Compound and organic light-emitting element 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 priority to and the benefit of Korean Patent Application No. 10-2020-0007825 filed in the Korean Intellectual Property Office on January 21, 2020, the entire contents of which are incorporated herein by reference.

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

[0003] The organic light-emitting phenomenon generally refers to the phenomenon of converting electrical energy into light energy using organic materials. An organic light-emitting device utilizing the organic light-emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is generally formed as a multilayer structure formed of different materials to improve the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in such an organic light-emitting device structure, holes and electrons are injected from the anode and the cathode into the organic material layer, respectively, and when the injected holes and electrons meet, excitons are formed, and light is emitted when these excitons fall back to the ground state.

[0004] There is an ongoing need to develop new materials for such organic light emitting devices. Summary of the invention

[0005] Technical issues

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

[0007] Technical Solution

[0008] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[0009] [Chemical formula 1]

[0010]

[0011] In Chemical Formula 1,

[0012] L1 is a direct bond; or a substituted or unsubstituted arylene group,

[0013] D is deuterium,

[0014] n1 is an integer from 0 to 8,

[0015] n2 is an integer from 0 to 8,

[0016] n3 is an integer from 0 to 7,

[0017] n4 is 0 or 1, and

[0018] 1≤n1+n2+n3+n4≤24.

[0019] Another embodiment of the present specification provides an organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contains the compound.

[0020] Beneficial Effects

[0021] The compound described in this specification can be used as a material of an organic material layer of an organic light emitting device. The compound according to another embodiment can improve efficiency, reduce driving voltage, and / or improve lifespan characteristics in an organic light emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figures 1 to 3 Each shows an example of an organic light-emitting device according to one embodiment of the present specification.

[0023] [reference numerals]

[0024] 1: Base

[0025] 2: First electrode

[0026] 3: Second electrode

[0027] 4: Luminous layer

[0028] 5: Hole injection layer

[0029] 5-1: First hole injection layer

[0030] 5-2: Second hole injection layer

[0031] 6: Hole transport layer

[0032] 6-1: First hole transport layer

[0033] 6-2: Second hole transport layer

[0034] 7: Electron blocking layer

[0035] 8: Electron transport layer

[0036] 8-1: First electron transport layer

[0037] 8-2: Second electron transport layer

[0038] 9: Electron injection layer DETAILED DESCRIPTION

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

[0040] One embodiment of the present specification provides a compound represented by Chemical Formula 1.

[0041] Chemical formula 1 according to one embodiment of the present specification includes 1) a naphthyl group and 2) a benzonaphthofuran bonded through L1 as a substituent in an anthracene nucleus, and Chemical formula 1 has a structure in which at least one hydrogen at a substitutable position is substituted with deuterium, and thus has structural characteristics of increasing electron and hole mobility and improving molecular stability. Therefore, an organic light-emitting device including the same is excellent in driving voltage, efficiency, and lifespan.

[0042] Examples of the substituent in the present specification are described below, however, the substituent is not limited thereto.

[0043] In this manual, It means the site of attachment.

[0044] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed into another substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is substituted, that is, a position where a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0045] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the following: deuterium; halogen group; hydroxyl group; cyano group; nitro group; alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; boron group; amine group; aryl group; and heteroaryl group, or substituted with substituents in which two or more of the above substituents are linked, or having no substituent.

[0046] In this specification, two or more substituents are connected to each other means that the hydrogen of any substituent is connected to another substituent. For example, two or more substituents connected to each other may include phenyl and naphthyl connected to form a substituent. In addition, three substituents connected together include not only (substituent 1)-(substituent 2)-(substituent 3) connected in succession, but also (substituent 2) and (substituent 3) connected to (substituent 1). For example, phenyl, naphthyl and isopropyl can be connected to form a substituent group. The same rules as above apply when four or more substituents are attached.

[0047] In the present specification, examples of the halogen group may include fluorine, chlorine, bromine or iodine.

[0048] In the present specification, the alkyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30. Specific examples thereof may 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, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0049] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms. Specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc., but are not limited thereto.

[0050] In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto.

[0051] In the present specification, the alkenyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 30. Specific examples thereof may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, and the like, but are not limited thereto.

[0052] In the present specification, the haloalkyl group means that in the definition of the alkyl group, the hydrogen of the alkyl group is substituted with at least one halogen group.

[0053] In the present specification, the aryl group is not particularly limited but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0054] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specific examples of the monocyclic aryl group may include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

[0055] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specific examples of the polycyclic aryl group may include naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, phenanthrenyl, perylene, fluorenyl, etc., but are not limited thereto.

[0056] In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0057] When the fluorenyl group is substituted, it may include etc., however, the structure is not limited thereto.

[0058] In this specification, an "adjacent" group may mean a substituent that replaces an atom directly connected to the atom substituted by the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or another substituent that replaces the atom substituted by the corresponding substituent. For example, two substituents that replace the ortho position in a benzene ring and two substituents that replace the same carbon in an aliphatic ring may be interpreted as groups that are "adjacent" to each other.

[0059] In the present specification, a heteroaryl group is a group containing one or more non-carbon atoms (i.e., heteroatoms), and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups may 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, phenanthridinyl, phenanthroline, isothiophene Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothioyl, phenanthroline Thiol, phenanthracene The present invention also includes, but is not limited to, oxazine, phenothiazine, dihydroindenocarbazolyl, spirofluorenylxanthenyl, spirofluorenylthioxanthenyl and the like.

[0060] In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc. As the alkyl group in the alkylsilyl group, the above-mentioned examples of the alkyl group may be applied, and as the aryl group in the arylsilyl group, the above-mentioned examples of the aryl group may be applied, and as the heteroaryl group in the heteroarylsilyl group, the examples of the heteroaryl group may be applied.

[0061] In this specification, the boron group can be -BR 100 R 101 . R 100 and R 101 The same or different from each other, and can 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 aromatic group having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaromatic group having 2 to 30 carbon atoms. Specific examples of the boron group may include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but are not limited thereto.

[0062] In the present specification, the amine group may be selected from -NH2, an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30. Specific examples of amine groups may include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl-anthrylamine, diphenylamine, dimethyltolylamine, N-phenyltolylamine, triphenylamine, N-phenylbiphenylamine, N-phenylnaphthylamine, N-biphenylnaphthylamine, N-naphthylfluorenylamine, N-phenylphenanthrenylamine, N-biphenylphenanthrenylamine, N-phenylfluorenylamine, N-phenylterphenylamine, N-phenanthrenylfluorenylamine, N-biphenylfluorenylamine and the like, but are not limited thereto.

[0063] In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.

[0064] In the present specification, the N-arylheteroarylamine group means an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl 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.

[0065] In the present specification, the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl 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.

[0066] In this specification, examples of alkylamino groups include substituted or unsubstituted monoalkylamino groups or substituted or unsubstituted dialkylamino groups. The alkyl group in the alkylamino group can be a linear or branched alkyl group. The alkylamino group comprising two or more alkyl groups can comprise a linear alkyl group, a branched alkyl group, or both a linear alkyl group and a branched alkyl group. For example, the alkyl group in the alkylamino group can be selected from the examples of the above-mentioned alkyl groups.

[0067] In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups or substituted or unsubstituted diarylamine groups. The aryl group in the arylamine group can be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more aryl groups can contain a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group can be selected from the examples of the above-mentioned aryl groups.

[0068] In this specification, examples of heteroarylamine include substituted or unsubstituted monoheteroarylamine, or substituted or unsubstituted diheteroarylamine. Heteroarylamine containing two or more heteroaryl groups may contain monocyclic heteroaryl, polycyclic heteroaryl, or both monocyclic heteroaryl and polycyclic heteroaryl. For example, the heteroaryl in the heteroarylamine may be selected from the examples of the above-mentioned heteroaryl.

[0069] In the present specification, an arylene group means an aryl group having two bonding sites, that is, a divalent group. The description about the aryl group provided above may be applied to the arylene group, except that each arylene group is a divalent group.

[0070] In the present specification, "deuteration" or "deuterated" means that hydrogen at a substitutable position of a compound is substituted with deuterium.

[0071] In the present specification, “perdeuterated” means a compound or group in which all hydrogens in a molecule are substituted with deuterium, and has the same meaning as “100% deuterated”.

[0072] In the present specification, "X% deuterated", "a degree of deuteration of X%" or "a deuterium substitution rate of X%" means that in the corresponding structure, X% of hydrogens at substitutable positions are substituted with deuterium. For example, when the corresponding structure is dibenzofuran, dibenzofuran is "25% deuterated", dibenzofuran has a "deuteration degree of 25%", or dibenzofuran has a "deuterium substitution rate of 25%" means that two of the eight hydrogens at the substitutable positions of dibenzofuran are substituted with deuterium.

[0073] In the present specification, known methods such as nuclear magnetic resonance spectroscopy ( 1 H NMR), TLC / MS (thin layer chromatography / mass spectrometry), or MALDI-TOF MS (matrix-assisted laser desorption / ionization time-of-flight mass spectrometry).

[0074] Unless otherwise limited in this specification, all technical and scientific terms used in this specification have the same meaning as the terms commonly understood by those skilled in the art. Although methods and materials similar or equivalent to those described in this specification can be used when implementing or testing the embodiments of the present disclosure, suitable methods and materials are described later. All publications, patent applications, patents and other references mentioned in this specification are incorporated into this specification by reference as a whole, and when conflicting, unless specific paragraphs are mentioned, the present specification containing definitions takes precedence. In addition, materials, methods and examples are only for illustrative purposes and do not limit this specification.

[0075] According to one embodiment of the present specification, 0 in the definitions of n1 to n4 means that hydrogen is bonded instead of deuterium.

[0076] According to one embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 1-1 or 1-2.

[0077] [Chemical formula 1-1]

[0078]

[0079] [Chemical formula 1-2]

[0080]

[0081] In Chemical Formulas 1-1 and 1-2,

[0082] L1, D, and n1 to n4 have the same definitions as in Chemical Formula 1.

[0083] According to one embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 1-3 or 1-4.

[0084] [Chemical formula 1-3]

[0085]

[0086] [Chemical formula 1-4]

[0087]

[0088] In Chemical Formulas 1-3 and 1-4,

[0089] L1, D, and n1 to n4 have the same definitions as in Chemical Formula 1.

[0090] According to one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-5 to 1-8.

[0091] [Chemical formula 1-5]

[0092]

[0093] [Chemical formula 1-6]

[0094]

[0095] [Chemical formula 1-7]

[0096]

[0097] [Chemical formula 1-8]

[0098]

[0099] In Chemical Formulas 1-5 to 1-8,

[0100] L1, D, and n1 to n4 have the same definitions as in Chemical Formula 1.

[0101] According to one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-9 or 1-10.

[0102] [Chemical formula 1-9]

[0103]

[0104] [Chemical formula 1-10]

[0105]

[0106] In Chemical Formulas 1-9 and 1-10,

[0107] D and n1 to n3 have the same definitions as in Chemical Formula 1, and

[0108] L11 is a substituted or unsubstituted arylene group.

[0109] 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 30 carbon atoms.

[0110] 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.

[0111] 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 10 carbon atoms.

[0112] According to one embodiment of the present specification, L1 is a direct bond; or an unsubstituted or deuterium-substituted arylene group.

[0113] According to one embodiment of the present specification, L1 is a direct bond; or an unsubstituted or deuterium-substituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0114] According to one embodiment of the present specification, L1 is a direct bond; or an unsubstituted or deuterium-substituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0115] According to one embodiment of the present specification, L1 is a direct bond; or an unsubstituted or deuterium-substituted monocyclic or polycyclic arylene group having 6 to 10 carbon atoms.

[0116] According to one embodiment of the present specification, L1 is a direct bond; an unsubstituted or deuterium-substituted phenylene group; or an unsubstituted or deuterium-substituted naphthylene group.

[0117] According to one embodiment of the present specification, L1 is a direct bond.

[0118] According to one embodiment of the present specification, L1 is a phenylene group.

[0119] According to one embodiment of the present specification, L1 is a naphthylene group.

[0120] According to one embodiment of the present specification, L1 is a deuterium-substituted phenylene group.

[0121] According to one embodiment of the present specification, L1 is a deuterium-substituted naphthylene group.

[0122] According to one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-11 or 1-12.

[0123] [Chemical formula 1-11]

[0124]

[0125] [Chemical formula 1-12]

[0126]

[0127] In Chemical Formulas 1-11 and 1-12,

[0128] D and n1 to n4 have the same definitions as in Chemical Formula 1,

[0129] n5 is an integer from 0 to 4, and

[0130] n6 is an integer from 1 to 6.

[0131] According to one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-13 to 1-16.

[0132] [Chemical formula 1-13]

[0133]

[0134] [Chemical formula 1-14]

[0135]

[0136] [Chemical formula 1-15]

[0137]

[0138] [Chemical formula 1-16]

[0139]

[0140] In Chemical Formulas 1-13 to 1-16,

[0141] D and n1 to n4 have the same definitions as in Chemical Formula 1,

[0142] n5 is an integer from 0 to 4, and

[0143] n6 is an integer from 1 to 6.

[0144] According to one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following structural formulas.

[0145]

[0146] In the structural formula,

[0147] L1, D and n4 have the same definitions as in Chemical Formula 1,

[0148] n11 is an integer from 1 to 8,

[0149] n12 is an integer from 1 to 8,

[0150] n13 is an integer from 1 to 7, and

[0151] n14 is 1.

[0152] According to one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following structural formulas.

[0153]

[0154] In the structural formula,

[0155] D and n4 have the same definitions as in Chemical Formula 1,

[0156] n11 is an integer from 1 to 8,

[0157] n12 is an integer from 1 to 8,

[0158] n13 is an integer from 1 to 7, and

[0159] n14 is 1.

[0160] According to one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following structural formulas.

[0161]

[0162]

[0163] In the structural formula,

[0164] D and n4 have the same definitions as in Chemical Formula 1,

[0165] n11 is an integer from 1 to 8,

[0166] n12 is an integer from 1 to 8,

[0167] n13 is an integer from 1 to 7,

[0168] n14 is 1, and

[0169] n15 is 1 to 4.

[0170] According to one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following structural formulas.

[0171]

[0172]

[0173] In the structural formula,

[0174] D and n4 have the same definitions as in Chemical Formula 1,

[0175] n11 is an integer from 1 to 8,

[0176] n12 is an integer from 1 to 8,

[0177] n13 is an integer from 1 to 7,

[0178] n14 is 1, and

[0179] n16 is 1 to 6.

[0180] According to one embodiment of the present specification, at least one hydrogen at a substitutable position in Chemical Formula 1 is substituted with deuterium.

[0181] According to one embodiment of the present specification, Chemical Formula 1 has a deuterium substitution rate of 100%.

[0182] According to one embodiment of the present specification, Chemical Formula 1 has a deuterium substitution rate of 10% to 90%.

[0183] According to one embodiment of the present specification, Chemical Formula 1 has a deuterium substitution rate of 20% to 80%.

[0184] According to one embodiment of the present specification, Chemical Formula 1 has a deuterium substitution rate of 30% to 70%.

[0185] According to one embodiment of the present specification, Chemical Formula 1 has a deuterium substitution rate of 40% to 60%.

[0186] According to one embodiment of the present specification, Chemical Formula 1 has a deuterium substitution rate of 50%.

[0187] According to one embodiment of the present specification, Chemical Formula 1 is any one selected from the following compounds.

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209] One embodiment of the present specification provides an organic light-emitting device including the above compound.

[0210] In this specification, a description that a certain member is disposed “on” another member includes not only a case where one member is in contact with another member but also a case where another member exists between the two members.

[0211] In the present specification, unless specifically described to the contrary, a description that a part “includes” certain constituent elements means that other constituent elements can also be included, and other constituent elements are not excluded.

[0212] In this specification, "layer" has the same meaning as "film" mainly used in the art, and means a coating covering a target area. The size of the "layer" is not limited, and each "layer" may have the same or different sizes. According to one embodiment, the size of the "layer" may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.

[0213] In this specification, the meaning that a specific A material is contained in the B layer includes both the following: i) one or more types of A materials are contained in one B layer, and ii) the B layer is formed into one or more layers and the A material is contained in one or more layers among the B layers as a multi-layer.

[0214] In this specification, the meaning that a specific A material is contained in a C layer or a D layer includes all of the following: i) contained in one or more layers among one or more C layers, ii) contained in one or more layers among one or more D layers, or iii) contained in each layer among one or more C layers and one or more D layers.

[0215] One embodiment of the present specification provides an organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contains a compound represented by Chemical Formula 1.

[0216] The organic material layer of the organic light-emitting device of the present specification may be formed as a single-layer structure, but may also be formed as a multilayer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device of the present specification 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.

[0217] According to one embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer contains the compound.

[0218] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound.

[0219] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host of the light-emitting layer.

[0220] According to one embodiment of the present specification, the light emitting layer includes a dopant, and the dopant includes one or more selected from a fluorescent dopant, a phosphorescent dopant, and a dopant based on thermal delayed fluorescence.

[0221] According to one embodiment of the present specification, the fluorescent dopant includes one or more selected from an arylamine-based compound and a boron-based compound.

[0222] According to one embodiment of the present specification, the fluorescent dopant is an arylamine-based compound.

[0223] According to one embodiment of the present specification, the fluorescent dopant is a boron-based compound.

[0224] According to one embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer includes a host and a dopant, the host includes the compound, and the dopant includes one or more selected from a fluorescent dopant, a phosphorescent dopant, and a dopant based on thermal delayed fluorescence.

[0225] According to one embodiment of the present specification, the arylamine-based compound is represented by the following Chemical Formula D-1.

[0226] [Chemical formula D-1]

[0227]

[0228] In chemical formula D-1,

[0229] L101 and L102 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group, and

[0230] Ar101 to Ar104 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0231] According to one embodiment of the present specification, L101 and L102 are direct bonds.

[0232] According to one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaromatic group having 2 to 30 carbon atoms.

[0233] According to one embodiment of the present specification, Ar101 to Ar104 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 which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaromatic group having 2 to 30 carbon atoms.

[0234] According to one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a phenyl group substituted with a methyl group; or a dibenzofuranyl group.

[0235] According to one embodiment of the present specification, Chemical Formula D-1 is represented by the following compounds.

[0236]

[0237] According to one embodiment of the present specification, the boron-based compound is represented by the following Chemical Formula D-2.

[0238] [Chemical formula D-2]

[0239]

[0240] In chemical formula D-2,

[0241] T1 to T5 are the same as or different from each other and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amino group; or a substituted or unsubstituted aryl group,

[0242] t3 and t4 are each an integer from 1 to 4,

[0243] t5 is an integer from 1 to 3,

[0244] When t3 is 2 or more, two or more T3 are the same as or different from each other,

[0245] When t4 is 2 or more, two or more T4 are the same as or different from each other, and

[0246] When t5 is 2 or more, two or more T5 are the same as or different from each other.

[0247] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aromatic amine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0248] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other and are each independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aromatic amine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

[0249] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and are each independently hydrogen; a tert-butyl group; a diphenylamino group; or a phenyl group which is unsubstituted or substituted with a tert-butyl group.

[0250] According to one embodiment of the present specification, Chemical Formula D-2 is represented by the following compounds.

[0251]

[0252] According to one embodiment of the present specification, those known in the art may be used as the phosphorescent dopant and the thermal delayed fluorescence-based dopant, however, the phosphorescent dopant and the thermal delayed fluorescence-based dopant are not limited thereto.

[0253] According to one embodiment of the present specification, the light emitting layer includes a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, the light emitting layer includes a host and a dopant in a weight ratio of 99:1 to 50:50, more specifically, in a weight ratio of 99:1 to 95:5.

[0254] According to one embodiment of the present specification, the organic light-emitting device further includes one, two or more layers selected from the following: a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer and an electron blocking layer.

[0255] According to one embodiment of the present specification, an 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 material layers arranged between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode.

[0256] According to one embodiment of the present specification, as two or more organic material layers arranged between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, two or more can be selected from a light-emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

[0257] According to one embodiment of the present specification, two or more hole injection layers are included between the light emitting layer and the first electrode. The two or more hole injection layers may include the same or different materials from each other.

[0258] 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 materials from each other.

[0259] According to one embodiment of the present specification, two or more electron transport layers are included between the light emitting layer and the second electrode. The two or more electron transport layers may include the same or different materials.

[0260] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0261] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0262] According to one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially laminated on a substrate.

[0263] According to one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a reverse structure (inverted type) in which a cathode, one or more organic material layers, and an anode are sequentially laminated on a substrate.

[0264] For example, the structure of the organic light-emitting device according to one embodiment of the present specification is Figures 1 to 3 Shown in. Figures 1 to 3Only an organic light emitting device is shown, and the organic light emitting device is not limited thereto.

[0265] Figure 1 The structure of an organic light emitting device is shown in which a first electrode 2, a light emitting layer 4, and a second electrode 3 are sequentially laminated on a substrate 1. The compound of Chemical Formula 1 is contained in the light emitting layer.

[0266] Figure 2 The structure of an organic light-emitting device is shown in which a first electrode 2, a hole injection layer 5, a first hole transport layer 6-1, a second hole transport layer 6-2, a light-emitting layer 4, an electron transport layer 8, an electron injection layer 9 and a second electrode 3 are sequentially laminated on a substrate 1. The compound of Chemical Formula 1 is contained in the light-emitting layer.

[0267] Figure 3 The structure of an organic light-emitting device is shown in which a first electrode 2, a first hole injection layer 5-1, a second hole injection layer 5-2, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 4, a first electron transport layer 8-1, a second electron transport layer 8-2, an electron injection layer 9, and a second electrode 3 are sequentially laminated on a substrate 1. The compound of Chemical Formula 1 is contained in the light-emitting layer.

[0268] The organic light-emitting device of the present specification may be manufactured using materials and methods known in the art, except that the light-emitting layer includes the compound, ie, the compound represented by Chemical Formula 1.

[0269] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0270] For example, the organic light-emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. Here, the organic light-emitting device can be manufactured by forming an anode on a substrate by depositing a metal, a conductive metal oxide, or an alloy thereof using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, and forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to such a method, the organic light-emitting device can also be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.

[0271] In addition, when manufacturing an organic light-emitting device, a solution coating method and a vacuum deposition method can be used to form the compound represented by Chemical Formula 1 into an organic material layer. Here, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0272] In addition to such a method, the organic light emitting device may also be manufactured by sequentially laminating the second electrode material, the organic material layer, and the first electrode material on the substrate. However, the manufacturing method is not limited thereto.

[0273] As the first electrode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. Examples thereof include: 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; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.

[0274] As the second electrode material, a material having a small work function is generally preferred so that electrons can be smoothly injected into the organic material layer. Examples thereof include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; etc., but are not limited thereto.

[0275] The light-emitting layer may include a host material and a dopant material. When an additional light-emitting layer is included in addition to the light-emitting layer including the compound represented by Chemical Formula 1 according to one embodiment of the present specification, the host material includes a fused aromatic ring derivative and / or a non-fused aromatic ring derivative, a heterocyclic compound, etc. Specifically, the fused aromatic ring derivative includes anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and the heterocyclic compound includes dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc. However, the material is not limited thereto.

[0276] Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, arylamine derivatives are fused aromatic ring derivatives having substituted or unsubstituted arylamine groups, and include pyrene, anthracene, In addition, the styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one, two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamine groups are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetramine, etc. are included, however, the styrylamine compound is not limited thereto. In addition, the metal complex includes iridium complex, platinum complex, etc., but is not limited thereto.

[0277] The hole injection layer is a layer that receives holes from an electrode. The hole injection material preferably has the effect of receiving holes from the anode by having the ability to transport holes, and has an excellent hole injection effect on the light-emitting layer or the light-emitting material. In addition, the hole injection material is preferably a material with excellent ability to prevent the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material. In addition, a material with excellent film forming ability is preferred. In addition, the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include: metal porphyrins, oligothiophenes, organic materials based on arylamines; organic materials based on hexanitrile hexaazatriphenylene; organic materials based on quinacridone; organic materials based on perylene; conductive polymers based on polythiophenes, such as anthraquinone or polyaniline; etc., but are not limited thereto.

[0278] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. As the hole transport material, a material having a high mobility for holes is preferably used as a material that can receive holes from the anode or the hole injection layer and move the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers having both a conjugated portion and a non-conjugated portion, etc., but are not limited thereto.

[0279] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. As an electron transport material, it is preferred that the material can advantageously receive electrons from the cathode, move the electrons to the light-emitting layer, and has a high mobility for electrons. Specific examples thereof include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes; and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in the art. In particular, suitable cathode materials are common materials having a low work function and followed by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium, samarium, and the like are included, and in each case, an aluminum layer or a silver layer is followed.

[0280] The electron injection layer is a layer that receives electrons from the electrode. As the electron injection material, it is preferred to have an excellent electron transport ability, an effect of receiving electrons from the second electrode, and an excellent electron injection effect to 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 moving to the hole injection layer and have an excellent thin film forming ability. Specific examples thereof include: fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc., and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

[0281] The metal complex compounds include 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, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0282] The electron blocking layer is a layer that can improve the life and efficiency of the device by preventing the electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. Known materials can be used without limitation, and the electron blocking layer can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and the layer that simultaneously performs hole injection and hole transport.

[0283] The 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. Specific examples thereof may include Oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., but not limited thereto.

[0284] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a dual emission type according to the materials used.

[0285] Embodiments of the invention

[0286] Hereinafter, the present specification will be described in detail with reference to embodiments, comparative examples, etc. However, the embodiments and comparative examples according to the present specification may be modified into various other forms, and the scope of the present specification should not be interpreted as being limited to the embodiments and comparative examples described below. The embodiments and comparative examples of the present specification are provided in order to more fully describe the present specification to those of ordinary skill in the art.

[0287] Synthesis example

[0288] Synthesis Example 1. Synthesis of BH-1

[0289]

[0290] <1-a> Preparation of Compound BH-1-a

[0291] After 9-bromo-10-(naphthalene-1-yl)anthracene (50g, 130.4mmol) and naphtho[2,3-b]benzofuran-1-ylboronic acid (37.6g, 143.44mmol) were dissolved in tetrahydrofuran (1000ml), 2M K2CO3 aqueous solution (200ml) was introduced thereto. Afterwards, Pd(PPh3)4 (1.50g, 1.3mmol) was introduced thereto, and the resultant was refluxed for 5 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and then dried over anhydrous magnesium sulfate. The organic solvent was removed under vacuum, and the resultant was purified using column chromatography to obtain compound BH-1-a (54.3g, yield 80%).

[0292] MS: [M+H]+=521

[0293] <1-b> Preparation of Compound BH-1

[0294] Compound BH-1-a (40g, 76.8mmol) and aluminum chloride (AlCl3) (5.0g, 38.4mmol) are introduced into C6D6 (800ml), and the mixture is stirred for 3 hours. After the reaction is completed, D2O (100ml) is introduced therein, the resultant is stirred for 30 minutes, and trimethylamine (10ml) is added dropwise thereto. The reaction solution is transferred to a separating funnel and extracted with water and toluene. The resultant is dried over anhydrous magnesium sulfate, and, after removing the organic solvent under vacuum, column chromatography is used to purify to obtain compound BH-1 (30.5g, yield 73%).

[0295] MS: [M+H]+=545

[0296] Synthesis Example 2. Synthesis of BH-2

[0297]

[0298] <2-a> Preparation of Compound BH-2-a

[0299] Compound BH-2-a was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-bromo-10-(naphthalene-2-yl)anthracene was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene.

[0300] MS: [M+H]+=521

[0301] <2-b> Preparation of Compound BH-2

[0302] Compound BH-2 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-2-a was used instead of Compound BH-1-a.

[0303] MS: [M+H]+=545

[0304] Synthesis Example 3. Synthesis of BH-3

[0305]

[0306] <3-a> Preparation of compound BH-3-a

[0307] Compound BH-3-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that 9-(naphthalene-1-yl)anthracene was used instead of Compound BH-1-a.

[0308] MS: [M+H]+=321

[0309] <3-b> Preparation of compound BH-3-b

[0310] After compound BH-3-a (30g, 93.6mmol) was dispersed in dimethylformamide (450ml), N-bromosuccinimide (16.7g, 93.6mmol) solution dissolved in dimethylformamide (50ml) was slowly added dropwise thereto. The resultant was reacted at room temperature for 3 hours, and then water (1L) was added dropwise thereto. The produced solid was filtered, dissolved in ethyl acetate, transferred to a separatory funnel, and washed several times with distilled water. The resultant was recrystallized in ethyl acetate to obtain compound BH-3-b (25.2g, yield 68%).

[0311] MS: [M+H]+=399

[0312] <3-c> Preparation of compound BH-3

[0313] Compound BH-3 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that Compound BH-3-b was used instead of 9-bromo-10-(naphthalen-1-yl)anthracene.

[0314] MS: [M+H]+=536

[0315] Synthesis Example 4. Synthesis of BH-4

[0316]

[0317] <4-a> Preparation of compound BH-4-a

[0318] Compound BH-4-a was obtained by synthesis and purification in the same manner as in Synthesis Example 1-b, except that 9-(naphthalen-2-yl)anthracene was used instead of Compound BH-1-a.

[0319] MS: [M+H]+=321

[0320] <4-b> Preparation of compound BH-4-b

[0321] Compound BH-4-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 3-b, except that Compound BH-4-a was used instead of Compound BH-3-a.

[0322] MS: [M+H]+=398

[0323] <4-c> Preparation of compound BH-4

[0324] Compound BH-4 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that Compound BH-4-b was used instead of 9-bromo-10-(naphthalen-1-yl)anthracene.

[0325] MS: [M+H]+=536

[0326] Synthesis Example 5. Synthesis of BH-5

[0327]

[0328] <5-a> Preparation of compound BH-5-a

[0329] Compound BH-5-a was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that 1-bromo-3-chlorobenzene was used instead of 9-bromo-10-(naphthalen-1-yl)anthracene.

[0330] MS: [M+H]+=329

[0331] <5-b> Preparation of compound BH-5-b

[0332] Compound BH-5-a (30 g, 91.2 mmol), bis(pinacol)diboron (34.7 g, 136.8 mmol), tricyclohexylphosphine (1.0 g, 3.64 mmol), potassium acetate (26.9 g, 273.6 mmol) and Pd(dba)2 (1.0 g, 1.82 mmol) were introduced into 1,4-dihydropyridine. The mixture was added into 4% ethyl acetate (450 ml) and refluxed for 6 hours. The reaction solution was cooled and the organic layer was extracted with ethyl acetate and then dried over anhydrous magnesium sulfate. The organic solvent was removed under vacuum and the resultant was purified by column chromatography to obtain compound BH-5-b (26.1 g, 68% yield).

[0333] MS: [M+H]+=421

[0334] <5-c> Preparation of compound BH-5

[0335] Compound BH-5 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that compound BH-4-b was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and compound BH-5-b was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0336] MS: [M+H]+=612

[0337] Synthesis Example 6. Synthesis of BH-6

[0338]

[0339] <6-a> Preparation of Compound BH-6

[0340] Compound BH-6 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that compound BH-3-b was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and compound BH-5-b was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0341] MS: [M+H]+=612

[0342] Synthesis Example 7. Synthesis of BH-7

[0343]

[0344] <7-a> Preparation of compound BH-7-a

[0345] Compound BH-7-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 1-bromo-4-chlorobenzene was used instead of 9-bromo-10-(naphthalen-1-yl)anthracene.

[0346] MS: [M+H]+=329

[0347] <7-b> Preparation of compound BH-7-b

[0348] Compound BH-7-b is obtained by synthesis and purification in the same manner as in Reaction Formula 5-b, except that Compound BH-7-a is used instead of Compound BH-5-a.

[0349] MS: [M+H]+=421

[0350] <7-c> Preparation of compound BH-7

[0351] Compound BH-7 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that compound BH-4-b was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and compound BH-7-b was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0352] MS: [M+H]+=612

[0353] Synthesis Example 8. Synthesis of BH-8

[0354]

[0355] <8-a> Preparation of Compound BH-8

[0356] Compound BH-8 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that compound BH-3-b was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and compound BH-7-b was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0357] MS: [M+H]+=612

[0358] Synthesis Example 9. Synthesis of BH-9

[0359]

[0360] <9-a> Preparation of Compound BH-9-a

[0361] Compound BH-9-a was obtained by synthesis and purification in the same manner as in Synthesis Example 3-b, except that 9-(naphthalen-1-yl)anthracene-1,2,3,4,5,6,7,8,10-d9 was used instead of Compound BH-3-a.

[0362] MS: [M+H]+=392

[0363] <9-b> Preparation of Compound BH-9

[0364] Compound BH-9 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that Compound BH-9-a was used instead of 9-bromo-10-(naphthalen-1-yl)anthracene.

[0365] MS: [M+H]+=529

[0366] Synthesis Example 10. Synthesis of BH-10

[0367]

[0368] <10-a> Preparation of Compound BH-10-a

[0369] Compound BH-10-a was obtained by synthesis and purification in the same manner as in Synthesis Example 3-b, except that 9-(naphthalen-2-yl)anthracene-1,2,3,4,5,6,7,8,10-d9 was used instead of Compound BH-3-a.

[0370] MS: [M+H]+=392

[0371] <10-b> Preparation of Compound BH-10

[0372] Compound BH-10 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that Compound BH-10-a was used instead of 9-bromo-10-(naphthalen-1-yl)anthracene.

[0373] MS: [M+H]+=529

[0374] Synthesis Example 11. Synthesis of BH-11

[0375]

[0376] <11-a> Preparation of Compound BH-11-a

[0377] Compound BH-11-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that naphtho[1,2-b]benzofuran-7-ylboronic acid was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0378] MS: [M+H]+=521

[0379] <11-b> Preparation of Compound BH-11

[0380] Compound BH-11 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-11-a was used instead of Compound BH-1-a.

[0381] MS: [M+H]+=545

[0382] Synthesis Example 12. Synthesis of BH-12

[0383]

[0384] <12-a> Preparation of Compound BH-12-a

[0385] Compound BH-12-a was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-bromo-10-(naphthalene-2-yl)anthracene was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and naphtho[1,2-b]benzofuran-7-ylboronic acid was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0386] MS: [M+H]+=521

[0387] <12-b> Preparation of Compound BH-12

[0388] Compound BH-12 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-12-a was used instead of Compound BH-1-a.

[0389] MS: [M+H]+=545

[0390] Synthesis Example 13. Synthesis of BH-13

[0391]

[0392] <3-a> Preparation of Compound BH-13

[0393] Compound BH-13 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that compound BH-3-b was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and naphtho[1,2-b]benzofuran-7-ylboronic acid was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0394] MS: [M+H]+=536

[0395] Synthesis Example 14. Synthesis of BH-14

[0396]

[0397] <14-a> Preparation of Compound BH-14

[0398] Compound BH-14 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that compound BH-4-b was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and naphtho[1,2-b]benzofuran-7-ylboronic acid was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0399] MS: [M+H]+=536

[0400] Synthesis Example 15. Synthesis of BH-15

[0401]

[0402] <15-a> Preparation of Compound BH-15-a

[0403] Compound BH-15-a was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that 1-bromo-3-chlorobenzene was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and naphtho[1,2-b]benzofuran-7-ylboronic acid was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0404] MS: [M+H]+=329

[0405] <15-b> Preparation of compound BH-15-b

[0406] Compound BH-15-b is obtained by synthesis and purification in the same manner as in Reaction Formula 5-b, except that Compound BH-15-a is used instead of Compound BH-5-a.

[0407] MS: [M+H]+=421

[0408] <15-c> Preparation of compound BH-15

[0409] Compound BH-15 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that compound BH-4-b was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and compound BH-15-b was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0410] MS: [M+H]+=612

[0411] Synthesis Example 16. Synthesis of BH-16

[0412]

[0413] <16-a> Preparation of Compound BH-16

[0414] Compound BH-16 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that compound BH-3-b was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and compound BH-15-b was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0415] MS: [M+H]+=612

[0416] Synthesis Example 17. Synthesis of BH-17

[0417]

[0418] <17-a> Preparation of Compound BH-17-a

[0419] Compound BH-17-a was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that 1-bromo-4-chlorobenzene was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and naphtho[1,2-b]benzofuran-7-ylboronic acid was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0420] MS: [M+H]+=329

[0421] <17-b> Preparation of compound BH-17-b

[0422] Compound BH-17-b is obtained by synthesis and purification in the same manner as in Reaction Formula 5-b, except that compound BH-17-a is used instead of compound BH-5-a.

[0423] MS: [M+H]+=421

[0424] <17-c> Preparation of Compound BH-17

[0425] Compound BH-17 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that compound BH-4-b was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and compound BH-17-b was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0426] MS: [M+H]+=612

[0427] Synthesis Example 18. Synthesis of BH-18

[0428]

[0429] <18-a> Preparation of Compound BH-18

[0430] Compound BH-18 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that compound BH-3-b was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and compound BH-17-b was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0431] MS: [M+H]+=612

[0432] Synthesis Example 19. Synthesis of BH-19

[0433]

[0434] <19-a> Preparation of Compound BH-19-a

[0435] Compound BH-19-a was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that 1-bromo-4-chloronaphthalene was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene.

[0436] MS: [M+H]+=379

[0437] <19-b> Preparation of compound BH-19-b

[0438] Compound BH-19-b is obtained by synthesis and purification in the same manner as in Reaction Formula 5-b, except that compound BH-19-a is used instead of compound BH-5-a.

[0439] MS: [M+H]+=471

[0440] <19-c> Preparation of compound BH-19-c

[0441] Compound BH-19-c was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that Compound BH-19-b was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0442] MS: [M+H]+=647

[0443] <19-d> Preparation of compound BH-19

[0444] Compound BH-19 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-19-c was used instead of Compound BH-1-a.

[0445] MS: [M+H]+=677

[0446] Synthesis Example 20. Synthesis of BH-20

[0447]

[0448]

[0449] <20-a> Preparation of Compound BH-20-a

[0450] Compound BH-20-a was obtained by synthesis and purification in the same manner as in Synthesis Example 1-a, except that 3-bromo-1-chloronaphthalene was used instead of 9-bromo-10-(naphthalene-1-yl)anthracene, and naphtho[1,2-b]benzofuran-7-ylboronic acid was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0451] MS: [M+H]+=379

[0452] <20-b> Preparation of compound BH-20-b

[0453] Compound BH-20-b is obtained by synthesis and purification in the same manner as in Reaction Formula 5-b, except that Compound BH-20-a is used instead of Compound BH-5-a.

[0454] MS: [M+H]+=471

[0455] <20-c> Preparation of compound BH-20-c

[0456] Compound BH-20-c was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that Compound BH-20-b was used instead of naphtho[2,3-b]benzofuran-1-ylboronic acid.

[0457] MS: [M+H]+=647

[0458] <20-d> Preparation of Compound BH-20

[0459] Compound BH-20 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-20-c was used instead of Compound BH-1-a.

[0460] MS: [M+H]+=677

[0461] <Experimental Example 1: Device Example>

[0462] Example 1

[0463] It is coated with a thickness of Indium tin oxide (ITO) of 1000nm is put into the distilled water dissolved with detergent as the glass substrate of film and carries out ultrasonic cleaning.Here, use the product of Fischer Co. as detergent, and as distilled water, use the distilled water filtered twice by the filter manufactured by Millipore Co..After ITO is cleaned for 30 minutes, use distilled water to repeat ultrasonic cleaning twice for 10 minutes.After finishing with distilled water cleaning, use isopropyl alcohol, acetone and methanol solvent to carry out ultrasonic cleaning to substrate, then dry, then transfer to plasma cleaning machine.In addition, use oxygen plasma to clean substrate for 5 minutes, then transfer to vacuum deposition device.

[0464] On the transparent ITO electrode prepared as above, the following HI-A and HATCN were thermally vacuum deposited to and To form a first hole injection layer and a second hole injection layer. On the hole injection layer, the following HT-A to The following HT-B is vacuum deposited on the hole transport layer to form a hole transport layer of thickness of 1000 nm. to form an electron blocking layer.

[0465] Subsequently, on the electron blocking layer, a layer with a thickness of 1000 nm was formed by vacuum depositing the following compound BD-A as a blue light-emitting dopant at 4 wt % relative to the total weight of the light-emitting layer and the following BH-1 as a host at 96 wt % relative to the total weight of the light-emitting layer. of the luminous layer.

[0466] Then, the following compounds ET-A to As the first electron transport layer, ET-B and LiQ were then vacuum deposited at a weight ratio of 1:1. The second electron transport layer is formed by vacuum depositing LiQ to On the electron injection layer, aluminum and silver were deposited in a weight ratio of 10:1 to form an electron injection layer. Aluminum is then deposited on top to a thickness of to form a cathode.

[0467] During the above process, the deposition rate of the organic material is maintained at to The deposition rate of aluminum at the cathode was maintained at The vacuum degree during deposition was maintained at 5 × 10 -8 Torr up to 1×10 -7 As a result, an organic light emitting device is manufactured.

[0468]

[0469] Examples 2 to 20

[0470] Each organic light-emitting device of Examples 2 to 20 was manufactured in the same manner as in Example 1, except that each compound described in the following Table 1 was used instead of Compound BH-1 as a host of the light-emitting layer.

[0471]

[0472]

[0473] Comparative Examples 1 to 7

[0474] Each organic light-emitting device of Comparative Examples 1 to 7 was manufactured in the same manner as in Example 1, except that each compound described in the following Table 1 was used as a host of the light-emitting layer instead of Compound BH-1.

[0475]

[0476] For each of the organic light emitting devices of Examples 1 to 20 and Comparative Examples 1 to 7, the 2 The voltage and efficiency (cd / A / y) at a current density of 20 mA / cm 2 The lifespan (LT95) at a current density of 20 mA / cm 2 When the initial brightness at the current density of 100 % is taken as 100 %, the time taken for the brightness to decrease to 95 % is shown, and the percentage is shown based on Comparative Example 1.

[0477] [Table 1]

[0478]

[0479] In Table 1, the compound of Chemical Formula 1 according to one embodiment of the present specification is a compound in which L1 is bonded to the 1st position of benzo[b]naphtho[2,3-d]furan or L1 is bonded to the 7th position of benzo[b]naphtho[2,1-d]furan, and has a structural characteristic of excellent electron and hole transport. In addition, Chemical Formula 1 has improved molecular stability by including deuterium as a substituent. Therefore, Examples 1 to 20 including the compound in the light-emitting layer of the organic light-emitting device have excellent efficiency, driving voltage and life efficiency compared with Comparative Example 1 including the compound of benzo[b]naphtho[2,3-d]furan or benzo[b]naphtho[2,1-d]furan not containing Chemical Formula 1.

[0480] Compared with Comparative Examples 2 to 7 comprising compounds in which L1 is bonded to positions 2 to 4 of benzo[b]naphtho[2,3-d]furan or L1 is bonded to positions 8 to 10 of benzo[b]naphtho[2,1-d]furan, Examples 1 to 20 exhibit excellent results in terms of driving voltage, efficiency and / or lifespan, and in particular, significantly excellent results are obtained in terms of lifespan.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; as well as one or more organic material layers disposed between the first electrode and the second electrode, One or more of the organic material layers includes a light-emitting layer, and the light-emitting layer contains any one selected from the following compounds as a host: The light-emitting layer further comprises a dopant, and the dopant is represented by the following chemical formula D-2: [Chemical formula D-2] In chemical formula D-2, T1 and T2 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 substituted with an alkyl group having 1 to 30 carbon atoms, T3 and T4 are the same as or different from each other and are each independently a linear or branched alkyl group having 1 to 30 carbon atoms, T5 is a monocyclic or polycyclic aromatic amine group having 6 to 30 carbon atoms, t3 and t4 are each an integer of 1, t5 is an integer of 1. 2 . The organic light-emitting device according to claim 1 , wherein the organic material layer further comprises a hole injection layer, a hole transport layer or an electron blocking layer.

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