 to R10 are the same as or different from each other and are each independently hydrogen or -L1-Ar1, When the R1 and R2 are combined with each other to form a fluorene ring substituted with -L1-Ar1, the R3 to R10 are hydrogen atoms, The R1 and R2 are each independently a phenyl group, or when they are combined with each other to form an unsubstituted fluorene ring, any one of the R3 to R10 is -L1-Ar1, and the rest are hydrogen, L1 is a direct bond, or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, Ar1 is a group represented by any of the following structures, In the structure described, * is the site that binds to L1 in the chemical formula 1, Y1 is a group represented by Chemical Formula 3, Y2 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, Y4 to Y8 are the same as or different from each other and are each independently hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms, y4 is 1 or 2, and when y4 is 2, two Y4 are the same as or different from each other, y5 is an integer from 1 to 4, and when y5 is 2 or more, two or more Y5 are the same or different from each other, y6 is an integer of 1 to 4, and when y6 is 2 or more, two or more Y6 are the same or different from each other, y7 is 1 or 2, and when y7 is 2, two Y7 are the same as or different from each other, and y8 is 1 or 2, and when y8 is 2, two Y8 are the same as or different from each other, Chemical formula 3 In the chemical formula 3, is a site that is combined with any one of the structures, L2 is a direct bond, a phenylene group or a biphenylene group, 1 to 4 of Q1 to Q5 are N, and the rest are CR, At least one of R is an aryl group selected from phenyl, biphenyl, terphenyl or naphthyl, and the others are the same as or different from each other and are each independently hydrogen or deuterium, and Ar1 is When L2 in the chemical formula 3 is a direct bond, at least two of R are aromatic groups selected from phenyl, biphenyl, terphenyl or naphthyl.

2. The compound according to claim 1, wherein The R1 and R2 are each independently phenyl.

3. The compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4: Chemical formula 1-1 Chemical formula 1-2 Chemical formula 1-3 Chemical formula 1-4 In the chemical formula 1-1, G1 and G2 are each independently phenyl, Any one of R3 to R10 is -L1-Ar1, and the rest are hydrogen, L1 and Ar1 are the same as those defined in the chemical formula 1, In the chemical formulas 1-2 to 1-4, Any one of R3 to R10 and R101 to R108 is -L1-Ar1, and the rest are hydrogen, and L1 and Ar1 are the same as defined in Chemical Formula 1.

4. The compound according to claim 1, wherein The chemical formula 3 is represented by any one of the following structures: In the structure described, The definition of L2 is the same as that in the chemical formula 3, At least one of Ra1 to Ra4 is an aryl group selected from phenyl, biphenyl, terphenyl or naphthyl, and the others are the same as or different from each other and are each independently hydrogen or deuterium, At least one of Rb1 to Rb3 is an aryl group selected from phenyl, biphenyl, terphenyl or naphthyl, and the others are the same as or different from each other and are each independently hydrogen or deuterium, At least one of Rc1 and Rc2 is an aryl group selected from phenyl, biphenyl, terphenyl or naphthyl, and the rest are hydrogen or deuterium, and Rd1 is an aryl group selected from phenyl, biphenyl, terphenyl or naphthyl.

5. The compound according to claim 1, wherein The chemical formula 1 is selected from the following compounds:

6. An organic light-emitting device, wherein: include: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 5.

7. The organic light emitting device according to claim 6, wherein: The organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.

8. The organic light emitting device according to claim 6, wherein: The organic layer includes a hole blocking layer, and the hole blocking layer contains the compound.

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