Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of Chemical Formula 1-2 or 1-5 and an organic light emitting device comprising the same. The compound according to the present invention can be used as a material for an organic layer of an organic light-emitting device, and can achieve an improvement in efficiency, a lower driving voltage, and / or an improvement in lifespan characteristics in an organic light-emitting device.

Description

[0001] This application is a divisional application of an application with an application date of January 20, 2021, application number 202180003732.4, and invention name “Compounds and organic light-emitting devices containing the same” (PCT / KR2021 / 095019, national phase entry date December 1, 2021). Technical Field

[0002] This application claims the priority 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.

[0003] The present invention relates to a compound and an organic light-emitting device including the same. Background Art

[0004] 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.

[0005] There is a continuous demand for the development of new materials for organic light-emitting devices as described above. Summary of the invention

[0006] Technical issues

[0007] The present specification provides a compound and an organic light-emitting device including the same.

[0008] Solution to the problem

[0009] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[0010] [Chemical formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] L1 is a direct bond, or a substituted or unsubstituted arylene group,

[0014] D is deuterium,

[0015] n1 is an integer from 0 to 9,

[0016] n2 is an integer from 0 to 8,

[0017] n3 is an integer from 0 to 7,

[0018] The above 1≤n1+n2+n3≤24.

[0019] 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, one or more of the organic layers containing the compound.

[0020] Effects of the Invention

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

[0022] Figures 1 to 3 An example of an organic light-emitting device according to an embodiment of the present specification is illustrated.

[0023] [Explanation of symbols]

[0024] 1: Substrate

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

[0040] One embodiment of the present specification provides a compound represented by the above 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 of an anthracene nucleus, and the above chemical formula 1 has a structure in which at least one hydrogen at a substitutable position is substituted by deuterium, and thus has structural characteristics of increasing the mobility of electrons and holes and improving molecular stability. Therefore, an organic light-emitting device including the same is excellent in driving voltage, efficiency, and lifespan.

[0042] In the present specification, examples of substituents are described below, but are not limited thereto.

[0043] In this manual, Indicates the connected part.

[0044] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by 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.

[0045] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a hydroxyl group, a cyano group, a nitro group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, a haloalkyl group, a silyl group, a boron group, an amino group, an aryl group, and a heteroaryl group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0046] In this specification, two or more substituents are linked together means that the hydrogen of any substituent is replaced by another substituent. For example, two substituents can be linked together to form a phenyl group and a naphthyl group. In addition, the connection of three substituents includes not only (substituent 1)-(substituent-2)-(substituent 3) connected continuously, but also (substituent 2) and (substituent 3) connected to (substituent 1). For example, phenyl, naphthyl and isopropyl can be connected to form The above definition also applies to the case where 4 or more substituents are connected.

[0047] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0048] 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, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] In the present specification, the above-mentioned halogenated alkyl group means that in the above-mentioned definition of alkyl, 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 is preferably an aryl group having 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 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.

[0055] 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.

[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] In the case where the above fluorenyl group is substituted,

[0058]

[0059] etc., but not limited thereto.

[0060] In this specification, "adjacent" groups refer to substituents substituted on atoms directly connected to the atoms substituted by the substituents, substituents closest to the substituents in terms of stereostructure, or other substituents substituted on the atoms substituted by the substituents. 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.

[0061] 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 (phenoxathine), phen Examples of the present invention include, but are not limited to, phenoxazine, phenothiazine, indenocarbazolyl, spirofluorenylxanthenyl and spirofluorenylthioxanthenyl.

[0062] 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.

[0063] 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.

[0064] 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, anthracenylamino, 9-methyl-anthrylamino, diphenylamino, dimethyltolylamino, N-phenylmethyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterbiphenylamino, N-phenanthrenylfluorenylamino, and N-biphenylfluorenylamino.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups or substituted or unsubstituted diarylamine groups. The aryl group in the above arylamine groups may be a monocyclic aryl group or a polycyclic aryl group. The arylamine groups containing two or more of the above aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the above arylamine groups may be selected from the examples of the above aryl groups.

[0070] 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.

[0071] In the present specification, an arylene group refers to a group having two bonding positions in an aryl group, that is, a divalent group. The above description of the aryl group is applicable to these groups except that they are each a divalent group.

[0072] In the present specification, "deuteration" or "deuterated" means that hydrogen at a substitutable position of a compound is substituted with deuterium.

[0073] In the present specification, "overdeuterated" refers to a compound or group in which all hydrogen in the molecule is replaced by deuterium, and has the same meaning as "100% deuterated".

[0074] In the present specification, "X% deuterated", "deuteration degree X%", or "deuterium substitution rate X%" means that X% of hydrogen atoms at substitutable positions in the corresponding structure are substituted with deuterium. For example, when the corresponding structure is dibenzofuran, "25% deuterated" dibenzofuran, "deuteration degree 25%" of the dibenzofuran, or "deuterium substitution rate 25%" of the dibenzofuran means that 2 of 8 hydrogen atoms at substitutable positions of the dibenzofuran are substituted with deuterium.

[0075] In this specification, the degree of deuteration can be determined by nuclear magnetic resonance spectroscopy ( 1 The protein can be confirmed by known methods such as H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or MALDI-TOF MS (Matrix assisted laser desorption / ionization Time-of-Flight Mass Spectrometry).

[0076] Unless otherwise defined in this specification, all technical terms and scientific terms used in this specification have the same meaning as those generally understood by those skilled in the art. Methods and materials similar to or equivalent to the description in this specification can be used for the implementation or test of embodiments of the present invention, but suitable methods and materials are described later. All publications, patent applications, patents and other references mentioned in this specification are included in this specification as a whole as a reference, and in the case of conflict, if no specific paragraph is mentioned, the present specification including the definition takes precedence. In addition, materials, methods and embodiments are only illustrative and not intended to be limited.

[0077] According to one embodiment of the present specification, 0 in the definitions of n1 to n3 means that hydrogen is bonded instead of deuterium.

[0078] According to one embodiment of the present specification, the above Chemical Formula 1 is represented by the following Chemical Formula 1-1.

[0079] [Chemical formula 1-1]

[0080]

[0081] In the above chemical formula 1-1,

[0082] Definitions of L1, D, and n1 to n3 are the same as those in the above Chemical Formula 1.

[0083] According to one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-2 to 1-5.

[0084] [Chemical formula 1-2]

[0085]

[0086] [Chemical formula 1-3]

[0087]

[0088] [Chemical formula 1-4]

[0089]

[0090] [Chemical formula 1-5]

[0091]

[0092] In the above chemical formulas 1-2 to 1-5,

[0093] Definitions of L1, D, and n1 to n3 are the same as those in the above Chemical Formula 1.

[0094] According to one embodiment of the present specification, the above Chemical Formula 1 is represented by the following Chemical Formula 1-6 or 1-7.

[0095] [Chemical formula 1-6]

[0096]

[0097] [Chemical formula 1-7]

[0098]

[0099] In the above chemical formulas 1-6 and 1-7,

[0100] Definitions of L1, D, and n1 to n3 are the same as those in the above Chemical Formula 1.

[0101] According to one embodiment of the present specification, the above Chemical Formula 1 is represented by Chemical Formula 1-8 or 1-9.

[0102] [Chemical formula 1-8]

[0103]

[0104] [Chemical formula 1-9]

[0105]

[0106] In the above chemical formulas 1-8 and 1-9,

[0107] The definitions of D and n1 to n3 are the same as those in the above Chemical Formula 1,

[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, the above-mentioned L1 is a direct bond, or an arylene group which may be substituted with deuterium or not.

[0113] According to one embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.

[0114] According to one embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.

[0115] According to one embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 10 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.

[0116] According to one embodiment of the present specification, L1 is a direct bond, a phenylene group which may be substituted by deuterium, or a naphthylene group which may be substituted by deuterium.

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

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

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

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

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

[0122] According to one embodiment of the present specification, the above Chemical Formula 1 is represented by the following Chemical Formula 1-10 or 1-11.

[0123] [Chemical formula 1-10]

[0124]

[0125] [Chemical formula 1-11]

[0126]

[0127] In the above chemical formulas 1-10 and 1-11,

[0128] The definitions of D and n1 to n3 are the same as those in the above Chemical Formula 1,

[0129] n4 is an integer from 0 to 4,

[0130] n5 is an integer from 0 to 6.

[0131] According to one embodiment of the present specification, the chemical formula 1 is represented by any one of the following structural formulas.

[0132]

[0133] In the above structural formula,

[0134] The definitions of L1 and D are the same as those in the above chemical formula 1,

[0135] n11 is an integer from 1 to 9,

[0136] n12 is an integer from 1 to 8,

[0137] n13 is an integer from 1 to 7.

[0138] According to one embodiment of the present specification, the chemical formula 1 is represented by any one of the following structural formulas.

[0139]

[0140] In the above structural formula,

[0141] The definition of D is the same as that in the above chemical formula 1,

[0142] n11 is an integer from 1 to 9,

[0143] n12 is an integer from 1 to 8,

[0144] n13 is an integer from 1 to 7.

[0145] According to one embodiment of the present specification, the chemical formula 1 is represented by any one of the following structural formulas.

[0146]

[0147] In the above structural formula,

[0148] The definition of D is the same as that in the above chemical formula 1,

[0149] n11 is an integer from 1 to 9,

[0150] n12 is an integer from 1 to 8,

[0151] n13 is an integer from 1 to 7,

[0152] n14 is an integer from 1 to 4.

[0153] According to one embodiment of the present specification, the chemical formula 1 is represented by any one of the following structural formulas.

[0154]

[0155]

[0156] In the above structural formula,

[0157] The definition of D is the same as that in the above chemical formula 1,

[0158] n11 is an integer from 1 to 9,

[0159] n12 is an integer from 1 to 8,

[0160] n13 is an integer from 1 to 7,

[0161] n15 is an integer from 1 to 6.

[0162] According to one embodiment of the present specification, at least one hydrogen at a substitutable position in the above Chemical Formula 1 is substituted with deuterium.

[0163] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 100%.

[0164] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 10% to 90%.

[0165] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 20% to 80%.

[0166] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 30% to 70%.

[0167] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 40% to 60%.

[0168] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 50%.

[0169] According to one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212] The present specification provides an organic light-emitting device including the above-mentioned compound.

[0213] 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.

[0214] 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.

[0215] 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.

[0216] In this specification, a specific substance A is contained in layer B, which means that i) more than one substance A is contained in one layer of layer B, and ii) layer B is composed of more than one layer and substance A is contained in one or more layers of the multiple layers of layer B.

[0217] In this specification, the specific substance A being contained in the C layer or the D layer means that i) it is contained in one or more layers of one or more C layers, or ii) it is contained in one or more layers of one or more D layers, or iii) it is contained in one or more C layers and one or more D layers respectively.

[0218] 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 contain the compound represented by the above chemical formula 1.

[0219] 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.

[0220] According to one embodiment of the present specification, the organic 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 includes the compound.

[0221] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

[0222] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound as a host of the light-emitting layer.

[0223] 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 thermally delayed fluorescent dopant.

[0224] According to one embodiment of the present specification, the fluorescent dopant includes one or more selected from arylamine compounds and boron compounds.

[0225] According to one embodiment of the present specification, the fluorescent dopant is an arylamine compound.

[0226] According to one embodiment of the present specification, the fluorescent dopant is a boron compound.

[0227] According to one embodiment of the present specification, the organic 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 thermally delayed fluorescent dopant.

[0228] According to one embodiment of the present specification, the arylamine compound is represented by the following chemical formula D-1.

[0229] [Chemical formula D-1]

[0230]

[0231] In the above chemical formula D-1,

[0232] L101 and L102 are the same as or different from each other, and are each independently a directly bonded, or substituted or unsubstituted arylene group,

[0233] 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.

[0234] According to one embodiment of the present specification, L101 and L102 are directly bonded.

[0235] 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 aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0236] According to one embodiment of the present specification, the above-mentioned Ar101 to Ar104 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0237] 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.

[0238] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

[0239]

[0240] According to one embodiment of the present specification, the boron compound is represented by the following chemical formula D-2.

[0241] [Chemical formula D-2]

[0242]

[0243] In the above chemical formula D-2,

[0244] 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 amine group, or a substituted or unsubstituted aryl group,

[0245] t3 and t4 are each an integer from 1 to 4,

[0246] t5 is an integer from 1 to 3,

[0247] When the above t3 is 2 or more, the above two or more T3 are the same or different from each other.

[0248] When the above t4 is 2 or more, the above two or more T4 are the same or different from each other.

[0249] When the above t5 is 2 or more, the above two or more T5s may be the same as or different from each other.

[0250] According to one embodiment of the present specification, the above-mentioned T1 to T5 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0251] According to one embodiment of the present specification, the above-mentioned T1 to T5 are the same as or different from each other, and are each independently hydrogen, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0252] According to one embodiment of the present specification, the above 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 may be substituted with a tert-butyl group.

[0253] According to one embodiment of the present specification, the chemical formula D-2 is represented by the following compound.

[0254]

[0255] According to one embodiment of the present specification, the phosphorescent dopant and the thermal delayed fluorescent dopant may use dopants known in the relevant technical field, but are not limited thereto.

[0256] According to one embodiment of the present specification, the light emitting layer includes the host and the dopant in a weight ratio of 99:1 to 1:99, specifically, in a weight ratio of 99:1 to 50:50, and more specifically, in a weight ratio of 99:1 to 95:5.

[0257] According to one embodiment of the present specification, the organic light-emitting device further includes one or more layers selected from 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.

[0258] 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.

[0259] According to one embodiment of the present specification, the two or more organic layers between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, can be selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer. Two or more.

[0260] 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 substances.

[0261] 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.

[0262] 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 substances.

[0263] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0264] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0265] 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 layers, and a cathode are sequentially stacked on a substrate.

[0266] 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.

[0267] 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.

[0268] Figure 1 exemplifies the structure of an organic light emitting device in which a first electrode 2, a light emitting layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The compound of the above Chemical Formula 1 is contained in the light emitting layer.

[0269] Figure 2 exemplifies the structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a first hole transport layer 6-1, 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 stacked on a substrate 1. The compound of the above chemical formula 1 is contained in the light-emitting layer.

[0270] Figure 3 exemplifies the structure of an organic light-emitting device 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 stacked on a substrate 1. The compound of the above chemical formula 1 is contained in the light-emitting layer.

[0271] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the technical field, except that the light-emitting layer includes the above compound, that is, the compound represented by the above Chemical Formula 1.

[0272] When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0273] 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 metal or a conductive metal oxide or an alloy thereof is evaporated on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, 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 evaporated on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a second electrode substance, an organic layer, and a first electrode substance on a substrate.

[0274] 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.

[0275] In addition to these methods, the organic light-emitting device can also be manufactured by sequentially vapor-depositing the second electrode material, the organic material layer, and the first electrode material on the substrate. However, the manufacturing method is not limited to this.

[0276] As the first electrode material, in order to smoothly inject holes into the organic layer, a material with a large work function is preferred. 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.

[0277] As the second electrode material, in order to facilitate the injection of electrons into the organic layer, a material with a small work function is preferably used, for example, 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.

[0278] The above-mentioned light-emitting layer may include a host material and a dopant material. In the case where 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 condensed and / or non-condensed aromatic ring derivative or a heterocyclic compound. Specifically, as aromatic condensed ring derivatives, 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, pyrimidine derivatives, etc., but are not limited thereto.

[0279] 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.

[0280] 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, has 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 preferably a material that 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 preferably a material with 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, polythiophene conductive polymers, etc., but are not limited to these.

[0281] The hole transport layer is a layer that receives holes from the hole injection layer and transports 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.

[0282] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, preferably a material with a large mobility for electrons. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to this. 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 material with a low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, etc., are accompanied by an aluminum layer or a silver layer in each case.

[0283] The electron injection layer is a layer that receives electrons from the electrode. As the electron injection material, the following materials are preferred: materials that have excellent ability to transport electrons, have the effect of receiving electrons from the second electrode, and have excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, materials that prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer and have excellent thin film forming ability are preferred. 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.

[0284] 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.

[0285] The electron blocking layer is a layer that prevents 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, 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.

[0286] The hole blocking layer is a layer that prevents holes from reaching the cathode and can be formed under the same conditions as the electron injection layer. Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0287] 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.

[0288] Examples of the invention

[0289] Below, in order to specifically describe this specification, examples and comparative examples will be cited to describe in detail. However, according to the examples and comparative examples of this specification, various different forms can be deformed, 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.

[0290] Synthesis Example 1. Synthesis of BH-1

[0291]

[0292] <1-a> Preparation of Compound BH-1-a

[0293] 9-(Naphthalene-1-yl)anthracene (23.4 g, 76.9 mmol) and aluminum chloride (AlCl3) (5.0 g, 38.4 mmol) were added to C6D6 (800 ml) and stirred for 3 hours. After the reaction was completed, D2O (100 ml) was added, and trimethylamine (10 ml) was added dropwise after stirring for 30 minutes. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. After drying with anhydrous magnesium sulfate, the organic solvent was removed under reduced pressure and purified by column chromatography to obtain compound BH-1-a (18.9 g, yield 77%).

[0294] MS: [M+H] + =321

[0295] <1-b> Preparation of Compound BH-1-b

[0296] After dispersing compound BH-1-a (15 g, 46.8 mmol) in 230 ml of dimethylformamide, slowly drop a solution of n-bromosuccinimide (8.4 g, 46.8 mmol) dissolved in 25 ml of dimethylformamide. After reacting at room temperature for 2 hours, drop 500 ml of water. When a solid is generated, filter it, dissolve it in ethyl acetate, put it in a separatory funnel, and wash it several times with distilled water. Recrystallize it in ethyl acetate to obtain compound BH-1-b (13.2 g, yield 72%).

[0297] MS: [M+H] + =399

[0298] <1-c> Preparation of Compound BH-1

[0299] After dissolving compound BH-1-b (10 g, 25.2 mmol) and naphtho[2,1-b]benzofuran-11-ylboronic acid (37.6 g, 143.44 mmol) in 200 ml of tetrahydrofuran, 40 ml of 2M K2CO3 aqueous solution was added. Then Pd(PPh3)4 (0.29 g, 0.25 mmol) was added and refluxed for 3 hours. After the reaction solution was cooled, the organic layer was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified by column chromatography to obtain compound BH-1 (10.1 g, yield 75%).

[0300] MS: [M+H] + =536

[0301] Synthesis Example 2. Synthesis of BH-2

[0302]

[0303] <2-a> Preparation of Compound BH-2-a

[0304] Compound BH-2-a was obtained by the same synthesis and purification method except that 9-bromo-10-(naphthalene-1-yl)anthracene was used instead of compound BH-1-b in the above-mentioned Synthesis Example 1-c.

[0305] MS: [M+H] + =521

[0306] <2-b> Preparation of Compound BH-2

[0307] Compound BH-2 was obtained by the same synthesis and purification as in Synthesis Example 1-a above, except that BH-2-a was used instead of 9-(naphthalene-1-yl)anthracene.

[0308] MS: [M+H]+ =545

[0309] Synthesis Example 3. Synthesis of BH-3

[0310]

[0311] <3-a> Preparation of Compound BH-3-a

[0312] Compound BH-3-a was obtained by the same synthesis and purification method except that 9-bromo-10-(naphthalene-2-yl)anthracene was used instead of compound BH-1-b in the above-mentioned Synthesis Example 1-c.

[0313] MS: [M+H] + =521

[0314] <3-b> Preparation of Compound BH-3

[0315] Compound BH-3 was obtained by the same synthesis and purification as in Synthesis Example 1-a above, except that Compound BH-3-a was used instead of 9-(naphthalene-1-yl)anthracene.

[0316] MS: [M+H] + =545

[0317] Synthesis Example 4. Synthesis of BH-4

[0318]

[0319] <4-a> Preparation of Compound BH-4-a

[0320] In the above-mentioned synthesis example 1-c, 11-bromonaphtho[2,1-b]benzofuran was used instead of compound BH-1-b, and (4-chlorophenyl)boronic acid was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-4-a.

[0321] MS: [M+H] + =329

[0322] <4-b> Preparation of Compound BH-4-b

[0323] Compound BH-4-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 added to 1,4-dihydro-1,4-diol. The reaction mixture was cooled, and the organic layer was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified by column chromatography to obtain compound BH-4-b (27.9 g, yield 73%).

[0324] MS: [M+H] + =421

[0325] <4-c> Preparation of compound BH-4-c

[0326] In the above-mentioned synthesis example 1-c, 9-bromo-10-(naphthalene-1-yl)anthracene was used instead of compound BH-1-b, and compound BH-4-b was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-4-c.

[0327] MS: [M+H] + =597

[0328] <4-d> Preparation of Compound BH-4

[0329] Compound BH-4 was obtained by the same synthesis and purification as in Synthesis Example 1-a above, except that Compound BH-4-c was used instead of 9-(naphthalene-1-yl)anthracene.

[0330] MS: [M+H] + =625

[0331] Synthesis Example 5. Synthesis of BH-5

[0332]

[0333] <5-a> Preparation of Compound BH-5-a

[0334] Compound BH-5-a was obtained by the same synthesis and purification method except that 9-(naphthalene-2-yl)anthracene was used instead of 9-(naphthalene-1-yl)anthracene in the above Synthesis Example 1-a.

[0335] MS: [M+H] + =321

[0336] <5-b> Preparation of Compound BH-5-b

[0337] Compound BH-5-b was obtained by the same method as above except that compound BH-5-a was used instead of compound BH-1-a in Synthesis Example 1-b.

[0338] MS: [M+H]+ =398

[0339] <5-c> Preparation of Compound BH-5

[0340] In the above-mentioned synthesis example 1-c, compound BH-5-b was used instead of compound BH-1-b, and naphtho[2,1-b]benzofuran-10-ylboronic acid was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid. Except for this, synthesis and purification were carried out by the same method to obtain compound BH-5.

[0341] MS: [M+H] + =536

[0342] Synthesis Example 6. Synthesis of BH-6

[0343]

[0344] <6-a> Preparation of Compound BH-6-a

[0345] In the above-mentioned synthesis example 1-c, 11-bromonaphtho[2,1-b]benzofuran was used instead of compound BH-1-b, and (3-chlorophenyl)boronic acid was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-6-a.

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

[0347] <6-b> Preparation of Compound BH-6-b

[0348] Compound BH-6-b was obtained by the same synthesis and purification method except that compound BH-6-a was used instead of compound BH-4-a in the above-mentioned Synthesis Example 4-b.

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

[0350] <6-c> Preparation of Compound BH-6

[0351] In the above-mentioned Synthesis Example 1-c, except that Compound BH-5-b was used instead of Compound BH-1-b, and Compound BH-6-b was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid, the same synthesis and purification were performed to obtain Compound BH-6.

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

[0353] Synthesis Example 7. Synthesis of BH-7

[0354]

[0355] <7-a> Preparation of Compound BH-7-a

[0356] In the above-mentioned synthesis example 1-c, 9-bromo-10-(naphthalene-1-yl)anthracene was used instead of compound BH-1-b, and naphtho[2,1-b]benzofuran-10-ylboronic acid was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-7-a.

[0357] MS: [M+H] + =521

[0358] <7-b> Preparation of Compound BH-7

[0359] Compound BH-7 was obtained by the same method as described above except that Compound BH-7-a was used instead of 9-(naphthalene-1-yl)anthracene.

[0360] MS: [M+H] + =545

[0361] Synthesis Example 8. Synthesis of BH-8

[0362]

[0363] <8-a> Preparation of Compound BH-8-a

[0364] In the above-mentioned synthesis example 1-c, 10-bromonaphtho[2,1-b]benzofuran was used instead of compound BH-1-b, and (6-chloronaphthalene-2-yl)boric acid was used instead of naphtho[2,1-b]benzofuran-11-ylboric acid. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-8-a.

[0365] MS: [M+H] + =379

[0366] <8-b> Preparation of Compound BH-8-b

[0367] Compound BH-8-b was obtained by the same method as above except that compound BH-8-a was used instead of compound BH-4-a in Synthesis Example 4-b.

[0368] MS: [M+H] + =471

[0369] <8-c> Preparation of Compound BH-8-c

[0370] In the above-mentioned synthesis example 1-c, compound BH-8-b was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid, and 9-bromo-10-(naphthalene-1-yl)anthracene was used instead of compound BH-1-b. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-8-c.

[0371] MS: [M+H] + =647

[0372] <8-d> Preparation of Compound BH-8

[0373] Compound BH-8 was obtained by the same method as above except that Compound BH-8-c was used instead of 9-(naphthalene-1-yl)anthracene in Synthesis Example 1-a.

[0374] MS: [M+H] + =677

[0375] Synthesis Example 9. Synthesis of BH-9

[0376]

[0377] <9-a> Preparation of Compound BH-9-a

[0378] In the above-mentioned synthesis example 1-c, 9-bromonaphtho[2,1-b]benzofuran was used instead of compound BH-1-b, and (4-chlorophenyl)boronic acid was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-9-a.

[0379] MS: [M+H] + =329

[0380] <9-b> Preparation of Compound BH-9-b

[0381] Compound BH-9-b was obtained by the same synthesis and purification method except that compound BH-9-a was used instead of compound BH-4-a in the above-mentioned Synthesis Example 4-b.

[0382] MS: [M+H] + =421

[0383] <9-c> Preparation of Compound BH-9-c

[0384] In the above-mentioned synthesis example 1-c, compound BH-9-b was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid, and 9-bromo-10-(naphthalene-2-yl)anthracene was used instead of compound BH-1-b. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-9-c.

[0385] MS: [M+H] + =597

[0386] <9-d> Preparation of Compound BH-9

[0387] Compound BH-9 was obtained by the same synthesis and purification method except that Compound BH-9-c was used instead of 9-(naphthalene-1-yl)anthracene in the above Synthesis Example 1-a.

[0388] MS: [M+H] + =625

[0389] Synthesis Example 10. Synthesis of BH-10

[0390]

[0391] <10-a> Preparation of Compound BH-10-a

[0392] In the above-mentioned synthesis example 1-c, 9-bromonaphtho[2,1-b]benzofuran was used instead of compound BH-1-b, and (3-chlorophenyl)boronic acid was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-10-a.

[0393] MS: [M+H] + =329

[0394] <10-b> Preparation of Compound BH-10-b

[0395] Compound BH-10-b was obtained by the same method as above except that compound BH-10-a was used instead of compound BH-4-a in Synthesis Example 4-b.

[0396] MS: [M+H] + =421

[0397] <10-c> Preparation of Compound BH-10-c

[0398] In the above-mentioned synthesis example 1-c, compound BH-10-b was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid, and 9-bromo-10-(naphthalene-1-yl)anthracene was used instead of compound BH-1-b. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-10-c.

[0399] MS: [M+H] + =597

[0400] <10-d> Preparation of Compound BH-10

[0401] Compound BH-10 was obtained by the same method as described above except that Compound BH-10-c was used instead of 9-(naphthalene-1-yl)anthracene.

[0402] MS: [M+H] + =625

[0403] Synthesis Example 11. Synthesis of BH-11

[0404]

[0405] <11-a> Preparation of Compound BH-11-a

[0406] In the above-mentioned synthesis example 1-c, 9-bromonaphtho[2,1-b]benzofuran was used instead of compound BH-1-b, and (3-chloronaphthalene-2-yl)boric acid was used instead of naphtho[2,1-b]benzofuran-11-ylboric acid. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-11-a.

[0407] MS: [M+H] + =379

[0408] <11-b> Preparation of Compound BH-11-b

[0409] Compound BH-11-b was obtained by the same method as above except that compound BH-11-a was used instead of compound BH-4-a in Synthesis Example 4-b.

[0410] MS: [M+H] + =471

[0411] <11-c> Preparation of Compound BH-11-c

[0412] In the above-mentioned synthesis example 1-c, compound BH-11-b was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid, and 9-bromo-10-(naphthalene-1-yl)anthracene was used instead of compound BH-1-b. Except for this, synthesis and purification were carried out by the same method to obtain compound BH-11-c.

[0413] MS: [M+H] + =647

[0414] <11-d> Preparation of Compound BH-11

[0415] Compound BH-11 was obtained by the same method as above except that Compound BH-11-c was used instead of 9-(naphthalene-1-yl)anthracene in Synthesis Example 1-a.

[0416] MS: [M+H] + =677

[0417] Synthesis Example 12. Synthesis of BH-12

[0418]

[0419] <12-a> Preparation of Compound BH-12-a

[0420] In the above-mentioned synthesis example 1-c, 9-bromo-10-(naphthalene-1-yl)anthracene was used instead of compound BH-1-b, and naphtho[2,1-b]benzofuran-8-ylboronic acid was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-12-a.

[0421] MS: [M+H] + =521

[0422] <12-b> Preparation of Compound BH-12

[0423] Compound BH-12 was obtained by the same method as described above except that Compound BH-12-a was used instead of 9-(naphthalene-1-yl)anthracene.

[0424] MS: [M+H] + =545

[0425] Synthesis Example 13. Synthesis of BH-13

[0426]

[0427] <13-a> Preparation of Compound BH-13-b

[0428] In the above-mentioned synthesis example 1-c, 9-bromo-10-(naphthalene-2-yl)anthracene was used instead of compound BH-1-b, and naphtho[2,1-b]benzofuran-8-ylboronic acid was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-13-b.

[0429] MS: [M+H] + =521

[0430] <13-b> Preparation of Compound BH-13

[0431] Compound BH-13 was obtained by the same method as described above except that Compound BH-13-b was used instead of 9-(naphthalene-1-yl)anthracene.

[0432] MS: [M+H] + =545

[0433] Synthesis Example 14. Synthesis of BH-14

[0434]

[0435] <14-a> Preparation of Compound BH-14-a

[0436] In the above-mentioned synthesis example 1-c, 8-bromonaphtho[2,1-b]benzofuran was used instead of compound BH-1-b, and (3-chlorophenyl)boronic acid was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid. Except for this, the synthesis and purification were carried out by the same method to obtain compound BH-14-a.

[0437] MS: [M+H] + =329

[0438] <14-b> Preparation of Compound BH-14-b

[0439] Compound BH-14-b was obtained by the same method as above except that compound BH-14-a was used instead of compound BH-4-a.

[0440] MS: [M+H] + =421

[0441] <14-c> Preparation of Compound BH-14

[0442] Compound BH-14 was obtained by the same method as above except that compound BH-14-b was used instead of naphtho[2,1-b]benzofuran-11-ylboronic acid in Synthesis Example 1-c.

[0443] MS: [M+H] + =612

[0444] <Experimental Example 1: Device Example>

[0445] Example 1.

[0446] 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.

[0447] On the ITO transparent electrode prepared as described above, the following HI-A and HATCN were respectively The first hole injection layer and the second hole injection layer were formed by thermal vacuum deposition with a thickness of 1000 mm / s. The following HT-B was deposited on the hole transport layer with a thickness of The electron blocking layer is formed by vacuum deposition of a thickness of .

[0448] Next, on the electron blocking layer, The light-emitting layer was formed by vacuum evaporating 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 main body at 96 wt % relative to the total weight of the light-emitting layer.

[0449] Then, on the above-mentioned light-emitting layer, as the first electron transport layer, the following compound ET-A was vacuum-deposited Next, the following ET-B and LiQ were vacuum-deposited at a weight ratio of 1:1, thereby A second electron transport layer is formed with a thickness of . On the second electron transport layer, LiQ is vacuum evaporated to The electron injection layer is formed by vacuum evaporation with a thickness of Aluminum and silver were evaporated at a weight ratio of 10:1, and Aluminum is evaporated to a thickness of , thereby forming a cathode.

[0450] In the above process, the evaporation rate of organic matter is maintained Aluminum cathode maintenance The evaporation speed is 1×10 -7 ~5×10 -8 A support is provided to produce an organic light-emitting device.

[0451]

[0452] Examples 2 to 14

[0453] Organic light-emitting devices of Examples 2 to 14 were prepared in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound BH-1 as the host of the light-emitting layer.

[0454]

[0455] Comparative Examples 1 and 2

[0456] Organic light-emitting devices of Comparative Examples 1 and 2 were prepared in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound BH-1 as the host of the light-emitting layer.

[0457]

[0458] The organic light emitting devices of Examples 1 to 14 and Comparative Examples 1 and 2 were measured by applying 10 mA / cm 2 The voltage, efficiency (cd / A / y) at a current density of 20 mA / cm 2 The results are shown in Table 1. At this time, LT95 means the lifespan (LT95) of the battery at a current density of 20 mA / cm 2 When the initial brightness under 100% is taken as 100%, the time required for the brightness to decrease to 95% is the ratio based on Comparative Example 1.

[0459] [Table 1]

[0460]

[0461] In the above Table 1, the compound of Chemical Formula 1 according to one embodiment of the present specification has a structural characteristic of excellent electron and hole transport. In addition, the above Chemical Formula 1 contains deuterium as a substituent, so that the stability of the molecule is improved. Therefore, Examples 1 to 14 in which it is included in the light-emitting layer of the organic light-emitting device show more excellent efficiency, driving voltage and life efficiency compared with the organic light-emitting devices of Comparative Examples 1 and 2 containing compounds not containing deuterium.

Claims

1. A compound represented by the following chemical formula 1-2 or 1-5: Chemical formula 1-2 Chemical formula 1-5 in, In the chemical formulas 1-2 and 1-5, L1 is a direct bond, or a substituted or unsubstituted arylene group, D is deuterium, n1 is an integer from 0 to 9, n2 is an integer from 0 to 8, n3 is an integer from 0 to 7, 1≤n1+n2+n3≤24.

2. The compound according to claim 1, wherein The above-mentioned L1 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, which is directly bonded or substituted or unsubstituted with deuterium.

3. The compound according to claim 1, wherein The chemical formula 1-2 or 1-5 is any one selected from the following compounds:

4. 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 layers disposed between the first electrode and the second electrode, One or more of the organic layers comprises the compound of any one of claims 1 to 3. 5 . The organic light-emitting device according to claim 4 , wherein the organic layer comprises 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 comprises the compound.

6. The organic light emitting device according to claim 4, wherein: The organic layer includes a light-emitting layer, and the light-emitting layer contains the compound.

7. The organic light emitting device according to claim 4, wherein: The organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host of the light-emitting layer.

8. The organic light emitting device according to claim 7, wherein: The light-emitting layer further includes a dopant, and the dopant includes one or more selected from a fluorescent dopant, a phosphorescent dopant, and a thermally delayed fluorescent dopant.

9. The organic light emitting device according to claim 8, wherein: The fluorescent dopant includes one or more selected from arylamine compounds and boron compounds.

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