Compound and organic light emitting device comprising same

Abstract

The present specification provides a compound represented by Chemical Formula 1 and an organic light-emitting diode comprising the same.

Description

Technology Field

[0001] This specification relates to compounds and organic light-emitting diodes containing the same. Background Technology

[0002] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) that utilize this phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the OLED; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic layer. When the injected holes and electrons meet, an exciton is formed, and light is emitted when this exciton returns to the ground state.

[0003] The development of new materials for organic light-emitting diodes as described above is continuously required. Prior art literature

[0004] (Patent Document 0001) KR 10-2012-119942 A The problem to be solved

[0005] The present specification provides a compound and an organic light-emitting diode containing the same. means of solving the problem

[0006] One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[0007] [Chemical Formula 1]

[0008]

[0009] In the above chemical formula 1,

[0010] L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted divalent hydrocarbon ring; or a substituted or unsubstituted divalent heteroring, and

[0011] R1 to R 10 are the same or different from one another, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0012] Ar2 is a substituted or unsubstituted hydrocarbon group; a substituted or unsubstituted amine group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted heterocyclic group, and

[0013] n1 and n2 are each independently integers from 0 to 2, and

[0014] Ar1 is a group represented by the following chemical formula 2, and

[0015] [Chemical Formula 2]

[0016]

[0017] In the above chemical formula 2,

[0018] X is O or S, and

[0019] Any one of A1 to A6 is (L1) of Chemical Formula 1 n1 It is connected to, and the remainders are the same or different from one another, and each independently is hydrogen; deuterium; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted hydrocarbon group; or substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring.

[0020] In addition, one embodiment of the present specification provides an organic light-emitting device comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprise a compound represented by Chemical Formula 1. Effects of the invention

[0021] The compounds described in this specification may be used as materials for the organic layer of an organic light-emitting diode. A compound according to at least one embodiment of this specification may improve efficiency, lower driving voltage, and / or lifespan characteristics in an organic light-emitting diode. Brief explanation of the drawing

[0022] FIG. 1 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (6), and a cathode (9) are sequentially stacked. FIG. 2 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light-emitting layer (6), a hole blocking layer (7), an electron injection and transport layer (8) and a cathode (9) are sequentially stacked. Specific details for implementing the invention

[0023] The present specification will be described in more detail below.

[0024] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0025] In this specification, when it is said that a member is located "on" another member, this includes not only cases where a member is in contact with another member, but also cases where another member exists between the two members.

[0026] In this specification, " " refers to the position where it is bonded to a chemical formula or compound.

[0027] Examples of substituents in this specification are described below, but are not limited thereto.

[0028] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0029] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group (-CN); nitro group; hydroxyl group; alkyl group; cycloalkyl group; alkoxy group; phosphine oxide group; aryloxy group; alkylthioxy group; arylthioxy group; alkyl sulfoxy group; aryl sulfoxy group; alkenyl group; silyl group; boron group; amine group; aryl group; or heterocyclic group, or is substituted with a substituent in which two or more of the exemplified substituents are connected, or has no substituents. For example, “a substituent in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

[0030] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxyl group; amino group; alkoxy group; aryloxy group; alkyl group; cycloalkyl group; aryl group; and heterocyclic group, or that it is substituted with a substituent in which two or more of the exemplified substituents are connected, or that it has no substituents.

[0031] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; alkyl group; aryl group; and heterocyclic group, or that it is substituted with two or more of the exemplified substituents linked together, or that it has no substituents.

[0032] Examples of the above substituents are described below, but are not limited thereto.

[0033] In this specification, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0034] In the present 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 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of alkyl groups include, butyl, n-butyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.

[0035] In this specification, the description of the alkyl group described above may apply except that the arylalkyl group is substituted with an aryl group.

[0036] In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferred to have 1 to 20 carbon atoms. Specifically, it may be 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, etc., but is not limited thereto.

[0037] Substituents comprising alkyl groups, alkoxy groups and other alkyl groups described in this specification include both straight-chain and broken-chain forms.

[0038] In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. 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, stilbenyl group, styrenyl group, etc., but are not limited to these.

[0039] In the present specification, the alkynyl group is a substituent comprising a triple bond between carbon atoms, and may be a straight chain or a branched chain. The number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkynyl group is 2 to 10.

[0040] In the present specification, the cycloalkyl group is not particularly limited, but it is preferable that it has 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, etc., are included but are not limited thereto.

[0041] In this specification, the amine group is -NH2, and the amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms in the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms in the amine group is 1 to 20. According to one embodiment, the number of carbon atoms in the amine group is 1 to 10. Specific examples of substituted amine groups include, but are not limited to, methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, 9,9-dimethylfluorenylphenylamine, pyridylphenylamine, diphenylamine, phenylpyridylamine, naphthylamine, biphenylamine, anthracenylamine, dibenzofuranylphenylamine, 9-methylanthracenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, and diphenylamine groups.

[0042] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. As a monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quadrphenyl group, etc., but is not limited thereto. As a polycyclic aryl group, the aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto.

[0043] In the present specification, the fluorenyl group may be substituted, and two substituents may be combined to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0044] When the above fluorenyl group is substituted, , , Spirofluorenyl group of the back, etc. (9,9-dimethylfluorenyl group), and It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited to this.

[0045] In this specification, the aryl group among the aryloxy group, arylamine group, and arylsilyl group may be subject to the description of the aryl group described above.

[0046] In this specification, the description of the alkyl group described above may be applied to the alkyl group among the alkyl thioxy group and the alkyl sulfoxy group.

[0047] In this specification, the description of the aryl group described above may be applied to the aryl group among the aryl thioxy group and the aryl sulfoxy group.

[0048] In the present specification, the heterocyclic group is a ring group comprising one or more heteroatoms N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of heterocyclic groups include, but are not limited to, pyridine groups, pyrrole groups, pyrimidine groups, quinoline groups, pyridazinyl groups, furan groups, thiophene groups, imidazole groups, pyrazol groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, benzocarbazole groups, naphthobenzofuran groups, benzonaphthiophene groups, indenocarbazole groups, triazinyl groups, etc.

[0049] In this specification, the description of the aforementioned heterocyclic group may apply, except that the heteroaryl group is aromatic.

[0050] In this specification, the description of the aryl group may apply except that the arylene group is divalent.

[0051] In this specification, the description of the heteroaryl group may apply except that the heteroaryl group is divalent.

[0052] In the present specification, in a substituted or unsubstituted ring formed by combining adjacent groups, "ring" means a hydrocarbon ring; or a heteroring.

[0053] The above hydrocarbon ring may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the above cycloalkyl group or aryl group.

[0054] In this specification, the meaning of forming a ring by combining with adjacent groups means forming a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heteroring; a substituted or unsubstituted aromatic heteroring; or a condensed ring thereof by combining with adjacent groups. The hydrocarbon ring means a ring composed only of carbon and hydrogen atoms. The heteroring means a ring comprising one or more elements selected from N, O, P, S, Si, and Se. In this specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heteroring, and aromatic heteroring may be monocyclic or polycyclic.

[0055] In this specification, an aliphatic hydrocarbon ring refers to a non-aromatic ring composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0056] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. In this specification, an aromatic hydrocarbon ring may be interpreted as having the same meaning as an aryl group.

[0057] In this specification, an aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephane, azocaine, thiocane, etc.

[0058] In this specification, an aromatic heterocycle means an aromatic ring comprising one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazol, oxazole, isooxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazolin, quinoxaline, naphthiridine, acridine, phenanthridine, diazanaphthalene, driazindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, Examples include imidazopyridine, phenoxazine, indolocarbazole, indenocabazole, etc., but are not limited to these.

[0059] In this specification, "X% deuterated," "degree of deuteration X%," or "deuterated substitution rate X%" means that X% of the hydrogens at substitutable positions in the structure are replaced with deuteration.

[0060] For example, if the structure is dibenzofuran, the dibenzofuran being "25% deuterated," the "deuteration of 25%" of the dibenzofuran, or the "deuteration of 25%" of the dibenzofuran may mean that two of the eight hydrogens at the substitutable positions of the dibenzofuran are substituted or unsubstituted with deuteration.

[0061] In the present specification, the hydrogens capable of deuterium substitutability in the structure may be substituted with deuterium in an amount greater than 0% and less than or equal to 100%, greater than or equal to 0.1% and less than or equal to 99.99%, or up to 100%. For example, if the structure is dibenzofuran, the dibenzofuran is "25% deuteriumized," the "deuteriumization degree of 25%" of the dibenzofuran, or the "deuterium substitution rate of 25%" of the dibenzofuran may mean that 8 of the 8 hydrogens at the substitutability positions of the dibenzofuran are substituted with 25% deuterium or 4 of the 8 hydrogens at the substitutability positions are substituted with 50% deuterium.

[0062] Preferred embodiments of the present invention are described in detail below. However, embodiments of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

[0063] Therefore, when a compound represented by the aforementioned chemical formula 1 is applied to an organic light-emitting device, an organic light-emitting device having high efficiency, low voltage, and / or long lifespan characteristics can be obtained.

[0064] Chemical Formula 1 will be explained in detail below.

[0065] [Chemical Formula 1]

[0066]

[0067] In the above chemical formula 1,

[0068] L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted divalent hydrocarbon ring; or a substituted or unsubstituted divalent heteroring, and

[0069] R1 to R 10 are the same or different from one another, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0070] Ar2 is a substituted or unsubstituted hydrocarbon group; a substituted or unsubstituted amine group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted heterocyclic group, and

[0071] n1 and n2 are each independently integers from 0 to 2, and

[0072] Ar1 is a group represented by the following chemical formula 2, and

[0073] [Chemical Formula 2]

[0074]

[0075] In the above chemical formula 2,

[0076] X is O or S, and

[0077] Any one of A1 to A6 is (L1) of Chemical Formula 1 n1 It is connected to, and the remainders are the same or different from one another, and each independently is hydrogen; deuterium; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted hydrocarbon group; or substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted ring.

[0078] According to one embodiment of the present specification, the Ar1 is represented by the chemical formula 2.

[0079] In one embodiment of the present specification, any one of A1 to A6 of Formula 2 is (L1) of Formula 1 n1 It is connected to.

[0080] In one embodiment of the present specification, A1 of Formula 2 is (L1) of Formula 1 n1 It is connected to.

[0081] In one embodiment of the present specification, A2 of Formula 2 is (L1) of Formula 1 n1 It is connected to.

[0082] In one embodiment of the present specification, A3 of Formula 2 is (L1) of Formula 1 n1 It is connected to.

[0083] In one embodiment of the present specification, A4 of Formula 2 is (L1) of Formula 1 n1 It is connected to.

[0084] In one embodiment of the present specification, A5 of Formula 2 is (L1) of Formula 1 n1 It is connected to.

[0085] In one embodiment of the present specification, A6 of Formula 2 is (L1) of Formula 1 n1 It is connected to.

[0086] In one embodiment of the present specification, (L1) of Formula 1 among A1 to A6 of Formula 2 n1 The remaining groups not connected to each other are the same or different, and each independently are hydrogen; deuterium; nitrile group; substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms; substituted or unsubstituted hydrocarbon group having 3 to 30 carbon atoms; or substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or are combined with adjacent groups to form a ring having 3 to 30 turns.

[0087] According to another embodiment, (L1) of Formula 1 among A1 to A6 of Formula 2 above n1 The remainder not connected to are the same or different from one another, and each independently hydrogen; deuterium; nitrile group; substituted or unsubstituted butyl group; substituted or unsubstituted phenyl group; substituted or unsubstituted tetrahydronaphthyl group ( ); substituted or unsubstituted naphthyl group; substituted or unsubstituted phenanthrene group; substituted or unsubstituted biphenyl group; substituted or unsubstituted terphenyl group; substituted or unsubstituted benzofuran group; substituted or unsubstituted benzothiophen group; substituted or unsubstituted pyridine group; substituted or unsubstituted pyrimidyl group; substituted or unsubstituted triazine group; substituted or unsubstituted carbazole group; substituted or unsubstituted silaflurene group; substituted or unsubstituted arylsilyl group; substituted or unsubstituted dibenzofuran group; or substituted or unsubstituted dibenzothiophen group, or combine with adjacent groups to form a substituted or unsubstituted six-membered ring.

[0088] According to another embodiment, (L1) of Formula 1 among A1 to A6 of Formula 2 above n1 The remainder not connected to are the same or different from one another, and each independently hydrogen; deuterium; nitrile group; tert-butyl group; phenyl group substituted or unsubstituted with a naphthyl group or pyridine group; tetrahydronaphthyl group substituted or unsubstituted with a methyl group ( ); naphthyl group; phenanthrene group; biphenyl group; terphenyl group; benzofuran group substituted or unsubstituted with a phenyl group; benzothiophen group substituted or unsubstituted with a phenyl group; pyridine group substituted or unsubstituted with a phenyl group; pyrimidyl group substituted or unsubstituted with a phenyl group; triazine group substituted or unsubstituted with a phenyl group; carbazole group substituted or unsubstituted with a phenyl group; silafluorene group substituted or unsubstituted with a phenyl group; triphenylsilyl group; dibenzofuran group; or dibenzothiophen group, or is combined with adjacent groups to form a substituted or unsubstituted cyclohexine ring; or a substituted or unsubstituted benzene ring. In this case, the substituents may be substituted with one or more deuterium atoms.

[0089] According to one embodiment of the present specification, the above chemical formula 1 is represented by the following chemical formula 1-1.

[0090] [Chemical Formula 1-1]

[0091]

[0092] In the above chemical formula 1-1,

[0093] L1, L2, R1 to R 10 The definitions of , n1, n2 and Ar2 are as in Chemical Formula 1 above, and the definitions of X, A1 and A3 to A6 are as in Chemical Formula 2 above.

[0094] According to one embodiment of the present specification, the above chemical formula 1 is represented by the following chemical formula 1-2.

[0095] [Chemical Formula 1-2]

[0096]

[0097] In the above chemical formula 1-2,

[0098] L1, L2, R1 to R 10 The definitions of , n1, n2 and Ar2 are as in Chemical Formula 1 above, and the definitions of X and A2 to A6 are as in Chemical Formula 2 above.

[0099] According to one embodiment of the present specification, the formula 1 is represented by any one of the following formulas 1-3 to 1-6.

[0100] [Chemical Formula 1-3]

[0101]

[0102] [Chemical Formula 1-4]

[0103]

[0104] [Chemical Formula 1-5]

[0105]

[0106] [Chemical Formula 1-6]

[0107]

[0108] In the above chemical formulas 1-3 to 1-6,

[0109] L1, L2, R1 to R 10The definitions of , n1, n2 and Ar2 are as in Chemical Formula 1 above, and the definitions of X and A1 to A6 are as in Chemical Formula 2 above.

[0110] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted divalent hydrocarbon ring; or a substituted or unsubstituted divalent heteroring.

[0111] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; a divalent hydrocarbon ring having 3 to 30 carbon atoms that is substituted or unsubstituted; or a divalent heterocyclic ring having 2 to 30 carbon atoms that is substituted or unsubstituted.

[0112] According to one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted divalent phenyl; a substituted or unsubstituted divalent biphenyl; a substituted or unsubstituted divalent naphthalene; a substituted or unsubstituted divalent phenanthrene; a substituted or unsubstituted divalent tetrahydronaphthalene; a substituted or unsubstituted divalent fluorene; a substituted or unsubstituted dibenzothiophene; or a substituted or unsubstituted dibenzofuran.

[0113] According to one embodiment of the present specification, L1 is a direct bond; a divalent phenyl substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; a divalent biphenyl substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; a divalent naphthalene substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; a divalent phenanthrene substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; a divalent tetrahydronaphthalene substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; a divalent fluorene substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; a divalent dibenzothiophene substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; Or it is a divalent dibenzofuran substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups. The alkyl group may have 1 to 20 carbon atoms, and the aryl group may have 6 to 30 carbon atoms.

[0114] In one embodiment of the present specification, L2 is a direct bond; a substituted or unsubstituted divalent phenyl; a substituted or unsubstituted divalent biphenyl; or a substituted or unsubstituted divalent naphthalene.

[0115] In one embodiment of the present specification, L2 is a direct bond; a divalent phenyl substituted or unsubstituted with one or more substituents among deuterium and aryl groups; a divalent biphenyl substituted or unsubstituted with one or more substituents among deuterium and aryl groups; or a divalent naphthalene substituted or unsubstituted with one or more substituents among deuterium and aryl groups.

[0116] According to one embodiment of the present specification, n1 and n2 are each independently 1 or 2.

[0117] According to one embodiment of the present specification, the Ar2 is a substituted or unsubstituted hydrocarbon group having 3 to 30 carbon atoms; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylsilyl group; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0118] According to another embodiment, the Ar2 comprises a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted tetrahydronaphthalene ( ); substituted or unsubstituted pyridine group; substituted or unsubstituted benzofuran group; substituted or unsubstituted dibenzofuran group; substituted or unsubstituted carbazole group; substituted or unsubstituted benzimidazole group; substituted or unsubstituted hexahydrocarbazole ( ); a substituted or unsubstituted arylsilyl group; or a substituted or unsubstituted arylamine group.

[0119] According to another embodiment, the Ar2 comprises: a phenyl group substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; a biphenyl group substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; a terphenyl group substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; a naphthyl group substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; a phenanthrene group substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; and tetrahydronaphthalene substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups ( ); pyridine group substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; benzofuran group substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; substituted or unsubstituted dibenzofuran group; carbazole group substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; benzimidazole group substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups; hexahydrocarbazole substituted or unsubstituted with one or more substituents selected from deuterium, alkyl groups, and aryl groups ( ); an arylsilyl group substituted or unsubstituted with one or more substituents among deuterium, alkyl groups and aryl groups; or an arylamine group substituted or unsubstituted with one or more substituents among deuterium, alkyl groups and aryl groups.

[0120] According to one embodiment of the present specification, the R1 to R 10 The groups are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0121] In one embodiment of the present specification, R1 to R 10 They are the same or different from each other, and each is independently hydrogen or deuterium.

[0122] In one embodiment of the present specification, the formula 1 is represented by any one of the following compounds.

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152] A compound represented by Chemical Formula 1 according to one embodiment of this specification may have a core structure prepared as shown in Reaction Scheme 1 below. Substituents may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

[0153] <Reaction Equation 1>

[0154]

[0155] Chemical formula 1 of the present invention can be synthesized by carrying out a coupling reaction using palladium catalyst from a bromochrysene starting material as shown in reaction formula 1 above, followed by a bromination reaction from the product obtained, and then a coupling reaction using a palladium catalyst again.

[0156] Although the above reaction scheme 1 illustrates a process for synthesizing a compound in which a specific substituent is attached to a specific position, compounds corresponding to the range of the above chemical formula 1 can be synthesized by a synthesis method known in the art using starting materials, intermediate materials, etc. known in the art.

[0157] In this specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of a compound represented by Chemical Formula 1. In addition, in this specification, the HOMO and LUMO energy levels of a compound can also be controlled by introducing various substituents into the core structure of such a structure.

[0158] In addition, the present specification provides an organic light-emitting device comprising the aforementioned compound.

[0159] In this specification, when it is stated that a component is located "on" another component, this includes not only cases where a component is in contact with another component, but also cases where another component exists between the two components.

[0160] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0161] An organic light-emitting device according to the present specification comprises an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprise a compound represented by the aforementioned chemical formula 1.

[0162] The organic light-emitting diode of the present specification can be manufactured by conventional methods and materials for manufacturing organic light-emitting diodes, except that an organic layer is formed using the compound of Formula 1 described above.

[0163] The above compound can be formed as an organic layer by vacuum deposition as well as by solution coating when manufacturing an organic light-emitting diode. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0164] The organic layer of the organic light-emitting device of the present specification may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure comprising one or more layers among a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as organic layers. However, the structure of the organic light-emitting device of the present specification is not limited thereto and may include a smaller or larger number of organic layers.

[0165] In the organic light-emitting device of the present specification, the organic light-emitting device comprises a light-emitting layer, and the light-emitting layer may comprise the compound.

[0166] At this time, the light-emitting layer may include the aforementioned compound as a dopant of the light-emitting layer and may include additional hosts and dopants. The additional host may be included together with the organic layer containing the aforementioned compound, or may be included in an adjacent organic layer. When the organic layer containing the aforementioned compound includes additional hosts and dopants, the additional host may be included in the organic layer at 99% to 80% by weight, and the dopant may be included at 1% to 20% by weight.

[0167] In the organic light-emitting device of the present specification, the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may comprise a compound represented by the aforementioned chemical formula 1.

[0168] In the organic light-emitting device of the present specification, the organic layer comprises a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may comprise a compound represented by the aforementioned chemical formula 1.

[0169] In one embodiment of the present specification, the organic layer comprises an electron blocking layer, and the electron blocking layer comprises a compound represented by the chemical formula 1.

[0170] In one embodiment of the present specification, the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer hole blocking layer, and the electron injection layer, electron transport layer, or electron injection and transport layer may comprise a compound represented by the aforementioned chemical formula 1.

[0171] In one embodiment of the present specification, the organic layer comprises a hole blocking layer, and the hole blocking layer comprises a compound represented by Chemical Formula 1.

[0172] The organic light-emitting device of the present specification may further include one or more organic layers among a hole transport layer, a hole injection layer, an electron blocking layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer.

[0173] In one embodiment of the present specification, the organic light-emitting element comprises an anode; a cathode; and two or more organic layers provided between the anode and the cathode, and at least one of the two or more organic layers comprises a compound represented by the chemical formula 1.

[0174] In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device of a normal type structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0175] In 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.

[0176] The structure of the organic light-emitting device of the present specification may have a structure such as that shown in FIGS. 1 and FIGS. 2, but is not limited thereto.

[0177] FIG. 1 illustrates the structure of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (6), and a cathode (9) are sequentially stacked. In such a structure, the compound may be included in the light-emitting layer (6).

[0178] FIG. 2 illustrates the structure of an organic light-emitting diode in which a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light-emitting layer (6), a hole blocking layer (7), an electron injection and transport layer (8), and a cathode (9) are sequentially stacked. In such a structure, the compound may be included in the hole injection layer (3), the hole transport layer (4), the electron blocking layer (5), the light-emitting layer (6), the hole blocking layer (7), or the electron injection and transport layer (8).

[0179] In one embodiment of the present specification, the electron blocking layer and the light-emitting layer may be provided adjacent to each other. For example, the electron blocking layer and the light-emitting layer may be provided in physical contact.

[0180] In one embodiment of the present specification, the hole transport layer and the electron blocking layer may be provided adjacent to each other. For example, the hole transport layer and the electron blocking layer may be provided in physical contact.

[0181] The organic light-emitting diode of this specification may be manufactured using materials and methods known in the art, except that one or more of the organic layers comprise the compound, i.e., the compound represented by Chemical Formula 1.

[0182] When the above organic light-emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0183] For example, an organic light-emitting diode according to the present specification can be manufactured by using a physical vapor deposition (PVD) method, such as sputtering or electron beam evaporation, to deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, then forming an organic layer including a hole injection layer, a hole transport layer, an emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting diode can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0184] In addition, if the organic layer of the organic light-emitting diode contains two or more compounds, it can be deposited using a co-deposition or pre-mixing method.

[0185] The above organic layer may further include one or more layers among a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer.

[0186] The above organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, an emissive layer and an electron transport layer, an electron injection layer, an electron injection and transport layer, etc., but is not limited thereto and may have a single layer structure. In addition, the above organic layer may be manufactured with a smaller number of layers by using various polymer materials and a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0187] The above anode is an electrode that injects holes, and as the anode material, it is generally preferable to use an organic layer with a high work function to facilitate hole injection. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0188] The above cathode is an electrode for injecting electrons, and the cathode material is typically an organic layer, preferably a material with a low work function to facilitate electron injection. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0189] The hole injection layer described above is a layer that facilitates the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material capable of receiving holes well from the anode at low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile-hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited to these.

[0190] The hole transport layer described above can facilitate the transport of holes. Suitable hole transport materials are those capable of receiving holes from the anode or hole injection layer and transferring them to the emissive layer, provided they possess high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0191] An electron blocking layer may be provided between the hole transport layer and the light-emitting layer. The aforementioned compound or a material known in the art may be used for the electron blocking layer.

[0192] The above-mentioned light-emitting layer may emit red, green, or blue light and may be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole, and benzimidazole series; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0193] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0194] When the emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the emitting dopant, but are not limited thereto. When the light-emitting layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distrylarylene (DSA), PFO-based polymers, and PPV-based polymers may be used as light-emitting dopants, but are not limited to these.

[0195] A hole blocking layer may be provided between the electron transport layer and the light-emitting layer, and materials known in the art may be used.

[0196] The electron transport layer described above can facilitate the transport of electrons. As an electron transport material, a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility, is suitable. Specific examples include the aforementioned compounds or Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes, but are not limited to these.

[0197] The electron injection layer described above can facilitate the injection of electrons. As an electron injection material, a compound is preferred that has the ability to transport electrons, has an excellent electron injection effect from the cathode, an excellent electron injection effect on the emissive layer or the emissive material, prevents the movement of excitons generated in the emissive layer to the hole injection layer, and also has excellent thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0198] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, Examples include bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited thereto.

[0199] The hole blocking layer described above is a layer that prevents holes from reaching the cathode and can generally be formed under the same conditions as the hole injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc. are used, but are not limited thereto.

[0200] The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0201] Hereinafter, to specifically explain this specification, examples will be described in detail. However, the embodiments according to this specification may be modified in various different forms, and the scope of this application is not to be interpreted as being limited to the embodiments described below. The embodiments of this application are provided to more completely explain this specification to those with average knowledge in the art.

[0203] < Synthetic example >

[0204] Synthetic example 1.

[0205]

[0206] Compounds 6-bromochrysene (30 g, 97.66 mmol, 1 eq.) and [1,1'-biphenyl]-2-ylboronic acid (21.27 g, 1.1 eq.) were dissolved in 970 ml of 1,4-dioxane in a round-bottom flask under a nitrogen atmosphere and stirred. Even if not completely dissolved, an aqueous potassium carbonate solution (27 g in 240 ml of H2O, 2 eq.) was added, followed by the addition of Bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 1 mol%) and heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, and the mixture was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized under toluene / EtOH conditions to prepare compound M-1 (33.8 g, 91%).

[0207] Compound M-1 (33.8 g, 88.87 mmol, 1 eq.) was dissolved in 300 mL of dimethylformamide in a round-bottom flask under a nitrogen atmosphere and stirred. N-Bromosuccinimide (48.2 g, 1.1 eq.) was added and stirred for 6 hours. If necessary, the temperature was raised to 60°C and stirred. After the reaction was complete, the temperature was lowered to room temperature, and 100 mL of water and 150 mL of ethanol were added and stirred for 30 minutes. After filtration, the solid was dissolved in chloroform, washed with aq. Na2S2O3 and aq. NaHCO3, and the water layer was removed. The organic layer was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized under toluene / hexane conditions to prepare Compound M-2 (29.8 g, 73%).

[0208] MS[M+H] + = 459

[0210] Synthetic example 2.

[0211]

[0212] Compound A-1 was synthesized using M-2 (15 g, 1 eq.) and M-3 as starting materials in the same manner as in Synthesis Example 1. Compound A-1 (10.7 g, 57%) was prepared by recrystallization under toluene conditions.

[0213] MS[M+H] + = 573

[0215] Synthetic example 3.

[0216]

[0217] Compound A-11 was synthesized using M-2 (15 g, 1 eq.) and M-4 as starting materials in the same manner as in Synthesis Example 2. Compound A-11 (16.2 g, 62%) was prepared by recrystallization under toluene conditions.

[0218] MS[M+H] + = 802

[0220] Synthetic example 4.

[0221]

[0222] M-5 was synthesized using 6-bromochrysene (80 g, 1 eq.) and phenylboronic acid as starting materials in the same manner as in Synthesis Example 1. Compound M-5 (74.5 g, 94%) was prepared by recrystallization under toluene / ethanol conditions.

[0223] M-6 was synthesized using M-5 (74.5 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-6 (73.2 g, 78%) was prepared by recrystallization under toluene conditions.

[0224] MS[M+H] + = 383

[0226] Synthetic example 5.

[0227]

[0228] Compound A-2 was synthesized using M-6 (11 g, 1 eq.) and M-7 as starting materials in the same manner as in Synthesis Example 2. Compound A-2 (11.7 g, 71%) was prepared by recrystallization under toluene conditions.

[0229] MS[M+H] + = 573

[0231] Synthetic example 6.

[0232]

[0233] Compound A-10 was synthesized using M-6 (11 g, 1 eq.) and M-8 as starting materials in the same manner as in Synthesis Example 2. Compound A-10 (12.1 g, 58%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0234] MS[M+H] + = 728

[0236] Synthetic example 7.

[0237]

[0238] Compound A-13 was synthesized using M-6 (11 g, 1 eq.) and M-9 as starting materials in the same manner as in Synthesis Example 2. Compound A-13 (9.0 g, 49%) was obtained by recrystallization under toluene / hexane conditions.

[0239] MS[M+H] + = 641

[0241] Synthetic example 8.

[0242]

[0243] Compound B-2 was synthesized using M-6 (11 g, 1 eq.) and M-10 as starting materials in the same manner as in Synthesis Example 2. Compound B-2 (12.0 g, 67%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0244] MS[M+H] + = 623

[0246] Synthetic example 9.

[0247]

[0248] Compound C-1 was synthesized using M-6 (11 g, 1 eq.) and M-11 as starting materials in the same manner as in Synthesis Example 2. Compound C-1 (10.5 g, 64%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0249] MS[M+H] + = 573

[0251] Synthetic example 10.

[0252]

[0253] Compound D-1 was synthesized using M-6 (11 g, 1 eq.) and M-12 as starting materials in the same manner as in Synthesis Example 2. Compound D-1 (9.9 g, 55%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0254] MS[M+H] + = 629

[0256] Synthetic example 11.

[0257]

[0258] Compound B-3 was synthesized using M-6 (7 g, 1 eq.) and M-13 as starting materials in the same manner as in Synthesis Example 2. Compound B-3 (7.7 g, 60%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0259] MS[M+H] + = 699

[0261] Synthetic example 12.

[0262]

[0263] Compounds 6,12-dibromochrysene (10 g, 26.05 mmol, 1 eq.) and [1,1'-biphenyl]-2-ylboronic acid (14.3 g, 2.3 eq.) were dissolved in 260 ml of 1,4-dioxane in a round-bottom flask under a nitrogen atmosphere and stirred. Even if the mixture was not completely dissolved, an aqueous potassium carbonate solution (18 g in 65 ml of H2O, 5 eq.) was added, followed by the addition of Bis(tri-tert-butylphosphine)palladium(0) (0.27 g, 2 mol%), and the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, and the mixture was dried with anhydrous magnesium sulfate. The mixture was then concentrated under reduced pressure and recrystallized under toluene conditions to prepare compound A-3 (13.1 g, 82%).

[0264] MS[M+H] + = 613

[0266] Synthetic example 13.

[0267]

[0268] M-15 was synthesized using 6-bromochrysene (50 g, 1 eq.) and M-14 (31 g, 1.1 eq) as starting materials in the same manner as in Synthesis Example 1. Compound M-15 (50.2 g, 87%) was prepared by recrystallization under toluene conditions.

[0269] M-16 was synthesized using M-15 (50.2 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-16 (43.6 g, 71%) was prepared by recrystallization under toluene / hexane conditions.

[0270] MS[M+H] + = 433

[0272] Synthetic example 14.

[0273]

[0274] Compound A-4 was synthesized using M-16 (15 g, 1 eq.) and M-17 as starting materials in the same manner as in Synthesis Example 2. Compound A-4 (16.4 g, 59%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0275] MS[M+H] + = 805

[0277] Synthetic example 15.

[0278]

[0279] Compound A-12 was synthesized using M-16 (15 g, 1 eq.) and M-18 as starting materials in the same manner as in Synthesis Example 2. Compound A-12 (14.7 g, 54%) was obtained by recrystallization under toluene / acetone conditions.

[0280] MS[M+H]+ = 787

[0282] Synthetic example 16.

[0283]

[0284] M-29 was synthesized using 6-bromochrysene (20 g, 1 eq.) and M-19 as starting materials in the same manner as in Synthesis Example 1. Compound M-20 (23.9 g, 78%) was prepared by recrystallization under toluene conditions.

[0285] M-21 was synthesized using M-20 (23.9 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-21 (21.5 g, 77%) was prepared by recrystallization under toluene conditions.

[0286] MS[M+H] + = 549

[0288] Synthetic example 17.

[0289]

[0290] Compound A-5 was synthesized using M-21 (15 g, 1 eq.) and M-22 as starting materials in the same manner as in Synthesis Example 2. Compound A-5 (12.3 g, 56%) was obtained by recrystallization under toluene / acetone conditions.

[0291] MS[M+H] + = 805

[0293] Synthetic example 18.

[0294]

[0295] Compound M-23 (46.2 g, 90%) was prepared by recrystallizing under toluene / ethanol conditions.

[0296] Compound M-24 (40.3 g, 70%) was synthesized using M-23 (46.2 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-24 was prepared by recrystallization under toluene / hexane conditions.

[0297] MS[M+H] + = 393

[0299] Synthetic example 19.

[0300]

[0301] Compound A-6 was synthesized using M-24 (15 g, 1 eq.) and M-25 as starting materials in the same manner as in Synthesis Example 2. Compound A-6 (12.8 g, 51%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0302] MS[M+H] + = 659

[0304] Synthetic example 20.

[0305]

[0306] Compound E-1 was synthesized using M-24 (15 g, 1 eq.) and M-26 as starting materials in the same manner as in Synthesis Example 2. Compound E-1 (12.5 g, 43%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0308] Synthetic example 21.

[0309]

[0310] M-28 was synthesized using 6-bromochrysene-d11 (30 g, 1 eq.) and M-27 as starting materials in the same manner as in Synthesis Example 1. Compound M-28 (26.3 g, 87%) was prepared by recrystallization under toluene / ethanol conditions.

[0311] M-29 was synthesized using M-28 (26.3 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-29 (23.8 g, 73%) was prepared by recrystallization under toluene / hexane conditions.

[0312] MS[M+H] + = 398

[0314] Synthetic example 22.

[0315]

[0316] Compound A-7 was synthesized using M-29 (15 g, 1 eq.) and M-30 (where the value of n+m is 6 based on the peak max of the MALDI-TOF MASS value, but at least 2 and up to 11 of the 11 hydrogen atoms of the aromatic ring are substituted) as starting materials in the same manner as in Synthesis Example 2. Compound A-7 (12 g, 56%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0317] MS[M+H] + = 568

[0319] Synthetic example 23.

[0320]

[0321] M-32 was synthesized using 6-bromochrysene (30 g, 1 eq.) and M-31 as starting materials in the same manner as in Synthesis Example 1. Compound M-32 (39.3 g, 81%) was prepared by recrystallization under toluene / hexane conditions.

[0322] M-33 was synthesized using M-32 (39.3 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-33 (31 g, 68%) was prepared by recrystallization under toluene / hexane conditions.

[0323] MS[M+H] + = 575

[0325] Synthetic example 24.

[0326]

[0327] Compound M-33 (15 g, 26.1 mmol, 1 eq.), carbazole (4.58 g, 1.05 eq.), and sodium tert-butoxide (3.8 g, 1.5 eq.) were dissolved in 200 mL of toluene in a round-bottom flask under a nitrogen atmosphere and stirred. Bis(tri-tert-butylphosphine)palladium (0) (0.13 g, 1 mol%) was added and heated and stirred for 6 hours. The temperature was lowered to room temperature, a q. of NH4Cl was added, and the mixture was stirred for 30 minutes. The aqueous layer was removed using a separatory funnel, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized under toluene conditions to prepare compound A-8 (9 g, 52%).

[0328] MS[M+H] + = 662

[0330] Synthetic example 25.

[0331]

[0332] M-35 was synthesized using 6-bromochrysene (30 g, 1 eq.) and M-34 as starting materials in the same manner as in Synthesis Example 1. Compound M-35 (34 g, 86%) was prepared by recrystallization under toluene conditions.

[0333] M-36 was synthesized using M-36 (34 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-36 (30 g, 74%) was prepared by recrystallization under toluene / ethyl acetate conditions.

[0334] MS[M+H] + = 483

[0336] Synthetic example 26.

[0337]

[0338] Compound A-9 was synthesized using M-36 (15 g, 1 eq.) and M-37 as starting materials in the same manner as in Synthesis Example 2. Compound A-9 (13.8 g, 66%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0340] Synthetic example 27.

[0341]

[0342] M-39 was synthesized using 6-bromochrysene (30 g, 1 eq.) and M-38 as starting materials in the same manner as in Synthesis Example 1. Compound M-39 (41.2 g, 84%) was prepared by recrystallization under toluene / hexane conditions.

[0343] M-40 was synthesized using M-39 (41.2, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-40 (36.7 g, 77%) was prepared by recrystallization under toluene / hexane conditions.

[0344] MS[M+H] + = 580

[0346] Synthetic example 28.

[0347]

[0348] Compound B-1 was synthesized using M-40 (15 g, 1 eq.) and carbazole-d8 as starting materials in the same manner as in Synthesis Example 24. Compound B-1 (10.1 g, 58%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0349] MS[M+H] + = 675

[0351] Synthetic example 29.

[0352]

[0353] M-42 was synthesized using 6-bromochrysene (30 g, 1 eq.) and M-41 as starting materials in the same manner as in Synthesis Example 1. Compound M-42 (30.5 g, 88%) was prepared by recrystallization under toluene conditions.

[0354] M-43 was synthesized using M-42 (30.5 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-43 (29.8 g, 80%) was prepared by recrystallization under toluene / hexane conditions.

[0355] MS[M+H] + = 433

[0357] Synthetic example 30.

[0358]

[0359] Compound D-2 was synthesized using M-43 (15 g, 1 eq.) and M-44 as starting materials in the same manner as in Synthesis Example 2. Compound D-2 (11.4 g, 49%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0360] MS[M+H] + = 749

[0362] Synthetic example 31.

[0363]

[0364] Compound M-46 (28.1 g, 85%) was prepared by recrystallizing under toluene / hexane conditions.

[0365] M-27 was synthesized using M-46 (28.1 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-47 (27.4 g, 79%) was prepared by recrystallization under toluene / hexane conditions.

[0366] MS[M+H] + = 417

[0368] Synthetic example 32.

[0369]

[0370] Compound M-49 was synthesized using M-47 (15 g, 1 eq.) and M-48 as starting materials in the same manner as in Synthesis Example 2. Compound M-49 (24.5 g, 82%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0371] MS[M+H] + = 455

[0372] Compound B-4 was synthesized using M-49 (15 g, 1 eq.) and M-50 as starting materials in the same manner as in Synthesis Example 24. Compound B-4 (10.4 g, 56%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0373] MS[M+H] + = 565

[0375] Synthetic example 33.

[0376]

[0377] M-52 was synthesized using 6-bromochrysene (30 g, 1 eq.) and M-51 as starting materials in the same manner as in Synthesis Example 1. Compound M-52 (23.8 g, 74%) was prepared by recrystallization under toluene / hexane conditions.

[0378] -53 was synthesized using M-52 (23.8 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-53 (18.9 g, 64%) was prepared by recrystallization under toluene / hexane conditions.

[0379] MS[M+H] + = 408

[0381] Synthetic example33.

[0382]

[0383] Compound D-3 was synthesized using M-53 (15 g, 1 eq.) and M-54 as starting materials in the same manner as in Synthesis Example 2. Compound D-3 (11.8 g, 44%) was obtained by recrystallization under toluene / ethyl acetate conditions.

[0384] MS[M+H] + = 728

[0386] Synthetic example 34.

[0387]

[0388] M-56 was synthesized using 6-bromochrysene (30 g, 1 eq.) and M-55 as starting materials in the same manner as in Synthesis Example 1. Compound M-56 (30.5 g, 82%) was prepared by recrystallization under toluene conditions.

[0389] -57 was synthesized using M-56 (30.5 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-57 (26.9, 73%) was prepared by recrystallization under toluene / hexane conditions.

[0390] MS[M+H] + = 459

[0392] Synthetic example 35.

[0393]

[0394] Compound B-5 was synthesized using M-57 (15 g, 1 eq.) and M-58 as starting materials in the same manner as in Synthesis Example 2. Compound B-5 (11.1 g, 53%) was obtained by recrystallization under toluene / acetone conditions.

[0395] MS[M+H] + = 641

[0397] Synthetic example36.

[0398]

[0399] M-60 was synthesized using 6-bromochrysene (30 g, 1 eq.) and M-59 as starting materials in the same manner as in Synthesis Example 1. Compound M-60 (34.4 g, 71%) was prepared by recrystallization under toluene conditions.

[0400] M-61 was synthesized using M-60 (34.4 g, 1 eq.) as a starting material in the same manner as in Synthesis Example 1. Compound M-61 (26.3 g, 66%) was prepared by recrystallization under toluene / hexane conditions.

[0401] MS[M+H] + = 575

[0403] Synthetic example 37.

[0404]

[0405] Compound C-2 was synthesized using M-61 (15 g, 1 eq.) and M-62 as starting materials in the same manner as in Synthesis Example 2. Compound C-2 (8.9 g, 48%) was obtained by recrystallization under toluene / acetone conditions.

[0406] MS[M+H] + = 726

[0408] <Experimental Example>

[0409] <Sojaye 1>

[0410] <Example 1-1> Preparation of an Organic Light-Emitting Device

[0411] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,000 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millerpore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0412] A hole injection layer was formed on the prepared ITO transparent electrode by thermal vacuum deposition of compounds [HI-1] and [HI-2] to a thickness of 80 Å in a ratio of 98:4 (molar ratio), and a hole transport layer was formed by vacuum deposition of HI-1, a material that transports holes, to a thickness of 1150 Å on top of it. Then, a hole control layer was formed using compound EB-1 (100 Å). Next, a light-emitting layer was formed by co-depositing compound A-1 prepared in the above synthesis example and blue fluorescent dopant BD-1 to a thickness of 250 Å in a weight ratio (wt%) of 95:5. Then, an electron control layer was formed by depositing compound HB-1 to a thickness of 50 Å, and an electron transport layer with a thickness of 250 Å was formed by mixing compound ET-1 and lithium quinoleate (Liq) in a ratio of 7:3. Sequentially, magnesium and lithium fluoride (LiF) with a thickness of 50 Å were formed as electron injection layers, and then aluminum was deposited to a thickness of 2,000 Å to form a cathode.

[0413] In the above process, the deposition rate of the organic material was maintained at 0.4–0.7 Å / sec, while the deposition rates for the cathode lithium fluoride and aluminum were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 2 × 10⁻¹⁰ -7~ 5 x 10 -6 An organic light-emitting diode was fabricated by maintaining torr.

[0414]

[0416] Examples 1-2 to 1-7

[0417] An organic light-emitting diode was prepared in the same manner as in Example 1-1, except that the compound listed in Table 1 below was used instead of compound A-1 of Example 1-1.

[0418] Comparative Examples 1-1 to 1-3

[0419] An organic light-emitting diode was prepared in the same manner as in Example 1-1, except that the compound listed in Table 1 below was used instead of compound A-1 of Example 1-1.

[0420]

[0422] The organic light-emitting diodes prepared in Examples 1-1 to 1-7 and Comparative Examples 1-1 to 1-3 at 10 mA / cm² 2 The driving voltage and luminous efficiency (cd / A) were measured at a current density of 20 mA / cm². 2 The time (T95) at which the initial brightness is reduced to 95% at the current density was measured, and a relative value based on Comparative Example 1-1 was expressed.

[0423] Host 10mA / cm 2 20mA / cm 2 Driving voltage (v) Efficiency (cd / A) lifespan, ratio Example 1-1 A-1 4.55 5.12 6.07 Examples 1-2 A-4 4.49 5.22 5.46 Examples 1-3 A-6 4.45 5.27 7.16 Examples 1-4 A-9 4.51 5.43 6.53 Examples 1-5 B-3 4.58 5.02 6.40 Examples 1-6 C-1 4.61 5.36 7.14 Examples 1-7 D-1 4.42 4.94 5.07 Comparative Example 1-1 X-1 4.02 3.87 1.00 Comparative Example 1-2 X-3 4.14 3.65 1.57 Comparative Examples 1-3 BH-1 4.97 5.48 1.88

[0424] As shown in the experimental results of Table 1 above, Examples 1-1 to 1-7, which used the compound of Formula 1 of the present invention as a blue fluorescent host, showed improved charge balance compared to the devices of Comparative Examples 1-1 and 1-2, which used compounds X-1 or X-3, resulting in significantly improved efficiency and lifespan. Although the driving voltage increased slightly, it was confirmed to be at an improved level compared to BH-1, which is based on anthracene and is typically used as a blue fluorescent host.

[0426] Examples 1-8 to 1-12

[0427] An organic light-emitting diode was prepared in the same manner as in Example 1-1, except that BH-1 was used instead of Compound A-1 of Example 1-1, and the compound listed in Table 2 below was used instead of ET-1.

[0428] Comparative Examples 1-4 to 1-5

[0429] An organic light-emitting diode was prepared in the same manner as in Example 1-1, except that the following BH-1 was used instead of compound A-1 of Example 1-1, and the compound listed in Table 2 below was used instead of ET-1.

[0430]

[0432] The organic light-emitting diodes prepared in Examples 1-8 to 1-12, Comparative Examples 1-4 and 1-5 at 10 mA / cm² 2 The driving voltage and luminous efficiency (cd / A) were measured at a current density of 20 mA / cm². 2 The time (T95) at which the initial brightness is reduced to 95% at the current density was measured, and the relative value based on Comparative Examples 1-3 was expressed.

[0433] Electron transport layer Driving voltage (v) Efficiency (cd / A) lifespan, ratio Examples 1-8 A-10 4.88 5.42 1.13 Examples 1-9 B-4 4.79 5.55 1.22 Examples 1-10 B-5 4.85 5.51 1.09 Example 1-11 C-2 4.91 5.43 1.16 Examples 1-12 D-3 4.74 5.64 1.05 Comparative Examples 1-4 X-2 5.06 4.82 1.02 Comparative Examples 1-5 X-3 5.26 5.21 1.06 Comparative Examples 1-3 ET-1 4.97 5.48 1.00

[0434] From the experimental results in Table 2 above, it can be confirmed that the compound of Formula 1 of the present invention can also be used as an electron transport layer. It was confirmed that the example using the compound of Formula 1 of the present invention showed improved electron injection characteristics compared to Comparative Examples 1-3 (Tables 1 and 2), resulting in a slight improvement in driving voltage and an increase in device lifespan. On the other hand, Compounds X-2 and X-3 are of the type where electrons are slower than Compound ET-1, so the driving voltage increased slightly and the device efficiency also decreased.

[0436] <Sojaye 2>

[0437] <Example 2-1> Preparation of an Organic Light-Emitting Device

[0438] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,000 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millerpore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0439] A hole injection layer was formed on the prepared ITO transparent electrode by thermal vacuum deposition of compounds of the chemical formula [HI-1] and the chemical formula [HI-2] to a thickness of 80 Å in a ratio of 98:4 (molar ratio), and a hole transport layer was formed by vacuum deposition of the compound HI-1, which is a material that transports holes, to a thickness of 1150 Å on top of it. Then, a hole control layer was formed using the compound EB-1 (100 Å). Then, a first emitting layer was formed by co-depositing the compound A-2 (first host) prepared in the synthesis example and the blue fluorescent dopant BD-2 in a weight ratio (wt%) of 95:5, and a second emitting layer was formed by co-depositing the compound BH-1 (second host) and the blue fluorescent dopant BD-2 in a weight ratio (wt%) of 95:5. The thicknesses of the first and second emitting layers were shown in Table 3 below, and the sum of the thicknesses of the two emitting layers was 250 Å. Then, the above compound HB-1 was deposited to form an electron control layer of 50 Å, and the above compound ET-1 and lithium quinolate (Liq) were mixed in a 7:3 ratio to form an electron transport layer of 250 Å thickness. Sequentially, magnesium and lithium fluoride (LiF) with a thickness of 50 Å were formed as an electron injection layer, and then aluminum was deposited to a thickness of 2,000 Å to form a cathode.

[0440] In the above process, the deposition rate of the organic material was maintained at 0.4–0.7 Å / sec, while the deposition rates for the cathode lithium fluoride and aluminum were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 2 × 10⁻¹⁰ -7 ~ 5 x 10 -6 An organic light-emitting diode was fabricated by maintaining torr.

[0441]

[0443] Examples 2-2 to 2-9

[0444] An organic light-emitting diode was manufactured in the same manner as in Example 2-1, except that a emitting layer of the thickness listed in Table 3 was formed using the compounds listed in Table 3 below instead of the first host, second host, and dopant used in Example 2-1.

[0445] Comparative Examples 2-1, 2-2, 2-4

[0446] An organic light-emitting diode was manufactured in the same manner as in Example 2-1, except that a emitting layer of the thickness listed in Table 3 was formed using the compounds listed in Table 3 below instead of the first host, second host, and dopant used in Example 2-1.

[0447] Comparative Example 2-3

[0448] An organic light-emitting diode was manufactured in the same manner as Comparative Example 1-3, except that the dopant BD-2 listed in Table 3 below was used instead of the dopant BD-1 of Comparative Example 1-3.

[0449]

[0450]

[0452] The organic light-emitting diodes prepared in Examples 2-1 to 2-9 and Comparative Examples 2-1 to 2-4 at 10 mA / cm² 2 The driving voltage and luminous efficiency (cd / A) were measured at a current density of 20 mA / cm². 2 The time (T95) at which the initial brightness is reduced to 95% at the current density was measured, and the relative value based on Comparative Examples 1-3 was expressed.

[0453] 1st host 2nd host dopant Driving voltage efficiency lifespan, ratio Example 2-1 A-2, 50Å BH-1, 200Å BD-2 4.87 5.84 1.10 Example 2-2 A-2, 125Å BH-1, 125Å BD-2 4.73 5.63 0.92 Examples 2-3 A-3, 50Å BH-1, 200Å BD-2 4.71 5.91 1.07 Examples 2-4 D-1, 50Å BH-2, 200Å BD-2 4.72 5.77 1.20 Examples 2-5 A-7, 50Å BH-2, 200Å BD-3 4.69 5.76 1.35 Examples 2-6 A-11, 50Å BH-2, 200Å BD-3 4.65 5.65 1.09 Examples 2-7 B-2, 50Å BH-3, 200Å BD-2 4.65 5.93 1.42 Examples 2-8 E-1, 50Å BH-3, 200Å BD-2 4.63 5.99 1.85 Examples 2-9 A-3, 50Å BH-3, 200Å BD-3 4.55 5.85 1.56 Comparative Example 2-1 X-1, 50Å BH-1, 200Å BD-2 4.72 5.56 0.79 Comparative Example 2-2 X-1, 50Å BH-2, 200Å BD-3 4.48 5.40 0.71 Comparative Example 2-3 BH-1, 250Å BD-2 4.99 5.59 0.91 Comparative Example 2-4 BH-1, 50Å BH-2, 200Å BD-2 4.70 5.37 0.96 Comparative Examples 1-3 BH-1, 250Å BD-1 4.97 5.48 1.00

[0454] By using a compound of Formula 1, which has a higher T1 than anthracene compounds, in the first light-emitting layer, the region where charges meet to form excitons and the region where excitons emit light are separated, thereby slightly improving the efficiency of the device and increasing its lifespan. From the experimental results in Table 3 above, it was confirmed that the efficiency and lifespan performance of the device differed depending on the thickness ratio of the first host and the second host, and that the effect was greater when the first host was used in smaller quantities.

[0456] <Sojaye 3>

[0457] <Example 3-1> Preparation of an Organic Light-Emitting Device

[0458] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,000 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millerpore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0459] On the ITO transparent electrode prepared in this way, 600 Å of BCFN was deposited, 50 Å of the first compound was deposited thereon, and on the first host mCBP and the second host A-12 were deposited thereon in a weight ratio (wt%) of 50:50, and the total host (first host + second host) and dopant BD-4 were deposited in a weight ratio (wt%) of 95:5 to form a light-emitting layer with a thickness of 300 Å.

[0460] Then, an electron transport layer with a thickness of 300 Å was formed by mixing mSiTrz and lithium quinolate (Liq) in a 7:3 ratio on top of 50 Å of mSiTrz.

[0461] Sequentially, magnesium and lithium fluoride (LiF) with a thickness of 50 Å were formed as electron injection layers, and then aluminum was deposited to a thickness of 2,000 Å to form a cathode.

[0462] In the above process, the deposition rate of the organic material was maintained at 0.4–0.7 Å / sec, while the deposition rates for the cathode lithium fluoride and aluminum were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 2 × 10⁻¹⁰ -7 ~ 5 x 10 -6 An organic light-emitting diode was fabricated by maintaining torr.

[0463]

[0464]

[0465]

[0467] Examples 3-2 to 3-7

[0468] An organic light-emitting diode was prepared in the same manner as in Example 3-1, except that the compounds listed in Table 4 below were used instead of the first host, second host, and dopant used in Example 3-1.

[0469] Comparative Examples 3-1 to 3-4

[0470] An organic light-emitting diode was prepared in the same manner as in Example 3-1, except that the compounds listed in Table 4 below were used instead of the first host, second host, and dopant used in Example 3-1.

[0472] The organic light-emitting diodes prepared in Examples 3-1 to 3-7 and Comparative Examples 3-1 to 3-4 at 10 mA / cm² 2 The driving voltage and luminous efficiency (EQE,%) were measured at a current density of 10 mA / cm². 2 The time (T80) at which the initial brightness is reduced to 80% at the current density was measured, and a relative value based on Comparative Example 3-1 was expressed.

[0473] 1st host 2nd host dopant Driving voltage EQE, % lifespan, ratio Example 3-1 mCBP A-12 BD-4 4.77 15.9 3.97 Example 3-2 mCBP A-13 BD-5 4.63 15.1 3.33 Example 3-3 CNmCBPCN A-8 BD-4 4.89 16.0 2.89 Examples 3-4 CNmCBPCN B-1 BD-5 4.83 15.4 3.41 Examples 3-5 CNmCBPCN A-5 BD-4 4.99 14.4 3.34 Examples 3-6 CNmCBPCN D-2 BD-5 4.92 14.7 3.26 Examples 3-7 B-1 A-12 BD-5 4.67 16.1 4.27 Comparative Example 3-1 mCBP - BD-4 5.61 12.7 1.00 Comparative Example 3-2 CNmCBPCN - BD-4 3.72 11.3 1.67 Comparative Example 3-3 mCBP X-2 BD-5 4.86 14.1 2.16 Comparative Example 3-4 mCBP CNmCBPCN BD-4 4.97 13.6 3.20

[0474] From the experimental results of Table 4 above, it was confirmed that the performance of the organic light-emitting device (Examples 3-1 to 3-7), in which one of the two hosts is a light-emitting layer of the compound of Formula 1 of the present invention, is superior to that of the device in Comparative Examples 3-1 to 3-4. Explanation of the symbols

[0475] 1: Substrate 2: Anode 3: Hole injection layer 4: Precision Transport Layer 5: Electromagnetic blocking layer 6: Emissive layer 7: Hole blocking layer 8: Electron injection and transport layer 9: Cathode

Claims

Claim 1 Compound represented by any one of the following chemical formulas 1-1 to 1-6: [Chemical Formula 1-1] In the above chemical formula 1-1, L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted divalent hydrocarbon ring; or a substituted or unsubstituted divalent heteroring, and R1 to R 10 is the same or different from each other and is each independently hydrogen; or deuterium; Ar2 is a substituted or unsubstituted hydrocarbon group; a substituted or unsubstituted amine group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted heterocyclic group; n1 and n2 are each independently integers from 0 to 2, X is O or S, A1 is a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted hydrocarbon group; or a substituted or unsubstituted heterocyclic group; A3 to A6 are the same or different from each other and are each independently hydrogen; deuterium; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted hydrocarbon group; or is a substituted or unsubstituted heterocyclic ring, or combines with adjacent groups to form a substituted or unsubstituted ring, and the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; amino group; alkoxy group; aryloxy group; alkyl group; cycloalkyl group; silyl group; aryl group; It means being substituted with one or more substituents selected from the group consisting of and heterocyclic groups, or being substituted with a substituent in which two or more of the substituents exemplified above are connected, or having no substituents, wherein the number of carbon atoms of the alkyl group and alkoxy group is 1 to 60, the number of carbon atoms of the hydrocarbon ring and cycloalkyl group is 3 to 60, the number of carbon atoms of the aryl group and aryloxy group is 6 to 60, the number of carbon atoms of the heterocyclic group and heterocyclic group is 2 to 60, and when X is O, it is any one of the following (1) to (3), (1) Ar2 is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted Hexahydrocarbazole group,(2) A1 is a substituted or unsubstituted arylsilyl group or a substituted or unsubstituted arylamine group, or A1 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted benzothiophen group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophen group, or (3) at least one of A3 to A6 is a deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylsilyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or Unsubstituted naphthyl group, substituted or unsubstituted phenanthrene group, substituted or unsubstituted tetrahydronaphthyl group, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophen group, substituted or unsubstituted pyridine group, substituted or unsubstituted pyrimidyl group, substituted or unsubstituted triazine group, substituted or unsubstituted carbazole group, substituted or unsubstituted benzimidazole group, substituted or unsubstituted silafluorene group, substituted or unsubstituted dibenzofuran group, or substituted or unsubstituted dibenzothiophen group, or is combined with an adjacent substituent to form a substituted or unsubstituted six-membered ring, [Chemical Formula 1-2], In the above chemical formula 1-2, L1 is a substituted or unsubstituted divalent hydrocarbon ring; or a substituted or unsubstituted divalent heteroring, L2 is a direct bond; a substituted or unsubstituted divalent hydrocarbon ring; or a substituted or unsubstituted divalent heteroring, and R1 to R 10 are equal to or different from each other and are each independently hydrogen; or deuterium, Ar2 is a substituted or unsubstituted hydrocarbon group; a substituted or unsubstituted amine group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted heterocyclic group, n1 is an integer from 1 to 2, n2 is an integer from 0 to 2, X is O or S, A2 is hydrogen; deuterium; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted hydrocarbon group; or a substituted or unsubstituted heterocyclic group, and A3 to A6 are equal to or different from each other and are each independently hydrogen; deuterium; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted hydrocarbon group; or is a substituted or unsubstituted heterocyclic ring, or combines with adjacent groups to form a substituted or unsubstituted ring, and the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; amino group; alkoxy group; aryloxy group; alkyl group; cycloalkyl group; silyl group; aryl group; It means being substituted with one or more substituents selected from the group consisting of and heterocyclic groups, or being substituted with a substituent in which two or more of the substituents exemplified above are connected, or having no substituents, wherein the number of carbon atoms of the alkyl group and alkoxy group is 1 to 60, the number of carbon atoms of the hydrocarbon ring and cycloalkyl group is 3 to 60, the number of carbon atoms of the aryl group and aryloxy group is 6 to 60, the number of carbon atoms of the heterocyclic group and heterocyclic group is 2 to 60, and when X is O, it is any one of the following (4) to (6), (4) Ar2 is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazine group,(5) A2 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted hexahydrocarbazole group, a substituted or unsubstituted arylsilyl group, or a substituted or unsubstituted arylamine group, or (5) A2 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted benzothiophen group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophen group, or (6) A3 to At least one of A6 is a deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylsilyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted benzothiophen group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted silafluorene group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophen group, or forms a substituted or unsubstituted six-membered ring by combining with an adjacent substituent, [Chemical Formula 1-3], [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-3 to 1-6, L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted divalent hydrocarbon ring; or a substituted or unsubstituted divalent heteroring, and R1 to R 10 ≠ or is a substituted or unsubstituted heterocyclic ring, and A3 to A6 are the same or different from one another, and each independently is hydrogen; deuterium; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted hydrocarbon ring; or substituted or unsubstituted heterocyclic ring, or is bonded to adjacent groups to form a substituted or unsubstituted ring, and the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; amino group; alkoxy group; aryloxy group; alkyl group; cycloalkyl group; silyl group; aryl group; It means being substituted with one or more substituents selected from the group consisting of and heterocyclic groups, or being substituted with a substituent in which two or more of the substituents exemplified above are connected, or having no substituents, wherein the number of carbon atoms of the alkyl group and alkoxy group is 1 to 60, the number of carbon atoms of the hydrocarbon ring and cycloalkyl group is 3 to 60, the number of carbon atoms of the aryl group and aryloxy group is 6 to 60, the number of carbon atoms of the heterocyclic group and heterocyclic group is 2 to 60, and when X is O, any one of the following (7) to (9).(7) Ar2 is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted hexahydrocarbazole group, a substituted or unsubstituted arylsilyl group, or a substituted or unsubstituted arylamine group, or (8) one or more of A1 and A2 are a substituted or unsubstituted alkyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted benzothiophen group, a substituted or unsubstituted (9) at least one of A3 to A6 is a deuterium, a nitrile group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted benzimidazole group, or at least one of A3 to A6 is a deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylsilyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted benzothiophen group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted benzimidazole group, or a substituted or unsubstituted silafluorene group, or forms a substituted or unsubstituted six-membered ring by combining with an adjacent substituent. Claim 2 delete Claim 3 delete Claim 4 A compound according to claim 1, wherein the formula 1 is represented by any one of formulas 1-3 to 1-6, L1 is a substituted or unsubstituted divalent hydrocarbon ring; or a substituted or unsubstituted divalent heteroring, and n1 is an integer from 1 to 2. Claim 5 In claim 1, in the formulas 1-1 and 1-2, X is S, and Ar2 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted tetrahydronaphthalene ( ); substituted or unsubstituted pyridine group; substituted or unsubstituted benzofuran group; substituted or unsubstituted dibenzofuran group; substituted or unsubstituted carbazole group; substituted or unsubstituted benzimidazole group; substituted or unsubstituted hexahydrocarbazole group ( ); a substituted or unsubstituted arylsilyl group; or a substituted or unsubstituted arylamine group, and in the formulas 1-3 to 1-6, X is S, and Ar2 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted tetrahydronaphthalene ( ); substituted or unsubstituted pyridine group; substituted or unsubstituted dibenzofuran group; substituted or unsubstituted carbazole group; substituted or unsubstituted benzimidazole group; substituted or unsubstituted hexahydrocarbazole group ( A compound that is a substituted or unsubstituted arylsilyl group; or a substituted or unsubstituted arylamine group. Claim 6 In claim 1, wherein in formula 1-1 and formulas 1-3 to 1-6, L1 is a direct bond; a substituted or unsubstituted divalent phenyl; a substituted or unsubstituted divalent biphenyl; a substituted or unsubstituted divalent naphthalene; a substituted or unsubstituted divalent phenanthrene; a substituted or unsubstituted divalent tetrahydronaphthalene; a substituted or unsubstituted divalent fluorene; a substituted or unsubstituted dibenzothiophene; or a substituted or unsubstituted dibenzofuran; and in formula 1-2, wherein L1 is a substituted or unsubstituted divalent phenyl; a substituted or unsubstituted divalent biphenyl; a substituted or unsubstituted divalent naphthalene; a substituted or unsubstituted divalent phenanthrene; a substituted or unsubstituted divalent tetrahydronaphthalene; A compound that is a substituted or unsubstituted divalent fluorene; a substituted or unsubstituted dibenzothiophene; or a substituted or unsubstituted dibenzofuran. Claim 7 A compound according to claim 1, wherein L2 is a direct bond; a substituted or unsubstituted divalent phenyl; a substituted or unsubstituted divalent biphenyl; or a substituted or unsubstituted divalent naphthalene. Claim 8 A compound according to claim 1, wherein any one of the formulas 1-1 to 1-6 is represented by any one of the following compounds: . Claim 9 An organic light-emitting device comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein the organic layers comprise a first light-emitting layer comprising a compound according to any one of claims 1 and 4 to 8 and a second light-emitting layer comprising an anthracene derivative, and wherein the thickness of the first light-emitting layer is less than or equal to the thickness of the second light-emitting layer. Claim 10 An organic light-emitting device comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein the organic layers comprise a light-emitting layer comprising a compound according to any one of claims 1 and 4 to 8 and a carbazole derivative. Claim 11 An organic light-emitting device comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein the organic layers comprise a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer comprises a compound according to any one of claims 1 and 4 to 8. Claim 12 An organic light-emitting device comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein the organic layers comprise an electron blocking layer, and the electron blocking layer comprises a compound according to any one of claims 1 and 4 to 8. Claim 13 An organic light-emitting device comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein the organic layers comprise an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, electron transport layer, or electron injection and transport layer comprises a compound according to any one of claims 1 and 4 to 8. Claim 14 An organic light-emitting device comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein the organic layers comprise a hole-blocking layer and the hole-blocking layer comprises a compound according to any one of claims 1 and 4 to 8.

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