Compound and organic light-emitting device including same

Abstract

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

Description

[Technical field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2021-0116104, filed with the Korean Intellectual Property Office on September 1, 2021, the entire contents of which are incorporated herein by reference.

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

[0003] In general, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often a multi-layer structure composed of different materials to improve the efficiency and safety of the organic light emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic light emitting device structure, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic material layer, and when the injected holes and electrons are recombined, excitons are formed, and when the excitons fall back to the ground state, light is emitted.

[0004] There is a continuing need to develop new materials for such organic light-emitting devices. Summary of the Invention [Problem to be solved by the invention]

[0005] The present specification provides a compound and an organic light-emitting device including the same. [Means for solving the problem]

[0006] One embodiment of the present specification provides a compound represented by the following chemical formula 1: [Chemical formula 1] [ka] In the above Chemical Formula 1, D is deuterium, L1 is a direct bond; or a substituted or unsubstituted arylene group; Ar1 is a substituted or unsubstituted aryl group; R1 to R9 are the same or different and each independently represents hydrogen or deuterium; a1 is an integer from 1 to 8.

[0007] The present specification also provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound. Effect of the Invention

[0008] The compounds described herein can be used as materials for the organic layers of organic light-emitting devices. The compounds according to one embodiment can improve the efficiency, lower the driving voltage, and / or improve the life characteristics of the organic light-emitting devices. [Brief description of the drawings]

[0009] [Figure 1] 1 illustrates an example of an organic light-emitting device according to an embodiment of the present specification. [Diagram 2] 1 illustrates an example of an organic light-emitting device according to an embodiment of the present specification. [Explanation of symbols]

[0010] 1. Circuit Board 2...1st electrode 3...Second electrode 4. Emitting layer 5. First hole injection layer 6 Second hole injection layer 7. Hole transport layer 8. Electron blocking layer 9...first electron transport layer 10...Second electron transport layer 11...electron injection layer DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] This specification will be explained in more detail below.

[0012] One embodiment of the present specification provides a compound represented by Chemical Formula 1.

[0013] According to one embodiment of the present specification, the anthracene core of Formula 1 includes 1) Ar1 and 2) L1 bonded to the 3-position of benzobisbenzofuran as a substituent, and at least one hydrogen atom at a substitutable position of the anthracene of Formula 1 is replaced with deuterium, thereby improving the mobility of electrons and holes and the molecular stability. Therefore, an organic light-emitting device including the anthracene core has excellent driving voltage, efficiency, and lifespan.

[0014] In this specification, examples of the substituents are described below, but are not limited to these.

[0015] In this specification, [ka] means the site to be linked.

[0016] Throughout this specification, the term "combinations thereof" contained in a Markush form expression means a mixture or combination of one or more selected from the group of elements set forth in the Markush form expression, and is meant to include one or more selected from the group of elements.

[0017] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0018] As used herein, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium; halogen groups; hydroxy groups; cyano groups; nitro groups; alkyl groups; cycloalkyl groups; alkoxy groups; alkenyl groups; haloalkyl groups; silyl groups; boron groups; amine groups; aryl groups; and heteroaryl groups, substituted with a substituent in which two or more of the substituents exemplified above are linked, or having no substituents at all.

[0019] In the present specification, the term "two or more substituents are linked" refers to the fact that a hydrogen atom of any one of the substituents is linked to another substituent. For example, the term "two substituents are linked" refers to the fact that a phenyl group and a naphthyl group are linked to each other. [ka] or [ka] In addition, the linking of three substituents includes not only the linking of (substituent 1)-(substituent 2)-(substituent 3) successively, but also the linking of (substituent 1) to (substituent 2) and (substituent 3). For example, a phenyl group, a naphthyl group, and an isopropyl group are linked to form [ka] The above definitions also apply to the case where four or more substituents are linked together.

[0020] As used herein, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0021] In this specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

[0022] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups, but are not limited to these.

[0023] In this specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferable that the number of carbon atoms is 1 to 30. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, and p-methylbenzyloxy.

[0024] In this specification, the alkenyl group may be linear 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-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, and a styrenyl group, but are not limited thereto.

[0025] As used herein, the haloalkyl group refers to an alkyl group defined above in which at least one halogen group is substituted for a hydrogen atom.

[0026] In this specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0027] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably is 6 to 30. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group.

[0028] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but preferably is 10 to 30. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, and a fluorene group.

[0029] As used herein, the fluorene groups may be substituted and adjacent groups may be linked together to form a ring.

[0030] When the fluorene group is substituted, [ka] These include, but are not limited to:

[0031] In this specification, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0032] In the present specification, a heteroaryl group includes one or more atoms other than carbon, i.e., heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The 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 the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group, a pyridazine group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phthalazine group, a pyridopyrimidine group, a pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene ... groups, dibenzothiophene groups, benzofuran groups, phenanthridine groups, phenanthroline groups, isoxazole groups, thiadiazole groups, dibenzofuran groups, dibenzosilole groups, phenoxathiine groups, phenoxazine groups, phenothiazine groups, dihydroindenocarbazole groups, spirofluorenexanthene groups, and spirofluorenethioxanthene groups, but are not limited to these.

[0033] In this 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 above-mentioned examples of the alkyl group, the aryl group in the arylsilyl group may be the above-mentioned examples of the aryl group, and the heteroaryl group in the heteroarylsilyl group may be the above-mentioned examples of the heteroaryl group.

[0034] As used herein, a boron group is -BR 100 R 101 wherein R 100 and R101 are the same or different and may each be independently selected from the group consisting of hydrogen, deuterium, halogen, a nitrile group, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. Specific examples of the boron group include, but are not limited to, a dimethyl boron group, a diethyl boron group, a t-butyl methyl boron group, and a diphenyl boron group.

[0035] In this specification, the amine group may be selected from the group consisting of -NH2, an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a ditolylamine group, an N-phenyltolylamine group, an N-phenylbiphenylamine group, an N-phenylnaphthylamine group, an N-biphenylnaphthylamine group, an N-naphthylfluorenylamine group, an N-phenylphenanthrenylamine group, an N-biphenylphenanthrenylamine group, an N-phenylfluorenylamine group, an N-phenylterphenylamine group, an N-phenanthrenylfluorenylamine group, an N-biphenylfluorenylamine group, and the like.

[0036] In the present specification, the term "N-alkylarylamine group" refers to an amine group in which an alkyl group and an aryl group are substituted at the N of the amine group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.

[0037] In the present specification, the term "N-arylheteroarylamine group" refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and the heteroaryl group described above.

[0038] In the present specification, the term "N-alkylheteroarylamine group" refers to an amine group in which an alkyl group and a heteroaryl group are substituted at the N of the amine group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the alkyl group and the heteroaryl group exemplified above.

[0039] In this specification, examples of alkylamine groups include substituted or unsubstituted monoalkylamine groups, or substituted or unsubstituted dialkylamine groups. The alkyl group in the alkylamine group may be a straight-chain or branched-chain alkyl group. The alkylamine group containing two or more alkyl groups may contain a straight-chain alkyl group, a branched-chain alkyl group, or both a straight-chain alkyl group and a branched-chain alkyl group. For example, the alkyl group in the alkylamine group may be selected from the alkyl group examples mentioned above.

[0040] In this specification, examples of the arylamine group include substituted or unsubstituted monoarylamine groups, or substituted or unsubstituted diarylamine groups. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of aryl groups mentioned above.

[0041] In this specification, examples of the heteroarylamine group include substituted or unsubstituted monoheteroarylamine groups, or substituted or unsubstituted diheteroarylamine groups.The heteroarylamine group containing two or more heteroaryl groups may contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.

[0042] In the present specification, an arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The above description of the aryl group may be applied to these groups, except that they are both divalent groups.

[0043] As used herein, "deuterated" or "deuterated" means that a hydrogen at a substitutable position of a compound has been replaced with deuterium.

[0044] As used herein, "perdeuterated" refers to a compound or group in which all hydrogens in the molecule have been replaced with deuterium, and has the same meaning as "100% deuterated."

[0045] As used herein, "X% deuterated", "deuteration rate X%", or "deuterium substitution rate X%" means that X% of hydrogen atoms at substitutable positions in the structure are substituted with deuterium. For example, when the structure is dibenzofuran, "25% deuterated" of the dibenzofuran, "deuteration rate 25%" of the dibenzofuran, or "deuterium substitution rate 25%" of the dibenzofuran means that two of eight hydrogen atoms at substitutable positions in the dibenzofuran are substituted with deuterium.

[0046] In this specification, the deuteration ratio is determined by nuclear magnetic resonance spectroscopy ( 1The identity of the compound can be confirmed by known methods such as 1 H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or MALDI-TOF MS (Matrix assisted laser desorption / ionization Time-of-Flight Mass Spectrometry).

[0047] In this specification, unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the present invention belongs. Methods and materials similar or equivalent to those described herein may be used in the practice or testing of embodiments of the present invention, and suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, the present specification, including definitions, will control unless a specific passage is mentioned. It should be noted that the materials, methods, and examples are merely illustrative and are not intended to be limiting.

[0048] According to one embodiment of the present specification, the above-mentioned Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2. [Chemical formula 1-1] [ka] [Chemical formula 1-2] [ka] In the above Chemical Formulas 1-1 and 1-2, The definitions of D, Ar1, a1, and R1 to R9 are the same as those in Chemical Formula 1. L11 is a substituted or unsubstituted arylene group.

[0049] According to one embodiment of the present specification, the above-mentioned Chemical Formula 1 is represented by the following Chemical Formula 1-3 or 1-4. [Chemical formula 1-3] [ka] [Chemical formula 1-4] [ka] In the above Chemical Formulas 1-3 and 1-4, The definitions of D, Ar1, a1, and R1 to R9 are the same as those in Chemical Formula 1. a2 is an integer from 0 to 4, a3 is an integer from 0 to 4, a4 is an integer from 0 to 4, 0≦a3+a4≦6.

[0050] According to one embodiment of the present specification, in the definitions of a2 to a4, 0 means that hydrogen is bonded in place of deuterium.

[0051] According to one embodiment of the present specification, a2 is an integer of 1-4.

[0052] According to one embodiment of the present specification, a2 is 0.

[0053] According to one embodiment of the present specification, a2 is 1.

[0054] According to one embodiment of the present specification, a2 is 2.

[0055] According to one embodiment of the present specification, a2 is 3.

[0056] According to one embodiment of the present specification, a2 is 4.

[0057] According to one embodiment of the present specification, a3 is an integer of 1-4.

[0058] According to one embodiment of the present specification, a3 is 0.

[0059] According to one embodiment of the present specification, a3 is 1.

[0060] According to one embodiment of the present specification, a3 is 2.

[0061] According to one embodiment of the present specification, a3 is 3.

[0062] According to one embodiment of the present specification, a3 is 4.

[0063] According to one embodiment of the present specification, a4 is an integer of 1-4.

[0064] According to one embodiment of the present specification, a4 is 0.

[0065] According to one embodiment of the present specification, a4 is 1.

[0066] According to one embodiment of the present specification, a4 is 2.

[0067] According to one embodiment of the present specification, a4 is 3.

[0068] According to one embodiment of the present specification, a4 is 4.

[0069] According to one embodiment of the present specification, a1 is 1.

[0070] According to one embodiment of the present specification, a1 is 2.

[0071] According to one embodiment of the present specification, a1 is 3.

[0072] According to one embodiment of the present specification, a1 is 4.

[0073] According to one embodiment of the present specification, a1 is 5.

[0074] According to one embodiment of the present specification, a1 is 6.

[0075] According to one embodiment of the present specification, a1 is 7.

[0076] According to one embodiment of the present specification, a1 is 8.

[0077] According to one embodiment of the present specification, at least one of R1 to R9 is deuterium, and the rest are hydrogen.

[0078] According to one embodiment of the present specification, any one of R1 to R9 is deuterium, and the rest are hydrogen.

[0079] According to one embodiment of the present specification, any two of R1 to R9 are deuterium, and the rest are hydrogen.

[0080] According to one embodiment of the present specification, any three of R1 to R9 are deuterium, and the rest are hydrogen.

[0081] According to one embodiment of the present specification, any four of R1 to R9 are deuterium, and the rest are hydrogen.

[0082] According to one embodiment of the present specification, any five of R1 to R9 are deuterium, and the remainder are hydrogen.

[0083] According to one embodiment of the present specification, any six of R1 to R9 are deuterium, and the remainder are hydrogen.

[0084] According to one embodiment of the present specification, any seven of R1 to R9 are deuterium, and the remainder are hydrogen.

[0085] According to one embodiment of the present specification, any eight of R1 to R9 are deuterium, and the remaining one is hydrogen.

[0086] According to one embodiment of the present specification, R1 to R9 are deuterium.

[0087] According to one embodiment of the present specification, R1 to R9 are hydrogen.

[0088] According to one embodiment of the present specification, the L1 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium, and the Ar1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with one or more substituents selected from deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof.

[0089] 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.

[0090] 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.

[0091] According to one embodiment of the present specification, the L1 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms which is unsubstituted or substituted with deuterium.

[0092] According to one embodiment of the present specification, the L1 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium.

[0093] According to one embodiment of the present specification, L1 is a direct bond; a deuterium-substituted or unsubstituted phenylene group; or a deuterium-substituted or unsubstituted naphthylene group.

[0094] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0095] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0096] According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof.

[0097] According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a combination thereof.

[0098] According to one embodiment of the present specification, Ar1 is a phenyl group substituted or unsubstituted with one or more of deuterium, naphthyl group, and combinations thereof; a biphenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium.

[0099] According to one embodiment of the present specification, the compound represented by Chemical Formula 1 is any one selected from the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] .

[0100] The present specification provides an organic light emitting device comprising the compound described above.

[0101] In this specification, when a member is said to be located "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member is present between the two members.

[0102] In this specification, when a part "comprises" a certain component, this does not mean excluding other components, but means that the part may further include other components, unless otherwise specified to the contrary.

[0103] In the present invention, the term "layer" is interchangeable with the term "film" commonly used in the art, and refers to a coating that covers a desired area. The size of the "layer" is not limited, and each "layer" may be the same or different in size. According to one embodiment, the size of the "layer" may be the same as the entire element, may correspond to the size of a specific functional area, or may be smaller by a single sub-pixel.

[0104] In this specification, the term "a specific substance A is contained in layer B" includes both i) one or more types of substance A are contained in one layer B, and ii) layer B is composed of one or more layers and substance A is contained in one or more of the multiple layer Bs.

[0105] In this specification, when a specific substance A is contained in layer C or layer D, it means that i) it is contained in one or more of one or more C layers, ii) it is contained in one or more of one or more D layers, or iii) it is contained in one or more C layers and one or more D layers.

[0106] The present specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by Chemical Formula 1.

[0107] The organic layer of the organic light-emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. For example, it may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0108] 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.

[0109] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

[0110] According to one embodiment of the present specification, the organic layer includes an emitting layer, and the emitting layer includes the compound as a host of the emitting layer.

[0111] According to one embodiment of the present specification, the light-emitting layer includes a dopant, and the dopant includes one or more selected from the group consisting of a fluorescent dopant, a phosphorescent dopant, and a thermally activated delayed fluorescent dopant.

[0112] According to one embodiment of the present specification, the fluorescent dopant includes one or more selected from the group consisting of an arylamine-based compound and a boron-based compound.

[0113] According to one embodiment of the present specification, the fluorescent dopant is an arylamine compound.

[0114] According to one embodiment of the present specification, the fluorescent dopant is a boron-based compound.

[0115] According to one embodiment of the present specification, the organic layer includes an emitting layer, the emitting layer includes a host and a dopant, the host includes the compound, and the dopant includes one or more selected from the group consisting of a fluorescent dopant, a phosphorescent dopant, and a thermally activated delayed fluorescent dopant.

[0116] According to one embodiment of the present specification, the arylamine compound is represented by the following chemical formula D-1. [Chemical formula D-1] [ka] In the above chemical formula D-1, L101 and L102 are the same or different and each independently represents a direct bond; or a substituted or unsubstituted arylene group; Ar101 to Ar104 are the same or different and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0117] According to one embodiment of the present specification, L101 and L102 are direct bonds.

[0118] According to one embodiment of the present specification, Ar101 to Ar104 are the same or different and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0119] According to one embodiment of the present specification, Ar101 to Ar104 are the same or different and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0120] According to one embodiment of the present specification, Ar101 to Ar104 are the same or different and each independently represents a phenyl group substituted with a methyl group; or a dibenzofuran group.

[0121] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound. [ka]

[0122] According to one embodiment of the present specification, the boron-based compound is represented by the following chemical formula D-2. [Chemical formula D-2] [ka] In the above chemical formula D-2, T1 to T5 are the same or different and each independently represents hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group; t3 and t4 are each an integer from 1 to 4, t5 is an integer from 1 to 3, When the t3 is 2 or more, the two or more T3 are the same or different, When t4 is 2 or more, the two or more T4 are the same or different, When the t5 is 2 or more, the two or more T5's may be the same or different.

[0123] According to one embodiment of the present specification, T1 to T5 are the same or different and each independently represent a hydrogen atom; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0124] According to one embodiment of the present specification, T1 to T5 are the same or different and each independently represent a hydrogen atom; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

[0125] According to one embodiment of the present specification, T1 to T5 are the same or different and each independently represent a hydrogen atom; a tert-butyl group; a diphenylamine group; or a phenyl group unsubstituted or substituted with a tert-butyl group.

[0126] According to one embodiment of the present specification, the chemical formula D-2 is represented by the following compound. [ka]

[0127] According to one embodiment of the present specification, the phosphorescent dopant and the thermally activated delayed fluorescent dopant are, but are not limited to, those well known in the art.

[0128] According to one embodiment of the present specification, the light emitting layer contains a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, the weight ratio is 99:1 to 50:50, more specifically, the weight ratio is 99:1 to 95:5.

[0129] According to one embodiment of the present specification, the organic light-emitting device further includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

[0130] According to one embodiment of the present specification, the organic light-emitting element includes a first electrode; a second electrode; an emitting layer provided between the first electrode and the second electrode; and two or more organic layers provided between the emitting layer and the first electrode or between the emitting layer and the second electrode.

[0131] According to one embodiment of the present specification, the two or more organic layers between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, may be two or more selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

[0132] According to one embodiment of the present specification, the device includes two or more hole injection layers between the light emitting layer and the first electrode. The two or more hole injection layers may contain the same or different materials.

[0133] According to one embodiment of the present specification, the device includes two or more hole transport layers between the light emitting layer and the first electrode. The two or more hole transport layers may contain the same or different materials.

[0134] According to one embodiment of the present specification, the device further includes two or more electron transport layers between the light emitting layer and the second electrode. The two or more electron transport layers may contain the same or different materials.

[0135] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0136] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0137] According to one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate.

[0138] According to one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0139] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is illustrated in Figures 1 and 2. Figures 1 and 2 are illustrative of, but not limiting of, the organic light-emitting device.

[0140] 1 illustrates a structure of an organic light emitting device in which a first electrode 2, an emitting layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The compound of Chemical Formula 1 is contained in the emitting layer 4.

[0141] 2 illustrates an example of a structure of an organic light-emitting device in which a substrate 1, a first electrode 2, a first hole injection layer 5, a second hole injection layer 6, a hole transport layer 7, an electron blocking layer 8, an emitting layer 4, a first electron transport layer 9, a second electron transport layer 10, an electron injection layer 11, and a second electrode 3 are sequentially laminated. In this structure, the compound may be contained in the emitting layer 4.

[0142] The organic light emitting device of the present specification may be manufactured by materials and methods well known in the art, except that the light emitting layer contains the above compound, ie, the compound represented by Chemical Formula 1 above.

[0143] When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0144] For example, the organic light emitting device of the present invention may be fabricated by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, a metal or a conductive metal oxide or an alloy thereof may be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode, and an organic layer including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer may be formed thereon, and a material usable as a cathode may be deposited thereon. In addition to this method, an organic light emitting device may be fabricated by sequentially depositing a second electrode material, an organic layer, and a first electrode material on a substrate.

[0145] In addition, the compound represented by Formula 1 may be formed in an organic layer by a solution coating method as well as a vacuum deposition method during the preparation of an organic light emitting device, where the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blade, inkjet printing, screen printing, spraying, roll coating, etc.

[0146] In addition to the above method, an organic light emitting device can be fabricated by sequentially depositing a second electrode material, an organic layer, and a first electrode material on a substrate, but the fabrication method is not limited to these.

[0147] The first electrode material is preferably a material having a large work function so that holes can be easily injected into the organic layer, and examples of the material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof, metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO), combinations of metals and oxides such as ZnO:Al or SnO2:Sb, and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0148] The second electrode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer, such as, but not limited to, metals or alloys thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; and materials having a multilayer structure, such as LiF / Al or LiO2 / Al.

[0149] 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 containing the compound represented by Chemical Formula 1 according to one embodiment of the present specification, the host material may include fused and / or non-fused aromatic ring derivatives or heterocycle-containing compounds. Specifically, fused aromatic ring derivatives may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds may include, but are not limited to, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.

[0150] The dopant material includes aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative includes fused aromatic ring derivatives having a substituted or unsubstituted arylamine group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamine group. The styrylamine compound includes a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. The metal complex includes, but are not limited to, an iridium complex, a platinum complex, etc.

[0151] The hole injection layer is a layer that receives holes from the electrode. The hole injection material has the ability to transport holes, and preferably has an excellent hole receiving effect from the anode and an excellent hole injection effect for the light emitting layer or light emitting material. In addition, a material having an excellent ability to prevent the movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material is preferable. In addition, a material having an excellent thin film forming ability is preferable. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrin, oligothiophene, and arylamine-based organic materials; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; polythiophene-based conductive polymers such as anthraquinone and polyaniline.

[0152] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but is not limited thereto. [Chemical formula HI-1] [ka] In the above chemical formula HI-1, R300 to R308 are the same or different and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are bonded to adjacent groups to form a substituted or unsubstituted ring; r301 and r302 each represent an integer of 1 to 4; r303 and r304 each represent an integer of 1 to 3; When the r301 is 2 or more, the R301 are the same or different, When the r302 is 2 or more, the R302 are the same or different, When the r303 is 2 or more, the R303 are the same or different, When r304 is 2 or more, R304 may be the same or different.

[0153] According to one embodiment of the present specification, R301 to R304 are hydrogen.

[0154] According to one embodiment of the present specification, R300 is a substituted or unsubstituted aryl group.

[0155] According to one embodiment of the present specification, R300 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0156] According to one embodiment of the present specification, R300 is a phenyl group.

[0157] According to one embodiment of the present specification, R300 is combined with R301 or R302 to form a substituted or unsubstituted ring.

[0158] According to one embodiment of the present specification, R300 is combined with R301 or R302 to form an indole ring.

[0159] According to one embodiment of the present specification, R305 to R308 are the same or different and each independently represent a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0160] According to one embodiment of the present specification, R305 to R308 are the same or different and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0161] According to one embodiment of the present specification, R305 to R308 are the same or different and each independently represents a phenyl group; or a carbazole group unsubstituted or substituted with a phenyl group.

[0162] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound. [ka]

[0163] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-2, but is not limited thereto. [Chemical formula HI-2] [ka] In the above chemical formula HI-2, At least one of X'1 to X'6 is N, and the rest are CH; R309 to R314 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are bonded to adjacent groups to form a substituted or unsubstituted ring.

[0164] According to one embodiment of the present specification, X'1 to X'6 are N.

[0165] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0166] According to one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound. [ka]

[0167] 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 is preferably a material that has high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0168] According to one embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HT-1, but is not limited thereto. [Chemical formula HT-1] [ka] In the formula HT-1, R315 to R317 are the same or different, and each independently represents one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring; r315 is an integer of 1 to 5, and when r315 is 2 or more, the two or more R315's are the same or different from each other, r316 is an integer of 1 to 5, and when said r316 is 2 or more, said 2 or more R316's are the same or different from each other.

[0169] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0170] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; and combinations thereof.

[0171] According to one embodiment of the present specification, R315 and R316 are the same or different from each other, and each independently represent a substituted or unsubstituted aryl group, or are bonded to adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0172] According to one embodiment of the present specification, R315 and R316 are the same or different and each independently represent a phenyl group, or are bonded to adjacent groups to form an indene substituted with a methyl group.

[0173] According to one embodiment of the present specification, the chemical formula HT-1 is represented by any one of the following compounds: [ka]

[0174] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material that can smoothly receive electrons injected from the cathode and transfer them to the light-emitting layer, and is preferably a material with high mobility for electrons. Specific examples include, but are not limited to, Al complex of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes, etc. The electron transport layer may be used with any desired cathode material as used in the prior art. In particular, suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each of which is followed by an aluminum or silver layer.

[0175] According to one embodiment of the present specification, the electron transport layer includes a compound represented by the following chemical formula ET-1. [Chemical formula ET-1] [ka] In the above formula ET-1, At least one of X'7 and X'8 is N, and the rest are CH; R318 to R323 are the same or different and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are bonded to adjacent groups to form a substituted or unsubstituted ring; L'1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; r322 is an integer of 1 to 7, and when r322 is 2 or more, R322 are the same or different, l'1 is an integer of 1 to 5, and when said l'1 is 2 or more, said L'1's are the same or different.

[0176] According to one embodiment of the present specification, R318 to R323 are the same or different and each independently represent a hydrogen atom or a substituted or unsubstituted aryl group, and adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0177] According to one embodiment of the present specification, R318 to R323 are the same or different and each independently represent a hydrogen atom; a phenyl group; or a naphthyl group, or adjacent groups are bonded to each other to form benzene.

[0178] According to one embodiment of the present specification, L'1 is a substituted or unsubstituted arylene group.

[0179] According to one embodiment of the present specification, L'1 is a phenylene group.

[0180] According to one embodiment of the present specification, the ET-1 is represented by the following compound. [ka]

[0181] According to one embodiment of the present specification, the electron transport layer includes a compound represented by the following chemical formula ET-2. [Chemical formula ET-2] [ka] In the above formula ET-2, T7 to T9 are the same or different and each independently represent one selected from the group consisting of hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group, and combinations thereof, or are bonded to adjacent groups to form a substituted or unsubstituted ring; t7 is an integer of 1 to 4, and when t7 is 2 or more, the two or more T7s are the same or different from each other, t8 is an integer of 1 to 4, and when t8 is 2 or more, the two or more T8 are the same or different from each other, t9 is an integer of 1 to 10, and when t9 is 2 or more, the two or more T9s are the same or different from each other.

[0182] According to one embodiment of the present specification, T7 to T9 are the same or different and each independently represent any one selected from the group consisting of hydrogen; a substituted or unsubstituted aryl group; and a substituted or unsubstituted heteroaryl group, and combinations thereof.

[0183] According to one embodiment of the present specification, T7 to T9 are the same or different and each independently represent any one selected from the group consisting of hydrogen; a carbazole group; a phenyl group; a biphenyl group; a triazine group; and combinations thereof.

[0184] According to one embodiment of the present specification, the ET-2 is represented by the following compound. [ka]

[0185] The electron transport layer may further include a metal complex. The metal may be any metal used in the art.

[0186] The electron injection layer is a layer that receives electrons from the electrode. The electron injection material is preferably excellent in the ability to transport electrons, has an effect of receiving electrons from the cathode, and has an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has an excellent thin-film forming ability is preferable. Specific examples of the material include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0187] Examples of the metal complex compound include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolate) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato) aluminum, and bis(2-methyl-8-quinolinato) (2-naphtholato) gallium.

[0188] The electron blocking layer is a layer capable of preventing electrons injected from the electron injection layer from entering the hole injection layer via the light emitting layer, thereby improving the life and efficiency of the device. Known materials can be used without limitation, and may be formed between the light emitting layer and the hole injection layer, between the light emitting layer and the hole transport layer, or between the light emitting layer and a layer that simultaneously injects and transports holes.

[0189] The hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer.Specific examples of the hole blocking layer include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0190] The organic light emitting devices according to the present invention may be top-emitting, bottom-emitting, or dual-sided emitting, depending on the materials used.

[0191] The organic light emitting device according to the present disclosure may be included in various electronic devices, such as, but not limited to, a display panel, a touch panel, a solar module, a lighting device, and the like. EXAMPLES

[0192] Hereinafter, the present specification will be described in detail with reference to examples and comparative examples. However, the examples and comparative examples according to the present specification may be modified in various different forms, and the scope of the present specification is not to be construed as being limited to the examples and comparative examples described below. The examples and comparative examples of the present specification are provided to more completely explain the present specification to those having average knowledge in the art.

[0193] Synthesis Example 1. Synthesis of Core-1 [ka] <1-a> Preparation of compound Core-1 3-Chloro-benzo[1,2-b:4,3-b']bisbenzofuran (50 g, 170.81 mmol), bis(pinacolato)diboron (54.3 g, 256.22 mmol), tricyclohexylphosphine (1.9 g, 6.7 mmol), potassium acetate (33.5 g, 341.6 mmol), and Pd(dba)2 (1.9 g, 3.4 mmol) were added to 1,4-dioxane (400 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 reduced pressure, and the product was purified using column chromatography to obtain compound Core-1 (44.0 g, 67% yield). MS:[M+H]+=385

[0194] Synthesis Example 2. Synthesis of Core-2 [ka] <2-a> Preparation of compound Core-2-a Compound Core-1 (40 g, 104.1 mmol) and 1-bromo-3-chlorobenzene (18.9 g, 98.9 mmol) were dissolved in THF (400 ml), and then Pd(PPh3)4 (1.2 g, 1.0 mmol) and 80 ml of 2M K2CO3 aqueous solution were added and refluxed for 4 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 reduced pressure, and the product was purified using column chromatography to obtain compound Core-2-a (23.7 g, 65% yield). MS:[M+H]+=369

[0195] <2-b> Preparation of compound Core-2 Compound Core-2 was obtained by synthesizing and purifying in the same manner as in the preparation of compound Core-1 <1-a> in Synthesis Example 1, except that compound Core-2-a was used instead of 3-chloro-benzo[1,2-b:4,3-b']bisbenzofuran. MS:[M+H]+=461

[0196] Synthesis Example 3. Synthesis of Core-3 [ka] <3-a> Preparation of compound Core-3-a Compound Core-3-a was obtained by synthesizing and purifying in the same manner as in the preparation of compound Core-2-a of Synthesis Example 2, except that 1-bromo-4-chlorobenzene was used instead of 1-bromo-3-chlorobenzene. MS:[M+H]+=369

[0197] <3-b> Preparation of compound Core-3 Compound Core-3 was obtained by synthesizing and purifying in the same manner as in the preparation of compound Core-1 <1-a> in Synthesis Example 1, except that compound Core-3-a was used instead of 3-chloro-benzo[1,2-b:4,3-b']bisbenzofuran. MS:[M+H]+=461

[0198] Synthesis Example 4. Synthesis of Core-4 [ka] <4-a> Preparation of compound Core-4-a Compound Core-4-a was obtained by synthesizing and purifying in the same manner as in the preparation of compound Core-2-a of Synthesis Example 2, except that 1-bromo-6-chloronaphthalene was used instead of 1-bromo-3-chlorobenzene. MS:[M+H]+=419

[0199] <4-b> Preparation of compound Core-4 Compound Core-4 was obtained by synthesizing and purifying in the same manner as in the preparation of compound Core-1 <1-a> in Synthesis Example 1, except that compound Core-4-a was used instead of 3-chloro-benzo[1,2-b:4,3-b']bisbenzofuran. MS:[M+H]+=511

[0200] Synthesis Example 5. Synthesis of BH-1 [ka] <5-a> Preparation of compound BH-1 Compound BH-1 was obtained by synthesizing and purifying in the same manner as in the preparation of compound Core-2-a of Synthesis Example 2, except that 9-bromo-10-phenylanthracene-1,2,3,4,5,6,7,8-d8 was used instead of 1-bromo-3-chlorobenzene. MS:[M+H]+=519

[0201] Synthesis Example 6. Synthesis of BH-2 [ka] <6-a> Preparation of compound BH-2 In the preparation of compound Core-2-a of Synthesis Example 2 <2-a>, except that 9-bromo-10-(naphthalen-1-yl)anthracene-1,2,3,4,5,6,7,8-d8 was used instead of 1-bromo-3-chlorobenzene and compound Core-2 was used instead of compound Core-1, the synthesis and purification were performed in the same manner to obtain compound BH-2. MS:[M+H]+=645

[0202] Synthesis Example 7. Synthesis of BH-3 [ka] <7-a> Preparation of compound BH-3-a Compound BH-3-a was obtained by synthesizing and purifying in the same manner as in the preparation of compound Core-2-a of Synthesis Example 2, except that 9-bromoanthracene was used instead of 1-bromo-3-chlorobenzene. MS:[M+H]+=435

[0203] <7-b> Preparation of compound BH-3-b Compound BH-3-a (40 g, 92.1 mmol) and AlCl3 (8 g, 60 mmol) were added to C6D6 (800 ml) and stirred for 5 hours. After the reaction was completed, D2O (50 ml) was added and stirred for 30 minutes, and then trimethylamine (5 ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried over MgSO4 and recrystallized with ethyl acetate to obtain BH-3-b (27.9 g, 67% yield). MS:[M+H]+=453

[0204] <7-c> Preparation of compound BH-3-c Compound BH-3-b (30 g, 66.3 mmol) was dispersed in 250 ml of dimethylformamide, and then a solution of n-bromosuccinimide (12.4 g, 69.6 mmol) dissolved in 50 ml of dimethylformamide was slowly added dropwise. After reacting at room temperature for 4 hours, 600 ml of water was added dropwise. When a solid was generated, it was filtered, dissolved in ethyl acetate, placed in a separatory funnel, and washed several times with distilled water. Compound BH-3-c (29.9 g, yield 85%) was obtained by recrystallization with EA. MS:[M+H]+=531

[0205] <7-d> Preparation of compound BH-3 In the preparation of compound Core-2-a of Synthesis Example 2, <2-a>, compound BH-3-c was used instead of 1-bromo-3-chlorobenzene, and [1,1'-biphenyl]-2-ylboronic acid was used instead of compound Core-1. Compound BH-3 was obtained by the same synthesis and purification. MS:[M+H]+=604

[0206] Synthesis Example 8. Synthesis of BH-4 [ka] <8-a> Preparation of compound BH-4 In the preparation of compound Core-2-a of Synthesis Example 2, <2-a>, the same synthesis and purification were carried out as above, except that 9-bromo-10-(naphthalen-1-yl)anthracene-1,2,3,4,5,6,7,8-d8 was used instead of 1-bromo-3-chlorobenzene, to obtain compound BH-4. MS:[M+H]+=569

[0207] Synthesis Example 9. Synthesis of BH-5 [ka] <9-a> Preparation of compound BH-5 Compound BH-5 was obtained by synthesizing and purifying in the same manner as in the preparation of compound Core-2-a of Synthesis Example 2 above, except that 9-bromo-10-(naphthalen-2-yl-d7)anthracene-1,2,3,4,5,6,7,8-d8 was used instead of 1-bromo-3-chlorobenzene. MS:[M+H]+=576

[0208] Synthesis Example 10. Synthesis of BH-6 [ka] <10-a> Preparation of compound BH-6-a In the preparation of compound Core-2-a of Synthesis Example 2, synthesis and purification were carried out in the same manner, except that 9-([1,1'-biphenyl]-3-yl)-10-bromoanthracene was used instead of 1-bromo-3-chlorobenzene, to obtain compound BH-6-a. MS:[M+H]+=587

[0209] <10-b> Preparation of compound BH-6 Compound BH-6 was obtained by synthesizing and purifying in the same manner as in the preparation of compound BH-3-b <7-b> in Synthesis Example 7, except that compound BH-6-a was used instead of compound BH-3-a. MS:[M+H]+=613

[0210] Synthesis Example 11. Synthesis of BH-7 [ka] <11-a> Preparation of compound BH-7-a Compound BH-7-a was obtained by synthesizing and purifying in the same manner as in the preparation of compound Core-2-a of Synthesis Example 2, except that 9-bromo-10-phenylanthracene was used instead of 1-bromo-3-chlorobenzene. MS:[M+H]+=511

[0211] <11-b> Preparation of compound BH-7 Compound BH-7 was obtained by synthesizing and purifying in the same manner as in the preparation of compound BH-3-b <7-b> in Synthesis Example 7, except that compound BH-7-a was used instead of compound BH-3-a. MS:[M+H]+=533

[0212] Synthesis Example 12. Synthesis of BH-8 [ka] <12-a> Preparation of compound BH-8-a In the preparation of compound Core-2-a of Synthesis Example 2, <2-a> compound Core-2-a was prepared in place of compound Core-1, and compound Core-3 was used in place of 1-bromo-3-chlorobenzene, but the same synthesis and purification were carried out to obtain compound BH-8-a. MS:[M+H]+=637

[0213] <12-b> Preparation of compound BH-8 Compound BH-8 was obtained by synthesizing and purifying in the same manner as in the preparation of compound BH-3-b of Synthesis Example 7 <7-b>, except that compound BH-8-a was used instead of compound BH-3-a. MS:[M+H]+=665

[0214] Synthesis Example 13. Synthesis of BH-9 [ka] <13-a> Preparation of compound BH-9 Compound BH-9 was obtained by synthesizing and purifying in the same manner as in the preparation of compound Core-2-a of Synthesis Example 2 above, except that 9-bromo-10-(naphthalen-1-yl-d7)anthracene-1,2,3,4,5,6,7,8-d8 was used instead of 1-bromo-3-chlorobenzene. MS:[M+H]+=576

[0215] Synthesis Example 14. Synthesis of BH-10 [ka] <14-a> Preparation of compound BH-10-a In the preparation of compound Core-2-a of Synthesis Example 2, <2-a> compound Core-2-a was prepared in place of compound Core-1, and compound Core-4 was used in place of compound Core-1, and compound BH-10-a was obtained by synthesizing and purifying the compound in the same manner, except that compound Core-4 was used in place of compound Core-1, and compound Core-2-a ... BH-10-a. MS:[M+H]+=713

[0216] <14-b> Preparation of compound BH-10 Compound BH-10 was obtained by synthesizing and purifying in the same manner as in the preparation of compound BH-3-b in Synthesis Example 7 <7-b>, except that compound BH-10-a was used instead of compound BH-3-a. MS:[M+H]+=746

[0217] Synthesis Example 15. Synthesis of BH-11 [ka] <15-a> Preparation of compound BH-11 In the preparation of compound Core-2-a of Synthesis Example 2, <2-a>, compound BH-3-c was used instead of 1-bromo-3-chlorobenzene, and [1,1'-biphenyl]-4-ylboronic acid was used instead of compound Core-1. Compound BH-11 was obtained by synthesis and purification in the same manner. MS:[M+H]+=604

[0218] Synthesis Example 16. Synthesis of BH-12 [ka] <12-a> Preparation of compound BH-12-a Compound BH-12-a was obtained by synthesizing and purifying in the same manner as in the preparation of compound Core-2-a in Synthesis Example 2 above, except that 9-bromoanthracene was used instead of 1-bromo-3-chlorobenzene and compound Core-3 was used instead of compound Core-1. MS:[M+H]+=511

[0219] <12-b> Preparation of compound BH-12-b Compound BH-12-b was obtained by synthesizing and purifying in the same manner as in the preparation of compound BH-3-b in Synthesis Example 7 <7-b>, except that compound BH-12-a was used instead of compound BH-3-a. MS:[M+H]+=533

[0220] <12-c> Preparation of compound BH-12-c Compound BH-12-c was obtained by synthesizing and purifying in the same manner as in the preparation of compound BH-3-c <7-c> in Synthesis Example 7, except that compound BH-12-b was used instead of compound BH-3-b. MS:[M+H]+=611

[0221] <12-d> Preparation of compound BH-12 In the preparation of compound Core-2-a of Synthesis Example 2, <2-a>, compound BH-12-c was used instead of 1-bromo-3-chlorobenzene, and [1,1'-biphenyl]-4-ylboronic acid was used instead of compound Core-1. Compound BH-12 was obtained by synthesis and purification in the same manner. MS:[M+H]+=684

[0222] <Experimental Example 1: Preparation of organic light-emitting device> Example 1 A glass substrate coated with a 1,400 Å-thick thin film of ITO (indium tin oxide) was placed in distilled water containing detergent and ultrasonically cleaned. The detergent used was a product from Fischer Co., and the distilled water used was distilled water that had been filtered a second time with a Millipore Co. filter. The ITO was washed for 30 minutes, then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was complete, the substrate was ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum deposition machine.

[0223] On the ITO transparent electrode prepared as above, the following HI-A and HATCN were thermally vacuum deposited to a thickness of 650 Å and 50 Å, respectively, to sequentially form a first hole injection layer and a second hole injection layer. On the second hole injection layer, the following HT-A was vacuum deposited to a thickness of 600 Å to form a hole transport layer. On the hole transport layer, the following HT-B was vacuum deposited to a thickness of 50 Å to form an electron blocking layer.

[0224] Next, on the electron blocking layer, 4 wt % of the following compound BD-A as a blue light-emitting dopant based on the total weight of the light-emitting layer and 96 wt % of the following compound BH-1 as a host based on the total weight of the light-emitting layer were vacuum-deposited to a thickness of 200 Å to form a light-emitting layer.

[0225] Next, the following compound ET-A was vacuum-deposited on the light-emitting layer to a thickness of 50 Å as a first electron transport layer, and then the following compound ET-B and LiQ were vacuum-deposited in a weight ratio of 1:1 to form a second electron transport layer to a thickness of 360 Å. LiQ was vacuum-deposited on the second electron transport layer to a thickness of 5 Å to form an electron injection layer. Aluminum and silver were vacuum-deposited on the electron injection layer to a thickness of 220 Å in a weight ratio of 10:1, and aluminum was vacuum-deposited thereon to a thickness of 1000 Å to form a cathode.

[0226] In the above process, the deposition rate of the organic material was maintained at 0.4-0.9 Å / sec, the deposition rate of the cathode aluminum was maintained at 2 Å / sec, and the degree of vacuum during deposition was 1×10 -7 ~5×10 -8 The organic light-emitting device was fabricated while maintaining the pressure at torr. [ka]

[0227] Examples 2 to 12 Organic light-emitting devices of Examples 2 to 12 were prepared in the same manner as in Example 1, except that the compounds shown in Table 1 below were used as the host of the light-emitting layer instead of the compound BH-1 in Example 1. [ka]

[0228] Comparative Examples 1 to 5 Organic light-emitting devices of Comparative Examples 1 to 5 were prepared in the same manner as in Example 1, except that the following compounds BH-a to BH-e were used as the host of the light-emitting layer instead of the compound BH-1 in Example 1. [ka]

[0229] The organic light-emitting devices of Examples 1 to 12 and Comparative Examples 1 to 5 were each supplied with a current of 10 mA / cm 2 The voltage, conversion efficiency (cd / A / y), and 2 The life (LT 95 The results are shown in Table 1 below. 95 is a current density of 20mA / cm 2 The figure shows the ratio of the time required for the brightness to decrease to 95% when the initial brightness at the time point was taken as 100%.

[0230] [Table 1]

[0231] The converted efficiency (cd / A / y) takes into consideration everything from the current efficiency (cd / A) to the color purity (CIEy) of the material, and is an important efficiency standard value for small and large organic light-emitting devices that aim for high brightness and high color reproduction.

[0232] In Table 1, Examples 1 to 12, which are organic light-emitting devices using the compound of Chemical Formula 1 according to an embodiment of the present specification, include compounds containing at least one deuterium in anthracene, Comparative Example 1 includes a compound that does not contain deuterium, and Comparative Examples 2 to 5 include compounds that do not contain deuterium in the anthracene core.

[0233] Specifically, the compound according to one embodiment of the present specification, which necessarily contains deuterium in the anthracene, has structural characteristics that improve the mobility of electrons and holes and the molecular stability compared to Comparative Examples 1 and 2, which do not contain deuterium, and Comparative Examples 3 to 5, which do not contain deuterium in the anthracene core. Therefore, it has been found that an organic light-emitting device including the compound has excellent driving voltage, efficiency, and life span.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] 【Chemistry 1】 In the above Chemical Formula 1, D is deuterium; L1 is a deuterium-substituted or unsubstituted naphthylene group; Ar1 is a phenyl group substituted or unsubstituted with one or more of deuterium, naphthyl, and combinations thereof; a biphenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium; R1 to R9 are the same or different and each independently represents hydrogen or deuterium; a1 is an integer from 1 to 8.

2. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-2: [Chemical formula 1-2] 【Chemistry 3】 In the above Chemical Formula 1-2, The definitions of D, Ar1, a1, and R1 to R9 are the same as those in Chemical Formula 1. L11 is a naphthylene group which is unsubstituted or substituted with deuterium.

3. The compound according to claim 1, wherein the formula 1 is represented by the following formulas 1-4: [Chemical formula 1-4] 【Chemistry 5】 In the above Chemical Formula 1-4, The definitions of D, Ar1, a1, and R1 to R9 are the same as those in Chemical Formula 1. a3 is an integer from 0 to 4, a4 is an integer from 0 to 4, 0≦a3+a4≦6.

4. The compound according to claim 1, wherein the formula 1 is any one selected from the following compounds: 【Chemistry 7】 【Chemistry 9】 【Chemistry 11】 【Chemistry 13】 【Chemistry 15】 【Chemistry 17】 【Chemistry 19】 【Chemistry 21】 。

5. An organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 4.

6. The organic light-emitting device according to claim 5 , 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.

7. The organic light-emitting element according to claim 5 , wherein the organic layer includes a light-emitting layer, the light-emitting layer including the compound.

8. The organic light-emitting device according to claim 5 , wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host for the light-emitting layer.

9. The organic light-emitting device according to claim 8 , wherein the light-emitting layer comprises a dopant, and the dopant comprises at least one selected from the group consisting of a fluorescent dopant, a phosphorescent dopant, and a thermally activated delayed fluorescent dopant.

10. The organic light emitting device according to claim 9 , wherein the fluorescent dopant comprises at least one selected from the group consisting of an arylamine-based compound and a boron-based compound.

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