WO2021049843A1 - Compound and organic light emitting device comprising same - Google Patents

Compound and organic light emitting device comprising same Download PDF

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WO2021049843A1
WO2021049843A1 PCT/KR2020/012085 KR2020012085W WO2021049843A1 WO 2021049843 A1 WO2021049843 A1 WO 2021049843A1 KR 2020012085 W KR2020012085 W KR 2020012085W WO 2021049843 A1 WO2021049843 A1 WO 2021049843A1
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formula
compound
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윤정민
홍성길
허동욱
한미연
이재탁
윤희경
박호윤
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주식회사 엘지화학
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Priority claimed from KR1020200102431A external-priority patent/KR102654051B1/en
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Priority to CN202080036911.3A priority Critical patent/CN113891885B/en
Publication of WO2021049843A1 publication Critical patent/WO2021049843A1/en

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Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material.
  • An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification provides a compound and an organic light emitting device including the same.
  • An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
  • At least one of X1 to X5 is N, and the others are each independently CR5,
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R1 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group,
  • R2, R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • an exemplary embodiment of the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
  • the compound according to the exemplary embodiment of the present specification may be used as a material of the organic material layer of the organic light emitting device, and by using the compound, it is possible to improve efficiency, low driving voltage, and/or life characteristics in the organic light emitting device.
  • 1 and 2 illustrate an example of an organic light-emitting device according to an exemplary embodiment of the present specification.
  • the compound according to an exemplary embodiment of the present specification includes L1 and L2, which are linking groups, to divalent naphthalene, which is a substituent that connects the electron donor, which is an imidazole derivative, and an electron acceptor including a 6-membered monocyclic or bicyclic heterocycle including N. It is a structure in which a substituent is bonded through.
  • R1 in Formula 1 when R1 in Formula 1 according to an exemplary embodiment of the present specification is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, the three-dimensional size is relatively larger and more robust than the conventional case where R1 is hydrogen, Due to this, since the compound has excellent sublimation properties and chemical structural stability, there is an advantage of having thermal stability. In addition, since R1 of Formula 1 is variously introduced, the amount of electrons flowing into the emission layer of the organic light emitting device is adjusted to induce a balance of charges in the emission layer, so that the organic light emitting device including the compound of Formula 1 is excellent. It has efficiency and longevity.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Cyano group; Alkyl group; Cycloalkyl group; Alkoxy group; Alkenyl group; Haloalkyl group; Silyl group; Boron group; Amine group; Aryl group; And it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, two or more of the above-exemplified substituents are substituted with a connected substituent, or it means that it does not have any substituents.
  • substituents when two or more substituents are connected, it means that hydrogen of any one substituent is connected with another substituent.
  • a phenyl group and a naphthyl group are connected, or It may be a substituent of.
  • the connection of three substituents is not only that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, but also (substituent 2) and (substituent 3) are connected to (substituent 1).
  • a phenyl group, a naphthyl group and an isopropyl group are connected, , or It may be a substituent of.
  • the above definition applies equally to those in which four or more substituents are connected.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl group, etc. , But is not limited thereto.
  • the alkoxy group may be a straight chain, branched chain, or cyclic chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 30 carbon atoms.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, and a styrenyl group, but are not limited thereto.
  • haloalkyl group means that at least one halogen group is substituted for hydrogen of the alkyl group in the definition of the alkyl group.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms.
  • the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.
  • the fluorene group may be substituted, and adjacent groups may be bonded to each other to form a ring.
  • the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent located three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted.
  • I can.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
  • the heteroaryl group includes one or more atoms other than carbon and one or more heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, and S.
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group , Pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthroline group, isoxazole group, thia Dia
  • the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, and the like.
  • the alkyl group of the alkylsilyl group may be exemplified by the aforementioned alkyl group
  • the aryl group of the arylsilyl group may be exemplified by the aryl group described above
  • the heteroaryl group of the heteroarylsilyl group may be exemplified by the heteroaryl group Can be applied.
  • the boron group may be -BR 100 R 101 , the R 100 and R 101 are the same or different, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.
  • the amine group is from the group consisting of -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre Nilfluorenylamine group, N-biphenylfluorenylamine group, N
  • the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.
  • the alkyl group and aryl group in the N-alkylarylamine group are the same as those of the aforementioned alkyl group and aryl group.
  • the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.
  • the aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and the heteroaryl group described above.
  • the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.
  • the alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as those of the aforementioned alkyl group and heteroaryl group.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group.
  • the arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
  • the meaning of "bonding with adjacent groups to form a ring" among the substituents refers to a substituted or unsubstituted hydrocarbon ring by bonding with an adjacent group; Or it means to form a substituted or unsubstituted heterocycle.
  • ring is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.
  • the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from examples of the cycloalkyl group or an aryl group, except for the non-monovalent ones.
  • the heterocycle is an atom other than carbon and includes one or more heteroatoms, and specifically, the heterocycle may include one or more atoms selected from the group consisting of O, N, Se, and S.
  • the heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.
  • the aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, and azocaine , Thiocane, and the like, but are not limited thereto.
  • an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
  • the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.
  • R2 and R3 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 6 to 30 monocyclic or polycyclic aromatic hydrocarbon rings; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed.
  • R2 and R3 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 6 to 20 monocyclic or polycyclic aromatic hydrocarbon rings; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms is formed.
  • R2 and R3 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a linear or branched alkyl group having 1 to 30 carbon atoms by bonding to each other , C 6 to C 30 monocyclic or polycyclic aryl group, or C 1 to C 30 straight or branched alkyl group substituted or unsubstituted C 2 to C 30 monocyclic or polycyclic heteroaryl group substituted or unsubstituted C 6 Monocyclic or polycyclic aromatic hydrocarbon rings of to 30; Or to form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
  • R2 and R3 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a linear or branched alkyl group having 1 to 20 carbon atoms by bonding to each other.
  • R2 and R3 are a phenyl group, or benzene unsubstituted or substituted with a methyl group, a phenyl group, a pyridine group unsubstituted or substituted with a methyl group, or a dibenzofuran group by bonding to each other; naphthalene; Dibenzothiophene; Or to form dibenzofuran.
  • Chemical Formula 1 is represented by the following Chemical Formula 2.
  • X1 to X5, L1, L2 and R1 are the same as defined in Formula 1,
  • R4 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
  • r4 is an integer of 1 to 4, and when r4 is 2 or more, the two or more R4s are the same as or different from each other.
  • R4 is hydrogen
  • R4 is a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • R4 is a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
  • R4 is a linear or branched alkyl group having 1 to 30 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a C2 to C30 monocyclic or polycyclic heteroaryl group substituted or unsubstituted with a C1 to C30 linear or branched alkyl group.
  • R4 is a linear or branched alkyl group having 1 to 20 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a C2 to C20 monocyclic or polycyclic heteroaryl group substituted or unsubstituted with a C1 to C20 linear or branched alkyl group.
  • R4 is a methyl group; Phenyl group; A pyridine group unsubstituted or substituted with a methyl group; Or a dibenzofuran group.
  • R4 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding with an adjacent group to each other; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed.
  • R4 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding with an adjacent group to each other; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms is formed.
  • R4 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding to each other with adjacent groups; Or to form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
  • R4 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding to each other with an adjacent group; Or to form a monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.
  • R4 is benzene by bonding with an adjacent group; Benzothiophene; Or to form benzofuran.
  • Chemical Formula 1 is represented by any one of Chemical Formulas 3 to 16 below.
  • X1 to X5, L1, L2, and R1 to R3 are the same as defined in Formula 1 above.
  • At least one of X1 to X5 is N, and the rest are each CR5.
  • At least two of X1 to X5 are N, and the rest are each CR5.
  • At least three of X1 to X5 are N, and the rest are each independently CR5.
  • any one of X1 to X5 is N, and the others are each independently CR5.
  • any two of X1 to X5 are N, and the others are each independently CR5.
  • any three of X1 to X5 are N, and the rest are each independently CR5.
  • X1 is N
  • X2 to X5 are the same as or different from each other, and each independently is R5.
  • X2 is N
  • X1 and X3 to X5 are the same as or different from each other, and each independently is R5.
  • X3 is N
  • X1, X2, X4, and X5 are the same as or different from each other, and each independently is R5.
  • X1 and X5 are N, X2 to X4 are the same as or different from each other, and each independently is R5.
  • X1 and X3 are N
  • X2, X4 and X5 are the same as or different from each other, and each independently is R5.
  • X2 and X4 are N
  • X1, X3 and X5 are the same as or different from each other, and each independently is R5.
  • X3 and X5 are N, X1, X2 and X4 are the same as or different from each other, and each independently is R5.
  • X1 and X2 are N, X3 to X5 are the same as or different from each other, and each independently is R5.
  • X4 and X5 are N, X1 to X3 are the same as or different from each other, and each independently is R5.
  • X2 and X3 are N
  • X1, X4 and X5 are the same as or different from each other, and each independently is R5.
  • X3 and X4 are N
  • X1, X2 and X5 are the same as or different from each other, and each independently is R5.
  • X1 and X4 are N, X2, X3, and X5 are the same as or different from each other, and each independently is R5.
  • X2 and X5 are N, X1, X3, and X4 are the same as or different from each other, and each independently is R5.
  • X1, X3, and X5 are N
  • X2 and X4 are the same as or different from each other, and each independently is R5.
  • Formula 1 is represented by any one of the following Formulas 1-1 to 1-10.
  • L1, L2 and R1 to R3 are the same as defined in Formula 1,
  • R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-11 to 1-20.
  • L1, L2 and R1 are the same as defined in Formula 1,
  • R4 and R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
  • r4 is an integer of 1 to 4, and when r4 is 2 or more, the two or more R4s are the same as or different from each other.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms, wherein R 1 is a linear or branched alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, and R2 and R3 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a straight chain having 1 to 30 carbon atoms by bonding to each other Or substituted with a branched alkyl group, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substitute
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; A monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Phenylene group; Naphthylene group; Biphenylylene group; A divalent pyridine group; Divalent dibenzofuran group; Or a divalent dibenzothiophene group.
  • R1 is a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms.
  • R1 is a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms.
  • R1 is an alkyl group; Or a cycloalkyl group.
  • R1 is a linear or branched alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms.
  • R1 is a linear or branched alkyl group having 1 to 20 carbon atoms; Or a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms.
  • R1 is a methyl group; Ethyl group; Isopropyl group; tert-butyl group; Cyclohexyl group; Or an adamantyl group.
  • R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or combined with adjacent groups to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, or combined with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; Unsubstituted or substituted with a cyano group, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a straight or branched chain alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or combined with an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; Unsubstituted or substituted with a cyano group, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms unsubstituted or substituted with a straight or branched chain alkyl group having 1 to 20 carbon atoms A monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, or combined with an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with a naphthyl group or a pyridine group unsubstituted or substituted with a methyl group; A biphenyl group unsubstituted or substituted with a cyano group; A naphthyl group unsubstituted or substituted with a cyano group; Phenanthrene group; Fluoranthene group; Pyridine group; Dibenzofuran group; Or it is a dibenzothiophene group, or it combines with an adjacent group to form benzene.
  • R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or combined with adjacent groups to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, or combined with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Unsubstituted or substituted with a cyano group, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a straight or branched alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or combined with an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Unsubstituted or substituted with a cyano group, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms unsubstituted or substituted with a straight or branched chain alkyl group having 1 to 20 carbon atoms A monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, or combined with an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with a naphthyl group or a pyridine group unsubstituted or substituted with a methyl group; A biphenyl group unsubstituted or substituted with a cyano group; A naphthyl group unsubstituted or substituted with a cyano group; Phenanthrene group; Fluoranthene group; Pyridine group; Dibenzofuran group; Or it is a dibenzothiophene group, or it combines with an adjacent group to form benzene.
  • Formula 1 is any one selected from the following compounds and compounds of Tables 1 to 36 below.
  • ** is in the formula 1 And of Formula 1 Refers to the site to which is bonded.
  • the present specification provides an organic light-emitting device including the compound represented by Chemical Formula 1.
  • the'layer' is meant to be compatible with the'film' mainly used in the present technical field, and means a coating covering a desired area.
  • the size of the'layer' is not limited, and each'layer' may be the same or different in size. According to an exemplary embodiment, the size of the'layer' may be the same as the entire device, may correspond to the size of a specific functional region, and may be as small as a single sub-pixel.
  • the meaning that a specific A material is included in the B layer means that i) at least one A material is included in one layer B, and ii) the B layer is composed of one or more layers, and the A material is a multilayer B Includes all those included in one or more of the floors.
  • the meaning that a specific A substance is included in the C layer or the D layer means i) is included in one or more of the C layers, ii) is included in one or more of the D layers, or iii ) It means both included in one or more layers C and one or more layers D, respectively.
  • the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Formula 1 do.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.
  • the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.
  • the organic material layer includes an emission layer.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or the hole injection and transport layer includes the compound.
  • the organic material layer includes an electron blocking layer.
  • the organic material layer includes a hole blocking layer.
  • the organic light emitting device is a group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer. It further includes one or two or more layers selected from.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; A light emitting layer provided between the first electrode and the second electrode; And two or more organic material layers provided between the emission layer and the first electrode or between the emission layer and the second electrode.
  • the two or more organic material layers are formed of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer. Two or more may be selected from the group.
  • two or more hole transport layers are included between the emission layer and the first electrode.
  • the two or more hole transport layers may include the same or different materials.
  • the first electrode is an anode or a cathode.
  • the second electrode is a cathode or an anode.
  • the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light-emitting device may be an inverted type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 illustrate an organic light emitting device, but are not limited thereto.
  • FIG. 1 illustrates a structure of an organic light-emitting device in which a first electrode 102, an organic material layer 111, and a second electrode 110 are sequentially stacked on a substrate 101.
  • the compound represented by Formula 1 is included in the organic material layer.
  • a first electrode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 105, an electron injection and transport layer 106, and a second electrode 110 are sequentially formed on the substrate 101.
  • the structure of the stacked organic light emitting device is illustrated.
  • the compound represented by Formula 1 is included in the electron injection and transport layer.
  • the organic light-emitting device of the present specification includes an electron injection layer, an electron transport layer, an electron injection and transport layer, a hole blocking layer, a hole injection layer, a hole transport layer, or a hole injection and transport layer. Except for that, it can be manufactured by materials and methods known in the art.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate.
  • the manufacturing method is not limited thereto.
  • anode material a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof;
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO);
  • a combination of a metal and an oxide such as ZnO:Al or SnO 2 :Sb;
  • Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof;
  • There are a multi-layered material such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And pyrimidine derivatives, but are not limited thereto.
  • the dopant material examples include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamine group.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and is selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Substituents are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto.
  • examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.
  • the hole injection layer is a layer that receives holes from an electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injection effect with respect to the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent the movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in thin film formation ability is preferred. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organic matter; Perylene-based organics; There are polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.
  • the hole transport material a material capable of receiving holes from an anode or a hole injection layer and transferring them to the light emitting layer, and a material having high mobility for holes is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • an additional electron transport layer other than the electron transport layer including Formula 1 as an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer
  • a material having high mobility for electrons is preferred.
  • Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired negative electrode material, as used according to the prior art.
  • suitable cathode materials have a low work function and are conventional materials followed by an aluminum layer or a silver layer.
  • the electron injection layer is a layer that receives electrons from an electrode.
  • the organic light-emitting device according to the exemplary embodiment of the present specification includes an additional electron injection layer other than the electron injection layer including Formula 1, the electron injection material has excellent ability to transport electrons, and the second electrode It is preferable to have an effect of receiving electrons from and an excellent electron injection effect to the light emitting layer or the light emitting material.
  • a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, Metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • 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, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , But is not limited thereto.
  • the electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer.
  • Known materials may be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.
  • the hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer.
  • the organic light-emitting device according to the exemplary embodiment of the present specification includes an additional hole blocking layer other than the hole blocking layer including Formula 1, specifically, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, There are aluminum complexes and the like, but are not limited thereto.
  • the organic light-emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • the compound 2-2 (13.5 g, 30 mmol) and the compound 2-3 (7.9 g, 33 mmol) were added to tetrahydrofuran (300 mL).
  • 2M K 2 CO 3 200 mL
  • Palladium acetate (0.14 g)
  • s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. .
  • the compound 30-2 (17.0 g, 30 mmol) and the compound 30-3 (14.4 g, 33 mmol) were added to tetrahydrofuran (300 mL).
  • 2M K 2 CO 3 200 mL
  • Palladium acetate (0.14 g)
  • s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. .
  • a glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000 ⁇ was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following compound [HI-A] was thermally vacuum deposited to a thickness of 600 ⁇ on the prepared ITO transparent electrode to form a hole injection layer.
  • a hole transport layer was formed by sequentially vacuum depositing 50 ⁇ of hexaazatriphenylene (HAT) of the following formula on the hole injection layer and the following compound [HT-A] (600 ⁇ ).
  • HAT hexaazatriphenylene
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.9 ⁇ /sec
  • the deposition rate of lithium fluoride at the cathode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum degree during deposition was 1 ⁇ 10. Maintaining -7 ⁇ 5 ⁇ 10 -8 torr, an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 8 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1 as the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 10 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 11 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 12 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 13 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 14 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 15 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 16 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 17 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 18 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 19 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 20 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 21 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 22 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 23 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 24 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 25 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 26 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 27 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 28 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 29 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 30 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 31 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 32 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 33 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 34 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 35 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 36 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET1 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET2 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET3 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET4 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
  • the driving voltage and luminous efficiency of the organic light emitting devices prepared in Examples 1 to 36 and Comparative Examples 1 to 4 were measured at a current density of 10 mA/cm 2 , and 98% of the initial luminance at a current density of 20 mA/cm 2 The time to become (LT98) was measured.
  • Formula 1 represents the linking groups L1 and L2 to divalent naphthalene, which is a substituent connecting the electron acceptor, which is an imidazole derivative, and an electron acceptor including a 6-membered monocyclic or bicyclic heterocycle including N. Since the substituent is bonded through the structure, the electron donor and the electron acceptor disposed on both sides are appropriately controlled by the connector to efficiently control the electron distribution and flow in the electron injection and transport layer. Accordingly, it was confirmed that the driving voltage, current efficiency, and life of the organic light emitting devices of Examples 1 to 36 exhibited superior characteristics than the compounds of Comparative Examples 1 to 4.

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Abstract

The present specification relates to a compound of chemical formula 1 and an organic light emitting device comprising same.

Description

화합물 및 이를 포함하는 유기 발광 소자Compound and organic light-emitting device comprising the same
본 출원은 2019년 9월 11일에 한국특허청에 제출된 한국 특허 출원 제 10-2019-0112880호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0112880 filed with the Korean Intellectual Property Office on September 11, 2019, the entire contents of which are incorporated herein.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present specification relates to a compound and an organic light emitting device including the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.Development of a new material for the organic light emitting device as described above is continuously required.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.The present specification provides a compound and an organic light emitting device including the same.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
[화학식 1][Formula 1]
Figure PCTKR2020012085-appb-I000001
Figure PCTKR2020012085-appb-I000001
상기 화학식 1에 있어서,In Formula 1,
X1 내지 X5 중 적어도 하나는 N이고, 나머지는 각각 독립적으로 CR5이며,At least one of X1 to X5 is N, and the others are each independently CR5,
L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R1은 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 시클로알킬기이고,R1 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group,
R2, R3 및 R5는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.R2, R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
또한, 본 명세서의 일 실시상태는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In addition, an exemplary embodiment of the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
본 명세서의 일 실시상태에 따른 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있고, 이를 사용함으로써 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성의 향상이 가능하다.The compound according to the exemplary embodiment of the present specification may be used as a material of the organic material layer of the organic light emitting device, and by using the compound, it is possible to improve efficiency, low driving voltage, and/or life characteristics in the organic light emitting device.
도 1 및 2는 본 명세서의 일 실시상태에 따른 유기 발광 소자의 예를 도시한 것이다.1 and 2 illustrate an example of an organic light-emitting device according to an exemplary embodiment of the present specification.
[부호의 설명][Explanation of code]
101: 기판101: substrate
102: 제1 전극102: first electrode
111: 유기물층111: organic material layer
110: 제2 전극110: second electrode
103: 정공주입층103: hole injection layer
104: 정공수송층104: hole transport layer
105: 발광층105: light-emitting layer
106: 전자 주입 및 수송층106: electron injection and transport layer
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, the present specification will be described in more detail.
본 명세서는 상기 화학식 1로 표시되는 화합물을 제공한다.The present specification provides a compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 따른 화합물은 이미다졸 유도체인 전자주개와 N을 포함하는 6원의 단환 또는 2환의 헤테로고리를 포함하는 전자받개를 연결해주는 치환기인 2가의 나프탈렌에 연결기인 L1 및 L2을 통하여 치환기가 결합된 구조이다. 각각 양쪽으로 배치된 전자주개와 전자받개를 상기 연결기가 적절히 조절함으로써 전자수송층, 또는 전자 주입 및 수송층 내의 전자 분포와 흐름을 효율적으로 제어하여 이를 포함하는 유기 발광 소자의 구동전압, 효율과 수명을 극대화할 수 있다.The compound according to an exemplary embodiment of the present specification includes L1 and L2, which are linking groups, to divalent naphthalene, which is a substituent that connects the electron donor, which is an imidazole derivative, and an electron acceptor including a 6-membered monocyclic or bicyclic heterocycle including N. It is a structure in which a substituent is bonded through. By appropriately controlling the electron donor and electron acceptor arranged on both sides, the connector effectively controls the distribution and flow of electrons in the electron transport layer or the electron injection and transport layer, maximizing the driving voltage, efficiency and lifespan of the organic light emitting device including the same. can do.
또한, 본 명세서의 일 실시상태에 따른 화학식 1의 R1이 치환 또는 비치환된 알킬기, 또는 치환 또는 비치환된 시클로알킬기인 경우, R1이 수소인 종래의 경우 보다 상대적으로 입체적 크기가 크고 견고하며, 이로 인하여 화합물의 우수한 승화성 및 화학 구조적 안정성을 가지므로, 열적 안정성을 가지는 이점이 있다. 또한, 상기 화학식 1의 R1을 다양하게 도입하여, 유기 발광 소자의 발광층 내로 유입되는 전자의 양을 조절하여, 발광층 내의 전하의 균형을 유도하므로, 상기 화학식 1의 화합물을 포함하는 유기 발광 소자는 우수한 효율 및 수명을 갖는다.In addition, when R1 in Formula 1 according to an exemplary embodiment of the present specification is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, the three-dimensional size is relatively larger and more robust than the conventional case where R1 is hydrogen, Due to this, since the compound has excellent sublimation properties and chemical structural stability, there is an advantage of having thermal stability. In addition, since R1 of Formula 1 is variously introduced, the amount of electrons flowing into the emission layer of the organic light emitting device is adjusted to induce a balance of charges in the emission layer, so that the organic light emitting device including the compound of Formula 1 is excellent. It has efficiency and longevity.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of the substituent in the present specification are described below, but are not limited thereto.
본 명세서에 있어서,
Figure PCTKR2020012085-appb-I000002
는 연결되는 부위를 의미한다.In this specification,
Figure PCTKR2020012085-appb-I000002
Means the connected part.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 같거나 상이할 수 있다.The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 알킬기; 시클로알킬기; 알콕시기; 알케닐기; 할로알킬기; 실릴기; 붕소기; 아민기; 아릴기; 및 헤테로아릴기로 이루어진 군으로부터 선택되는 1 이상의 치환기로 치환되었거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Alkyl group; Cycloalkyl group; Alkoxy group; Alkenyl group; Haloalkyl group; Silyl group; Boron group; Amine group; Aryl group; And it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, two or more of the above-exemplified substituents are substituted with a connected substituent, or it means that it does not have any substituents.
본 명세서에 있어서, 2 이상의 치환기가 연결된다는 것은 어느 하나의 치환기의 수소가 다른 치환기와 연결된 것을 말한다. 예컨대, 2개의 치환기가 연결되는 것은 페닐기와 나프틸기가 연결되어
Figure PCTKR2020012085-appb-I000003
또는
Figure PCTKR2020012085-appb-I000004
의 치환기가 될 수 있다. 또한, 3개의 치환기가 연결되는 것은 (치환기 1)-(치환기 2)-(치환기 3)이 연속하여 연결되는 것뿐만 아니라, (치환기 1)에 (치환기 2) 및 (치환기 3)이 연결되는 것도 포함한다. 예컨대, 페닐기, 나프틸기 및 이소프로필기가 연결되어,
Figure PCTKR2020012085-appb-I000005
,
Figure PCTKR2020012085-appb-I000006
또는
Figure PCTKR2020012085-appb-I000007
의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 정의가 동일하게 적용된다.In the present specification, when two or more substituents are connected, it means that hydrogen of any one substituent is connected with another substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected,
Figure PCTKR2020012085-appb-I000003
or
Figure PCTKR2020012085-appb-I000004
It may be a substituent of. In addition, the connection of three substituents is not only that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, but also (substituent 2) and (substituent 3) are connected to (substituent 1). Includes. For example, a phenyl group, a naphthyl group and an isopropyl group are connected,
Figure PCTKR2020012085-appb-I000005
,
Figure PCTKR2020012085-appb-I000006
or
Figure PCTKR2020012085-appb-I000007
It may be a substituent of. The above definition applies equally to those in which four or more substituents are connected.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 30인 것이 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 30인 것이 바람직하며, 구체적으로 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸, 아다만틸기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl group, etc. , But is not limited thereto.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시, 벤질옥시, p-메틸벤질옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be a straight chain, branched chain, or cyclic chain. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but It is not limited.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, and a styrenyl group, but are not limited thereto.
본 명세서에 있어서, 상기 할로알킬기는 상기 알킬기의 정의 중 알킬기의 수소 대신 적어도 하나의 할로겐기가 치환되는 것을 의미한다.In the present specification, the haloalkyl group means that at least one halogen group is substituted for hydrogen of the alkyl group in the definition of the alkyl group.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하며, 상기 아릴기는 단환식 또는 다환식일 수 있다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 30인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라센기, 페난트렌기, 트리페닐렌기, 파이렌기, 페날렌기, 페릴렌기, 크라이센기, 플루오렌기 등이 될 수 있으나, 이에 한정되는 것은 아니다. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 플루오렌기는 치환될 수 있으며, 인접한 기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorene group may be substituted, and adjacent groups may be bonded to each other to form a ring.
상기 플루오렌기가 치환되는 경우,
Figure PCTKR2020012085-appb-I000008
등이 있으나, 이에 한정되지 않는다.When the fluorene group is substituted,
Figure PCTKR2020012085-appb-I000008
And the like, but are not limited thereto.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오르토(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한" 기로 해석될 수 있다.In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent located three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
본 명세서에 있어서, 헤테로아릴기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 30인 것이 바람직하며, 상기 헤테로아릴기는 단환식 또는 다환식일 수 있다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 피리딘기, 바이피리딘기, 피리미딘기, 트리아진기, 트리아졸기, 아크리딘기, 피리다진기, 피라진기, 퀴놀린기, 퀴나졸린기, 퀴녹살린기, 프탈라진기, 피리도 피리미딘기, 피리도 피라진기, 피라지노 피라진기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨란기, 페난트리딘기(phenanthridine), 페난쓰롤린기(phenanthroline), 이소옥사졸기, 티아디아졸기, 디벤조퓨란기, 디벤조실롤기, 페노크산틴기(phenoxathiine), 페녹사진기(phenoxazine), 페노티아진기(phenothiazine), 디하이드로인데노카바졸기, 스피로플루오렌잔텐기 및 스피로플루오렌티옥산텐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the heteroaryl group includes one or more atoms other than carbon and one or more heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group , Pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxathiine group, phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), dihydroindenocarbazole group, spirofluorenxanthene group and spirofluorene Thioxanthene groups, and the like, but are not limited thereto.
본 명세서 있어서, 상기 실릴기는 알킬실릴기, 아릴실릴기, 헤테로아릴실릴기 등일 수 있다. 상기 알킬실릴기 중 알킬기는 전술한 알킬기의 예시가 적용될 수 있고, 상기 아릴실릴기 중 아릴기는 전술한 아릴기의 예시가 적용될 수 있으며, 상기 헤테로아릴실릴기 중 헤테로아릴기는 상기 헤테로아릴기의 예시가 적용될 수 있다.In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, and the like. The alkyl group of the alkylsilyl group may be exemplified by the aforementioned alkyl group, the aryl group of the arylsilyl group may be exemplified by the aryl group described above, and the heteroaryl group of the heteroarylsilyl group may be exemplified by the heteroaryl group Can be applied.
본 명세서에 있어서, 붕소기는 -BR100R101일 수 있으며, 상기 R100 및 R101은 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐; 니트릴기; 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 및 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 이루어진 군으로부터 선택될 수 있다. 상기 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group may be -BR 100 R 101 , the R 100 and R 101 are the same or different, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.
본 명세서에 있어서, 아민기는 -NH2, 알킬아민기, N-알킬아릴아민기, 아릴아민기, N-아릴헤테로아릴아민기, N-알킬헤테로아릴아민기, 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, 디톨릴아민기, N-페닐톨릴아민기, 트리페닐아민기, N-페닐바이페닐아민기, N-페닐나프틸아민기, N-바이페닐나프틸아민기; N-나프틸플루오레닐아민기, N-페닐페난트레닐아민기, N-바이페닐페난트레닐아민기, N-페닐플루오레닐아민기, N-페닐터페닐아민기, N-페난트레닐플루오레닐아민기, N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the amine group is from the group consisting of -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre Nilfluorenylamine group, N-biphenylfluorenylamine group, and the like, but are not limited thereto.
본 명세서에 있어서, N-알킬아릴아민기는 아민기의 N에 알킬기 및 아릴기가 치환된 아민기를 의미한다. 상기 N-알킬아릴아민기 중의 알킬기와 아릴기는 전술한 알킬기 및 아릴기의 예시와 같다.In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group. The alkyl group and aryl group in the N-alkylarylamine group are the same as those of the aforementioned alkyl group and aryl group.
본 명세서에 있어서, N-아릴헤테로아릴아민기는 아민기의 N에 아릴기 및 헤테로아릴기가 치환된 아민기를 의미한다. 상기 N-아릴헤테로아릴아민기 중의 아릴기와 헤테로아릴기는 전술한 아릴기 및 헤테로아릴기의 예시와 같다.In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group. The aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and the heteroaryl group described above.
본 명세서에 있어서, N-알킬헤테로아릴아민기는 아민기의 N에 알킬기 및 헤테로아릴기가 치환된 아민기를 의미한다. 상기 N-알킬헤테로아릴아민기 중의 알킬기와 헤테로아릴기는 전술한 알킬기 및 헤테로아릴기의 예시와 같다.In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group. The alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as those of the aforementioned alkyl group and heteroaryl group.
본 명세서에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 또는 치환 또는 비치환된 디아릴아민기가 있다. 상기 아릴기가 2 이상을 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식 아릴기와 다환식 아릴기를 동시에 포함할 수 있다. 예컨대, 상기 아릴아민기 중의 아릴기는 전술한 아릴기의 예시 중에서 선택될 수 있다.In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
본 명세서에 있어서, 헤테로아릴아민기의 예로는 치환 또는 비치환된 모노헤테로아릴아민기, 또는 치환 또는 비치환된 디헤테로아릴아민기가 있다. 상기 헤테로아릴기가 2 이상을 포함하는 헤테로아릴아민기는 단환식 헤테로아릴기, 다환식 헤테로아릴기, 또는 단환식 헤테로아릴기와 다환식 헤테로아릴기를 동시에 포함할 수 있다. 예컨대, 상기 헤테로아릴아민기 중의 헤테로아릴기는 전술한 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
본 명세서에 있어서, 치환기 중 "인접한 기와 서로 결합하여 고리를 형성한다"는 의미는 인접한 기와 서로 결합하여 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 형성하는 것을 의미한다.In the present specification, the meaning of "bonding with adjacent groups to form a ring" among the substituents refers to a substituted or unsubstituted hydrocarbon ring by bonding with an adjacent group; Or it means to form a substituted or unsubstituted heterocycle.
본 명세서에 있어서, 서로 결합하여 형성되는 치환 또는 비치환된 고리에서, "고리"는 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 의미한다.In the present specification, in a substituted or unsubstituted ring formed by bonding to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.
본 명세서에 있어서, 탄화수소고리는 방향족 탄화수소 고리, 지방족 탄화수소고리, 또는 방향족 탄화수소와 지방족 탄화수소의 축합고리일 수 있으며, 상기 1가가 아닌 것을 제외하고 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있다.In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from examples of the cycloalkyl group or an aryl group, except for the non-monovalent ones.
본 명세서에 있어서, 헤테로고리는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 상기 헤테로고리는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 방향족 헤테로고리는 1가가 아닌 것을 제외하고 상기 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, the heterocycle is an atom other than carbon and includes one or more heteroatoms, and specifically, the heterocycle may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.
본 명세서에 있어서, 지방족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 지방족 고리를 의미한다. 지방족 헤테로고리의 예로는, 옥시레인(oxirane), 테트라하이드로퓨란, 1,4-디옥세인(1,4-dioxane), 피롤리딘, 피페리딘, 모르폴린(morpholine), 옥세판, 아조케인, 티오케인 등이 있으나, 이에 한정되지 않는다.In the present specification, the aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, and azocaine , Thiocane, and the like, but are not limited thereto.
본 명세서에 있어서, 아릴렌기는 아릴기에 결합 위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 아릴기의 설명이 적용될 수 있다.In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
본 명세서에 있어서, 헤테로아릴렌기는 헤테로아릴기에 결합 위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 헤테로아릴기의 설명이 적용될 수 있다.In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.
이하, 상기 화학식 1로 표시되는 화합물에 관하여 상세히 설명한다.Hereinafter, the compound represented by Chemical Formula 1 will be described in detail.
본 명세서의 일 실시상태에 따르면, 상기 R2 및 R3는 서로 같거나 상이하며, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 6 to 30 monocyclic or polycyclic aromatic hydrocarbon rings; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed.
본 명세서의 일 실시상태에 따르면, 상기 R2 및 R3는 서로 같거나 상이하며, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기이거나, 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 6 to 20 monocyclic or polycyclic aromatic hydrocarbon rings; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms is formed.
본 명세서의 일 실시상태에 따르면, 상기 R2 및 R3는 서로 같거나 상이하며, 각각 독립적으로 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a linear or branched alkyl group having 1 to 30 carbon atoms by bonding to each other , C 6 to C 30 monocyclic or polycyclic aryl group, or C 1 to C 30 straight or branched alkyl group substituted or unsubstituted C 2 to C 30 monocyclic or polycyclic heteroaryl group substituted or unsubstituted C 6 Monocyclic or polycyclic aromatic hydrocarbon rings of to 30; Or to form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R2 및 R3는 서로 같거나 상이하며, 각각 독립적으로 탄소수 6 내지 20의 단환 또는 다환의 아릴기이거나, 서로 결합하여 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기, 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 또는 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a linear or branched alkyl group having 1 to 20 carbon atoms by bonding to each other. , C 6 to C 20 monocyclic or polycyclic aryl group, or C 2 to C 20 monocyclic or polycyclic heteroaryl group substituted or unsubstituted with C 1 to C 20 straight or branched alkyl group substituted or unsubstituted C 6 Monocyclic or polycyclic aromatic hydrocarbon rings of to 20; Or to form a monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R2 및 R3는 페닐기이거나, 서로 결합하여 메틸기, 페닐기, 메틸기로 치환 또는 비치환된 피리딘기, 또는 디벤조퓨란기로 치환 또는 비치환된 벤젠; 나프탈렌; 디벤조티오펜; 또는 디벤조퓨란을 형성한다.According to an exemplary embodiment of the present specification, R2 and R3 are a phenyl group, or benzene unsubstituted or substituted with a methyl group, a phenyl group, a pyridine group unsubstituted or substituted with a methyl group, or a dibenzofuran group by bonding to each other; naphthalene; Dibenzothiophene; Or to form dibenzofuran.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 2로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 2.
[화학식 2][Formula 2]
Figure PCTKR2020012085-appb-I000009
Figure PCTKR2020012085-appb-I000009
상기 화학식 2에 있어서,In Formula 2,
X1 내지 X5, L1, L2 및 R1는 상기 화학식 1에서 정의한 바와 동일하고,X1 to X5, L1, L2 and R1 are the same as defined in Formula 1,
R4는 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 결합하여, 치환 또는 비치환된 고리를 형성할 수 있고,R4 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
r4는 1 내지 4의 정수이며, 상기 r4가 2 이상인 경우, 상기 2 이상의 R4는 서로 같거나 상이하다.r4 is an integer of 1 to 4, and when r4 is 2 or more, the two or more R4s are the same as or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 R4는 수소이다.According to an exemplary embodiment of the present specification, R4 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R4는 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, R4 is a linear or branched alkyl group having 1 to 30 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a C2 to C30 monocyclic or polycyclic heteroaryl group substituted or unsubstituted with a C1 to C30 linear or branched alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 R4는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, R4 is a linear or branched alkyl group having 1 to 20 carbon atoms; A monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a C2 to C20 monocyclic or polycyclic heteroaryl group substituted or unsubstituted with a C1 to C20 linear or branched alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 R4는 메틸기; 페닐기; 메틸기로 치환 또는 비치환된 피리딘기; 또는 디벤조퓨란기이다.According to an exemplary embodiment of the present specification, R4 is a methyl group; Phenyl group; A pyridine group unsubstituted or substituted with a methyl group; Or a dibenzofuran group.
본 명세서의 일 실시상태에 따르면, 상기 R4는 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding with an adjacent group to each other; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed.
본 명세서의 일 실시상태에 따르면, 상기 R4는 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding with an adjacent group to each other; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms is formed.
본 명세서의 일 실시상태에 따르면, 상기 R4는 인접한 기와 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R4 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding to each other with adjacent groups; Or to form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 인접한 기와 서로 결합하여 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리; 또는 탄소수 2 내지 20의 단환 또는 다환의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, R4 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding to each other with an adjacent group; Or to form a monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 인접한 기와 서로 결합하여 벤젠; 벤조티오펜; 또는 벤조퓨란을 형성한다.According to an exemplary embodiment of the present specification, R4 is benzene by bonding with an adjacent group; Benzothiophene; Or to form benzofuran.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 3 내지 16 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 3 to 16 below.
[화학식 3][Formula 3]
Figure PCTKR2020012085-appb-I000010
Figure PCTKR2020012085-appb-I000010
[화학식 4][Formula 4]
Figure PCTKR2020012085-appb-I000011
Figure PCTKR2020012085-appb-I000011
[화학식 5][Formula 5]
Figure PCTKR2020012085-appb-I000012
Figure PCTKR2020012085-appb-I000012
[화학식 6][Formula 6]
Figure PCTKR2020012085-appb-I000013
Figure PCTKR2020012085-appb-I000013
[화학식 7][Formula 7]
Figure PCTKR2020012085-appb-I000014
Figure PCTKR2020012085-appb-I000014
[화학식 8][Formula 8]
Figure PCTKR2020012085-appb-I000015
Figure PCTKR2020012085-appb-I000015
[화학식 9][Formula 9]
Figure PCTKR2020012085-appb-I000016
Figure PCTKR2020012085-appb-I000016
[화학식 10][Formula 10]
Figure PCTKR2020012085-appb-I000017
Figure PCTKR2020012085-appb-I000017
[화학식 11][Formula 11]
Figure PCTKR2020012085-appb-I000018
Figure PCTKR2020012085-appb-I000018
[화학식 12][Formula 12]
Figure PCTKR2020012085-appb-I000019
Figure PCTKR2020012085-appb-I000019
[화학식 13][Formula 13]
Figure PCTKR2020012085-appb-I000020
Figure PCTKR2020012085-appb-I000020
[화학식 14][Formula 14]
Figure PCTKR2020012085-appb-I000021
Figure PCTKR2020012085-appb-I000021
[화학식 15][Formula 15]
Figure PCTKR2020012085-appb-I000022
Figure PCTKR2020012085-appb-I000022
[화학식 16][Formula 16]
Figure PCTKR2020012085-appb-I000023
Figure PCTKR2020012085-appb-I000023
상기 화학식 3 내지 16에 있어서,In Formulas 3 to 16,
X1 내지 X5, L1, L2 및 R1 내지 R3는 상기 화학식 1에서 정의한 바와 동일하다.X1 to X5, L1, L2, and R1 to R3 are the same as defined in Formula 1 above.
본 명세서의 일 실시상태에 따르면, 상기 X1 내지 X5 중 적어도 1개는 N이고, 나머지는 각각 CR5이다.According to an exemplary embodiment of the present specification, at least one of X1 to X5 is N, and the rest are each CR5.
본 명세서의 일 실시상태에 따르면, 상기 X1 내지 X5 중 적어도 2개는 N이고, 나머지는 각각 CR5이다.According to an exemplary embodiment of the present specification, at least two of X1 to X5 are N, and the rest are each CR5.
본 명세서의 일 실시상태에 따르면, 상기 X1 내지 X5 중 적어도 3개는 N이고, 나머지는 각각 독립적으로 CR5이다.According to an exemplary embodiment of the present specification, at least three of X1 to X5 are N, and the rest are each independently CR5.
본 명세서의 일 실시상태에 따르면, 상기 X1 내지 X5 중 어느 1개는 N이고, 나머지는 각각 독립적으로 CR5이다.According to an exemplary embodiment of the present specification, any one of X1 to X5 is N, and the others are each independently CR5.
본 명세서의 일 실시상태에 따르면, 상기 X1 내지 X5 중 어느 2개는 N이고, 나머지는 각각 독립적으로 CR5이다.According to an exemplary embodiment of the present specification, any two of X1 to X5 are N, and the others are each independently CR5.
본 명세서의 일 실시상태에 따르면, 상기 X1 내지 X5 중 어느 3개는 N이고, 나머지는 각각 독립적으로 CR5이다.According to an exemplary embodiment of the present specification, any three of X1 to X5 are N, and the rest are each independently CR5.
본 명세서의 일 실시상태에 따르면, 상기 X1는 N이고, X2 내지 X5는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X1 is N, X2 to X5 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X2는 N이고, X1, 및 X3 내지 X5는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X2 is N, X1, and X3 to X5 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X3는 N이고, X1, X2, X4, 및 X5는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X3 is N, X1, X2, X4, and X5 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X1 및 X5는 N이고, X2 내지 X4는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X1 and X5 are N, X2 to X4 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X1 및 X3는 N이고, X2, X4 및 X5는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X1 and X3 are N, X2, X4 and X5 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X2 및 X4는 N이고, X1, X3 및 X5 는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X2 and X4 are N, X1, X3 and X5 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X3 및 X5는 N이고, X1, X2 및 X4 는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X3 and X5 are N, X1, X2 and X4 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X1 및 X2는 N이고, X3 내지 X5는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X1 and X2 are N, X3 to X5 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X4 및 X5는 N이고, X1 내지 X3는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X4 and X5 are N, X1 to X3 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X2 및 X3는 N이고, X1, X4 및 X5는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X2 and X3 are N, X1, X4 and X5 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X3 및 X4는 N이고, X1, X2 및 X5 는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X3 and X4 are N, X1, X2 and X5 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X1 및 X4는 N이고, X2, X3, 및 X5는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X1 and X4 are N, X2, X3, and X5 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X2 및 X5는 N이고, X1, X3, 및 X4는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X2 and X5 are N, X1, X3, and X4 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 X1, X3 및 X5는 N이고, X2 및 X4 는 서로 같거나 상이하며, 각각 독립적으로 R5이다.According to an exemplary embodiment of the present specification, X1, X3, and X5 are N, X2 and X4 are the same as or different from each other, and each independently is R5.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-1 내지 1-10 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 1-1 to 1-10.
[화학식 1-1][Formula 1-1]
Figure PCTKR2020012085-appb-I000024
Figure PCTKR2020012085-appb-I000024
[화학식 1-2][Formula 1-2]
Figure PCTKR2020012085-appb-I000025
Figure PCTKR2020012085-appb-I000025
[화학식 1-3][Formula 1-3]
Figure PCTKR2020012085-appb-I000026
Figure PCTKR2020012085-appb-I000026
[화학식 1-4][Formula 1-4]
Figure PCTKR2020012085-appb-I000027
Figure PCTKR2020012085-appb-I000027
[화학식 1-5][Formula 1-5]
Figure PCTKR2020012085-appb-I000028
Figure PCTKR2020012085-appb-I000028
[화학식 1-6][Formula 1-6]
Figure PCTKR2020012085-appb-I000029
Figure PCTKR2020012085-appb-I000029
[화학식 1-7][Formula 1-7]
Figure PCTKR2020012085-appb-I000030
Figure PCTKR2020012085-appb-I000030
[화학식 1-8][Formula 1-8]
Figure PCTKR2020012085-appb-I000031
Figure PCTKR2020012085-appb-I000031
[화학식 1-9][Formula 1-9]
Figure PCTKR2020012085-appb-I000032
Figure PCTKR2020012085-appb-I000032
[화학식 1-10][Formula 1-10]
Figure PCTKR2020012085-appb-I000033
Figure PCTKR2020012085-appb-I000033
상기 화학식 1-1 내지 1-10에 있어서,In Formulas 1-1 to 1-10,
L1, L2 및 R1 내지 R3는 상기 화학식 1에서 정의한 바와 동일하고,L1, L2 and R1 to R3 are the same as defined in Formula 1,
R51 내지 R55는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-11 내지 1-20 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-11 to 1-20.
[화학식 1-11][Formula 1-11]
Figure PCTKR2020012085-appb-I000034
Figure PCTKR2020012085-appb-I000034
[화학식 1-12][Formula 1-12]
Figure PCTKR2020012085-appb-I000035
Figure PCTKR2020012085-appb-I000035
[화학식 1-13][Formula 1-13]
Figure PCTKR2020012085-appb-I000036
Figure PCTKR2020012085-appb-I000036
[화학식 1-14][Formula 1-14]
Figure PCTKR2020012085-appb-I000037
Figure PCTKR2020012085-appb-I000037
[화학식 1-15][Formula 1-15]
Figure PCTKR2020012085-appb-I000038
Figure PCTKR2020012085-appb-I000038
[화학식 1-16][Formula 1-16]
Figure PCTKR2020012085-appb-I000039
Figure PCTKR2020012085-appb-I000039
[화학식 1-17][Formula 1-17]
Figure PCTKR2020012085-appb-I000040
Figure PCTKR2020012085-appb-I000040
[화학식 1-18][Formula 1-18]
Figure PCTKR2020012085-appb-I000041
Figure PCTKR2020012085-appb-I000041
[화학식 1-19][Formula 1-19]
Figure PCTKR2020012085-appb-I000042
Figure PCTKR2020012085-appb-I000042
[화학식 1-20][Formula 1-20]
Figure PCTKR2020012085-appb-I000043
Figure PCTKR2020012085-appb-I000043
상기 화학식 1-11 내지 1-20에 있어서,In Formulas 1-11 to 1-20,
L1, L2 및 R1는 상기 화학식 1에서 정의한 바와 동일하고,L1, L2 and R1 are the same as defined in Formula 1,
R4 및 R51 내지 R55는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,R4 and R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
r4는 1 내지 4의 정수이며, 상기 r4가 2 이상인 경우, 상기 2 이상의 R4는 서로 같거나 상이하다.r4 is an integer of 1 to 4, and when r4 is 2 or more, the two or more R4s are the same as or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기이며, 상기 R1은 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기이고, 상기 R2 및 R3는 서로 같거나 상이하며, 각각 독립적으로 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성하며, 상기 X1 내지 X5 중 적어도 1개는 N이며, 나머지는 각각 독립적으로 CR5이며, 상기 R5는 수소; 중수소; 시아노기, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms, wherein R 1 is a linear or branched alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, and R2 and R3 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a straight chain having 1 to 30 carbon atoms by bonding to each other Or substituted with a branched alkyl group, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a straight or branched chain alkyl group having 1 to 30 carbon atoms, or An unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, and at least one of X1 to X5 is N, the rest are each independently CR5, and R5 is hydrogen; heavy hydrogen; Unsubstituted or substituted with a cyano group, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a straight or branched alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or combined with an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 탄소수 6 내지 20의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; A monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 나프틸렌기; 바이페닐릴렌기; 2가의 피리딘기; 2가의 디벤조퓨란기; 또는 2가의 디벤조티오펜기이다.According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Phenylene group; Naphthylene group; Biphenylylene group; A divalent pyridine group; Divalent dibenzofuran group; Or a divalent dibenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 R1은 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기이다.According to an exemplary embodiment of the present specification, R1 is a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1은 치환 또는 비치환된 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 또는 치환 또는 비치환된 탄소수 3 내지 20의 단환 또는 다환의 시클로알킬기이다.According to an exemplary embodiment of the present specification, R1 is a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1은 알킬기; 또는 시클로알킬기이다.[0348] According to an exemplary embodiment of the present specification, R1 is an alkyl group; Or a cycloalkyl group.
본 명세서의 일 실시상태에 따르면, 상기 R1은 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기이다.According to an exemplary embodiment of the present specification, R1 is a linear or branched alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1은 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 3 내지 20의 단환 또는 다환의 시클로알킬기이다.According to an exemplary embodiment of the present specification, R1 is a linear or branched alkyl group having 1 to 20 carbon atoms; Or a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1은 메틸기; 에틸기; 이소프로필기; tert-부틸기; 시클로헥실기; 또는 아다만틸기이다.According to an exemplary embodiment of the present specification, R1 is a methyl group; Ethyl group; Isopropyl group; tert-butyl group; Cyclohexyl group; Or an adamantyl group.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.[0348] According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or combined with adjacent groups to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.[0348] According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, or combined with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 시아노기, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.[0348] According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; Unsubstituted or substituted with a cyano group, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a straight or branched chain alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or combined with an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 시아노기, 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.[0348] According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; Unsubstituted or substituted with a cyano group, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms unsubstituted or substituted with a straight or branched chain alkyl group having 1 to 20 carbon atoms A monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, or combined with an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 나프틸기, 또는 메틸기로 치환 또는 비치환된 피리딘기로 치환 또는 비치환된 페닐기; 시아노기로 치환 또는 비치환된 바이페닐기; 시아노기로 치환 또는 비치환된 나프틸기; 페난트렌기; 플루오란텐기; 피리딘기; 디벤조퓨란기; 또는 디벤조티오펜기이거나, 인접한 기와 서로 결합하여 벤젠을 형성한다.[0348] According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with a naphthyl group or a pyridine group unsubstituted or substituted with a methyl group; A biphenyl group unsubstituted or substituted with a cyano group; A naphthyl group unsubstituted or substituted with a cyano group; Phenanthrene group; Fluoranthene group; Pyridine group; Dibenzofuran group; Or it is a dibenzothiophene group, or it combines with an adjacent group to form benzene.
본 명세서의 일 실시상태에 따르면, 상기 R51 내지 R55는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or combined with adjacent groups to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.[0348] According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, or combined with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R51 내지 R55는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 시아노기, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Unsubstituted or substituted with a cyano group, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a straight or branched alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or combined with an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R51 내지 R55는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 시아노기, 탄소수 6 내지 20의 단환 또는 다환의 아릴기, 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 20의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Unsubstituted or substituted with a cyano group, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms unsubstituted or substituted with a straight or branched chain alkyl group having 1 to 20 carbon atoms A monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, or combined with an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R51 내지 R55는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 나프틸기, 또는 메틸기로 치환 또는 비치환된 피리딘기로 치환 또는 비치환된 페닐기; 시아노기로 치환 또는 비치환된 바이페닐기; 시아노기로 치환 또는 비치환된 나프틸기; 페난트렌기; 플루오란텐기; 피리딘기; 디벤조퓨란기; 또는 디벤조티오펜기이거나, 인접한 기와 서로 결합하여 벤젠을 형성한다.According to an exemplary embodiment of the present specification, R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with a naphthyl group or a pyridine group unsubstituted or substituted with a methyl group; A biphenyl group unsubstituted or substituted with a cyano group; A naphthyl group unsubstituted or substituted with a cyano group; Phenanthrene group; Fluoranthene group; Pyridine group; Dibenzofuran group; Or it is a dibenzothiophene group, or it combines with an adjacent group to form benzene.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화합물 및 하기 표 1 내지 36의 화합물 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one selected from the following compounds and compounds of Tables 1 to 36 below.
Figure PCTKR2020012085-appb-I000044
Figure PCTKR2020012085-appb-I000044
Figure PCTKR2020012085-appb-I000045
Figure PCTKR2020012085-appb-I000045
Figure PCTKR2020012085-appb-T000001
Figure PCTKR2020012085-appb-T000001
Figure PCTKR2020012085-appb-I000046
Figure PCTKR2020012085-appb-I000046
Figure PCTKR2020012085-appb-I000047
Figure PCTKR2020012085-appb-I000047
Figure PCTKR2020012085-appb-I000048
Figure PCTKR2020012085-appb-I000048
Figure PCTKR2020012085-appb-I000049
Figure PCTKR2020012085-appb-I000049
Figure PCTKR2020012085-appb-T000002
Figure PCTKR2020012085-appb-T000002
Figure PCTKR2020012085-appb-I000050
Figure PCTKR2020012085-appb-I000050
Figure PCTKR2020012085-appb-I000051
Figure PCTKR2020012085-appb-I000051
Figure PCTKR2020012085-appb-I000052
Figure PCTKR2020012085-appb-I000052
Figure PCTKR2020012085-appb-I000053
Figure PCTKR2020012085-appb-I000053
Figure PCTKR2020012085-appb-I000054
Figure PCTKR2020012085-appb-I000054
Figure PCTKR2020012085-appb-T000003
Figure PCTKR2020012085-appb-T000003
Figure PCTKR2020012085-appb-I000055
Figure PCTKR2020012085-appb-I000055
Figure PCTKR2020012085-appb-I000056
Figure PCTKR2020012085-appb-I000056
Figure PCTKR2020012085-appb-I000057
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Figure PCTKR2020012085-appb-T000004
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Figure PCTKR2020012085-appb-I000060
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Figure PCTKR2020012085-appb-I000061
Figure PCTKR2020012085-appb-I000061
Figure PCTKR2020012085-appb-I000062
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Figure PCTKR2020012085-appb-I000063
Figure PCTKR2020012085-appb-I000063
Figure PCTKR2020012085-appb-I000064
Figure PCTKR2020012085-appb-I000064
Figure PCTKR2020012085-appb-T000005
Figure PCTKR2020012085-appb-T000005
Figure PCTKR2020012085-appb-I000065
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Figure PCTKR2020012085-appb-I000066
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Figure PCTKR2020012085-appb-I000067
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Figure PCTKR2020012085-appb-I000068
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Figure PCTKR2020012085-appb-T000006
Figure PCTKR2020012085-appb-T000006
Figure PCTKR2020012085-appb-I000070
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Figure PCTKR2020012085-appb-T000021
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Figure PCTKR2020012085-appb-I000200
Figure PCTKR2020012085-appb-I000201
Figure PCTKR2020012085-appb-I000201
Figure PCTKR2020012085-appb-I000202
Figure PCTKR2020012085-appb-I000202
Figure PCTKR2020012085-appb-I000203
Figure PCTKR2020012085-appb-I000203
Figure PCTKR2020012085-appb-T000029
Figure PCTKR2020012085-appb-T000029
Figure PCTKR2020012085-appb-I000204
Figure PCTKR2020012085-appb-I000204
Figure PCTKR2020012085-appb-I000205
Figure PCTKR2020012085-appb-I000205
Figure PCTKR2020012085-appb-I000206
Figure PCTKR2020012085-appb-I000206
Figure PCTKR2020012085-appb-I000207
Figure PCTKR2020012085-appb-I000207
Figure PCTKR2020012085-appb-I000208
Figure PCTKR2020012085-appb-I000208
Figure PCTKR2020012085-appb-I000209
Figure PCTKR2020012085-appb-I000209
Figure PCTKR2020012085-appb-T000030
Figure PCTKR2020012085-appb-T000030
Figure PCTKR2020012085-appb-I000210
Figure PCTKR2020012085-appb-I000210
Figure PCTKR2020012085-appb-I000211
Figure PCTKR2020012085-appb-I000211
Figure PCTKR2020012085-appb-I000212
Figure PCTKR2020012085-appb-I000212
Figure PCTKR2020012085-appb-I000213
Figure PCTKR2020012085-appb-I000213
Figure PCTKR2020012085-appb-I000214
Figure PCTKR2020012085-appb-I000214
Figure PCTKR2020012085-appb-I000215
Figure PCTKR2020012085-appb-I000215
Figure PCTKR2020012085-appb-T000031
Figure PCTKR2020012085-appb-T000031
Figure PCTKR2020012085-appb-I000216
Figure PCTKR2020012085-appb-I000216
Figure PCTKR2020012085-appb-I000217
Figure PCTKR2020012085-appb-I000217
Figure PCTKR2020012085-appb-I000218
Figure PCTKR2020012085-appb-I000218
Figure PCTKR2020012085-appb-I000219
Figure PCTKR2020012085-appb-I000219
Figure PCTKR2020012085-appb-I000220
Figure PCTKR2020012085-appb-I000220
Figure PCTKR2020012085-appb-I000221
Figure PCTKR2020012085-appb-I000221
Figure PCTKR2020012085-appb-T000032
Figure PCTKR2020012085-appb-T000032
Figure PCTKR2020012085-appb-I000222
Figure PCTKR2020012085-appb-I000222
Figure PCTKR2020012085-appb-I000223
Figure PCTKR2020012085-appb-I000223
Figure PCTKR2020012085-appb-I000224
Figure PCTKR2020012085-appb-I000224
Figure PCTKR2020012085-appb-I000225
Figure PCTKR2020012085-appb-I000225
Figure PCTKR2020012085-appb-I000226
Figure PCTKR2020012085-appb-I000226
Figure PCTKR2020012085-appb-I000227
Figure PCTKR2020012085-appb-I000227
Figure PCTKR2020012085-appb-T000033
Figure PCTKR2020012085-appb-T000033
Figure PCTKR2020012085-appb-I000228
Figure PCTKR2020012085-appb-I000228
Figure PCTKR2020012085-appb-I000229
Figure PCTKR2020012085-appb-I000229
Figure PCTKR2020012085-appb-I000230
Figure PCTKR2020012085-appb-I000230
Figure PCTKR2020012085-appb-I000231
Figure PCTKR2020012085-appb-I000231
Figure PCTKR2020012085-appb-I000232
Figure PCTKR2020012085-appb-I000232
Figure PCTKR2020012085-appb-I000233
Figure PCTKR2020012085-appb-I000233
Figure PCTKR2020012085-appb-T000034
Figure PCTKR2020012085-appb-T000034
Figure PCTKR2020012085-appb-I000234
Figure PCTKR2020012085-appb-I000234
Figure PCTKR2020012085-appb-I000235
Figure PCTKR2020012085-appb-I000235
Figure PCTKR2020012085-appb-I000236
Figure PCTKR2020012085-appb-I000236
Figure PCTKR2020012085-appb-I000237
Figure PCTKR2020012085-appb-I000237
Figure PCTKR2020012085-appb-I000238
Figure PCTKR2020012085-appb-I000238
Figure PCTKR2020012085-appb-I000239
Figure PCTKR2020012085-appb-I000239
Figure PCTKR2020012085-appb-T000035
Figure PCTKR2020012085-appb-T000035
Figure PCTKR2020012085-appb-I000240
Figure PCTKR2020012085-appb-I000240
Figure PCTKR2020012085-appb-I000241
Figure PCTKR2020012085-appb-I000241
Figure PCTKR2020012085-appb-I000242
Figure PCTKR2020012085-appb-I000242
Figure PCTKR2020012085-appb-I000243
Figure PCTKR2020012085-appb-I000243
Figure PCTKR2020012085-appb-I000244
Figure PCTKR2020012085-appb-I000244
Figure PCTKR2020012085-appb-I000245
Figure PCTKR2020012085-appb-I000245
Figure PCTKR2020012085-appb-T000036
Figure PCTKR2020012085-appb-T000036
Figure PCTKR2020012085-appb-I000246
Figure PCTKR2020012085-appb-I000246
Figure PCTKR2020012085-appb-I000247
Figure PCTKR2020012085-appb-I000247
Figure PCTKR2020012085-appb-I000248
Figure PCTKR2020012085-appb-I000248
Figure PCTKR2020012085-appb-I000249
Figure PCTKR2020012085-appb-I000249
Figure PCTKR2020012085-appb-I000250
Figure PCTKR2020012085-appb-I000250
Figure PCTKR2020012085-appb-I000251
Figure PCTKR2020012085-appb-I000251
상기 표 1 내지 36에 있어서,In Tables 1 to 36,
Figure PCTKR2020012085-appb-I000252
은 상기 화학식 1의
Figure PCTKR2020012085-appb-I000253
와 상기 화학식 1의
Figure PCTKR2020012085-appb-I000254
가 결합되는 부위, 또는 상기 화학식 1의
Figure PCTKR2020012085-appb-I000255
와 상기 화학식 1의
Figure PCTKR2020012085-appb-I000256
가 결합되는 부위를 의미하고,
Figure PCTKR2020012085-appb-I000252
Is in the formula 1
Figure PCTKR2020012085-appb-I000253
And of Formula 1
Figure PCTKR2020012085-appb-I000254
The site to which is bonded, or of Formula 1
Figure PCTKR2020012085-appb-I000255
And of Formula 1
Figure PCTKR2020012085-appb-I000256
Means the site to which is bonded,
*는 상기 화학식 1의
Figure PCTKR2020012085-appb-I000257
와 상기 화학식 1의
Figure PCTKR2020012085-appb-I000258
가 결합되는 부위를 의미하며,* Is in the formula 1
Figure PCTKR2020012085-appb-I000257
And of Formula 1
Figure PCTKR2020012085-appb-I000258
Refers to the site to which is bonded,
**는 상기 화학식 1의
Figure PCTKR2020012085-appb-I000259
와 상기 화학식 1의
Figure PCTKR2020012085-appb-I000260
가 결합되는 부위를 의미한다.** is in the formula 1
Figure PCTKR2020012085-appb-I000259
And of Formula 1
Figure PCTKR2020012085-appb-I000260
Refers to the site to which is bonded.
본 명세서는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다.The present specification provides an organic light-emitting device including the compound represented by Chemical Formula 1.
본 명세서에서 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, when a member is positioned "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.
본 명세서에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless specifically stated to the contrary.
본 명세서에 있어서, 상기 '층'은 본 기술분야에 주로 사용되는 '필름'과 호환되는 의미이며, 목적하는 영역을 덮는 코팅을 의미한다. 상기 '층'의 크기는 한정되지 않으며, 각각의 '층'은 그 크기가 같거나 상이할 수 있다. 일 실시상태에 따르면, '층'의 크기는 전체 소자와 같을 수 있고, 특정 기능성 영역의 크기에 해당할 수 있으며, 단일 서브픽셀(sub-pixel)만큼 작을 수도 있다. In the present specification, the'layer' is meant to be compatible with the'film' mainly used in the present technical field, and means a coating covering a desired area. The size of the'layer' is not limited, and each'layer' may be the same or different in size. According to an exemplary embodiment, the size of the'layer' may be the same as the entire device, may correspond to the size of a specific functional region, and may be as small as a single sub-pixel.
본 명세서에 있어서, 특정한 A 물질이 B층에 포함된다는 의미는 i) 1종 이상의 A 물질이 하나의 B층에 포함되는 것과 ii) B층이 1층 이상으로 구성되고, A 물질이 다층의 B층 중 1층 이상에 포함되는 것을 모두 포함한다.In the present specification, the meaning that a specific A material is included in the B layer means that i) at least one A material is included in one layer B, and ii) the B layer is composed of one or more layers, and the A material is a multilayer B Includes all those included in one or more of the floors.
본 명세서에 있어서, 특정한 A 물질이 C층 또는 D층에 포함된다는 의미는 i) 1층 이상의 C층 중 1층 이상에 포함되거나, ii) 1층 이상의 D층 중 1층 이상에 포함되거나, iii) 1층 이상의 C층 및 1층 이상의 D층에 각각 포함되는 것을 모두 의미하는 것이다.In the present specification, the meaning that a specific A substance is included in the C layer or the D layer means i) is included in one or more of the C layers, ii) is included in one or more of the D layers, or iii ) It means both included in one or more layers C and one or more layers D, respectively.
본 명세서는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다.The present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Formula 1 do.
본 명세서의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 차단층, 정공 차단층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 전자주입층, 전자 수송층, 또는 전자 주입 및 수송층을 포함하고, 상기 전자주입층, 전자 수송층, 또는 전자 주입 및 수송층은 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공차단층을 포함하고, 상기 정공차단층은 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공 주입층, 정공 수송층, 또는 정공주입 및 수송층을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공 주입층, 정공 수송층, 또는 정공주입 및 수송층을 포함하고, 상기 정공 주입층, 정공 수송층, 또는 정공주입 및 수송층은 상기 화합물을 포함한다. According to an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or the hole injection and transport layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 전자 차단층을 포함한다. According to an exemplary embodiment of the present specification, the organic material layer includes an electron blocking layer.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공 차단층을 포함한다. According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 정공 주입층, 정공 수송층, 정공 주입 및 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 주입 및 수송층, 정공 차단층 및 전자 차단층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device is a group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer. It further includes one or two or more layers selected from.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층; 및 상기 발광층과 상기 제1 전극 사이, 또는 상기 발광층과 상기 제2 전극 사이에 구비된 2층 이상의 유기물층을 포함한다. According to an exemplary embodiment of the present specification, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; A light emitting layer provided between the first electrode and the second electrode; And two or more organic material layers provided between the emission layer and the first electrode or between the emission layer and the second electrode.
본 명세서의 일 실시상태에 따르면, 상기 2층 이상의 유기물층은 정공 주입층, 정공 수송층, 정공 주입 및 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 주입 및 수송층, 정공 차단층 및 전자 차단층으로 이루어진 군에서 2 이상이 선택될 수 있다.According to an exemplary embodiment of the present specification, the two or more organic material layers are formed of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer. Two or more may be selected from the group.
본 명세서의 일 실시상태에 따르면, 상기 발광층과 상기 제1 전극 사이에 2층 이상의 정공수송층을 포함한다. 상기 2층 이상의 정공수송층은 서로 동일하거나 상이한 물질을 포함할 수 있다.According to an exemplary embodiment of the present specification, two or more hole transport layers are included between the emission layer and the first electrode. The two or more hole transport layers may include the same or different materials.
본 명세서의 일 실시상태에 따르면, 상기 제1 전극은 양극 또는 음극이다.According to an exemplary embodiment of the present specification, the first electrode is an anode or a cathode.
본 명세서의 일 실시상태에 따르면, 상기 제2 전극은 음극 또는 양극이다. According to an exemplary embodiment of the present specification, the second electrode is a cathode or an anode.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. According to the exemplary embodiment of the present specification, the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다.According to the exemplary embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
예컨대, 본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조가 도 1 및 2에 예시되어 있다. 상기 도 1 및 2는 유기 발광 소자를 예시한 것이며 이에 한정되는 것은 아니다. For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2. 1 and 2 illustrate an organic light emitting device, but are not limited thereto.
도 1에는 기판(101) 위에 제1 전극(102), 유기물층(111) 및 제2 전극(110)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 화학식 1로 표시되는 화합물은 유기물층에 포함된다. 1 illustrates a structure of an organic light-emitting device in which a first electrode 102, an organic material layer 111, and a second electrode 110 are sequentially stacked on a substrate 101. The compound represented by Formula 1 is included in the organic material layer.
도 2에는 기판(101) 위에 제1 전극(102), 정공주입층(103), 정공수송층(104), 발광층(105), 전자 주입 및 수송층(106), 및 제2 전극(110)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 화학식 1로 표시되는 화합물은 전자 주입 및 수송층에 포함된다.2, a first electrode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 105, an electron injection and transport layer 106, and a second electrode 110 are sequentially formed on the substrate 101. The structure of the stacked organic light emitting device is illustrated. The compound represented by Formula 1 is included in the electron injection and transport layer.
본 명세서의 유기 발광 소자는 전자주입층, 전자 수송층, 전자 주입 및 수송층, 정공차단층, 정공 주입층, 정공 수송층, 또는 정공주입 및 수송층이 상기 화합물, 즉 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic light-emitting device of the present specification includes an electron injection layer, an electron transport layer, an electron injection and transport layer, a hole blocking layer, a hole injection layer, a hole transport layer, or a hole injection and transport layer. Except for that, it can be manufactured by materials and methods known in the art.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다.When the organic light-emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질, 유기물층 및 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다. For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하나, 이에 한정되는 것은 아니다. In addition, the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다. 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate. However, the manufacturing method is not limited thereto.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 예를 들어, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이에 한정되는 것은 아니다. As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 예를 들어, 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이에 한정되는 것은 아니다.It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are a multi-layered material such as LiF/Al or LiO 2 /Al, but are not limited thereto.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로, 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되는 것은 아니다. The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And pyrimidine derivatives, but are not limited thereto.
상기 도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로, 방향족 아민 유도체로는 치환 또는 비치환된 아릴아민기를 갖는 축합 방향족환 유도체로서, 아릴아민기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있다. 또한, 스티릴아민 화합물은 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 시클로알킬기 및 아릴아민기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되는 것은 아니다. Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and is selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Substituents are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.
상기 정공 주입층은 전극으로부터 정공을 수취하는 층이다. 정공 주입 물질은 정공을 수송하는 능력을 가져 양극으로부터 정공 수취 효과 및 발광층 또는 발광 재료에 대하여 우수한 정공 주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 엑시톤의 전자 주입층 또는 전자 주입 재료에의 이동을 방지할 수 있는 능력이 우수한 물질이 바람직하다. 또한, 박막 형성 능력이 우수한 물질이 바람직하다. 또한, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는, 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물; 헥사니트릴헥사아자트리페닐렌 계열의 유기물; 퀴나크리돈(quinacridone)계열의 유기물; 페릴렌(perylene) 계열의 유기물; 안트라퀴논, 폴리아닐린과 같은 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이에 한정 되는 것은 아니다. The hole injection layer is a layer that receives holes from an electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injection effect with respect to the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent the movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in thin film formation ability is preferred. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organic matter; Perylene-based organics; There are polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층이다. 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수취하여 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이에 한정되는 것은 아니다.The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer. As the hole transport material, a material capable of receiving holes from an anode or a hole injection layer and transferring them to the light emitting layer, and a material having high mobility for holes is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
상기 전자 수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층이다. 본 명세서의 일 실시상태에 따른 유기 발광 소자가 상기 화학식 1을 포함하는 전자수송층 이외의 추가의 전자수송층을 포함하는 경우, 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 8-히드록시퀴놀린의 Al착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이에 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이, 임의의 원하는 음극 물질과 함께 사용할 수 있다. 특히, 적절한 음극 물질은 낮은 일함수를 가지며, 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로, 세슘, 바륨, 칼슘, 이테르븀 및 사마륨 등이 있고, 각 경우 알루미늄층 또는 실버층이 뒤따른다.The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. When the organic light-emitting device according to an exemplary embodiment of the present specification includes an additional electron transport layer other than the electron transport layer including Formula 1, as an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer As, a material having high mobility for electrons is preferred. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer can be used with any desired negative electrode material, as used according to the prior art. In particular, suitable cathode materials have a low work function and are conventional materials followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows.
상기 전자 주입층은 전극으로부터 전자를 수취하는 층이다. 본 명세서의 일 실시상태에 따른 유기 발광 소자가 상기 화학식 1을 포함하는 전자주입층 이외의 추가의 전자주입층을 포함하는 경우, 전자 주입물로는 전자를 수송하는 능력이 우수하고, 제2 전극으로부터의 전자 수취 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 엑시톤이 정공 주입층으로 이동하는 것을 방지하고, 박막 형성 능력이 우수한 물질이 바람직하다. 구체적으로는, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되는 것은 아니다. The electron injection layer is a layer that receives electrons from an electrode. When the organic light-emitting device according to the exemplary embodiment of the present specification includes an additional electron injection layer other than the electron injection layer including Formula 1, the electron injection material has excellent ability to transport electrons, and the second electrode It is preferable to have an effect of receiving electrons from and an excellent electron injection effect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, Metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
상기 금속 착체 화합물로는 8-히드록시퀴놀리나토 리튬, 비스(8-히드록시퀴놀리나토)아연, 비스(8-히드록시퀴놀리나토)구리, 비스(8-히드록시퀴놀리나토)망간, 트리스(8-히드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-히드록시퀴놀리나토)알루미늄, 트리스(8-히드록시퀴놀리나토)갈륨, 비스(10-히드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-히드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되는 것은 아니다.As the metal complex compound, 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, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , But is not limited thereto.
상기 전자 차단층은 전자 주입층으로부터 주입된 전자가 발광층을 지나 정공 주입층으로 진입하는 것을 방지하여 소자의 수명과 효율을 향상시킬 수 있는 층이다. 공지된 재료는 제한 없이 사용 가능하며, 발광층과 정공 주입층 사이에, 또는 발광층과 정공 주입 및 정공 수송을 동시에 하는 층 사이에 형성될 수 있다. The electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer. Known materials may be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.
상기 정공 차단층은 정공이 음극으로 도달을 저지하는 층으로, 일반적으로 전자 주입층과 동일한 조건으로 형성될 수 있다. 본 명세서의 일 실시상태에 따른 유기 발광 소자가 상기 화학식 1을 포함하는 정공차단층 이외의 추가의 정공차단층을 포함하는 경우, 구체적으로, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되는 것은 아니다. The hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. When the organic light-emitting device according to the exemplary embodiment of the present specification includes an additional hole blocking layer other than the hole blocking layer including Formula 1, specifically, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, There are aluminum complexes and the like, but are not limited thereto.
본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light-emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예 및 비교예 등을 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예 및 비교예는 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예 및 비교예에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예 및 비교예는 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, examples and comparative examples will be described in detail to describe the present specification in detail. However, the Examples and Comparative Examples according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the Examples and Comparative Examples described below. Examples and comparative examples of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.
합성예 1-1Synthesis Example 1-1
Figure PCTKR2020012085-appb-I000261
Figure PCTKR2020012085-appb-I000261
상기 화합물 2-bromo-1-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2(2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 1-1를 제조하였다. (11.9 g, 수율 43 %, MS:[M+H]+= 307).The compound 2-bromo-1-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol) were added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 1-1. (11.9 g, yield 43%, MS:[M+H]+= 307).
합성예 1-2Synthesis Example 1-2
Figure PCTKR2020012085-appb-I000262
Figure PCTKR2020012085-appb-I000262
상기 화합물 1-1 (60.5 g, 197.3 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol)을 1,4-다이옥산 (1000 mL)에 투입하였다. Potassium acetate (58.0 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 1-2를 제조하였다. (63.7 g, 수율 81 %, MS:[M+H]+= 399).Compound 1-1 (60.5 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol) was added to 1,4-dioxane (1000 mL). Potassium acetate (58.0 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) were added and then stirred and refluxed for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare Compound 1-2. (63.7 g, yield 81%, MS:[M+H]+= 399).
합성예 1Synthesis Example 1
Figure PCTKR2020012085-appb-I000263
Figure PCTKR2020012085-appb-I000263
상기 화합물 1-2 (11.9 g, 30 mmol) 및 상기 화합물 1-3 (6.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 1를 제조하였다. (9.1 g, 수율 71 %, MS:[M+H]+= 427).Compound 1-2 (11.9 g, 30 mmol) and compound 1-3 (6.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 1. (9.1 g, yield 71%, MS:[M+H]+= 427).
합성예 2-1Synthesis Example 2-1
Figure PCTKR2020012085-appb-I000264
Figure PCTKR2020012085-appb-I000264
상기 화합물 3-bromo-1-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-3H-naphtho[1,2-d]imidazole (17.7 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 2-1를 제조하였다. (16.4g, 수율 51 %, MS:[M+H]+= 357).The compound 3-bromo-1-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-3H-naphtho[1,2-d]imidazole (17.7 g, 90 mmol) were added to toluene (900 mL). . After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 2-1. (16.4 g, yield 51%, MS:[M+H]+= 357).
합성예 2-2Synthesis Example 2-2
Figure PCTKR2020012085-appb-I000265
Figure PCTKR2020012085-appb-I000265
상기 화합물 2-1 (70.4 g, 197.3 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol)을 1,4-다이옥산 (1000 mL)에 투입하였다. Potassium acetate (58.0 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 2-2를 제조하였다. (78.7 g, 수율 89 %, MS:[M+H]+= 449).Compound 2-1 (70.4 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol) was added to 1,4-dioxane (1000 mL). Potassium acetate (58.0 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 2-2. (78.7 g, 89% yield, MS:[M+H]+=449).
합성예 2Synthesis Example 2
Figure PCTKR2020012085-appb-I000266
Figure PCTKR2020012085-appb-I000266
상기 화합물 2-2 (13.5 g, 30 mmol) 및 상기 화합물 2-3 (7.9 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 2를 제조하였다. (11.4 g, 수율 72 %, MS:[M+H]+= 527).The compound 2-2 (13.5 g, 30 mmol) and the compound 2-3 (7.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 2. (11.4 g, yield 72%, MS:[M+H]+= 527).
합성예 3-1Synthesis Example 3-1
Figure PCTKR2020012085-appb-I000267
Figure PCTKR2020012085-appb-I000267
상기 화합물 1-bromo-4-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 3-1를 제조하였다. (12.4g, 수율 45 %, MS:[M+H]+= 307).The compound 1-bromo-4-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol) were added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 3-1. (12.4g, yield 45%, MS:[M+H]+= 307).
합성예 3-2Synthesis Example 3-2
Figure PCTKR2020012085-appb-I000268
Figure PCTKR2020012085-appb-I000268
상기 화합물 3-1 (60.5 g, 197.3 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol)을 1,4-다이옥산 (1000 mL)에 투입하였다. Potassium acetate (58.0 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 3-2를 제조하였다. (61.3 g, 수율 78 %, MS:[M+H]+= 399).The compound 3-1 (60.5 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol) was added to 1,4-dioxane (1000 mL). Potassium acetate (58.0 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) were added and then stirred and refluxed for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 3-2. (61.3 g, yield 78%, MS:[M+H]+= 399).
합성예 3Synthesis Example 3
Figure PCTKR2020012085-appb-I000269
Figure PCTKR2020012085-appb-I000269
상기 화합물 3-2 (11.9 g, 30 mmol) 및 상기 화합물 3-3 (12.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 3를 제조하였다. (11.9 g, 수율 65 %, MS:[M+H]+= 610).Compound 3-2 (11.9 g, 30 mmol) and compound 3-3 (12.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 3. (11.9 g, yield 65%, MS:[M+H]+= 610).
합성예 4-1Synthesis Example 4-1
Figure PCTKR2020012085-appb-I000270
Figure PCTKR2020012085-appb-I000270
상기 화합물 1-bromo-5-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-4,5-diphenyl-1H-imidazole (22.3 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 4-1를 제조하였다. (16.9g, 수율 46 %, MS:[M+H]+= 409).The compound 1-bromo-5-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-4,5-diphenyl-1H-imidazole (22.3 g, 90 mmol) were added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized twice with ethyl acetate to prepare compound 4-1. (16.9 g, yield 46%, MS:[M+H]+=409).
합성예 4-2Synthesis Example 4-2
Figure PCTKR2020012085-appb-I000271
Figure PCTKR2020012085-appb-I000271
상기 화합물 4-1 (80.7 g, 197.3 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol)을 1,4-다이옥산 (1000 mL)에 투입하였다. Potassium acetate (58.0 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 4-2를 제조하였다. (76.0 g, 수율 77 %, MS:[M+H]+= 501).Compound 4-1 (80.7 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol) was added to 1,4-dioxane (1000 mL). Potassium acetate (58.0 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) were added and then stirred and refluxed for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 4-2. (76.0 g, yield 77%, MS:[M+H]+=501).
합성예 4Synthesis Example 4
Figure PCTKR2020012085-appb-I000272
Figure PCTKR2020012085-appb-I000272
상기 화합물 4-2 (15.0 g, 30 mmol) 및 상기 화합물 4-3 (6.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 4를 제조하였다. (8.7 g, 수율 55 %, MS:[M+H]+= 528).Compound 4-2 (15.0 g, 30 mmol) and compound 4-3 (6.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 4. (8.7 g, yield 55%, MS:[M+H]+= 528).
합성예 5-1Synthesis Example 5-1
Figure PCTKR2020012085-appb-I000273
Figure PCTKR2020012085-appb-I000273
상기 화합물 6-bromo-1-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 5-1를 제조하였다. (11.9g, 수율 43 %, MS:[M+H]+= 307).The compound 6-bromo-1-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol) were added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 5-1. (11.9g, yield 43%, MS:[M+H]+=307).
합성예 5-2Synthesis Example 5-2
Figure PCTKR2020012085-appb-I000274
Figure PCTKR2020012085-appb-I000274
상기 화합물 5-1 (60.5 g, 197.3 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol)을 1,4-다이옥산 (1000 mL)에 투입하였다. Potassium acetate (58.0 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 5-2를 제조하였다. (64.4 g, 수율 82 %, MS:[M+H]+= 399).The compound 5-1 (60.5 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol) was added to 1,4-dioxane (1000 mL). Potassium acetate (58.0 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 5-2. (64.4 g, yield 82%, MS:[M+H]+= 399).
합성예 5Synthesis Example 5
Figure PCTKR2020012085-appb-I000275
Figure PCTKR2020012085-appb-I000275
상기 화합물 5-2 (11.9 g, 30 mmol) 및 상기 화합물 5-3 (12.9 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 5를 제조하였다. (10.5 g, 수율 56 %, MS:[M+H]+= 628).Compound 5-2 (11.9 g, 30 mmol) and compound 5-3 (12.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 5. (10.5 g, yield 56%, MS:[M+H]+=628).
합성예 6-1Synthesis Example 6-1
Figure PCTKR2020012085-appb-I000276
Figure PCTKR2020012085-appb-I000276
상기 화합물 1-bromo-8-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 6-1를 제조하였다. (14.4g, 수율 52 %, MS:[M+H]+= 307).The compound 1-bromo-8-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol) were added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 6-1. (14.4 g, yield 52%, MS:[M+H]+= 307).
합성예 6-2Synthesis Example 6-2
Figure PCTKR2020012085-appb-I000277
Figure PCTKR2020012085-appb-I000277
상기 화합물 6-1 (60.5 g, 197.3 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol)을 1,4-다이옥산 (1000 mL)에 투입하였다. Potassium acetate (58.0 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 6-2를 제조하였다. (65.2 g, 수율 83 %, MS:[M+H]+= 399).Compound 6-1 (60.5 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol) was added to 1,4-dioxane (1000 mL). Potassium acetate (58.0 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 6-2. (65.2 g, 83% yield, MS:[M+H]+= 399).
합성예 6Synthesis Example 6
Figure PCTKR2020012085-appb-I000278
Figure PCTKR2020012085-appb-I000278
상기 화합물 6-2 (11.9 g, 30 mmol) 및 상기 화합물 6-3 (12.2 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 6를 제조하였다. (10.0 g, 수율 55 %, MS:[M+H]+= 605).Compound 6-2 (11.9 g, 30 mmol) and compound 6-3 (12.2 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 6. (10.0 g, yield 55%, MS:[M+H]+=605).
합성예 7-1Synthesis Example 7-1
Figure PCTKR2020012085-appb-I000279
Figure PCTKR2020012085-appb-I000279
상기 화합물 2-bromo-3-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-isopropyl-6-(pyridin-2-yl)-1H-benzo[d]imidazole (21.4 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 7-1를 제조하였다. (19.7g, 수율 55 %, MS:[M+H]+= 398).The compound 2-bromo-3-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-isopropyl-6-(pyridin-2-yl)-1H-benzo[d]imidazole (21.4 g, 90 mmol) were added to toluene ( 900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 7-1. (19.7 g, yield 55%, MS:[M+H]+= 398).
합성예 7-2Synthesis Example 7-2
Figure PCTKR2020012085-appb-I000280
Figure PCTKR2020012085-appb-I000280
상기 화합물 7-1 (78.5 g, 197.3 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol)을 1,4-다이옥산 (1000 mL)에 투입하였다. Potassium acetate (58.0 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 7-2를 제조하였다. (78.2 g, 수율 81 %, MS:[M+H]+= 490).The compound 7-1 (78.5 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol) was added to 1,4-dioxane (1000 mL). Potassium acetate (58.0 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) were added and then stirred and refluxed for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 7-2. (78.2 g, yield 81%, MS:[M+H]+= 490).
합성예 7Synthesis Example 7
Figure PCTKR2020012085-appb-I000281
Figure PCTKR2020012085-appb-I000281
상기 화합물 7-2 (14.7 g, 30 mmol) 및 상기 화합물 7-3 (10.5 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 7를 제조하였다. (13.0 g, 수율 67 %, MS:[M+H]+= 645).Compound 7-2 (14.7 g, 30 mmol) and compound 7-3 (10.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 7. (13.0 g, yield 67%, MS:[M+H]+= 645).
합성예 8-1Synthesis Example 8-1
Figure PCTKR2020012085-appb-I000282
Figure PCTKR2020012085-appb-I000282
상기 화합물 2-bromo-6-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-isopropyl-6-methyl-1H-benzo[d]imidazole (15.7 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 8-1를 제조하였다. (15.1g, 수율 50 %, MS:[M+H]+= 335).The compound 2-bromo-6-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-isopropyl-6-methyl-1H-benzo[d]imidazole (15.7 g, 90 mmol) were added to toluene (900 mL). . After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 8-1. (15.1 g, yield 50%, MS:[M+H]+= 335).
합성예 8-2Synthesis Example 8-2
Figure PCTKR2020012085-appb-I000283
Figure PCTKR2020012085-appb-I000283
상기 화합물 8-1 (66.1 g, 197.3 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol)을 1,4-다이옥산 (1000 mL)에 투입하였다. Potassium acetate (58.0 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 8-2를 제조하였다. (67.3 g, 수율 80 %, MS:[M+H]+= 427).Compound 8-1 (66.1 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol) was added to 1,4-dioxane (1000 mL). Potassium acetate (58.0 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 8-2. (67.3 g, yield 80%, MS:[M+H]+= 427).
합성예 8Synthesis Example 8
Figure PCTKR2020012085-appb-I000284
Figure PCTKR2020012085-appb-I000284
상기 화합물 8-2 (12.8 g, 30 mmol) 및 상기 화합물 8-3 (11.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 8를 제조하였다. (10.8 g, 수율 58 %, MS:[M+H]+= 623).Compound 8-2 (12.8 g, 30 mmol) and compound 8-3 (11.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare Compound 8. (10.8 g, yield 58%, MS:[M+H]+= 623).
합성예 9-1Synthesis Example 9-1
Figure PCTKR2020012085-appb-I000285
Figure PCTKR2020012085-appb-I000285
상기 화합물 2-bromo-7-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 9-1를 제조하였다. (13.8g, 수율 50 %, MS:[M+H]+= 307).The compound 2-bromo-7-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol) were added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 9-1. (13.8 g, yield 50%, MS:[M+H]+= 307).
합성예 9-2Synthesis Example 9-2
Figure PCTKR2020012085-appb-I000286
Figure PCTKR2020012085-appb-I000286
상기 화합물 9-1 (60.5 g, 197.3 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol)을 1,4-다이옥산 (1000 mL)에 투입하였다. Potassium acetate (58.0 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 9-2를 제조하였다. (60.5 g, 수율 77 %, MS:[M+H]+= 399).Compound 9-1 (60.5 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol) was added to 1,4-dioxane (1000 mL). Potassium acetate (58.0 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 9-2. (60.5 g, yield 77%, MS:[M+H]+= 399).
합성예 9Synthesis Example 9
Figure PCTKR2020012085-appb-I000287
Figure PCTKR2020012085-appb-I000287
상기 화합물 9-2 (11.9 g, 30 mmol) 및 상기 화합물 9-3 (8.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 9를 제조하였다. (9.8 g, 수율 65 %, MS:[M+H]+= 504).Compound 9-2 (11.9 g, 30 mmol) and compound 9-3 (8.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 9. (9.8 g, yield 65%, MS:[M+H]+= 504).
합성예 10-1Synthesis Example 10-1
Figure PCTKR2020012085-appb-I000288
Figure PCTKR2020012085-appb-I000288
상기 화합물 2-bromo-1-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 10-1를 제조하였다. (13.8g, 수율 50 %, MS:[M+H]+= 307).The compound 2-bromo-1-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol) were added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 10-1. (13.8 g, yield 50%, MS:[M+H]+= 307).
합성예 10Synthesis Example 10
Figure PCTKR2020012085-appb-I000289
Figure PCTKR2020012085-appb-I000289
상기 화합물 10-1 (9.2 g, 30 mmol) 및 상기 화합물 10-2 (11.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 10를 제조하였다. (10.5 g, 수율 70 %, MS:[M+H]+= 502).Compound 10-1 (9.2 g, 30 mmol) and compound 10-2 (11.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 10. (10.5 g, yield 70%, MS:[M+H]+= 502).
합성예 11-1Synthesis Example 11-1
Figure PCTKR2020012085-appb-I000290
Figure PCTKR2020012085-appb-I000290
상기 화합물 3-bromo-1-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 11-1를 제조하였다. (12.4g, 수율 45 %, MS:[M+H]+= 307).The compound 3-bromo-1-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol) were added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 11-1. (12.4g, yield 45%, MS:[M+H]+= 307).
합성예 11Synthesis Example 11
Figure PCTKR2020012085-appb-I000291
Figure PCTKR2020012085-appb-I000291
상기 화합물 11-1 (9.2 g, 30 mmol) 및 상기 화합물 11-2 (16.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 11를 제조하였다. (11.4 g, 수율 58 %, MS:[M+H]+= 655).Compound 11-1 (9.2 g, 30 mmol) and compound 11-2 (16.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 11. (11.4 g, yield 58%, MS:[M+H]+= 655).
합성예 12-1Synthesis Example 12-1
Figure PCTKR2020012085-appb-I000292
Figure PCTKR2020012085-appb-I000292
상기 화합물 1-bromo-4-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 12-1를 제조하였다. (12.1g, 수율 44 %, MS:[M+H]+= 307).The compound 1-bromo-4-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol) were added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized twice with ethyl acetate to prepare compound 12-1. (12.1 g, yield 44%, MS:[M+H]+=307).
합성예 12Synthesis Example 12
Figure PCTKR2020012085-appb-I000293
Figure PCTKR2020012085-appb-I000293
상기 화합물 12-1 (9.2 g, 30 mmol) 및 상기 화합물 12-2 (17.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 12를 제조하였다. (12.5 g, 수율 62 %, MS:[M+H]+= 670).Compound 12-1 (9.2 g, 30 mmol) and compound 12-2 (17.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare Compound 12. (12.5 g, yield 62%, MS:[M+H]+= 670).
합성예 13-1Synthesis Example 13-1
Figure PCTKR2020012085-appb-I000294
Figure PCTKR2020012085-appb-I000294
상기 화합물 1-bromo-5-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-isopropyl-1H-benzo[4',5']thieno[2',3':4,5]benzo[1,2-d]imidazole (24.0 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 13-1를 제조하였다. (23.4g, 수율 61 %, MS:[M+H]+= 427).The compound 1-bromo-5-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-isopropyl-1H-benzo[4',5']thieno[2',3':4,5]benzo[1,2 -d]imidazole (24.0 g, 90 mmol) was added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 13-1. (23.4 g, yield 61%, MS:[M+H]+= 427).
합성예 13Synthesis Example 13
Figure PCTKR2020012085-appb-I000295
Figure PCTKR2020012085-appb-I000295
상기 화합물 13-1 (12.8 g, 30 mmol) 및 상기 화합물 13-2 (17.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 13를 제조하였다. (16.8 g, 수율 71 %, MS:[M+H]+= 790).Compound 13-1 (12.8 g, 30 mmol) and compound 13-2 (17.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 13. (16.8 g, yield 71%, MS:[M+H]+= 790).
합성예 14-1Synthesis Example 14-1
Figure PCTKR2020012085-appb-I000296
Figure PCTKR2020012085-appb-I000296
상기 화합물 6-bromo-1-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-1H-naphtho[2,3-d]imidazole (17.7 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 14-1를 제조하였다. (17.7g, 수율 55 %, MS:[M+H]+= 357).The compound 6-bromo-1-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-1H-naphtho[2,3-d]imidazole (17.7 g, 90 mmol) were added to toluene (900 mL). . After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 14-1. (17.7 g, yield 55%, MS:[M+H]+= 357).
합성예 14Synthesis Example 14
Figure PCTKR2020012085-appb-I000297
Figure PCTKR2020012085-appb-I000297
상기 화합물 14-1 (10.7 g, 30 mmol) 및 상기 화합물 14-2 (13.5 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 14를 제조하였다. (13.0 g, 수율 72 %, MS:[M+H]+= 604).Compound 14-1 (10.7 g, 30 mmol) and compound 14-2 (13.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 14. (13.0 g, yield 72%, MS:[M+H]+= 604).
합성예 15-1Synthesis Example 15-1
Figure PCTKR2020012085-appb-I000298
Figure PCTKR2020012085-appb-I000298
상기 화합물 1-bromo-8-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-methyl-1H-benzo[d]imidazole (11.9 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 15-1를 제조하였다. (14.8g, 수율 56 %, MS:[M+H]+= 293).The compound 1-bromo-8-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-methyl-1H-benzo[d]imidazole (11.9 g, 90 mmol) were added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 15-1. (14.8g, yield 56%, MS:[M+H]+=293).
합성예 15Synthesis Example 15
Figure PCTKR2020012085-appb-I000299
Figure PCTKR2020012085-appb-I000299
상기 화합물 15-1 (8.8 g, 30 mmol) 및 상기 화합물 15-2 (10.9 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 15를 제조하였다. (8.6 g, 수율 62 %, MS:[M+H]+= 462).Compound 15-1 (8.8 g, 30 mmol) and compound 15-2 (10.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 15. (8.6 g, yield 62%, MS:[M+H]+= 462).
합성예 16-1Synthesis Example 16-1
Figure PCTKR2020012085-appb-I000300
Figure PCTKR2020012085-appb-I000300
상기 화합물 2-bromo-3-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-((1r,3r,5r,7r)-adamantan-2-yl)-5-phenyl-1H-benzo[d]imidazole (29.6 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 16-1를 제조하였다. (22.0g, 수율 50 %, MS:[M+H]+= 490).The compound 2-bromo-3-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-((1r,3r,5r,7r)-adamantan-2-yl)-5-phenyl-1H-benzo[d]imidazole (29.6 g, 90 mmol) was added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 16-1. (22.0 g, yield 50%, MS:[M+H]+=490).
합성예 16Synthesis Example 16
Figure PCTKR2020012085-appb-I000301
Figure PCTKR2020012085-appb-I000301
상기 화합물 16-1 (14.0 g, 30 mmol) 및 상기 화합물 16-2 (17.7 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 16를 제조하였다. (18.4 g, 수율 71 %, MS:[M+H]+= 864).Compound 16-1 (14.0 g, 30 mmol) and compound 16-2 (17.7 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 16. (18.4 g, yield 71%, MS:[M+H]+= 864).
합성예 17-1Synthesis Example 17-1
Figure PCTKR2020012085-appb-I000302
Figure PCTKR2020012085-appb-I000302
상기 화합물 2-bromo-6-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 17-1를 제조하였다. (15.2g, 수율 55 %, MS:[M+H]+= 307).The compound 2-bromo-6-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol) were added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized twice with ethyl acetate to prepare compound 17-1. (15.2 g, yield 55%, MS:[M+H]+= 307).
합성예 17Synthesis Example 17
Figure PCTKR2020012085-appb-I000303
Figure PCTKR2020012085-appb-I000303
상기 화합물 17-1 (9.2 g, 30 mmol) 및 상기 화합물 17-2 (18.5 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 17를 제조하였다. (14.8 g, 수율 70 %, MS:[M+H]+= 706).Compound 17-1 (9.2 g, 30 mmol) and compound 17-2 (18.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 17. (14.8 g, yield 70%, MS:[M+H]+= 706).
합성예 18-1Synthesis Example 18-1
Figure PCTKR2020012085-appb-I000304
Figure PCTKR2020012085-appb-I000304
상기 화합물 2-bromo-7-chloronaphthalene (21.7 g, 90 mmol) 및 상기 화합물 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol)을 톨루엔 (900 mL)에 투입하였다. NatBuO (26 g), Pd(PtBu3)2 (2.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 18-1를 제조하였다. (14.4g, 수율 52 %, MS:[M+H]+= 307).The compound 2-bromo-7-chloronaphthalene (21.7 g, 90 mmol) and the compound 2-ethyl-1H-benzo[d]imidazole (13.2 g, 90 mmol) were added to toluene (900 mL). After adding NatBuO (26 g) and Pd(PtBu 3 ) 2 (2.7 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 18-1. (14.4 g, yield 52%, MS:[M+H]+= 307).
합성예 18Synthesis Example 18
Figure PCTKR2020012085-appb-I000305
Figure PCTKR2020012085-appb-I000305
상기 화합물 18-1 (9.2 g, 30 mmol) 및 상기 화합물 18-2 (17.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 18를 제조하였다. (13.1 g, 수율 65 %, MS:[M+H]+= 670).Compound 18-1 (9.2 g, 30 mmol) and compound 18-2 (17.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 18. (13.1 g, yield 65%, MS:[M+H]+= 670).
합성예 19-1Synthesis Example 19-1
Figure PCTKR2020012085-appb-I000306
Figure PCTKR2020012085-appb-I000306
상기 화합물 2-bromo-1-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 19-1 (10.4 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 19-2를 제조하였다. (5.2 g, 수율 45 %, MS:[M+H]+= 383).The compound 2-bromo-1-chloronaphthalene (7.2 g, 30 mmol) and compound 19-1 (10.4 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 19-2. (5.2 g, yield 45%, MS:[M+H]+= 383).
합성예 19-2Synthesis Example 19-2
Figure PCTKR2020012085-appb-I000307
Figure PCTKR2020012085-appb-I000307
상기 화합물 19-2 (15.1 g, 39.5 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol)을 1,4-다이옥산 (300 mL)에 투입하였다. Potassium acetate (11.6 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 19-3를 제조하였다. (15.2 g, 수율 81 %, MS:[M+H]+= 475).Compound 19-2 (15.1 g, 39.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol) was added to 1,4-dioxane (300 mL). Potassium acetate (11.6 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 19-3. (15.2 g, yield 81%, MS:[M+H]+= 475).
합성예 19Synthesis Example 19
Figure PCTKR2020012085-appb-I000308
Figure PCTKR2020012085-appb-I000308
상기 화합물 19-3 (14.2 g, 30 mmol) 및 상기 화합물 19-4 (5.2 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 19를 제조하였다. (8.7 g, 수율 68 %, MS:[M+H]+= 426).Compound 19-3 (14.2 g, 30 mmol) and compound 19-4 (5.2 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 19. (8.7 g, yield 68%, MS:[M+H]+= 426).
합성예 20-1Synthesis Example 20-1
Figure PCTKR2020012085-appb-I000309
Figure PCTKR2020012085-appb-I000309
상기 화합물 3-bromo-1-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 20-1 (12.7 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 20-2를 제조하였다. (6.5 g, 수율 47 %, MS:[M+H]+= 459).The compound 3-bromo-1-chloronaphthalene (7.2 g, 30 mmol) and compound 20-1 (12.7 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 20-2. (6.5 g, yield 47%, MS:[M+H]+= 459).
합성예 20-2Synthesis Example 20-2
Figure PCTKR2020012085-appb-I000310
Figure PCTKR2020012085-appb-I000310
상기 화합물 20-2 (18.1 g, 39.5 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol)을 1,4-다이옥산 (300 mL)에 투입하였다. Potassium acetate (11.6 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 20-3를 제조하였다. (16.7 g, 수율 77 %, MS:[M+H]+= 551).The compound 20-2 (18.1 g, 39.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol) was added to 1,4-dioxane (300 mL). Potassium acetate (11.6 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 20-3. (16.7 g, yield 77%, MS:[M+H]+= 551).
합성예 20Synthesis Example 20
Figure PCTKR2020012085-appb-I000311
Figure PCTKR2020012085-appb-I000311
상기 화합물 20-3 (16.5 g, 30 mmol) 및 상기 화합물 20-4 (8.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 20를 제조하였다. (12.2 g, 수율 62 %, MS:[M+H]+= 655).The compound 20-3 (16.5 g, 30 mmol) and the compound 20-4 (8.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare Compound 20. (12.2 g, yield 62%, MS:[M+H]+= 655).
합성예 21-1Synthesis Example 21-1
Figure PCTKR2020012085-appb-I000312
Figure PCTKR2020012085-appb-I000312
상기 화합물 1-bromo-4-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 21-1 (10.5 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 21-2를 제조하였다. (5.9 g, 수율 51 %, MS:[M+H]+= 384).The compound 1-bromo-4-chloronaphthalene (7.2 g, 30 mmol) and compound 21-1 (10.5 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized twice with ethyl acetate to prepare compound 21-2. (5.9 g, yield 51%, MS:[M+H]+= 384).
합성예 21-2Synthesis Example 21-2
Figure PCTKR2020012085-appb-I000313
Figure PCTKR2020012085-appb-I000313
상기 화합물 21-2 (15.2 g, 39.5 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol)을 1,4-다이옥산 (300 mL)에 투입하였다. Potassium acetate (11.6 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 21-3를 제조하였다. (15.4 g, 수율 82 %, MS:[M+H]+= 476).Compound 21-2 (15.2 g, 39.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol) was added to 1,4-dioxane (300 mL). Potassium acetate (11.6 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 21-3. (15.4 g, yield 82%, MS:[M+H]+= 476).
합성예 21Synthesis Example 21
Figure PCTKR2020012085-appb-I000314
Figure PCTKR2020012085-appb-I000314
상기 화합물 21-3 (14.3 g, 30 mmol) 및 상기 화합물 21-4 (12.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 21를 제조하였다. (13.4 g, 수율 65 %, MS:[M+H]+= 687).Compound 21-3 (14.3 g, 30 mmol) and compound 21-4 (12.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 21. (13.4 g, yield 65%, MS:[M+H]+= 687).
합성예 22-1Synthesis Example 22-1
Figure PCTKR2020012085-appb-I000315
Figure PCTKR2020012085-appb-I000315
상기 화합물 1-bromo-5-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 22-1 (17.1 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 22-2를 제조하였다. (8.7 g, 수율 48 %, MS:[M+H]+= 606).The compound 1-bromo-5-chloronaphthalene (7.2 g, 30 mmol) and compound 22-1 (17.1 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 22-2. (8.7 g, yield 48%, MS:[M+H]+=606).
합성예 22-2Synthesis Example 22-2
Figure PCTKR2020012085-appb-I000316
Figure PCTKR2020012085-appb-I000316
상기 화합물 22-2 (23.9 g, 39.5 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol)을 1,4-다이옥산 (300 mL)에 투입하였다. Potassium acetate (11.6 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 22-3를 제조하였다. (23.4 g, 수율 85 %, MS:[M+H]+= 697).Compound 22-2 (23.9 g, 39.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol) was added to 1,4-dioxane (300 mL). Potassium acetate (11.6 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 22-3. (23.4 g, yield 85%, MS:[M+H]+= 697).
합성예 22Synthesis Example 22
Figure PCTKR2020012085-appb-I000317
Figure PCTKR2020012085-appb-I000317
상기 화합물 22-3 (20.9 g, 30 mmol) 및 상기 화합물 22-4 (6.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 22를 제조하였다. (9.8 g, 수율 45 %, MS:[M+H]+= 725).Compound 22-3 (20.9 g, 30 mmol) and compound 22-4 (6.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 22. (9.8 g, yield 45%, MS:[M+H]+=725).
합성예 23-1Synthesis Example 23-1
Figure PCTKR2020012085-appb-I000318
Figure PCTKR2020012085-appb-I000318
상기 화합물 6-bromo-1-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 23-1 (11.9 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 23-2를 제조하였다. (5.7 g, 수율 44 %, MS:[M+H]+= 433).The compound 6-bromo-1-chloronaphthalene (7.2 g, 30 mmol) and compound 23-1 (11.9 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 23-2. (5.7 g, yield 44%, MS:[M+H]+= 433).
합성예 23-2Synthesis Example 23-2
Figure PCTKR2020012085-appb-I000319
Figure PCTKR2020012085-appb-I000319
상기 화합물 23-2 (17.1 g, 39.5 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol)을 1,4-다이옥산 (300 mL)에 투입하였다. Potassium acetate (11.6 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 23-3를 제조하였다. (14.9 g, 수율 72 %, MS:[M+H]+= 525).Compound 23-2 (17.1 g, 39.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol) was added to 1,4-dioxane (300 mL). Potassium acetate (11.6 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 23-3. (14.9 g, yield 72%, MS:[M+H]+= 525).
합성예 23Synthesis Example 23
Figure PCTKR2020012085-appb-I000320
Figure PCTKR2020012085-appb-I000320
상기 화합물 23-3 (15.7 g, 30 mmol) 및 상기 화합물 23-4 (7.9 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 23를 제조하였다. (8.0 g, 수율 44 %, MS:[M+H]+= 603).Compound 23-3 (15.7 g, 30 mmol) and compound 23-4 (7.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 23. (8.0 g, yield 44%, MS:[M+H]+=603).
합성예 24-1Synthesis Example 24-1
Figure PCTKR2020012085-appb-I000321
Figure PCTKR2020012085-appb-I000321
상기 화합물 1-bromo-8-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 24-1 (11.9 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 24-2를 제조하였다. (6.8 g, 수율 52 %, MS:[M+H]+= 433).The compound 1-bromo-8-chloronaphthalene (7.2 g, 30 mmol) and compound 24-1 (11.9 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 24-2. (6.8 g, yield 52%, MS:[M+H]+= 433).
합성예 24-2Synthesis Example 24-2
Figure PCTKR2020012085-appb-I000322
Figure PCTKR2020012085-appb-I000322
상기 화합물 24-2(17.1 g, 39.5 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol)을 1,4-다이옥산 (300 mL)에 투입하였다. Potassium acetate (11.6 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 24-3를 제조하였다. (15.7 g, 수율 76 %, MS:[M+H]+= 525).Compound 24-2 (17.1 g, 39.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol) was added to 1,4-dioxane (300 mL). Potassium acetate (11.6 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 24-3. (15.7 g, yield 76%, MS:[M+H]+= 525).
합성예 24Synthesis Example 24
Figure PCTKR2020012085-appb-I000323
Figure PCTKR2020012085-appb-I000323
상기 화합물 24-3 (15.7 g, 30 mmol) 및 상기 화합물 24-4 (8.9 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 24를 제조하였다. (10.6 g, 수율 56 %, MS:[M+H]+= 631).Compound 24-3 (15.7 g, 30 mmol) and compound 24-4 (8.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 24. (10.6 g, yield 56%, MS:[M+H]+= 631).
합성예 25-1Synthesis Example 25-1
Figure PCTKR2020012085-appb-I000324
Figure PCTKR2020012085-appb-I000324
상기 화합물 2-bromo-3-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 25-1 (13.2 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 25-2를 제조하였다. (7.1 g, 수율 50 %, MS:[M+H]+= 475).The compound 2-bromo-3-chloronaphthalene (7.2 g, 30 mmol) and compound 25-1 (13.2 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 25-2. (7.1 g, yield 50%, MS:[M+H]+= 475).
합성예 25-2Synthesis Example 25-2
Figure PCTKR2020012085-appb-I000325
Figure PCTKR2020012085-appb-I000325
상기 화합물 25-2(18.7 g, 39.5 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol)을 1,4-다이옥산 (300 mL)에 투입하였다. Potassium acetate (11.6 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 25-3를 제조하였다. (18.1 g, 수율 81 %, MS:[M+H]+= 656).Compound 25-2 (18.7 g, 39.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol) was added to 1,4-dioxane (300 mL). Potassium acetate (11.6 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 25-3. (18.1 g, yield 81%, MS:[M+H]+= 656).
합성예 25Synthesis Example 25
Figure PCTKR2020012085-appb-I000326
Figure PCTKR2020012085-appb-I000326
상기 화합물 25-3 (17.0 g, 30 mmol) 및 상기 화합물 25-4 (10.5 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 25를 제조하였다. (11.9 g, 수율 55 %, MS:[M+H]+= 721).Compound 25-3 (17.0 g, 30 mmol) and compound 25-4 (10.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 25. (11.9 g, yield 55%, MS:[M+H]+=721).
합성예 26-1Synthesis Example 26-1
Figure PCTKR2020012085-appb-I000327
Figure PCTKR2020012085-appb-I000327
상기 화합물 2-bromo-6-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 26-1 (13.1 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 26-2를 제조하였다. (8.5 g, 수율 60 %, MS:[M+H]+= 473).The compound 2-bromo-6-chloronaphthalene (7.2 g, 30 mmol) and compound 26-1 (13.1 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 26-2. (8.5 g, yield 60%, MS:[M+H]+= 473).
합성예 26-2Synthesis Example 26-2
Figure PCTKR2020012085-appb-I000328
Figure PCTKR2020012085-appb-I000328
상기 화합물 26-2(18.7 g, 39.5 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol)을 1,4-다이옥산 (300 mL)에 투입하였다. Potassium acetate (11.6 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 26-3를 제조하였다. (19.6 g, 수율 88 %, MS:[M+H]+= 565).Compound 26-2 (18.7 g, 39.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol) was added to 1,4-dioxane (300 mL). Potassium acetate (11.6 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 26-3. (19.6 g, yield 88%, MS:[M+H]+=565).
합성예 26Synthesis Example 26
Figure PCTKR2020012085-appb-I000329
Figure PCTKR2020012085-appb-I000329
상기 화합물 26-3 (16.9 g, 30 mmol) 및 상기 화합물 26-4 (12.2 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 26를 제조하였다. (13.4 g, 수율 58 %, MS:[M+H]+= 771).Compound 26-3 (16.9 g, 30 mmol) and compound 26-4 (12.2 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 26. (13.4 g, yield 58%, MS:[M+H]+= 771).
합성예 27-1Synthesis Example 27-1
Figure PCTKR2020012085-appb-I000330
Figure PCTKR2020012085-appb-I000330
상기 화합물 2-bromo-7-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 27-1 (13.1 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 27-2를 제조하였다. (7.8 g, 수율 55 %, MS:[M+H]+= 473).The compound 2-bromo-7-chloronaphthalene (7.2 g, 30 mmol) and compound 27-1 (13.1 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 27-2. (7.8 g, yield 55%, MS:[M+H]+= 473).
합성예 27-2Synthesis Example 27-2
Figure PCTKR2020012085-appb-I000331
Figure PCTKR2020012085-appb-I000331
상기 화합물 27-2(18.7 g, 39.5 mmol) 및 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol)을 1,4-다이옥산 (300 mL)에 투입하였다. Potassium acetate (11.6 g) 및 Pd(dppf)Cl2([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g)를 투입한 후 12시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 27-3를 제조하였다. (18.3 g, 수율 82 %, MS:[M+H]+= 565).Compound 27-2 (18.7 g, 39.5 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.0 g, 43.4 mmol) was added to 1,4-dioxane (300 mL). Potassium acetate (11.6 g) and Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.9 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 27-3. (18.3 g, yield 82%, MS:[M+H]+= 565).
합성예 27Synthesis Example 27
Figure PCTKR2020012085-appb-I000332
Figure PCTKR2020012085-appb-I000332
상기 화합물 27-3 (16.9 g, 30 mmol) 및 상기 화합물 27-4 (8.8 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 27를 제조하였다. (12.5 g, 수율 62 %, MS:[M+H]+= 670).Compound 27-3 (16.9 g, 30 mmol) and compound 27-4 (8.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 27. (12.5 g, yield 62%, MS:[M+H]+= 670).
합성예 28-1Synthesis Example 28-1
Figure PCTKR2020012085-appb-I000333
Figure PCTKR2020012085-appb-I000333
상기 화합물 2-bromo-1-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 28-1 (10.4 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 28-2를 제조하였다. (5.9 g, 수율 51 %, MS:[M+H]+= 383).The compound 2-bromo-1-chloronaphthalene (7.2 g, 30 mmol) and compound 28-1 (10.4 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 28-2. (5.9 g, yield 51%, MS:[M+H]+= 383).
합성예 28Synthesis Example 28
Figure PCTKR2020012085-appb-I000334
Figure PCTKR2020012085-appb-I000334
상기 화합물 28-2 (11.5 g, 30 mmol) 및 상기 화합물 28-3 (13.5 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 28를 제조하였다. (12.8 g, 수율 68 %, MS:[M+H]+= 629).The compound 28-2 (11.5 g, 30 mmol) and the compound 28-3 (13.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 28. (12.8 g, yield 68%, MS:[M+H]+= 629).
합성예 29-1Synthesis Example 29-1
Figure PCTKR2020012085-appb-I000335
Figure PCTKR2020012085-appb-I000335
상기 화합물 3-bromo-1-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 29-1 (12.7 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 29-2를 제조하였다. (7.6 g, 수율 55 %, MS:[M+H]+= 459).The compound 3-bromo-1-chloronaphthalene (7.2 g, 30 mmol) and compound 29-1 (12.7 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 29-2. (7.6 g, yield 55%, MS:[M+H]+= 459).
합성예 29Synthesis Example 29
Figure PCTKR2020012085-appb-I000336
Figure PCTKR2020012085-appb-I000336
상기 화합물 29-2 (13.8 g, 30 mmol) 및 상기 화합물 29-3 (14.4 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 29를 제조하였다. (13.6 g, 수율 62 %, MS:[M+H]+= 733).The compound 29-2 (13.8 g, 30 mmol) and the compound 29-3 (14.4 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 29. (13.6 g, yield 62%, MS:[M+H]+= 733).
합성예 30-1Synthesis Example 30-1
Figure PCTKR2020012085-appb-I000337
Figure PCTKR2020012085-appb-I000337
상기 화합물 1-bromo-4-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 30-1 (15.9 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 30-2를 제조하였다. (9.2 g, 수율 54 %, MS:[M+H]+= 566).The compound 1-bromo-4-chloronaphthalene (7.2 g, 30 mmol) and the compound 30-1 (15.9 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 30-2. (9.2 g, yield 54%, MS:[M+H]+=566).
합성예 30Synthesis Example 30
Figure PCTKR2020012085-appb-I000338
Figure PCTKR2020012085-appb-I000338
상기 화합물 30-2 (17.0 g, 30 mmol) 및 상기 화합물 30-3 (14.4 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 30를 제조하였다. (16.4 g, 수율 65 %, MS:[M+H]+= 841).The compound 30-2 (17.0 g, 30 mmol) and the compound 30-3 (14.4 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the compound 30. (16.4 g, yield 65%, MS:[M+H]+= 841).
합성예 31-1Synthesis Example 31-1
Figure PCTKR2020012085-appb-I000339
Figure PCTKR2020012085-appb-I000339
상기 화합물 1-bromo-5-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 31-1 (11.9 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 31-2를 제조하였다. (8.1 g, 수율 62 %, MS:[M+H]+= 433).The compound 1-bromo-5-chloronaphthalene (7.2 g, 30 mmol) and the compound 31-1 (11.9 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized twice with ethyl acetate to prepare compound 31-2. (8.1 g, yield 62%, MS:[M+H]+= 433).
합성예 31Synthesis Example 31
Figure PCTKR2020012085-appb-I000340
Figure PCTKR2020012085-appb-I000340
상기 화합물 31-2 (13.0 g, 30 mmol) 및 상기 화합물 31-3 (17.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 31를 제조하였다. (17.2 g, 수율 72 %, MS:[M+H]+= 796).Compound 31-2 (13.0 g, 30 mmol) and compound 31-3 (17.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 31. (17.2 g, yield 72%, MS:[M+H]+= 796).
합성예 32-1Synthesis Example 32-1
Figure PCTKR2020012085-appb-I000341
Figure PCTKR2020012085-appb-I000341
상기 화합물 6-bromo-1-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 32-1 (12.7 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 32-2를 제조하였다. (9.2 g, 수율 67 %, MS:[M+H]+= 459).Compound 6-bromo-1-chloronaphthalene (7.2 g, 30 mmol) and compound 32-1 (12.7 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 32-2. (9.2 g, yield 67%, MS:[M+H]+= 459).
합성예 32Synthesis Example 32
Figure PCTKR2020012085-appb-I000342
Figure PCTKR2020012085-appb-I000342
상기 화합물 32-2 (13.8 g, 30 mmol) 및 상기 화합물 32-3 (14.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 32를 제조하였다. (16.4 g, 수율 75 %, MS:[M+H]+= 731).Compound 32-2 (13.8 g, 30 mmol) and compound 32-3 (14.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 32. (16.4 g, yield 75%, MS:[M+H]+=731).
합성예 33-1Synthesis Example 33-1
Figure PCTKR2020012085-appb-I000343
Figure PCTKR2020012085-appb-I000343
상기 화합물 1-bromo-8-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 33-1 (13.1 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 33-2를 제조하였다. (9.2 g, 수율 65 %, MS:[M+H]+= 473).The compound 1-bromo-8-chloronaphthalene (7.2 g, 30 mmol) and the compound 33-1 (13.1 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 33-2. (9.2 g, yield 65%, MS:[M+H]+= 473).
합성예 33Synthesis Example 33
Figure PCTKR2020012085-appb-I000344
Figure PCTKR2020012085-appb-I000344
상기 화합물 33-2 (14.2 g, 30 mmol) 및 상기 화합물 33-3 (14.3 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 33를 제조하였다. (15.9 g, 수율 71 %, MS:[M+H]+= 745).Compound 33-2 (14.2 g, 30 mmol) and compound 33-3 (14.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 33. (15.9 g, yield 71%, MS:[M+H]+= 745).
합성예 34-1Synthesis Example 34-1
Figure PCTKR2020012085-appb-I000345
Figure PCTKR2020012085-appb-I000345
상기 화합물 2-bromo-3-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 34-1 (13.2 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 34-2를 제조하였다. (7.8 g, 수율 55 %, MS:[M+H]+= 475).The compound 2-bromo-3-chloronaphthalene (7.2 g, 30 mmol) and the compound 34-1 (13.2 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 34-2. (7.8 g, yield 55%, MS:[M+H]+= 475).
합성예 34Synthesis Example 34
Figure PCTKR2020012085-appb-I000346
Figure PCTKR2020012085-appb-I000346
상기 화합물 34-2 (14.2 g, 30 mmol) 및 상기 화합물 34-3 (16.0 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 34를 제조하였다. (16.3 g, 수율 68 %, MS:[M+H]+= 797).Compound 34-2 (14.2 g, 30 mmol) and compound 34-3 (16.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 34. (16.3 g, yield 68%, MS:[M+H]+=797).
합성예 35-1Synthesis Example 35-1
Figure PCTKR2020012085-appb-I000347
Figure PCTKR2020012085-appb-I000347
상기 화합물 2-bromo-6-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 35-1 (12.7 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7 g) 을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 35-2를 제조하였다. (6.9 g, 수율 50 %, MS:[M+H]+= 459).The compound 2-bromo-6-chloronaphthalene (7.2 g, 30 mmol) and compound 35-1 (12.7 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7 g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was recrystallized twice with ethyl acetate to prepare compound 35-2. (6.9 g, yield 50%, MS:[M+H]+= 459).
합성예 35Synthesis Example 35
Figure PCTKR2020012085-appb-I000348
Figure PCTKR2020012085-appb-I000348
상기 화합물 35-2 (13.8 g, 30 mmol) 및 상기 화합물 35-3 (14.4 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 35를 제조하였다. (14.3 g, 수율 65 %, MS:[M+H]+= 733).Compound 35-2 (13.8 g, 30 mmol) and compound 35-3 (14.4 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 35. (14.3 g, yield 65%, MS:[M+H]+= 733).
합성예 36-1Synthesis Example 36-1
Figure PCTKR2020012085-appb-I000349
Figure PCTKR2020012085-appb-I000349
상기 화합물 2-bromo-7-chloronaphthalene (7.2 g, 30 mmol) 및 상기 화합물 36-1 (13.5 g, 30 mmol)을 테트라하이드로퓨란 (300 mL)에 투입하였다. 2M K2CO3(200 mL), Pd(dppf)Cl2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g)을 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 에틸아세테이트로 2회 재결정하여 상기 화합물 36-2를 제조하였다. (9.0 g, 수율 62 %, MS:[M+H]+= 484).The compound 2-bromo-7-chloronaphthalene (7.2 g, 30 mmol) and compound 36-1 (13.5 g, 30 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Pd(dppf)Cl 2 ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 0.7g) was added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare compound 36-2. (9.0 g, yield 62%, MS:[M+H]+= 484).
합성예 36Synthesis Example 36
Figure PCTKR2020012085-appb-I000350
Figure PCTKR2020012085-appb-I000350
상기 화합물 36-2 (14.5 g, 30 mmol) 및 상기 화합물 36-3 (13.5 g, 33 mmol)을 테트라하이드로퓨란(300 mL)에 투입하였다. 2M K2CO3(200 mL), Palladium acetate (0.14 g) 및, s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand를 투입한 후, 5시간 동안 교반 및 환류하였다. 상온으로 식힌 후 여과하여 생성된 고체를 톨루엔으로 2회 재결정하여 상기 화합물 36를 제조하였다. (16.4 g, 수율 75 %, MS:[M+H]+= 729).Compound 36-2 (14.5 g, 30 mmol) and compound 36-3 (13.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K 2 CO 3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring and refluxing for 5 hours. . After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare compound 36. (16.4 g, yield 75%, MS:[M+H]+= 729).
실시예 1Example 1
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 화합물 [HI-A]를 600Å의 두께로 열진공증착하여 정공 주입층을 형성하였다. 상기 정공 주입층 위에 하기 화학식의 헥사니트릴 헥사아자트리페닐렌 (hexaazatriphenylene; HAT)를 50Å 및 하기 화합물 [HT-A] (600Å)를 순차적으로 진공증착하여 정공 수송층을 형성하였다.The following compound [HI-A] was thermally vacuum deposited to a thickness of 600Å on the prepared ITO transparent electrode to form a hole injection layer. A hole transport layer was formed by sequentially vacuum depositing 50Å of hexaazatriphenylene (HAT) of the following formula on the hole injection layer and the following compound [HT-A] (600Å).
이어서, 상기 정공 수송층 위에 막 두께 200Å으로 하기 화합물 [BH]와 [BD]를 25:1의 중량비로 진공증착하여 발광층을 형성하였다. 상기 발광층 위에 상기 화합물 1과 [LiQ](Lithiumquinolate)를 1:1 중량비로 진공증착하여 350Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 10Å 두께로 리튬 플루라이드(LiF)와 1,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다.Subsequently, the following compounds [BH] and [BD] were vacuum-deposited at a weight ratio of 25:1 to a film thickness of 200 Å on the hole transport layer to form an emission layer. Compound 1 and [LiQ] (Lithium quinolate) were vacuum-deposited at a 1:1 weight ratio on the emission layer to form an electron injection and transport layer with a thickness of 350Å. Lithium fluoride (LiF) in a thickness of 10 Å and aluminum in a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.9 Å/sec를 유지하였고, 음극의 리튬플루오라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1 × 10-7 ~ 5 × 10-8torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.9 Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 1 × 10. Maintaining -7 ~ 5 × 10 -8 torr, an organic light emitting device was manufactured.
Figure PCTKR2020012085-appb-I000351
Figure PCTKR2020012085-appb-I000351
실시예 2Example 2
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 2를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 3Example 3
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 3을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 4Example 4
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 4를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 5Example 5
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 5를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 6Example 6
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 6을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 7Example 7
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 7을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 8Example 8
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 8을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 8 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 9Example 9
상기 실시예 1에서 전자 주입 및 수송층으로 화합물 1 대신 화합물 9를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1 as the electron injection and transport layer in Example 1.
실시예 10Example 10
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 10을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 10 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 11Example 11
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 11을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 11 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 12Example 12
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 12를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 12 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 13Example 13
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 13을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 13 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 14Example 14
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 14를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 14 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 15Example 15
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 15를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 15 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 16Example 16
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 16을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 16 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 17Example 17
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 17을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 17 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 18Example 18
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 18을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 18 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 19Example 19
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 19를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 19 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 20Example 20
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 20을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 20 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 21Example 21
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 21을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 21 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 22Example 22
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 22을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 22 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 23Example 23
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 23을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 23 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 24Example 24
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 24을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 24 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 25Example 25
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 25을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 25 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 26Example 26
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 26을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 26 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 27Example 27
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 27을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 27 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 28Example 28
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 28을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 28 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 29Example 29
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 29을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 29 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 30Example 30
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 30을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 30 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 31Example 31
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 31을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 31 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 32Example 32
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 32을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 32 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 33Example 33
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 33을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 33 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 34Example 34
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 34을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 34 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 35Example 35
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 35을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 35 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
실시예 36Example 36
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 화합물 36을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 36 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
비교예 1Comparative Example 1
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 하기 화합물 ET1을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET1 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
Figure PCTKR2020012085-appb-I000352
Figure PCTKR2020012085-appb-I000352
비교예 2Comparative Example 2
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 하기 화합물 ET2를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET2 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
Figure PCTKR2020012085-appb-I000353
Figure PCTKR2020012085-appb-I000353
비교예 3Comparative Example 3
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 하기 화합물 ET3을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET3 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
Figure PCTKR2020012085-appb-I000354
Figure PCTKR2020012085-appb-I000354
비교예 4Comparative Example 4
상기 실시예 1에서 전자 주입 및 수송층의 화합물 1 대신 하기 화합물 ET4을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET4 was used instead of Compound 1 in the electron injection and transport layer in Example 1.
Figure PCTKR2020012085-appb-I000355
Figure PCTKR2020012085-appb-I000355
상기 실시예 1 내지 36 및 비교예 1 내지 4에서 제조한 유기 발광 소자를 10 mA/cm2의 전류밀도에서 구동전압과 발광 효율을 측정하였고, 20mA/cm2의 전류밀도에서 초기 휘도 대비 98%가 되는 시간(LT98)을 측정하였다. The driving voltage and luminous efficiency of the organic light emitting devices prepared in Examples 1 to 36 and Comparative Examples 1 to 4 were measured at a current density of 10 mA/cm 2 , and 98% of the initial luminance at a current density of 20 mA/cm 2 The time to become (LT98) was measured.
그 결과를 하기 표 37에 나타내었다.The results are shown in Table 37 below.
구분division 화합물compound 전압(V)Voltage(V) 전류효율(cd/A)Current efficiency (cd/A) Life Time 98 at 20mA/cm2 Life Time 98 at 20mA/cm 2
실시예 1Example 1 화합물 1Compound 1 3.693.69 5.515.51 102102
실시예 2Example 2 화합물 2Compound 2 3.753.75 5.455.45 112112
실시예 3Example 3 화합물 3Compound 3 3.653.65 5.325.32 8888
실시예 4Example 4 화합물 4Compound 4 3.703.70 5.35.3 8888
실시예 5Example 5 화합물 5Compound 5 3.693.69 5.245.24 9898
실시예 6Example 6 화합물 6Compound 6 3.863.86 5.525.52 8888
실시예 7Example 7 화합물 7Compound 7 3.563.56 5.245.24 8383
실시예 8Example 8 화합물 8Compound 8 4.044.04 5.525.52 8888
실시예 9Example 9 화합물 9Compound 9 3.883.88 5.125.12 102102
실시예 10Example 10 화합물 10Compound 10 3.883.88 5.155.15 9898
실시예 11Example 11 화합물 11Compound 11 3.883.88 5.215.21 8888
실시예 12Example 12 화합물 12Compound 12 3.733.73 5.255.25 9898
실시예 13Example 13 화합물 13Compound 13 3.883.88 5.225.22 8383
실시예 14Example 14 화합물 14Compound 14 4.054.05 4.84.8 8888
실시예 15Example 15 화합물 15Compound 15 3.913.91 5.35.3 8383
실시예 16Example 16 화합물 16Compound 16 3.733.73 5.45.4 8888
실시예 17Example 17 화합물 17Compound 17 3.813.81 5.515.51 9393
실시예 18Example 18 화합물 18Compound 18 3.813.81 5.255.25 8888
실시예 19Example 19 화합물 19Compound 19 3.743.74 5.215.21 9898
실시예 20Example 20 화합물 20Compound 20 3.843.84 5.225.22 9393
실시예 21Example 21 화합물 21Compound 21 3.733.73 5.45.4 8888
실시예 22Example 22 화합물 22Compound 22 3.813.81 5.25.2 9393
실시예 23Example 23 화합물 23Compound 23 3.803.80 5.265.26 9393
실시예 24Example 24 화합물 24Compound 24 3.863.86 5.35.3 8888
실시예 25Example 25 화합물 25Compound 25 3.563.56 5.245.24 8383
실시예 26Example 26 화합물 26Compound 26 3.793.79 5.525.52 8888
실시예 27Example 27 화합물 27Compound 27 3.843.84 5.125.12 102102
실시예 28Example 28 화합물 28Compound 28 3.863.86 5.155.15 9898
실시예 29Example 29 화합물 29Compound 29 3.953.95 5.515.51 8888
실시예 30Example 30 화합물 30Compound 30 4.044.04 5.255.25 8888
실시예 31Example 31 화합물 31Compound 31 3.573.57 5.215.21 8888
실시예 32Example 32 화합물 32Compound 32 3.883.88 5.225.22 8383
실시예 33Example 33 화합물 33Compound 33 3.883.88 5.45.4 8888
실시예 34Example 34 화합물 34Compound 34 3.883.88 5.555.55 102102
실시예 35Example 35 화합물 35Compound 35 3.883.88 4.84.8 8383
실시예 36Example 36 화합물 36Compound 36 3.883.88 5.35.3 8383
비교예 1Comparative Example 1 ET1ET1 4.424.42 3.323.32 4040
비교예 2Comparative Example 2 ET2ET2 5.325.32 3.313.31 5050
비교예 3Comparative Example 3 ET3ET3 4.354.35 3.803.80 5050
비교예 4Comparative Example 4 ET4ET4 5.415.41 3.333.33 3030
상기 표 37의 결과와 같이 상기 화학식 1은 이미다졸 유도체인 전자주개와 N을 포함하는 6원의 단환 또는 2환의 헤테로고리를 포함하는 전자받개를 연결해주는 치환기인 2가의 나프탈렌에 연결기인 L1 및 L2을 통하여 치환기가 결합된 구조이므로, 각각 양쪽으로 배치된 전자주개와 전자받개를 상기 연결기가 적절히 조절함으로써 전자 주입 및 수송층 내의 전자 분포와 흐름을 효율적으로 제어한다. 따라서, 상기 실시예 1 내지 36의 유기 발광 소자의 구동전압, 전류효율, 및 수명이 비교예 1 내지 4의 화합물 보다 우수한 특성을 나타내는 것을 확인할 수 있었다.As shown in the result of Table 37, Formula 1 represents the linking groups L1 and L2 to divalent naphthalene, which is a substituent connecting the electron acceptor, which is an imidazole derivative, and an electron acceptor including a 6-membered monocyclic or bicyclic heterocycle including N. Since the substituent is bonded through the structure, the electron donor and the electron acceptor disposed on both sides are appropriately controlled by the connector to efficiently control the electron distribution and flow in the electron injection and transport layer. Accordingly, it was confirmed that the driving voltage, current efficiency, and life of the organic light emitting devices of Examples 1 to 36 exhibited superior characteristics than the compounds of Comparative Examples 1 to 4.

Claims (11)

  1. 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2020012085-appb-I000356
    Figure PCTKR2020012085-appb-I000356
    상기 화학식 1에 있어서,In Formula 1,
    X1 내지 X5 중 적어도 하나는 N이고, 나머지는 각각 독립적으로 CR5이며,At least one of X1 to X5 is N, and the others are each independently CR5,
    L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    R1은 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 시클로알킬기이고,R1 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group,
    R2, R3 및 R5는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.R2, R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  2. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 2로 표시되는 것인 화합물:The compound of claim 1, wherein Formula 1 is represented by the following Formula 2:
    [화학식 2][Formula 2]
    Figure PCTKR2020012085-appb-I000357
    Figure PCTKR2020012085-appb-I000357
    상기 화학식 2에 있어서,In Formula 2,
    X1 내지 X5, L1, L2 및 R1는 상기 화학식 1에서 정의한 바와 동일하고,X1 to X5, L1, L2 and R1 are the same as defined in Formula 1,
    R4는 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 결합하여, 치환 또는 비치환된 고리를 형성할 수 있고,R4 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
    r4는 1 내지 4의 정수이며, 상기 r4가 2 이상인 경우, 상기 2 이상의 R4는 서로 같거나 상이하다.r4 is an integer of 1 to 4, and when r4 is 2 or more, the two or more R4s are the same as or different from each other.
  3. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 3 내지 16 중 어느 하나로 표시되는 것인 화합물:The compound of claim 1, wherein Formula 1 is represented by any one of the following Formulas 3 to 16:
    [화학식 3][Formula 3]
    Figure PCTKR2020012085-appb-I000358
    Figure PCTKR2020012085-appb-I000358
    [화학식 4][Formula 4]
    Figure PCTKR2020012085-appb-I000359
    Figure PCTKR2020012085-appb-I000359
    [화학식 5][Formula 5]
    Figure PCTKR2020012085-appb-I000360
    Figure PCTKR2020012085-appb-I000360
    [화학식 6][Formula 6]
    Figure PCTKR2020012085-appb-I000361
    Figure PCTKR2020012085-appb-I000361
    [화학식 7][Formula 7]
    Figure PCTKR2020012085-appb-I000362
    Figure PCTKR2020012085-appb-I000362
    [화학식 8][Formula 8]
    Figure PCTKR2020012085-appb-I000363
    Figure PCTKR2020012085-appb-I000363
    [화학식 9][Formula 9]
    Figure PCTKR2020012085-appb-I000364
    Figure PCTKR2020012085-appb-I000364
    [화학식 10][Formula 10]
    Figure PCTKR2020012085-appb-I000365
    Figure PCTKR2020012085-appb-I000365
    [화학식 11][Formula 11]
    Figure PCTKR2020012085-appb-I000366
    Figure PCTKR2020012085-appb-I000366
    [화학식 12][Formula 12]
    Figure PCTKR2020012085-appb-I000367
    Figure PCTKR2020012085-appb-I000367
    [화학식 13][Formula 13]
    Figure PCTKR2020012085-appb-I000368
    Figure PCTKR2020012085-appb-I000368
    [화학식 14][Formula 14]
    Figure PCTKR2020012085-appb-I000369
    Figure PCTKR2020012085-appb-I000369
    [화학식 15][Formula 15]
    Figure PCTKR2020012085-appb-I000370
    Figure PCTKR2020012085-appb-I000370
    [화학식 16][Formula 16]
    Figure PCTKR2020012085-appb-I000371
    Figure PCTKR2020012085-appb-I000371
    상기 화학식 3 내지 16에 있어서,In Formulas 3 to 16,
    X1 내지 X5, L1, L2 및 R1 내지 R3는 상기 화학식 1에서 정의한 바와 동일하다.X1 to X5, L1, L2, and R1 to R3 are the same as defined in Formula 1 above.
  4. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 1-1 내지 1-10 중 어느 하나로 표시되는 것인 화합물:The compound of claim 1, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-10:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2020012085-appb-I000372
    Figure PCTKR2020012085-appb-I000372
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2020012085-appb-I000373
    Figure PCTKR2020012085-appb-I000373
    [화학식 1-3][Formula 1-3]
    Figure PCTKR2020012085-appb-I000374
    Figure PCTKR2020012085-appb-I000374
    [화학식 1-4][Formula 1-4]
    Figure PCTKR2020012085-appb-I000375
    Figure PCTKR2020012085-appb-I000375
    [화학식 1-5][Formula 1-5]
    Figure PCTKR2020012085-appb-I000376
    Figure PCTKR2020012085-appb-I000376
    [화학식 1-6][Formula 1-6]
    Figure PCTKR2020012085-appb-I000377
    Figure PCTKR2020012085-appb-I000377
    [화학식 1-7][Formula 1-7]
    Figure PCTKR2020012085-appb-I000378
    Figure PCTKR2020012085-appb-I000378
    [화학식 1-8][Formula 1-8]
    Figure PCTKR2020012085-appb-I000379
    Figure PCTKR2020012085-appb-I000379
    [화학식 1-9][Formula 1-9]
    Figure PCTKR2020012085-appb-I000380
    Figure PCTKR2020012085-appb-I000380
    [화학식 1-10][Formula 1-10]
    Figure PCTKR2020012085-appb-I000381
    Figure PCTKR2020012085-appb-I000381
    상기 화학식 1-1 내지 1-10에 있어서,In Formulas 1-1 to 1-10,
    L1, L2 및 R1 내지 R3는 상기 화학식 1에서 정의한 바와 동일하고,L1, L2 and R1 to R3 are the same as defined in Formula 1,
    R51 내지 R55는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다.R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring.
  5. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 1-11 내지 1-20 중 어느 하나로 표시되는 것인 화합물:The compound of claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-11 to 1-20:
    [화학식 1-11][Formula 1-11]
    Figure PCTKR2020012085-appb-I000382
    Figure PCTKR2020012085-appb-I000382
    [화학식 1-12][Formula 1-12]
    Figure PCTKR2020012085-appb-I000383
    Figure PCTKR2020012085-appb-I000383
    [화학식 1-13][Formula 1-13]
    Figure PCTKR2020012085-appb-I000384
    Figure PCTKR2020012085-appb-I000384
    [화학식 1-14][Formula 1-14]
    Figure PCTKR2020012085-appb-I000385
    Figure PCTKR2020012085-appb-I000385
    [화학식 1-15][Formula 1-15]
    Figure PCTKR2020012085-appb-I000386
    Figure PCTKR2020012085-appb-I000386
    [화학식 1-16][Formula 1-16]
    Figure PCTKR2020012085-appb-I000387
    Figure PCTKR2020012085-appb-I000387
    [화학식 1-17][Formula 1-17]
    Figure PCTKR2020012085-appb-I000388
    Figure PCTKR2020012085-appb-I000388
    [화학식 1-18][Formula 1-18]
    Figure PCTKR2020012085-appb-I000389
    Figure PCTKR2020012085-appb-I000389
    [화학식 1-19][Formula 1-19]
    Figure PCTKR2020012085-appb-I000390
    Figure PCTKR2020012085-appb-I000390
    [화학식 1-20][Formula 1-20]
    Figure PCTKR2020012085-appb-I000391
    Figure PCTKR2020012085-appb-I000391
    상기 화학식 1-11 내지 1-20에 있어서,In Formulas 1-11 to 1-20,
    L1, L2 및 R1는 상기 화학식 1에서 정의한 바와 동일하고,L1, L2 and R1 are the same as defined in Formula 1,
    R4 및 R51 내지 R55는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있고,R4 and R51 to R55 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,
    r4는 1 내지 4의 정수이며, 상기 r4가 2 이상인 경우, 상기 2 이상의 R4는 서로 같거나 상이하다.r4 is an integer of 1 to 4, and when r4 is 2 or more, the two or more R4s are the same as or different from each other.
  6. 청구항 1에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴렌기이며,The method according to claim 1, wherein L1 and L2 are the same as or different from each other, and each independently a direct bond; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms,
    상기 R1은 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 또는 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기이고,R1 is a C1-C30 linear or branched alkyl group; Or a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms,
    상기 R2 및 R3는 서로 같거나 상이하며, 각각 독립적으로 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리를 형성하며,The R2 and R3 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a straight or branched alkyl group having 1 to 30 carbon atoms by bonding to each other, a monocyclic or polycyclic chain having 6 to 30 carbon atoms A monocyclic or polycyclic aromatic hydrocarbon having 6 to 30 carbon atoms unsubstituted or substituted with a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a ring aryl group or a straight or branched chain alkyl group having 1 to 30 carbon atoms ring; Or to form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms,
    상기 X1 내지 X5 중 적어도 1개는 N이며, 나머지는 각각 독립적으로 CR5이며, 상기 R5는 수소; 중수소; 시아노기, 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성하는 것인 화합물.At least one of X1 to X5 is N, the rest are each independently CR5, and R5 is hydrogen; heavy hydrogen; Unsubstituted or substituted with a cyano group, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a straight or branched alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or a compound that forms a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding with adjacent groups.
  7. 청구항 1에 있어서, 상기 화학식 1은 하기 화합물 및 하기 표 1 내지 36의 화합물 중에서 선택되는 어느 하나인 것인 화합물:The compound of claim 1, wherein Formula 1 is any one selected from the following compounds and compounds of Tables 1 to 36:
    Figure PCTKR2020012085-appb-I000392
    Figure PCTKR2020012085-appb-I000392
    Figure PCTKR2020012085-appb-I000393
    Figure PCTKR2020012085-appb-I000393
    [표 1][Table 1]
    Figure PCTKR2020012085-appb-I000394
    Figure PCTKR2020012085-appb-I000394
    Figure PCTKR2020012085-appb-I000395
    Figure PCTKR2020012085-appb-I000395
    Figure PCTKR2020012085-appb-I000396
    Figure PCTKR2020012085-appb-I000396
    Figure PCTKR2020012085-appb-I000397
    Figure PCTKR2020012085-appb-I000397
    Figure PCTKR2020012085-appb-I000398
    Figure PCTKR2020012085-appb-I000398
    [표 2][Table 2]
    Figure PCTKR2020012085-appb-I000399
    Figure PCTKR2020012085-appb-I000399
    Figure PCTKR2020012085-appb-I000400
    Figure PCTKR2020012085-appb-I000400
    Figure PCTKR2020012085-appb-I000401
    Figure PCTKR2020012085-appb-I000401
    Figure PCTKR2020012085-appb-I000402
    Figure PCTKR2020012085-appb-I000402
    Figure PCTKR2020012085-appb-I000403
    Figure PCTKR2020012085-appb-I000403
    Figure PCTKR2020012085-appb-I000404
    Figure PCTKR2020012085-appb-I000404
    [표 3][Table 3]
    Figure PCTKR2020012085-appb-I000405
    Figure PCTKR2020012085-appb-I000405
    Figure PCTKR2020012085-appb-I000406
    Figure PCTKR2020012085-appb-I000406
    Figure PCTKR2020012085-appb-I000407
    Figure PCTKR2020012085-appb-I000407
    Figure PCTKR2020012085-appb-I000408
    Figure PCTKR2020012085-appb-I000408
    Figure PCTKR2020012085-appb-I000409
    Figure PCTKR2020012085-appb-I000409
    Figure PCTKR2020012085-appb-I000410
    Figure PCTKR2020012085-appb-I000410
    [표 4][Table 4]
    Figure PCTKR2020012085-appb-I000411
    Figure PCTKR2020012085-appb-I000411
    Figure PCTKR2020012085-appb-I000412
    Figure PCTKR2020012085-appb-I000412
    Figure PCTKR2020012085-appb-I000413
    Figure PCTKR2020012085-appb-I000413
    Figure PCTKR2020012085-appb-I000414
    Figure PCTKR2020012085-appb-I000414
    Figure PCTKR2020012085-appb-I000415
    Figure PCTKR2020012085-appb-I000415
    Figure PCTKR2020012085-appb-I000416
    Figure PCTKR2020012085-appb-I000416
    [표 5][Table 5]
    Figure PCTKR2020012085-appb-I000417
    Figure PCTKR2020012085-appb-I000417
    Figure PCTKR2020012085-appb-I000418
    Figure PCTKR2020012085-appb-I000418
    Figure PCTKR2020012085-appb-I000419
    Figure PCTKR2020012085-appb-I000419
    Figure PCTKR2020012085-appb-I000420
    Figure PCTKR2020012085-appb-I000420
    Figure PCTKR2020012085-appb-I000421
    Figure PCTKR2020012085-appb-I000421
    Figure PCTKR2020012085-appb-I000422
    Figure PCTKR2020012085-appb-I000422
    [표 6][Table 6]
    Figure PCTKR2020012085-appb-I000423
    Figure PCTKR2020012085-appb-I000423
    Figure PCTKR2020012085-appb-I000424
    Figure PCTKR2020012085-appb-I000424
    Figure PCTKR2020012085-appb-I000425
    Figure PCTKR2020012085-appb-I000425
    Figure PCTKR2020012085-appb-I000426
    Figure PCTKR2020012085-appb-I000426
    Figure PCTKR2020012085-appb-I000427
    Figure PCTKR2020012085-appb-I000427
    Figure PCTKR2020012085-appb-I000428
    Figure PCTKR2020012085-appb-I000428
    [표 7][Table 7]
    Figure PCTKR2020012085-appb-I000429
    Figure PCTKR2020012085-appb-I000429
    Figure PCTKR2020012085-appb-I000430
    Figure PCTKR2020012085-appb-I000430
    Figure PCTKR2020012085-appb-I000431
    Figure PCTKR2020012085-appb-I000431
    Figure PCTKR2020012085-appb-I000432
    Figure PCTKR2020012085-appb-I000432
    Figure PCTKR2020012085-appb-I000433
    Figure PCTKR2020012085-appb-I000433
    Figure PCTKR2020012085-appb-I000434
    Figure PCTKR2020012085-appb-I000434
    [표 8][Table 8]
    Figure PCTKR2020012085-appb-I000435
    Figure PCTKR2020012085-appb-I000435
    Figure PCTKR2020012085-appb-I000436
    Figure PCTKR2020012085-appb-I000436
    Figure PCTKR2020012085-appb-I000437
    Figure PCTKR2020012085-appb-I000437
    Figure PCTKR2020012085-appb-I000438
    Figure PCTKR2020012085-appb-I000438
    Figure PCTKR2020012085-appb-I000439
    Figure PCTKR2020012085-appb-I000439
    Figure PCTKR2020012085-appb-I000440
    Figure PCTKR2020012085-appb-I000440
    [표 9][Table 9]
    Figure PCTKR2020012085-appb-I000441
    Figure PCTKR2020012085-appb-I000441
    Figure PCTKR2020012085-appb-I000442
    Figure PCTKR2020012085-appb-I000442
    Figure PCTKR2020012085-appb-I000443
    Figure PCTKR2020012085-appb-I000443
    Figure PCTKR2020012085-appb-I000444
    Figure PCTKR2020012085-appb-I000444
    Figure PCTKR2020012085-appb-I000445
    Figure PCTKR2020012085-appb-I000445
    Figure PCTKR2020012085-appb-I000446
    Figure PCTKR2020012085-appb-I000446
    [표 10][Table 10]
    Figure PCTKR2020012085-appb-I000447
    Figure PCTKR2020012085-appb-I000447
    Figure PCTKR2020012085-appb-I000448
    Figure PCTKR2020012085-appb-I000448
    Figure PCTKR2020012085-appb-I000449
    Figure PCTKR2020012085-appb-I000449
    Figure PCTKR2020012085-appb-I000450
    Figure PCTKR2020012085-appb-I000450
    Figure PCTKR2020012085-appb-I000451
    Figure PCTKR2020012085-appb-I000451
    Figure PCTKR2020012085-appb-I000452
    Figure PCTKR2020012085-appb-I000452
    Figure PCTKR2020012085-appb-I000453
    Figure PCTKR2020012085-appb-I000453
    [표 11][Table 11]
    Figure PCTKR2020012085-appb-I000454
    Figure PCTKR2020012085-appb-I000454
    Figure PCTKR2020012085-appb-I000455
    Figure PCTKR2020012085-appb-I000455
    Figure PCTKR2020012085-appb-I000456
    Figure PCTKR2020012085-appb-I000456
    Figure PCTKR2020012085-appb-I000457
    Figure PCTKR2020012085-appb-I000457
    Figure PCTKR2020012085-appb-I000458
    Figure PCTKR2020012085-appb-I000458
    Figure PCTKR2020012085-appb-I000459
    Figure PCTKR2020012085-appb-I000459
    Figure PCTKR2020012085-appb-I000460
    Figure PCTKR2020012085-appb-I000460
    [표 12][Table 12]
    Figure PCTKR2020012085-appb-I000461
    Figure PCTKR2020012085-appb-I000461
    Figure PCTKR2020012085-appb-I000462
    Figure PCTKR2020012085-appb-I000462
    Figure PCTKR2020012085-appb-I000463
    Figure PCTKR2020012085-appb-I000463
    Figure PCTKR2020012085-appb-I000464
    Figure PCTKR2020012085-appb-I000464
    Figure PCTKR2020012085-appb-I000465
    Figure PCTKR2020012085-appb-I000465
    Figure PCTKR2020012085-appb-I000466
    Figure PCTKR2020012085-appb-I000466
    Figure PCTKR2020012085-appb-I000467
    Figure PCTKR2020012085-appb-I000467
    [표 13][Table 13]
    Figure PCTKR2020012085-appb-I000468
    Figure PCTKR2020012085-appb-I000468
    Figure PCTKR2020012085-appb-I000469
    Figure PCTKR2020012085-appb-I000469
    Figure PCTKR2020012085-appb-I000470
    Figure PCTKR2020012085-appb-I000470
    Figure PCTKR2020012085-appb-I000471
    Figure PCTKR2020012085-appb-I000471
    Figure PCTKR2020012085-appb-I000472
    Figure PCTKR2020012085-appb-I000472
    Figure PCTKR2020012085-appb-I000473
    Figure PCTKR2020012085-appb-I000473
    Figure PCTKR2020012085-appb-I000474
    Figure PCTKR2020012085-appb-I000474
    [표 14][Table 14]
    Figure PCTKR2020012085-appb-I000475
    Figure PCTKR2020012085-appb-I000475
    Figure PCTKR2020012085-appb-I000476
    Figure PCTKR2020012085-appb-I000476
    Figure PCTKR2020012085-appb-I000477
    Figure PCTKR2020012085-appb-I000477
    Figure PCTKR2020012085-appb-I000478
    Figure PCTKR2020012085-appb-I000478
    Figure PCTKR2020012085-appb-I000479
    Figure PCTKR2020012085-appb-I000479
    Figure PCTKR2020012085-appb-I000480
    Figure PCTKR2020012085-appb-I000480
    Figure PCTKR2020012085-appb-I000481
    Figure PCTKR2020012085-appb-I000481
    [표 15][Table 15]
    Figure PCTKR2020012085-appb-I000482
    Figure PCTKR2020012085-appb-I000482
    Figure PCTKR2020012085-appb-I000483
    Figure PCTKR2020012085-appb-I000483
    Figure PCTKR2020012085-appb-I000484
    Figure PCTKR2020012085-appb-I000484
    Figure PCTKR2020012085-appb-I000485
    Figure PCTKR2020012085-appb-I000485
    Figure PCTKR2020012085-appb-I000486
    Figure PCTKR2020012085-appb-I000486
    Figure PCTKR2020012085-appb-I000487
    Figure PCTKR2020012085-appb-I000487
    Figure PCTKR2020012085-appb-I000488
    Figure PCTKR2020012085-appb-I000488
    [표 16][Table 16]
    Figure PCTKR2020012085-appb-I000489
    Figure PCTKR2020012085-appb-I000489
    Figure PCTKR2020012085-appb-I000490
    Figure PCTKR2020012085-appb-I000490
    Figure PCTKR2020012085-appb-I000491
    Figure PCTKR2020012085-appb-I000491
    Figure PCTKR2020012085-appb-I000492
    Figure PCTKR2020012085-appb-I000492
    Figure PCTKR2020012085-appb-I000493
    Figure PCTKR2020012085-appb-I000493
    Figure PCTKR2020012085-appb-I000494
    Figure PCTKR2020012085-appb-I000494
    Figure PCTKR2020012085-appb-I000495
    Figure PCTKR2020012085-appb-I000495
    [표 17][Table 17]
    Figure PCTKR2020012085-appb-I000496
    Figure PCTKR2020012085-appb-I000496
    Figure PCTKR2020012085-appb-I000497
    Figure PCTKR2020012085-appb-I000497
    Figure PCTKR2020012085-appb-I000498
    Figure PCTKR2020012085-appb-I000498
    Figure PCTKR2020012085-appb-I000499
    Figure PCTKR2020012085-appb-I000499
    Figure PCTKR2020012085-appb-I000500
    Figure PCTKR2020012085-appb-I000500
    Figure PCTKR2020012085-appb-I000501
    Figure PCTKR2020012085-appb-I000501
    Figure PCTKR2020012085-appb-I000502
    Figure PCTKR2020012085-appb-I000502
    [표 18][Table 18]
    Figure PCTKR2020012085-appb-I000503
    Figure PCTKR2020012085-appb-I000503
    Figure PCTKR2020012085-appb-I000504
    Figure PCTKR2020012085-appb-I000504
    Figure PCTKR2020012085-appb-I000505
    Figure PCTKR2020012085-appb-I000505
    Figure PCTKR2020012085-appb-I000506
    Figure PCTKR2020012085-appb-I000506
    Figure PCTKR2020012085-appb-I000507
    Figure PCTKR2020012085-appb-I000507
    Figure PCTKR2020012085-appb-I000508
    Figure PCTKR2020012085-appb-I000508
    Figure PCTKR2020012085-appb-I000509
    Figure PCTKR2020012085-appb-I000509
    [표 19][Table 19]
    Figure PCTKR2020012085-appb-I000510
    Figure PCTKR2020012085-appb-I000510
    Figure PCTKR2020012085-appb-I000511
    Figure PCTKR2020012085-appb-I000511
    Figure PCTKR2020012085-appb-I000512
    Figure PCTKR2020012085-appb-I000512
    Figure PCTKR2020012085-appb-I000513
    Figure PCTKR2020012085-appb-I000513
    Figure PCTKR2020012085-appb-I000514
    Figure PCTKR2020012085-appb-I000514
    Figure PCTKR2020012085-appb-I000515
    Figure PCTKR2020012085-appb-I000515
    Figure PCTKR2020012085-appb-I000516
    Figure PCTKR2020012085-appb-I000516
    [표 20][Table 20]
    Figure PCTKR2020012085-appb-I000517
    Figure PCTKR2020012085-appb-I000517
    Figure PCTKR2020012085-appb-I000518
    Figure PCTKR2020012085-appb-I000518
    Figure PCTKR2020012085-appb-I000519
    Figure PCTKR2020012085-appb-I000519
    Figure PCTKR2020012085-appb-I000520
    Figure PCTKR2020012085-appb-I000520
    Figure PCTKR2020012085-appb-I000521
    Figure PCTKR2020012085-appb-I000521
    Figure PCTKR2020012085-appb-I000522
    Figure PCTKR2020012085-appb-I000522
    Figure PCTKR2020012085-appb-I000523
    Figure PCTKR2020012085-appb-I000523
    [표 21][Table 21]
    Figure PCTKR2020012085-appb-I000524
    Figure PCTKR2020012085-appb-I000524
    Figure PCTKR2020012085-appb-I000525
    Figure PCTKR2020012085-appb-I000525
    Figure PCTKR2020012085-appb-I000526
    Figure PCTKR2020012085-appb-I000526
    Figure PCTKR2020012085-appb-I000527
    Figure PCTKR2020012085-appb-I000527
    Figure PCTKR2020012085-appb-I000528
    Figure PCTKR2020012085-appb-I000528
    Figure PCTKR2020012085-appb-I000529
    Figure PCTKR2020012085-appb-I000529
    Figure PCTKR2020012085-appb-I000530
    Figure PCTKR2020012085-appb-I000530
    [표 22][Table 22]
    Figure PCTKR2020012085-appb-I000531
    Figure PCTKR2020012085-appb-I000531
    Figure PCTKR2020012085-appb-I000532
    Figure PCTKR2020012085-appb-I000532
    Figure PCTKR2020012085-appb-I000533
    Figure PCTKR2020012085-appb-I000533
    Figure PCTKR2020012085-appb-I000534
    Figure PCTKR2020012085-appb-I000534
    Figure PCTKR2020012085-appb-I000535
    Figure PCTKR2020012085-appb-I000535
    Figure PCTKR2020012085-appb-I000536
    Figure PCTKR2020012085-appb-I000536
    Figure PCTKR2020012085-appb-I000537
    Figure PCTKR2020012085-appb-I000537
    [표 23][Table 23]
    Figure PCTKR2020012085-appb-I000538
    Figure PCTKR2020012085-appb-I000538
    Figure PCTKR2020012085-appb-I000539
    Figure PCTKR2020012085-appb-I000539
    Figure PCTKR2020012085-appb-I000540
    Figure PCTKR2020012085-appb-I000540
    Figure PCTKR2020012085-appb-I000541
    Figure PCTKR2020012085-appb-I000541
    Figure PCTKR2020012085-appb-I000542
    Figure PCTKR2020012085-appb-I000542
    Figure PCTKR2020012085-appb-I000543
    Figure PCTKR2020012085-appb-I000543
    Figure PCTKR2020012085-appb-I000544
    Figure PCTKR2020012085-appb-I000544
    [표 24][Table 24]
    Figure PCTKR2020012085-appb-I000545
    Figure PCTKR2020012085-appb-I000545
    Figure PCTKR2020012085-appb-I000546
    Figure PCTKR2020012085-appb-I000546
    Figure PCTKR2020012085-appb-I000547
    Figure PCTKR2020012085-appb-I000547
    Figure PCTKR2020012085-appb-I000548
    Figure PCTKR2020012085-appb-I000548
    Figure PCTKR2020012085-appb-I000549
    Figure PCTKR2020012085-appb-I000549
    Figure PCTKR2020012085-appb-I000550
    Figure PCTKR2020012085-appb-I000550
    Figure PCTKR2020012085-appb-I000551
    Figure PCTKR2020012085-appb-I000551
    [표 25][Table 25]
    Figure PCTKR2020012085-appb-I000552
    Figure PCTKR2020012085-appb-I000552
    Figure PCTKR2020012085-appb-I000553
    Figure PCTKR2020012085-appb-I000553
    Figure PCTKR2020012085-appb-I000554
    Figure PCTKR2020012085-appb-I000554
    Figure PCTKR2020012085-appb-I000555
    Figure PCTKR2020012085-appb-I000555
    Figure PCTKR2020012085-appb-I000556
    Figure PCTKR2020012085-appb-I000556
    Figure PCTKR2020012085-appb-I000557
    Figure PCTKR2020012085-appb-I000557
    Figure PCTKR2020012085-appb-I000558
    Figure PCTKR2020012085-appb-I000558
    [표 26][Table 26]
    Figure PCTKR2020012085-appb-I000559
    Figure PCTKR2020012085-appb-I000559
    Figure PCTKR2020012085-appb-I000560
    Figure PCTKR2020012085-appb-I000560
    Figure PCTKR2020012085-appb-I000561
    Figure PCTKR2020012085-appb-I000561
    Figure PCTKR2020012085-appb-I000562
    Figure PCTKR2020012085-appb-I000562
    Figure PCTKR2020012085-appb-I000563
    Figure PCTKR2020012085-appb-I000563
    Figure PCTKR2020012085-appb-I000564
    Figure PCTKR2020012085-appb-I000564
    Figure PCTKR2020012085-appb-I000565
    Figure PCTKR2020012085-appb-I000565
    [표 27][Table 27]
    Figure PCTKR2020012085-appb-I000566
    Figure PCTKR2020012085-appb-I000566
    Figure PCTKR2020012085-appb-I000567
    Figure PCTKR2020012085-appb-I000567
    Figure PCTKR2020012085-appb-I000568
    Figure PCTKR2020012085-appb-I000568
    Figure PCTKR2020012085-appb-I000569
    Figure PCTKR2020012085-appb-I000569
    Figure PCTKR2020012085-appb-I000570
    Figure PCTKR2020012085-appb-I000570
    Figure PCTKR2020012085-appb-I000571
    Figure PCTKR2020012085-appb-I000571
    Figure PCTKR2020012085-appb-I000572
    Figure PCTKR2020012085-appb-I000572
    [표 28][Table 28]
    Figure PCTKR2020012085-appb-I000573
    Figure PCTKR2020012085-appb-I000573
    Figure PCTKR2020012085-appb-I000574
    Figure PCTKR2020012085-appb-I000574
    Figure PCTKR2020012085-appb-I000575
    Figure PCTKR2020012085-appb-I000575
    Figure PCTKR2020012085-appb-I000576
    Figure PCTKR2020012085-appb-I000576
    Figure PCTKR2020012085-appb-I000577
    Figure PCTKR2020012085-appb-I000577
    Figure PCTKR2020012085-appb-I000578
    Figure PCTKR2020012085-appb-I000578
    Figure PCTKR2020012085-appb-I000579
    Figure PCTKR2020012085-appb-I000579
    [표 29][Table 29]
    Figure PCTKR2020012085-appb-I000580
    Figure PCTKR2020012085-appb-I000580
    Figure PCTKR2020012085-appb-I000581
    Figure PCTKR2020012085-appb-I000581
    Figure PCTKR2020012085-appb-I000582
    Figure PCTKR2020012085-appb-I000582
    Figure PCTKR2020012085-appb-I000583
    Figure PCTKR2020012085-appb-I000583
    Figure PCTKR2020012085-appb-I000584
    Figure PCTKR2020012085-appb-I000584
    Figure PCTKR2020012085-appb-I000585
    Figure PCTKR2020012085-appb-I000585
    Figure PCTKR2020012085-appb-I000586
    Figure PCTKR2020012085-appb-I000586
    [표 30][Table 30]
    Figure PCTKR2020012085-appb-I000587
    Figure PCTKR2020012085-appb-I000587
    Figure PCTKR2020012085-appb-I000588
    Figure PCTKR2020012085-appb-I000588
    Figure PCTKR2020012085-appb-I000589
    Figure PCTKR2020012085-appb-I000589
    Figure PCTKR2020012085-appb-I000590
    Figure PCTKR2020012085-appb-I000590
    Figure PCTKR2020012085-appb-I000591
    Figure PCTKR2020012085-appb-I000591
    Figure PCTKR2020012085-appb-I000592
    Figure PCTKR2020012085-appb-I000592
    Figure PCTKR2020012085-appb-I000593
    Figure PCTKR2020012085-appb-I000593
    [표 31][Table 31]
    Figure PCTKR2020012085-appb-I000594
    Figure PCTKR2020012085-appb-I000594
    Figure PCTKR2020012085-appb-I000595
    Figure PCTKR2020012085-appb-I000595
    Figure PCTKR2020012085-appb-I000596
    Figure PCTKR2020012085-appb-I000596
    Figure PCTKR2020012085-appb-I000597
    Figure PCTKR2020012085-appb-I000597
    Figure PCTKR2020012085-appb-I000598
    Figure PCTKR2020012085-appb-I000598
    Figure PCTKR2020012085-appb-I000599
    Figure PCTKR2020012085-appb-I000599
    Figure PCTKR2020012085-appb-I000600
    Figure PCTKR2020012085-appb-I000600
    [표 32][Table 32]
    Figure PCTKR2020012085-appb-I000601
    Figure PCTKR2020012085-appb-I000601
    Figure PCTKR2020012085-appb-I000602
    Figure PCTKR2020012085-appb-I000602
    Figure PCTKR2020012085-appb-I000603
    Figure PCTKR2020012085-appb-I000603
    Figure PCTKR2020012085-appb-I000604
    Figure PCTKR2020012085-appb-I000604
    Figure PCTKR2020012085-appb-I000605
    Figure PCTKR2020012085-appb-I000605
    Figure PCTKR2020012085-appb-I000606
    Figure PCTKR2020012085-appb-I000606
    Figure PCTKR2020012085-appb-I000607
    Figure PCTKR2020012085-appb-I000607
    [표 33][Table 33]
    Figure PCTKR2020012085-appb-I000608
    Figure PCTKR2020012085-appb-I000608
    Figure PCTKR2020012085-appb-I000609
    Figure PCTKR2020012085-appb-I000609
    Figure PCTKR2020012085-appb-I000610
    Figure PCTKR2020012085-appb-I000610
    Figure PCTKR2020012085-appb-I000611
    Figure PCTKR2020012085-appb-I000611
    Figure PCTKR2020012085-appb-I000612
    Figure PCTKR2020012085-appb-I000612
    Figure PCTKR2020012085-appb-I000613
    Figure PCTKR2020012085-appb-I000613
    Figure PCTKR2020012085-appb-I000614
    Figure PCTKR2020012085-appb-I000614
    [표 34][Table 34]
    Figure PCTKR2020012085-appb-I000615
    Figure PCTKR2020012085-appb-I000615
    Figure PCTKR2020012085-appb-I000616
    Figure PCTKR2020012085-appb-I000616
    Figure PCTKR2020012085-appb-I000617
    Figure PCTKR2020012085-appb-I000617
    Figure PCTKR2020012085-appb-I000618
    Figure PCTKR2020012085-appb-I000618
    Figure PCTKR2020012085-appb-I000619
    Figure PCTKR2020012085-appb-I000619
    Figure PCTKR2020012085-appb-I000620
    Figure PCTKR2020012085-appb-I000620
    Figure PCTKR2020012085-appb-I000621
    Figure PCTKR2020012085-appb-I000621
    [표 35][Table 35]
    Figure PCTKR2020012085-appb-I000622
    Figure PCTKR2020012085-appb-I000622
    Figure PCTKR2020012085-appb-I000623
    Figure PCTKR2020012085-appb-I000623
    Figure PCTKR2020012085-appb-I000624
    Figure PCTKR2020012085-appb-I000624
    Figure PCTKR2020012085-appb-I000625
    Figure PCTKR2020012085-appb-I000625
    Figure PCTKR2020012085-appb-I000626
    Figure PCTKR2020012085-appb-I000626
    Figure PCTKR2020012085-appb-I000627
    Figure PCTKR2020012085-appb-I000627
    Figure PCTKR2020012085-appb-I000628
    Figure PCTKR2020012085-appb-I000628
    [표 36][Table 36]
    Figure PCTKR2020012085-appb-I000629
    Figure PCTKR2020012085-appb-I000629
    Figure PCTKR2020012085-appb-I000630
    Figure PCTKR2020012085-appb-I000630
    Figure PCTKR2020012085-appb-I000631
    Figure PCTKR2020012085-appb-I000631
    Figure PCTKR2020012085-appb-I000632
    Figure PCTKR2020012085-appb-I000632
    Figure PCTKR2020012085-appb-I000633
    Figure PCTKR2020012085-appb-I000633
    Figure PCTKR2020012085-appb-I000634
    Figure PCTKR2020012085-appb-I000634
    Figure PCTKR2020012085-appb-I000635
    Figure PCTKR2020012085-appb-I000635
    상기 표 1 내지 36에 있어서,In Tables 1 to 36,
    Figure PCTKR2020012085-appb-I000636
    은 상기 화학식 1의
    Figure PCTKR2020012085-appb-I000637
    와 상기 화학식 1의
    Figure PCTKR2020012085-appb-I000638
    가 결합되는 부위, 또는 상기 화학식 1의
    Figure PCTKR2020012085-appb-I000639
    와 상기 화학식 1의
    Figure PCTKR2020012085-appb-I000640
    가 결합되는 부위를 의미하고,
    Figure PCTKR2020012085-appb-I000636
    Is in the formula 1
    Figure PCTKR2020012085-appb-I000637
    And of Formula 1
    Figure PCTKR2020012085-appb-I000638
    The site to which is bonded, or of Formula 1
    Figure PCTKR2020012085-appb-I000639
    And of Formula 1
    Figure PCTKR2020012085-appb-I000640
    Means the site to which is bonded,
    *는 상기 화학식 1의
    Figure PCTKR2020012085-appb-I000641
    와 상기 화학식 1의
    Figure PCTKR2020012085-appb-I000642
    가 결합되는 부위를 의미하며,    * Is in the formula 1
    Figure PCTKR2020012085-appb-I000641
    And of Formula 1
    Figure PCTKR2020012085-appb-I000642
    Refers to the site to which is bonded,
    **는 상기 화학식 1의
    Figure PCTKR2020012085-appb-I000643
    와 상기 화학식 1의
    Figure PCTKR2020012085-appb-I000644
    가 결합되는 부위를 의미한다.    ** is in the formula 1
    Figure PCTKR2020012085-appb-I000643
    And of Formula 1
    Figure PCTKR2020012085-appb-I000644
    Refers to the site to which is bonded.
  8. 제1 전극; 상기 제1 전극에 대향하여 구비된 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 청구항 1 내지 7 중 어느 한 항의 화합물을 포함하는 것인 유기 발광 소자.A first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of any one of claims 1 to 7.
  9. 청구항 8에 있어서, 상기 유기물층은 전자주입층, 전자 수송층, 또는 전자 주입 및 수송층을 포함하고, 상기 전자주입층, 전자 수송층, 또는 전자 주입 및 수송층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light-emitting device of claim 8, wherein the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.
  10. 청구항 8에 있어서, 상기 유기물층은 정공차단층을 포함하고, 상기 정공차단층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light-emitting device of claim 8, wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.
  11. 청구항 8에 있어서, 상기 유기물층은 정공주입층, 정공 수송층, 또는 정공 주입 및 수송층을 포함하고, 상기 정공주입층, 정공 수송층, 또는 정공 주입 및 수송층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light-emitting device of claim 8, wherein the organic material layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or a hole injection and transport layer comprises the compound.
PCT/KR2020/012085 2019-09-11 2020-09-08 Compound and organic light emitting device comprising same WO2021049843A1 (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022211500A1 (en) * 2021-03-30 2022-10-06 주식회사 엘지화학 Novel compound and organic light-emitting device using same
US11785847B2 (en) * 2020-10-26 2023-10-10 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
WO2024010336A1 (en) * 2022-07-04 2024-01-11 주식회사 엘지화학 Novel compound and organic light-emitting device using same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102654051B1 (en) * 2019-09-11 2024-04-03 주식회사 엘지화학 Compound and organic light emitting device comprising the same

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150002417A (en) * 2013-06-28 2015-01-07 주식회사 엘지화학 Hetero-cyclic compound and organic light emitting device comprising the same
CN106946852A (en) * 2017-04-26 2017-07-14 江苏三月光电科技有限公司 It is a kind of using triazine and benzimidazole as the organic compound of core and its application on OLED
KR20170138730A (en) * 2016-06-08 2017-12-18 이-레이 옵토일렉트로닉스 테크놀로지 컴퍼니 리미티드 New imidazole compound, material for electronic device use, electroluminescent device, and electronic device thereof
KR20180128417A (en) * 2017-04-20 2018-12-03 장쑤 선에라 테크놀로지 컴퍼니 리미티드 Organic compounds with a core of triazine and benzimidazole as a core and related applications on organic electroluminescent devices
KR20190078533A (en) * 2017-12-26 2019-07-04 엘티소재주식회사 Heterocyclic compound and organic light emitting device comprising the same

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10135513B4 (en) 2001-07-20 2005-02-24 Novaled Gmbh Light-emitting component with organic layers
KR101466150B1 (en) * 2010-12-31 2014-11-27 제일모직 주식회사 Compound for organic photoelectric device and organic photoelectric device including the same
CN108699054B (en) * 2016-03-15 2022-06-28 陶氏环球技术有限责任公司 Organic electroluminescent compound and organic electroluminescent device thereof
KR102654051B1 (en) * 2019-09-11 2024-04-03 주식회사 엘지화학 Compound and organic light emitting device comprising the same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150002417A (en) * 2013-06-28 2015-01-07 주식회사 엘지화학 Hetero-cyclic compound and organic light emitting device comprising the same
KR20170138730A (en) * 2016-06-08 2017-12-18 이-레이 옵토일렉트로닉스 테크놀로지 컴퍼니 리미티드 New imidazole compound, material for electronic device use, electroluminescent device, and electronic device thereof
KR20180128417A (en) * 2017-04-20 2018-12-03 장쑤 선에라 테크놀로지 컴퍼니 리미티드 Organic compounds with a core of triazine and benzimidazole as a core and related applications on organic electroluminescent devices
CN106946852A (en) * 2017-04-26 2017-07-14 江苏三月光电科技有限公司 It is a kind of using triazine and benzimidazole as the organic compound of core and its application on OLED
KR20190078533A (en) * 2017-12-26 2019-07-04 엘티소재주식회사 Heterocyclic compound and organic light emitting device comprising the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11785847B2 (en) * 2020-10-26 2023-10-10 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
WO2022211500A1 (en) * 2021-03-30 2022-10-06 주식회사 엘지화학 Novel compound and organic light-emitting device using same
WO2024010336A1 (en) * 2022-07-04 2024-01-11 주식회사 엘지화학 Novel compound and organic light-emitting device using same

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