WO2023234749A1 - Compound and organic light-emitting device comprising same - Google Patents

Compound and organic light-emitting device comprising same Download PDF

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WO2023234749A1
WO2023234749A1 PCT/KR2023/007638 KR2023007638W WO2023234749A1 WO 2023234749 A1 WO2023234749 A1 WO 2023234749A1 KR 2023007638 W KR2023007638 W KR 2023007638W WO 2023234749 A1 WO2023234749 A1 WO 2023234749A1
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substituted
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김민준
서상덕
송종수
이성재
홍성길
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주식회사 엘지화학
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Priority to CN202380013340.5A priority Critical patent/CN117940423A/en
Publication of WO2023234749A1 publication Critical patent/WO2023234749A1/en

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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Definitions

  • This specification relates to compounds and organic light-emitting devices containing the same.
  • an organic light-emitting device is a light-emitting device using an organic semiconductor material and requires exchange of holes and/or electrons between an electrode and an organic semiconductor material.
  • Organic light-emitting devices can be broadly divided into two types according to their operating principles as follows. First, excitons are formed in the organic layer by photons flowing into the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as current sources (voltage sources). It is a type of light emitting device. The second type is a light-emitting device that applies voltage or current to two or more electrodes to inject holes and/or electrons into the organic semiconductor material layer forming the interface with the electrodes, and operates by the injected electrons and holes.
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them.
  • the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device. For example, it consists of a hole injection layer, a hole transport layer, a light-emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer. You can lose.
  • this organic light-emitting device when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
  • These organic light-emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.
  • Materials used as organic layers in organic light-emitting devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, and electron injection materials, depending on their function.
  • charge transport materials such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, and electron injection materials, depending on their function.
  • color of the light there are blue, green, and red light emitting materials, as well as yellow and orange light emitting materials needed to achieve better natural colors.
  • a host/dopant system can be used as a luminescent material.
  • the principle is that when a small amount of dopant, which has a smaller energy band gap and higher luminous efficiency than the host that mainly constitutes the light-emitting layer, is mixed into the light-emitting layer, excitons generated in the host are transported to the dopant, producing highly efficient light.
  • the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.
  • the materials that make up the organic layer within the device such as hole injection material, hole transport material, light-emitting material, electron suppressor material, electron transport material, and electron injection material, must be stable and efficient materials. As this is supported by , the development of new materials continues to be required.
  • An exemplary embodiment of the present specification provides a compound of Formula 1 below.
  • L1 to L3 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
  • Ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
  • Ar3 is of the formula 2 below,
  • X11 and X12 are the same or different from each other and are each independently CR
  • R is hydrogen or deuterium
  • X9 or It is a cyclic arylene group, or a substituted or unsubstituted heteroarylene group
  • Ar1 and Ar2 are the same or different from each other, and each independently represents a substituted or unsubstituted polycyclic aryl group or a substituted or unsubstituted heteroaryl group.
  • a first electrode a second electrode provided opposite the first electrode; and an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the above-mentioned compounds.
  • the compound of the present invention can be used as a material for the organic layer of an organic light-emitting device.
  • an organic light-emitting device including the compound of the present invention an organic light-emitting device with high efficiency, low voltage, and long lifespan characteristics can be obtained, and when the compound of the present invention is included in the electron transport layer of the organic light-emitting device, intramolecular Due to its high polarity, the effect of electron transfer is high, making it possible to manufacture organic light-emitting devices with long-life characteristics.
  • FIG. 1 and 2 show examples of organic light-emitting devices according to the present invention.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent.
  • the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; Cyano group (-CN); silyl group; boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents.
  • a substituent group in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.
  • halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).
  • the silyl group is deuterium; Substituted or unsubstituted alkyl group; Alternatively, it may be substituted or unsubstituted with a substituted or unsubstituted aryl group.
  • the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.
  • the boron group is deuterium; Substituted or unsubstituted alkyl group; Alternatively, it may be substituted or unsubstituted with a substituted or unsubstituted aryl group.
  • the boron group specifically includes, but is not limited to, dimethyl boron group, diethyl boron group, t-butylmethyl boron group, diphenyl boron group, and phenyl boron group.
  • the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the carbon number of the alkyl group is 1 to 30. According to another embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, and octyl groups.
  • the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine group and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine groups include methylamine groups; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methylanthracenylamine 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-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, etc.
  • N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group.
  • N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group.
  • N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group.
  • alkyl groups in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group are the same as examples of the alkyl groups described above.
  • the alkylthioxy group includes methylthioxy group; ethylthioxy group; tert-butylthioxy group; hexylthioxy group; Octylthioxy groups, etc.
  • examples of alkylsulfoxy groups include mesyl; ethyl sulfoxy group; Propyl alcohol oxygen group; Butyl sulfoxy group, etc., but is not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, or terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylene group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
  • the heteroaryl group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30.
  • heterocyclic groups include pyridine group, pyrrole group, pyrimidine group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, carbazole group, etc. However, it is not limited to these.
  • the arylene group is the same as defined for the aryl group above, except that it is a divalent group.
  • heteroarylene group is the same as defined for the heteroaryl group above, except that it is a divalent group.
  • Formula 1 is any one of Formulas 1-1 to 1-6 below.
  • L1 to L3, X1 to X12, Ar1 and Ar2 are as defined in Formulas 1 and 2 above.
  • Formula 2 is any one of the structures below.
  • one of the carbons included in each structure is bonded to L3 in Chemical Formula 1.
  • Formula 2 is any one of the structures below.
  • one of the carbons included in each structure is bonded to L3 in Chemical Formula 1.
  • one of X1 to X4 is N.
  • X1 to X4 among X1 to X4, X2 or X3 is N.
  • X1 is N
  • one of X2 to X12 is C combined with L3
  • the others are CR.
  • X2 is N, X1, and one of X3 to X12 is C combined with L3, and the others are CR.
  • X3 is N
  • one of X1, X2, and X4 to X12 is C that combines with L3, and the others are CR.
  • X4 is N
  • X5 to X12 is C that combines with L3
  • the others are CR.
  • X5 is N
  • one of X1 to X4 and X6 to X12 is C that combines with L3, and the others are CR.
  • X6 is N
  • one of X1 to X5 is C that combines with L3
  • the others are CR.
  • X7 is N
  • one of X1 to X6, and X8 to X12 is C that combines with L3, and the others are CR.
  • X8 is N
  • one of X1 to X7, and X9 to X12 is C that combines with L3, and the others are CR.
  • X9 is N
  • one of X1 to X8 and X10 to X12 is C that combines with L3, and the others are CR.
  • X10 is N
  • one of X1 to X9, X11, and X12 is C that combines with L3, and the others are CR.
  • L1 to L3 are the same as or different from each other, and each independently is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 30 carbon atoms. It is a heteroarylene group.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 20 carbon atoms. It is a heteroarylene group.
  • L1 to L3 are the same as or different from each other and are each independently a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
  • L1 to L3 are the same as or different from each other and are each independently a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
  • L1 to L3 are the same as or different from each other, and are each independently directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted biphenyl group.
  • Divalent terphenyl group substituted or unsubstituted divalent naphthyl group, substituted or unsubstituted divalent anthracene group, substituted or unsubstituted divalent phenanthrene group, substituted or unsubstituted divalent pyrene group, substituted or unsubstituted divalent carbazole group, substituted or unsubstituted divalent pyridine group, substituted or unsubstituted divalent pyrimidine group, substituted or unsubstituted divalent triazine group, substituted or unsubstituted divalent dibenzofuran group, substituted Or an unsubstituted divalent dibenzothiophene group, a substituted or unsubstituted divalent furan group, a substituted or unsubstituted divalent thiophene group, a substituted or unsubstituted divalent benzimidazole group, or a substituted or unsubstituted
  • L1 to L3 are the same as or different from each other, and are each independently directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted biphenyl group.
  • Divalent naphthyl group substituted or unsubstituted divalent terphenyl group, substituted or unsubstituted divalent carbazole group, substituted or unsubstituted divalent pyridine group, substituted or unsubstituted divalent pyrimidine group, substituted or unsubstituted divalent triazine group, substituted or unsubstituted divalent dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted divalent furan group, substituted or unsubstituted divalent thiophene group, a substituted or unsubstituted divalent benzimidazole group, or a substituted or unsubstituted divalent benzoxazole group.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, Divalent phenanthrene group, divalent pyrene group, divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, divalent dibenzofuran group, divalent dibenzothiophene group, divalent furan group, a divalent thiophene group, a divalent benzimidazole group, or a divalent benzoxazole group.
  • L1 to L3 are the same or different from each other, and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent terphenyl group, a divalent carbazole group, A divalent pyridine group, a divalent pyrimidine group, a divalent triazine group, a dibenzofuran group, a dibenzothiophene group, a divalent furan group, a divalent thiophene group, a divalent benzimidazole group, or It is a divalent benzoxazole group.
  • L1 to L3 are the same as or different from each other, and are each independently directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted biphenyl group. It is a divalent naphthyl group, or a substituted or unsubstituted divalent terphenyl group.
  • L1 to L3 are the same or different from each other, and are each independently directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a divalent substituted or It is an unsubstituted naphthyl group.
  • L1 to L3 are the same as or different from each other and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, or a divalent terphenyl group.
  • L1 to L3 are the same or different from each other and are each independently a direct bond, a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, Divalent phenanthrene group, divalent pyrene group, divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, divalent dibenzofuran group, divalent dibenzothiophene group, divalent furan group, a divalent thiophene group, a divalent benzimidazole group, or a divalent benzoxazole group.
  • L1 to L3 are direct bonds.
  • L1 to L3 are phenylene groups.
  • L1 to L3 are divalent naphthyl groups.
  • L1 to L3 are divalent biphenyl groups
  • L1 to L3 are substituted or unsubstituted phenylene groups.
  • L1 to L3 are substituted or unsubstituted divalent naphthyl groups.
  • L1 to L3 are substituted or unsubstituted divalent biphenyl groups.
  • L1 and L2 are the same as each other and are a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.
  • L1 and L2 are the same as each other and are a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.
  • L1 and L2 are the same as each other and are a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
  • L1 and L2 are the same as each other and are a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
  • L1 and L2 are the same as each other, and are directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or Unsubstituted divalent naphthyl group, substituted or unsubstituted divalent anthracene group, substituted or unsubstituted divalent phenanthrene group, substituted or unsubstituted divalent pyrene group, substituted or unsubstituted divalent carbazole group, substituted or an unsubstituted divalent pyridine group, a substituted or unsubstituted divalent pyrimidine group, a substituted or unsubstituted divalent triazine group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsub
  • L1 and L2 are the same as each other, and are a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, a divalent phenanthrene group, 2 Divalent pyrene group, divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, divalent dibenzofuran group, divalent dibenzothiophene group, divalent furan group, divalent thiophene group , a divalent benzimidazole group, or a divalent benzoxazole group.
  • L1 and L2 are different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 30 carbon atoms. It is an arylene group.
  • L1 and L2 are different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 20 carbon atoms. It is an arylene group.
  • L1 and L2 are different from each other and are each independently a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
  • L1 and L2 are different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 20 carbon atoms. It is an arylene group.
  • L1 and L2 are different from each other and are each independently directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent group.
  • Terphenyl group substituted or unsubstituted divalent naphthyl group, substituted or unsubstituted divalent anthracene group, substituted or unsubstituted divalent phenanthrene group, substituted or unsubstituted divalent pyrene group, substituted or unsubstituted 2 A divalent carbazole group, a substituted or unsubstituted divalent pyridine group, a substituted or unsubstituted divalent pyrimidine group, a substituted or unsubstituted divalent triazine group, a substituted or unsubstituted divalent dibenzofuran group, substituted or unsubstituted A substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted divalent furan group, a substituted or unsubstituted divalent thiophene group, a substituted or unsubstituted divalent benzimidazole
  • L1 and L2 are different from each other and are each independently a direct bond, a phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent naphthyl group.
  • L1 and L2 are different from each other and are each independently a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
  • L1 and L2 are different from each other and each independently, a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, a divalent Phenanthrene group, divalent pyrene group, divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, divalent dibenzofuran group, divalent dibenzothiophene group, divalent furan group, It is a divalent thiophene group, a divalent benzimidazole group, or a divalent benzoxazole group.
  • L1 and L2 are different from each other and are each independently a direct bond, a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.
  • L1 and L2 are a direct bond.
  • L1 and L2 are phenylene groups.
  • L1 and L2 are divalent naphthyl groups.
  • L1 and L2 are divalent biphenyl groups.
  • L1 is a direct bond.
  • L1 is a phenylene group.
  • L1 is a divalent naphthyl group.
  • L1 is a divalent biphenyl group.
  • L2 is a direct bond.
  • L2 is a phenylene group.
  • L2 is a divalent naphthyl group.
  • L2 is a divalent biphenyl group.
  • L3 is a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
  • L3 is a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
  • L3 is a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, a divalent phenanthrene group, a divalent pyrene group, 2 divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, dibenzofuran group, dibenzothiophene group, divalent furan group, divalent thiophene group, divalent benzimi It is a polyazole group, or a divalent benzoxazole group. It is a benzoxazole group. It is a benzoxazole group. It is a benzoxazole group. Accordingly, L3 is a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, or a divalent terphenyl group.
  • L3 is a direct bond, a phenylene group, or a divalent naphthyl group.
  • L3 is a direct bond.
  • L3 is a phenylene group, a divalent naphthyl group, a divalent biphenyl group, or a divalent terphenyl group.
  • L3 is a phenylene group or a divalent naphthyl group.
  • L3 is a direct bond.
  • L3 is a phenylene group.
  • L3 is a divalent naphthyl group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. .
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms. .
  • Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group of 6 to 20 carbon atoms, or a heteroaryl group of 3 to 20 carbon atoms substituted with an aryl group of 6 to 30 carbon atoms. .
  • Ar1 and Ar2 are the same as or different from each other, and are each independently substituted or provided with an aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently substituted or provided with an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluoranthene group, a phenanthrene group, a triphenylene group, and a dibenzofuran group.
  • a dibenzothiophene group a benzofuropyridine group, a benzothiopyridine group, a benzonaphthofuran group, or a carbazole group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.
  • At least one of Ar1 and Ar2 is a substituted or unsubstituted aryl group with three or more rings, or a substituted or unsubstituted heteroaryl group with two or more rings.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluoranthene group, a phenanthrene group, a triphenylene group, and a dibenzofuran group.
  • a dibenzothiophene group a benzofuropyridine group, a benzothiopyridine group, a benzonaphthofuran group, or a carbazole group substituted or unsubstituted by a phenyl group.
  • L3 is a direct bond, a substituted or unsubstituted polycyclic arylene group having 10 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms,
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  • X9 or is a direct bond when X9 or is a direct bond, a polycyclic arylene group having 10 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms,
  • Ar1 and Ar2 are the same or different from each other, and are each independently a polycyclic aryl group having 10 to 30 carbon atoms; Or it is a heteroaryl group having 3 to 30 carbon atoms that is substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.
  • X9 or is a direct bond when X9 or is a direct bond, a polycyclic arylene group having 10 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms,
  • Ar1 and Ar2 are the same or different from each other, and are each independently a polycyclic aryl group having 10 to 30 carbon atoms; Or it is a phenyl group or a naphthyl group, a heteroaryl group having 3 to 30 carbon atoms.
  • Ar1 and Ar2 are the same or different from each other, and are each independently a biphenyl group, naphthyl group, terphenyl group, fluoranthene group, phenanthrene group, triphenylene group, dibenzofuran group, dibenzothiophene group, and benzofuropyridine group. , a benzothiopyridine group, a benzonaphthofuran group, or a carbazole group substituted or unsubstituted with a phenyl group.
  • R is hydrogen or deuterium.
  • R is hydrogen
  • R is deuterium
  • Formula 1 is one of the structural formulas below.
  • Substituents of the compound of Formula 1 may be combined by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.
  • the organic light emitting device includes a first electrode; a second electrode provided opposite the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the above-described compound.
  • the organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.
  • the compound may be formed into 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 application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer.
  • the structure of the organic light emitting device is not limited to this and may include fewer or more organic material layers.
  • the organic material layer includes a light-emitting layer.
  • the light-emitting layer includes the compound of Formula 1 as a host.
  • the light emitting layer includes a dopant and a host.
  • the light-emitting layer includes a dopant and a host at a mass ratio of 1:99 to 30:70.
  • the light-emitting layer includes a dopant and a host at a mass ratio of 1:99 to 25:75.
  • the light-emitting layer includes a dopant and a host at a mass ratio of 1:99 to 20:80.
  • the light-emitting layer includes a dopant and a host at a mass ratio of 1:99 to 15:85.
  • the light-emitting layer includes a dopant and a host at a mass ratio of 1:99 to 5:95.
  • the organic material layer may include one or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more of the layers includes the compound represented by Formula 1 can do.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Formula 1.
  • the electron injection and transport layer includes the compound of Formula 1 and a metal complex.
  • the electron injection and transport layer includes the compound of Formula 1 and lithium quinolate.
  • the electron injection and transport layer may include the compound of Formula 1 and the metal complex at a weight ratio of 1:10 to 10:1.
  • the electron injection and transport layer may include the compound of Formula 1 and the metal complex at a weight ratio of 1:5 to 5:1.
  • the electron injection and transport layer may include the compound of Formula 1 and the metal complex at a weight ratio of 1:3 to 3:1.
  • the electron injection and transport layer may include the compound of Formula 1 and lithium quinolate at a weight ratio of 1:10 to 10:1.
  • the electron injection and transport layer may include the compound of Formula 1 and lithium quinolate in a weight ratio of 1:5 to 5:1.
  • the electron injection and transport layer may include the compound of Formula 1 and lithium quinolate at a weight ratio of 1:3 to 3:1.
  • the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound of Formula 1.
  • the organic material layer may include one or more layers among a hole injection layer, a hole transport layer, and a layer that performs both hole injection and hole transport, and one or more of the layers is represented by the formula (1) It may contain compounds.
  • the organic material layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include the compound represented by Formula 1.
  • a hole injection layer or a hole transport layer is additionally provided between the light emitting layer and the organic material.
  • a hole injection layer or a hole transport layer is additionally provided between the light emitting layer and the organic material.
  • the first electrode is an anode and the second electrode is a cathode.
  • the first electrode is a cathode and the second electrode is an anode.
  • the structure of the organic light emitting device of the present invention may have the same structure as shown in FIG. 1, but is not limited thereto.
  • Figure 1 illustrates the structure of an organic light-emitting device in which an anode 2, an organic material layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound represented by Formula 1 may be included in the organic layer 3.
  • an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), a hole blocking layer (9), an electron injection and transport layer The structure of an organic light emitting device in which the cathode 10) and the cathode 4 are sequentially stacked is illustrated. In this structure, the compound represented by Formula 1 may be included in the light-emitting layer 8.
  • the organic light emitting device deposits a metal, a conductive metal oxide, or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • An anode is formed by depositing a layer on which a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, a light emitting layer, an electron transport layer, an electron injection layer, and a layer that performs both electron transport and electron injection are selected from the group consisting of It can be manufactured by forming an organic material layer containing one or more selected layers and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, but is not limited to this and may have a single-layer structure.
  • the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.
  • the anode is an electrode that injects holes
  • the anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer.
  • anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combination of metal and 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 are included, but are not limited to these.
  • the cathode is an electrode that injects electrons
  • the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer.
  • Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof;
  • There are multi-layer structure materials such as LiF/Al or LiO 2 /Al, but they are not limited to these.
  • the hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage.
  • HOMO highest occupied
  • the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage to preventing this.
  • the hole injection layer includes, but is not limited to, a compound represented by the following formula HI-1.
  • R400 to R402 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with adjacent groups to form a substituted or unsubstituted ring,
  • L402 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  • R400 to R402 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
  • R402 is a phenyl group substituted with a carbazole group or an arylamine group; Biphenyl group substituted with carbazole group or arylamine group; and any one selected from the group consisting of combinations thereof.
  • R400 and R401 are the same or different from each other and are each independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.
  • R400 and R401 are the same or different from each other, and each independently represents an aryl group substituted or unsubstituted by an alkyl group.
  • R400 and R401 are the same or different from each other, and are each independently a phenyl group or a dimethylfluorene group.
  • the formula HI-1 is selected from the following compounds.
  • the hole injection layer includes a compound represented by the following formula HI-2, but is not limited thereto.
  • X'1 to X'3 are the same or different from each other and are each independently hydrogen, deuterium, or halogen group,
  • R309 to R314 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • x1' to x3' are each integers from 1 to 4, and when they are 2 or more, the substituents in parentheses are the same or different from each other.
  • X'1 to X'3 are halogen groups.
  • X'1 to X'3 are F or Cl.
  • X'1 to X'3 are F.
  • R309 to R314 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted amine group.
  • R309 to R314 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or nitrile.
  • R309 to R314 are nitrile groups.
  • the formula HI-2 is represented by the following compound.
  • the hole transport layer may play a role in facilitating the transport of holes.
  • the hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.
  • the hole transport layer includes a compound represented by the following chemical formula HT-2, but is not limited thereto.
  • R403 to R406 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with adjacent groups to form a substituted or unsubstituted ring,
  • L403 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
  • l403 is an integer from 1 to 3, and if l403 is 2 or more, L403 is the same or different from each other.
  • R403 to R406 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
  • R403 to R406 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms.
  • R403 to R406 are the same as or different from each other, and each independently represents a phenyl group, a biphenyl group, or a naphthyl group.
  • R403 to R406 are the same or different from each other, and each independently represents a phenyl group.
  • L403 is an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms substituted with an arylene group.
  • L403 is a divalent carbazole group unsubstituted or substituted with a phenylene group, a divalent biphenyl group, or an aryl group.
  • L403 is a divalent carbazole group substituted with a naphthyl group.
  • the formula HT-2 is selected from the following compounds.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the electron blocking layer may be made of the spiro compound described above or a material known in the art.
  • the electron blocking layer includes, but is not limited to, a compound represented by the following formula EB-1.
  • L311 to L313 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R311 to R313 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and combinations thereof, or is combined with adjacent groups to form a substituted or unsubstituted ring.
  • R311 to R313 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
  • R311 to R313 are the same as or different from each other, and are each independently a biphenyl group; Or it is a phenanthrene group.
  • L311 to L313 are the same or different from each other and are each independently directly bonded; Arylene group; Or it is a heteroarylene group.
  • L311 to L313 are the same or different from each other and are each independently directly bonded; Or it is a phenylene group.
  • the formula EB-1 is represented by the following compound.
  • the light-emitting layer may emit red, green, or blue light and may be made of a phosphorescent material or a fluorescent material.
  • the light-emitting material is a material capable of emitting light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Compounds of the benzoxazole, benzthiazole and benzimidazole series Compounds of the benzoxazole, benzthiazole and benzimidazole series
  • Poly(p-phenylenevinylene) (PPV) series polymer Poly(p-phenylenevinylene) (PPV) series polymer
  • Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
  • the light-emitting dopants include PIQIr(acac)(bis(1-phenylsoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), and PQIr(tris(1-phenylquinoline)iridium).
  • phosphorescent materials such as PtOEP (octaethylporphyrin platinum), or fluorescent materials such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but are not limited to these.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used as the light-emitting dopant.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum)
  • Alq3 tris(8-hydroxyquinolino)aluminum
  • the light-emitting dopant may be a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited to these.
  • a metal complex may be used as the dopant.
  • the dopant may be an iridium complex.
  • the iridium complex used as the dopant may have any one of the structures below, but is not limited thereto.
  • the structure specified above is not limited to the dopant compound.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
  • the electron transport layer may play a role in facilitating the transport of electrons.
  • the electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these.
  • the thickness of the electron transport layer may be 1 to 50 nm.
  • the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There are benefits to this.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an excellent electron injection effect from the cathode, a light emitting layer or a light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also has an excellent electron injection effect from the cathode to the light emitting layer or light emitting material. , Compounds with excellent thin film forming ability are preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals.
  • fluorenone anthraquinodimethane
  • diphenoquinone diphenoquinone
  • thiopyran dioxide oxazole
  • oxadiazole triazole
  • imidazole imidazole
  • perylenetetracarboxylic acid
  • metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, Tris(2-methyl-8-hydroxyquinolinato)aluminum, Tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.
  • the electron injection and transport layer includes, but is not limited to, a compound of the following formula ET-1.
  • At least one of Z11 to Z13 is N, the others are CH,
  • L601 is directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar601 to Ar603 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • l601 is an integer from 1 to 5, and when l601 is 2 or more, the 2 or more L601s are the same or different from each other.
  • L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L601 is a phenylene group; Biphenylylene group; Or it is a naphthylene group.
  • Ar601 and Ar602 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar601 and Ar602 are phenyl groups.
  • Ar603 is a heteroaryl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar603 is a heteroaryl group substituted or unsubstituted with a phenyl group.
  • Ar603 is a triazine group substituted or unsubstituted by a phenyl group.
  • the formula ET-1 is represented by the following compound
  • the hole blocking layer of this specification is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.
  • the hole blocking layer includes a compound of the following formula HB-1.
  • At least one of Z1 to Z3 is N, the others are CH,
  • L601 and L602 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar601 to Ar603 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L601 and L602 are the same as or different from each other, and are each independently a phenylene group; Biphenylylene group; Or it is a naphthylene group.
  • Ar601 to Ar603 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms. .
  • Ar601 to Ar603 are phenyl groups or triphenylene groups.
  • the formula HB-1 is represented by the following compound.
  • the organic light emitting device may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
  • the organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.
  • Trz2 (15g, 35.9mmol) and sub2 (13.4g, 37.7mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.9g, 107.7mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • Trz16 (15g, 35.9mmol) and sub16 (16.3g, 37.7mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.9g, 107.7mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 ⁇ was placed in distilled water with a detergent dissolved in it and washed ultrasonically.
  • a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • the following HI-1 compound was formed as a hole injection layer to a thickness of 1150 ⁇ , and the following A-1 compound was p-doped at a concentration of 1.5%.
  • the following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer with a film thickness of 800 ⁇ .
  • the following EB-1 compound was vacuum deposited to a film thickness of 150 ⁇ on the hole transport layer to form an electron blocking layer.
  • Compound 1 as a host and Compound Dp-7 as a dopant were vacuum deposited on the EB-1 deposition film at a weight ratio of 98:2 to form a red light-emitting layer with a thickness of 400 ⁇ .
  • the following HB-1 compound was vacuum deposited to a film thickness of 30 ⁇ on the light emitting layer to form a hole blocking layer.
  • the following ET-1 compound and the following LiQ compound were vacuum deposited on the hole blocking layer at a weight ratio of 2:1 to form an electron injection and transport layer with a thickness of 300 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron injection and transport layer.
  • the deposition rate of organic matter was maintained at 0.4 ⁇ 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride of the cathode was maintained at 0.3 ⁇ /sec
  • the deposition rate of aluminum was maintained at 2 ⁇ /sec
  • the vacuum degree during deposition was 2 ⁇ 10 -7 ⁇
  • An organic light emitting device was manufactured by maintaining 5 ⁇ 10 -6 torr.
  • An organic light-emitting device was manufactured in the same manner as Example 1, except that the compound of Formula 1 was used as the host shown in Table 1 in the organic light-emitting device of Example 1.
  • An organic light-emitting device was manufactured in the same manner as Example 1, except that the comparative example compound was used as the host shown in Table 2 in the organic light-emitting device of Example 1.
  • Compounds B-1 and B-2 differ from the compounds of Formula 1 herein, where X11 or X12 is N.
  • Examples 1 to 53 show characteristics of high efficiency and long life compared to Comparative Examples 1 and 2.
  • R is a phenyl group rather than hydrogen or deuterium, and in this case, it can be seen that it is not better than Examples 1 to 53 in terms of voltage, efficiency, and lifespan.
  • the red organic light emitting device of Example 1 used widely used materials and had a structure using compound [EB-1] as an electron blocking layer and Dp-7 as a red dopant.

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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 소자Compounds and organic light-emitting devices containing them
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. This specification relates to compounds and organic light-emitting devices containing the same.
본 출원은 2022년 06월 03일 한국특허청에 제출된 한국 특허 출원 제10-2022-0068224호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0068224 filed with the Korea Intellectual Property Office on June 3, 2022, the entire contents of which are included in this specification.
본 명세서에서, 유기 발광 소자란 유기 반도체 물질을 이용한 발광 소자로서, 전극과 유기 반도체 물질 사이에서의 정공 및/또는 전자의 교류를 필요로 한다. 유기 발광 소자는 동작 원리에 따라 하기와 같이 크게 두 가지로 나눌 수 있다. 첫째는 외부의 광원으로부터 소자로 유입된 광자에 의하여 유기물층에서 엑시톤(exiton)이 형성되고, 이 엑시톤이 전자와 정공으로 분리되고, 이 전자와 정공이 각각 다른 전극으로 전달되어 전류원(전압원)으로 사용되는 형태의 발광 소자이다. 둘째는 2개 이상의 전극에 전압 또는 전류를 가하여 전극과 계면을 이루는 유기 반도체 물질층에 정공 및/또는 전자를 주입하고, 주입된 전자와 정공에 의하여 작동하는 형태의 발광 소자이다.In this specification, an organic light-emitting device is a light-emitting device using an organic semiconductor material and requires exchange of holes and/or electrons between an electrode and an organic semiconductor material. Organic light-emitting devices can be broadly divided into two types according to their operating principles as follows. First, excitons are formed in the organic layer by photons flowing into the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as current sources (voltage sources). It is a type of light emitting device. The second type is a light-emitting device that applies voltage or current to two or more electrodes to inject holes and/or electrons into the organic semiconductor material layer forming the interface with the electrodes, and operates by the injected electrons and holes.
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, 전자억제층, 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. 이러한 유기 발광 소자는 자발광, 고휘도, 고효율, 낮은 구동 전압, 넓은 시야각, 높은 콘트라스트 등의 특성을 갖는 것으로 알려져 있다.In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device. For example, it consists of a hole injection layer, a hole transport layer, a light-emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer. You can lose. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows. These organic light-emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.
유기 발광 소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하 수송 재료, 예컨대 정공 주입 재료, 정공 수송 재료, 전자 억제 물질, 전자 수송 재료, 전자 주입 재료 등으로 분류될 수 있다. 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료가 있다.Materials used as organic layers in organic light-emitting devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, and electron injection materials, depending on their function. Depending on the color of the light, there are blue, green, and red light emitting materials, as well as yellow and orange light emitting materials needed to achieve better natural colors.
또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도펀트를 발광층에 소량 혼합하면, 호스트에서 발생한 엑시톤이 도펀트로 수송되어 효율이 높은 빛을 내는 것이다. 이 때 호스트의 파장이 도펀트의 파장대로 이동하므로, 이용하는 도펀트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material. The principle is that when a small amount of dopant, which has a smaller energy band gap and higher luminous efficiency than the host that mainly constitutes the light-emitting layer, is mixed into the light-emitting layer, excitons generated in the host are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.
전술한 유기 발광 소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공 주입 물질, 정공 수송 물질, 발광 물질, 전자 억제 물질, 전자 수송 물질, 전자 주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되므로 새로운 재료의 개발이 계속 요구되고 있다.In order to fully demonstrate the excellent characteristics of the above-described organic light-emitting device, the materials that make up the organic layer within the device, such as hole injection material, hole transport material, light-emitting material, electron suppressor material, electron transport material, and electron injection material, must be stable and efficient materials. As this is supported by , the development of new materials continues to be required.
본 명세서에는 화합물 및 이를 포함하는 유기 발광 소자가 기재된다. Disclosed herein are compounds and organic light-emitting devices containing the same.
본 명세서의 일 실시상태는 하기 화학식 1의 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound of Formula 1 below.
[화학식 1][Formula 1]
Figure PCTKR2023007638-appb-img-000001
Figure PCTKR2023007638-appb-img-000001
상기 화학식 1에 있어서, In Formula 1,
L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합, 치환 또는 비치환된 아릴렌기 또는 치환 또는 비치환된 헤테로아릴렌기이고, L1 to L3 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이고, Ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
Ar3은 하기 화학식 2이고,Ar3 is of the formula 2 below,
[화학식 2][Formula 2]
Figure PCTKR2023007638-appb-img-000002
Figure PCTKR2023007638-appb-img-000002
상기 화학식 2에 있어서,In Formula 2,
X1 내지 X10 중 어느 하나는 N이고, 나머지는 서로 같거나 상이하고 각각 독립적으로 N 또는 CR이고, Any one of X1 to
X11 및 X12은 서로 같거나 상이하고, 각각 독립적으로 CR이고, X11 and X12 are the same or different from each other and are each independently CR,
X11, X12 및 X1 내지 X10 중 N이 아닌 나머지 중 하나는 L3과 결합하는 C이고, Among X11, X12, and X1 to
R은 수소, 또는 중수소이고,R is hydrogen or deuterium,
X9 또는 X10가 N일 때, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴렌기 또는 치환 또는 비치환된 헤테로아릴렌기이고, L3은 직접결합, 치환 또는 비치환된 다환의 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이고, Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 다환의 아릴기 또는 치환 또는 비치환된 헤테로아릴기이다. When X9 or It is a cyclic arylene group, or a substituted or unsubstituted heteroarylene group, and Ar1 and Ar2 are the same or different from each other, and each independently represents a substituted or unsubstituted polycyclic aryl group or a substituted or unsubstituted heteroaryl group.
또한, 본 발명의 일 실시상태에 따르면, 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상이 전술한 화합물을 포함하는 유기 발광 소자를 제공한다. Additionally, according to an exemplary embodiment of the present invention, a first electrode; a second electrode provided opposite the first electrode; and an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the above-mentioned compounds.
본 발명의 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 본 발명의 화합물을 포함하여 유기 발광 소자를 제조하는 경우, 고효율, 저전압 및 장수명 특성을 갖는 유기 발광 소자를 얻을 수 있으며, 본 발명의 화합물을 유기 발광 소자의 전자 수송층에 포함하는 경우, 분자 내 분극성이 높아 전자전달의 효과가 높아서 장수명 특성을 가지는 유기 발광 소자를 제조할 수 있다.The compound of the present invention can be used as a material for the organic layer of an organic light-emitting device. When manufacturing an organic light-emitting device including the compound of the present invention, an organic light-emitting device with high efficiency, low voltage, and long lifespan characteristics can be obtained, and when the compound of the present invention is included in the electron transport layer of the organic light-emitting device, intramolecular Due to its high polarity, the effect of electron transfer is high, making it possible to manufacture organic light-emitting devices with long-life characteristics.
도 1 및 2는 본 발명에 따른 유기 발광 소자의 예를 도시한 것이다.1 and 2 show examples of organic light-emitting devices according to the present invention.
[부호의 설명][Explanation of symbols]
1: 기판 1: substrate
2: 양극2: anode
3: 유기물층3: Organic layer
4: 음극4: cathode
5: 정공주입층5: Hole injection layer
6: 정공수송층 6: Hole transport layer
7: 전자차단층 7: Electronic blocking layer
8: 발광층8: Light-emitting layer
9: 정공저지층9: Hole blocking layer
10: 전자주입 및 수송층10: Electron injection and transport layer
이하 본 명세서에 대하여 더욱 상세히 설명한다. Hereinafter, this specification will be described in more detail.
본 명세서에 있어서, 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 this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.
본 명세서에 있어서, 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 said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of substituents in this specification are described below, but are not limited thereto.
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 동일하거나 상이할 수 있다.The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기(-CN); 실릴기; 붕소기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 사이클로알킬기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 도 있다.As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Cyano group (-CN); silyl group; boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents. For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of the above substituents are described below, but are not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소(F), 염소(Cl), 브롬(Br) 또는 요오드(I)가 있다.In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).
본 명세서에 있어서, 실릴기는 중수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기 등으로 치환 또는 비치환될 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group is deuterium; Substituted or unsubstituted alkyl group; Alternatively, it may be substituted or unsubstituted with a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.
본 명세서에 있어서, 붕소기는 중수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기로 치환 또는 비치환될 수 있다. 상기 붕소기는 구체적으로 디메틸붕소기, 디에틸붕소기, t-부틸메틸붕소기, 디페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In this specification, the boron group is deuterium; Substituted or unsubstituted alkyl group; Alternatively, it may be substituted or unsubstituted with a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, dimethyl boron group, diethyl boron group, t-butylmethyl boron group, diphenyl boron group, and phenyl boron group.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 30이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, 이소부틸기, tert-부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the carbon number of the alkyl group is 1 to 30. According to another embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, and octyl groups.
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-메틸안트라세닐아민기; 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 this specification, the amine group is -NH 2 ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine group and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine groups; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methylanthracenylamine 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-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, etc., but is not limited thereto.
본 명세서에 있어서, N-알킬아릴아민기는 아민기의 N에 알킬기 및 아릴기가 치환된 아민기를 의미한다.In the present specification, N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group.
본 명세서에 있어서, N-아릴헤테로아릴아민기는 아민기의 N에 아릴기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group.
본 명세서에 있어서, N-알킬헤테로아릴아민기는 아민기의 N에 알킬기 및 헤테로아릴기가 치환된 아민기를 의미한다.In the present specification, N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group.
본 명세서에 있어서, 알킬아민기, N-아릴알킬아민기, 알킬티옥시기, 알킬술폭시기, N-알킬헤테로아릴아민기 중의 알킬기는 전술한 알킬기의 예시와 같다. 구체적으로 알킬티옥시기로는 메틸티옥시기; 에틸티옥시기; tert－부틸티옥시기; 헥실티옥시기; 옥틸티옥시기 등이 있고, 알킬술폭시기로는 메실; 에틸술폭시기; 프로필술폭시기; 부틸술폭시기 등이 있으나, 이에 한정되는 것은 아니다.In this specification, the alkyl groups in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group are the same as examples of the alkyl groups described above. Specifically, the alkylthioxy group includes methylthioxy group; ethylthioxy group; tert-butylthioxy group; hexylthioxy group; Octylthioxy groups, etc., and examples of alkylsulfoxy groups include mesyl; ethyl sulfoxy group; Propyl alcohol oxygen group; Butyl sulfoxy group, etc., but is not limited thereto.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필기, 사이클로부틸기, 사이클로펜틸기, 사이클로헥실기, 사이클로헵틸기, 사이클로옥틸기 등이 있으나, 이에 한정되지 않는다. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 트리페닐렌기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, or terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylene group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
본 명세서에 있어서, 헤테로아릴기는 이종원자로 N, O, P, S, Si 및 Se 중 1개 이상을 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로고리기의 탄소수는 2 내지 30이다. 헤테로고리기의 예로는 피리딘기, 피롤기, 피리미딘기, 피리다지닐기, 퓨란기, 티오펜기, 이미다졸기, 피라졸기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heteroaryl group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. Examples of heterocyclic groups include pyridine group, pyrrole group, pyrimidine group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, carbazole group, etc. However, it is not limited to these.
본 명세서에 있어서, 아릴렌기는 2가기인 것을 제외하고, 상기 아릴기에서 정의한 바와 같다.In the present specification, the arylene group is the same as defined for the aryl group above, except that it is a divalent group.
본 명세서에 있어서, 헤테로아릴렌기는 2가기인 것을 제외하고, 상기 헤테로아릴기에서 정의한 바와 같다.In the present specification, the heteroarylene group is the same as defined for the heteroaryl group above, except that it is a divalent group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 아래 화학식 1-1 내지 1-6 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one of Formulas 1-1 to 1-6 below.
[화학식 1-1][Formula 1-1]
Figure PCTKR2023007638-appb-img-000003
Figure PCTKR2023007638-appb-img-000003
[화학식 1-2][Formula 1-2]
Figure PCTKR2023007638-appb-img-000004
Figure PCTKR2023007638-appb-img-000004
[화학식 1-3][Formula 1-3]
Figure PCTKR2023007638-appb-img-000005
Figure PCTKR2023007638-appb-img-000005
[화학식 1-4][Formula 1-4]
Figure PCTKR2023007638-appb-img-000006
Figure PCTKR2023007638-appb-img-000006
[화학식 1-5][Formula 1-5]
Figure PCTKR2023007638-appb-img-000007
Figure PCTKR2023007638-appb-img-000007
[화학식 1-6][Formula 1-6]
Figure PCTKR2023007638-appb-img-000008
Figure PCTKR2023007638-appb-img-000008
상기 화학식 1-1 내지 1-6에 있어서, L1 내지 L3, X1 내지 X12, Ar1 및 Ar2는 상기 화학식 1 및 2에서 정의한 바와 같다.In Formulas 1-1 to 1-6, L1 to L3, X1 to X12, Ar1 and Ar2 are as defined in Formulas 1 and 2 above.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2은 아래 구조 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 2 is any one of the structures below.
Figure PCTKR2023007638-appb-img-000009
Figure PCTKR2023007638-appb-img-000009
예컨대, 상기 각 구조에 포함된 탄소 중 어느 하나는 상기 화학식 1의 L3에 결합한다.For example, one of the carbons included in each structure is bonded to L3 in Chemical Formula 1.
본 명세서의 일 실시상태에 따르면, 상기 화학식 2은 아래 구조 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 2 is any one of the structures below.
Figure PCTKR2023007638-appb-img-000010
Figure PCTKR2023007638-appb-img-000010
예컨대, 상기 각 구조에 포함된 탄소 중 어느 하나는 상기 화학식 1의 L3에 결합한다.For example, one of the carbons included in each structure is bonded to L3 in Chemical Formula 1.
본 명세서의 일 실시상태에 따르면, 상기 X1 내지 X4 중 하나는 N이다.According to an exemplary embodiment of the present specification, one of X1 to X4 is N.
본 명세서의 일 실시상태에 따르면, 상기 X1 내지 X4 중 X2 또는 X3은 N이다.According to an exemplary embodiment of the present specification, among X1 to X4, X2 or X3 is N.
본 명세서의 일 실시상태에 따르면, 상기 X1은 N이고, X2 내지 X12 중 하나는 L3과 결합하는 C이고, 나머지는 CR이다.According to an exemplary embodiment of the present specification, X1 is N, one of X2 to X12 is C combined with L3, and the others are CR.
본 명세서의 일 실시상태에 따르면, 상기 X2는 N이고, X1, 및 X3 내지 X12 중 하나는 L3과 결합하는 C이고, 나머지는 CR이다.According to an exemplary embodiment of the present specification, X2 is N, X1, and one of X3 to X12 is C combined with L3, and the others are CR.
본 명세서의 일 실시상태에 따르면, 상기 X3은 N이고, X1, X2, 및 X4 내지 X12 중 하나는 L3과 결합하는 C이고, 나머지는 CR이다.According to an exemplary embodiment of the present specification, X3 is N, one of X1, X2, and X4 to X12 is C that combines with L3, and the others are CR.
본 명세서의 일 실시상태에 따르면, 상기 X4는 N이고, X1 내지 X3, 및 X5 내지 X12 중 하나는 L3과 결합하는 C이고, 나머지는 CR이다.According to an exemplary embodiment of the present specification, X4 is N, one of X1 to X3, and X5 to X12 is C that combines with L3, and the others are CR.
본 명세서의 일 실시상태에 따르면, 상기 X5는 N이고, X1 내지 X4, 및 X6 내지 X12 중 하나는 L3과 결합하는 C이고, 나머지는 CR이다.According to an exemplary embodiment of the present specification, X5 is N, one of X1 to X4, and X6 to X12 is C that combines with L3, and the others are CR.
본 명세서의 일 실시상태에 따르면, 상기 X6은 N이고, X1 내지 X5, 및 X7 내지 X12 중 하나는 L3과 결합하는 C이고, 나머지는 CR이다.According to an exemplary embodiment of the present specification, X6 is N, one of X1 to X5, and X7 to X12 is C that combines with L3, and the others are CR.
본 명세서의 일 실시상태에 따르면, 상기 X7은 N이고, X1 내지 X6, 및 X8 내지 X12 중 하나는 L3과 결합하는 C이고, 나머지는 CR이다.According to an exemplary embodiment of the present specification, X7 is N, one of X1 to X6, and X8 to X12 is C that combines with L3, and the others are CR.
본 명세서의 일 실시상태에 따르면, 상기 X8은 N이고, X1 내지 X7, 및 X9 내지 X12 중 하나는 L3과 결합하는 C이고, 나머지는 CR이다.According to an exemplary embodiment of the present specification, X8 is N, one of X1 to X7, and X9 to X12 is C that combines with L3, and the others are CR.
본 명세서의 일 실시상태에 따르면, 상기 X9는 N이고, X1 내지 X8, 및 X10 내지 X12 중 하나는 L3과 결합하는 C이고, 나머지는 CR이다.According to an exemplary embodiment of the present specification, X9 is N, one of X1 to X8, and X10 to X12 is C that combines with L3, and the others are CR.
본 명세서의 일 실시상태에 따르면, 상기 X10은 N이고, X1 내지 X9, X11 및 X12 중 하나는 L3과 결합하는 C이고, 나머지는 CR이다.According to an exemplary embodiment of the present specification, X10 is N, one of X1 to X9, X11, and X12 is C that combines with L3, and the others are CR.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 30 carbon atoms. It is a heteroarylene group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 20 carbon atoms. It is a heteroarylene group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 탄소수 6 내지 30의 아릴렌기, 또는 탄소수 3 내지 30의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other and are each independently a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 탄소수 6 내지 20의 아릴렌기, 또는 탄소수 3 내지 20의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other and are each independently a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 2가의 비페닐기, 치환 또는 비치환된 2가의 터페닐기, 치환 또는 비치환된 2가의 나프틸기, 치환 또는 비치환된 2가의 안트라센기, 치환 또는 비치환된 2가의 페난트렌기, 치환 또는 비치환된 2가의 파이렌기, 치환 또는 비치환된 2가의 카바졸기, 치환 또는 비치환된 2가의 피리딘기, 치환 또는 비치환된 2가의 피리미딘기, 치환 또는 비치환된 2가의 트리아진기, 치환 또는 비치환된 2가의 디벤조퓨란기, 치환 또는 비치환된 2가의 디벤조티오펜기, 치환 또는 비치환된 2가의 퓨란기, 치환 또는 비치환된 2가의 티오펜기, 치환 또는 비치환된 2가의 벤즈이미다졸기, 또는 치환 또는 비치환된 2가의 벤즈옥사졸기이다..According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted biphenyl group. Divalent terphenyl group, substituted or unsubstituted divalent naphthyl group, substituted or unsubstituted divalent anthracene group, substituted or unsubstituted divalent phenanthrene group, substituted or unsubstituted divalent pyrene group, substituted or unsubstituted divalent carbazole group, substituted or unsubstituted divalent pyridine group, substituted or unsubstituted divalent pyrimidine group, substituted or unsubstituted divalent triazine group, substituted or unsubstituted divalent dibenzofuran group, substituted Or an unsubstituted divalent dibenzothiophene group, a substituted or unsubstituted divalent furan group, a substituted or unsubstituted divalent thiophene group, a substituted or unsubstituted divalent benzimidazole group, or a substituted or unsubstituted group. It is a divalent benzoxazole group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 2가의 비페닐기, 치환 또는 비치환된 2가의 나프틸기, 치환 또는 비치환된 2가의 터페닐기, 치환 또는 비치환된 2가의 카바졸기, 치환 또는 비치환된 2가의 피리딘기, 치환 또는 비치환된 2가의 피리미딘기, 치환 또는 비치환된 2가의 트리아진기, 치환 또는 비치환된 2가의 디벤조퓨란기, 치환 또는 비치환된 2가의 디벤조티오펜기, 치환 또는 비치환된 2가의 퓨란기, 치환 또는 비치환된 2가의 티오펜기, 치환 또는 비치환된 2가의 벤즈이미다졸기, 또는 치환 또는 비치환된 2가의 벤즈옥사졸기이다..According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted biphenyl group. Divalent naphthyl group, substituted or unsubstituted divalent terphenyl group, substituted or unsubstituted divalent carbazole group, substituted or unsubstituted divalent pyridine group, substituted or unsubstituted divalent pyrimidine group, substituted or unsubstituted divalent triazine group, substituted or unsubstituted divalent dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted divalent furan group, substituted or unsubstituted divalent thiophene group, a substituted or unsubstituted divalent benzimidazole group, or a substituted or unsubstituted divalent benzoxazole group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 페닐렌기, 2가의 비페닐기, 2가의 터페닐기, 2가의 나프틸기, 2가의 안트라센기, 2가의 페난트렌기, 2가의 파이렌기, 2가의 카바졸기, 2가의 피리딘기, 2가의 피리미딘기, 2가의 트리아진기, 2가의 디벤조퓨란기, 2가의 디벤조티오펜기, 2가의 퓨란기, 2가의 티오펜기, 2가의 벤즈이미다졸기, 또는 2가의 벤즈옥사졸기이다..According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, Divalent phenanthrene group, divalent pyrene group, divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, divalent dibenzofuran group, divalent dibenzothiophene group, divalent furan group, a divalent thiophene group, a divalent benzimidazole group, or a divalent benzoxazole group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 페닐렌기, 2가의 비페닐기, 2가의 나프틸기, 2가의 터페닐기, 2가의 카바졸기, 2가의 피리딘기, 2가의 피리미딘기, 2가의 트리아진기, 2가의 디벤조퓨란기, 2가의 디벤조티오펜기, 2가의 퓨란기, 2가의 티오펜기, 2가의 벤즈이미다졸기, 또는 2가의 벤즈옥사졸기이다..According to an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent terphenyl group, a divalent carbazole group, A divalent pyridine group, a divalent pyrimidine group, a divalent triazine group, a dibenzofuran group, a dibenzothiophene group, a divalent furan group, a divalent thiophene group, a divalent benzimidazole group, or It is a divalent benzoxazole group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 2가의 비페닐기, 치환 또는 비치환된 2가의 나프틸기, 또는 치환 또는 비치환된 2가의 터페닐기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted biphenyl group. It is a divalent naphthyl group, or a substituted or unsubstituted divalent terphenyl group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 2가의 비페닐기, 또는 2가의 치환 또는 비치환된 나프틸기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a divalent substituted or It is an unsubstituted naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 페닐렌기, 2가의 비페닐기, 2가의 나프틸기, 또는 2가의 터페닐기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, or a divalent terphenyl group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 페닐렌기, 2가의 비페닐기, 또는 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other and are each independently a direct bond, a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 페닐렌기, 2가의 비페닐기, 2가의 터페닐기, 2가의 나프틸기, 2가의 안트라센기, 2가의 페난트렌기, 2가의 파이렌기, 2가의 카바졸기, 2가의 피리딘기, 2가의 피리미딘기, 2가의 트리아진기, 2가의 디벤조퓨란기, 2가의 디벤조티오펜기, 2가의 퓨란기, 2가의 티오펜기, 2가의 벤즈이미다졸기, 또는 2가의 벤즈옥사졸기이다..According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, Divalent phenanthrene group, divalent pyrene group, divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, divalent dibenzofuran group, divalent dibenzothiophene group, divalent furan group, a divalent thiophene group, a divalent benzimidazole group, or a divalent benzoxazole group.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 직접결합이다.According to an exemplary embodiment of the present specification, L1 to L3 are direct bonds.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 페닐렌기이다.According to an exemplary embodiment of the present specification, L1 to L3 are phenylene groups.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L1 to L3 are divalent naphthyl groups.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 2가의 비페닐기이다,According to an exemplary embodiment of the present specification, L1 to L3 are divalent biphenyl groups,
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 치환 또는 비치환된 페닐렌기이다.According to an exemplary embodiment of the present specification, L1 to L3 are substituted or unsubstituted phenylene groups.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 치환 또는 비치환된 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L1 to L3 are substituted or unsubstituted divalent naphthyl groups.
본 명세서의 일 실시상태에 따르면, 상기 L1 내지 L3은 치환 또는 비치환된 2가의 비페닐기이다.According to an exemplary embodiment of the present specification, L1 to L3 are substituted or unsubstituted divalent biphenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 같고, 직접결합, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are the same as each other and are a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 같고, 직접결합, 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are the same as each other and are a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 같고, 직접결합, 탄소수 6 내지 30의 아릴렌기, 또는 탄소수 3 내지 30의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are the same as each other and are a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 같고, 직접결합, 탄소수 6 내지 20의 아릴렌기, 또는 탄소수 3 내지 20의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are the same as each other and are a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 같고, 직접결합, 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 2가의 비페닐기, 치환 또는 비치환된 2가의 터페닐기, 치환 또는 비치환된 2가의 나프틸기, 치환 또는 비치환된 2가의 안트라센기, 치환 또는 비치환된 2가의 페난트렌기, 치환 또는 비치환된 2가의 파이렌기, 치환 또는 비치환된 2가의 카바졸기, 치환 또는 비치환된 2가의 피리딘기, 치환 또는 비치환된 2가의 피리미딘기, 치환 또는 비치환된 2가의 트리아진기, 치환 또는 비치환된 2가의 디벤조퓨란기, 치환 또는 비치환된 2가의 디벤조티오펜기, 치환 또는 비치환된 2가의 퓨란기, 치환 또는 비치환된 2가의 티오펜기, 치환 또는 비치환된 2가의 벤즈이미다졸기, 또는 치환 또는 비치환된 2가의 벤즈옥사졸기이다..According to an exemplary embodiment of the present specification, L1 and L2 are the same as each other, and are directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or Unsubstituted divalent naphthyl group, substituted or unsubstituted divalent anthracene group, substituted or unsubstituted divalent phenanthrene group, substituted or unsubstituted divalent pyrene group, substituted or unsubstituted divalent carbazole group, substituted or an unsubstituted divalent pyridine group, a substituted or unsubstituted divalent pyrimidine group, a substituted or unsubstituted divalent triazine group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted divalent dibenzofuran group. It is a benzothiophene group, a substituted or unsubstituted divalent furan group, a substituted or unsubstituted divalent thiophene group, a substituted or unsubstituted divalent benzimidazole group, or a substituted or unsubstituted divalent benzoxazole group. ..
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 같고, 직접결합, 페닐렌기, 2가의 비페닐기, 2가의 터페닐기, 2가의 나프틸기, 2가의 안트라센기, 2가의 페난트렌기, 2가의 파이렌기, 2가의 카바졸기, 2가의 피리딘기, 2가의 피리미딘기, 2가의 트리아진기, 2가의 디벤조퓨란기, 2가의 디벤조티오펜기, 2가의 퓨란기, 2가의 티오펜기, 2가의 벤즈이미다졸기, 또는 2가의 벤즈옥사졸기이다..According to an exemplary embodiment of the present specification, L1 and L2 are the same as each other, and are a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, a divalent phenanthrene group, 2 Divalent pyrene group, divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, divalent dibenzofuran group, divalent dibenzothiophene group, divalent furan group, divalent thiophene group , a divalent benzimidazole group, or a divalent benzoxazole group.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 상이하고, 각각 독립적으로, 직접결합, 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 30 carbon atoms. It is an arylene group.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 상이하고, 각각 독립적으로, 직접결합, 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 20 carbon atoms. It is an arylene group.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 상이하고, 각각 독립적으로, 직접결합, 탄소수 6 내지 30의 아릴렌기, 또는 탄소수 3 내지 30의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are different from each other and are each independently a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 상이하고, 각각 독립적으로, 직접결합, 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 20 carbon atoms. It is an arylene group.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 상이하고, 각각 독립적으로, 직접결합, 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 2가의 비페닐기, 치환 또는 비치환된 2가의 터페닐기, 치환 또는 비치환된 2가의 나프틸기, 치환 또는 비치환된 2가의 안트라센기, 치환 또는 비치환된 2가의 페난트렌기, 치환 또는 비치환된 2가의 파이렌기, 치환 또는 비치환된 2가의 카바졸기, 치환 또는 비치환된 2가의 피리딘기, 치환 또는 비치환된 2가의 피리미딘기, 치환 또는 비치환된 2가의 트리아진기, 치환 또는 비치환된 2가의 디벤조퓨란기, 치환 또는 비치환된 2가의 디벤조티오펜기, 치환 또는 비치환된 2가의 퓨란기, 치환 또는 비치환된 2가의 티오펜기, 치환 또는 비치환된 2가의 벤즈이미다졸기, 또는 치환 또는 비치환된 2가의 벤즈옥사졸기이다..According to an exemplary embodiment of the present specification, L1 and L2 are different from each other and are each independently directly bonded, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent group. Terphenyl group, substituted or unsubstituted divalent naphthyl group, substituted or unsubstituted divalent anthracene group, substituted or unsubstituted divalent phenanthrene group, substituted or unsubstituted divalent pyrene group, substituted or unsubstituted 2 A divalent carbazole group, a substituted or unsubstituted divalent pyridine group, a substituted or unsubstituted divalent pyrimidine group, a substituted or unsubstituted divalent triazine group, a substituted or unsubstituted divalent dibenzofuran group, substituted or unsubstituted A substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted divalent furan group, a substituted or unsubstituted divalent thiophene group, a substituted or unsubstituted divalent benzimidazole group, or a substituted or unsubstituted 2 It is a benzoxazole group.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 상이하고, 각각 독립적으로, 직접결합, 페닐렌기, 치환 또는 비치환된 2가의 비페닐기, 또는 치환 또는 비치환된 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L1 and L2 are different from each other and are each independently a direct bond, a phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 상이하고, 각각 독립적으로, 직접결합, 탄소수 6 내지 20의 아릴렌기, 또는 탄소수 3 내지 20의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are different from each other and are each independently a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 상이하고, 각각 독립적으로, 직접결합, 페닐렌기, 2가의 비페닐기, 2가의 터페닐기, 2가의 나프틸기, 2가의 안트라센기, 2가의 페난트렌기, 2가의 파이렌기, 2가의 카바졸기, 2가의 피리딘기, 2가의 피리미딘기, 2가의 트리아진기, 2가의 디벤조퓨란기, 2가의 디벤조티오펜기, 2가의 퓨란기, 2가의 티오펜기, 2가의 벤즈이미다졸기, 또는 2가의 벤즈옥사졸기이다..According to an exemplary embodiment of the present specification, L1 and L2 are different from each other and each independently, a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, a divalent Phenanthrene group, divalent pyrene group, divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, divalent dibenzofuran group, divalent dibenzothiophene group, divalent furan group, It is a divalent thiophene group, a divalent benzimidazole group, or a divalent benzoxazole group.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 서로 상이하고, 각각 독립적으로, 직접결합, 페닐렌기, 2가의 비페닐기, 또는 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L1 and L2 are different from each other and are each independently a direct bond, a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 직접결합이다.According to an exemplary embodiment of the present specification, L1 and L2 are a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 페닐렌기이다.According to an exemplary embodiment of the present specification, L1 and L2 are phenylene groups.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L1 and L2 are divalent naphthyl groups.
본 명세서의 일 실시상태에 따르면, 상기 L1 및 L2는 2가의 비페닐기이다.According to an exemplary embodiment of the present specification, L1 and L2 are divalent biphenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 L1은 직접결합이다.According to an exemplary embodiment of the present specification, L1 is a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 L1은 페닐렌기이다.According to an exemplary embodiment of the present specification, L1 is a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 L1은 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L1 is a divalent naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 L1은 2가의 비페닐기이다.According to an exemplary embodiment of the present specification, L1 is a divalent biphenyl group.
본 명세서의 일 실시상태에 따르면, 상기 L2는 직접결합이다.According to an exemplary embodiment of the present specification, L2 is a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 L2는 페닐렌기이다.According to an exemplary embodiment of the present specification, L2 is a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 L2는 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L2 is a divalent naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 L2는 2가의 비페닐기이다.According to an exemplary embodiment of the present specification, L2 is a divalent biphenyl group.
본 명세서의 일 실시상태에 따르면, 상기 L3은 직접결합, 탄소수 6 내지 30의 아릴렌기, 또는 탄소수 3 내지 30의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L3 is a direct bond, an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L3은 직접결합, 탄소수 6 내지 20의 아릴렌기, 또는 탄소수 3 내지 20의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L3 is a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L3은 직접결합, 페닐렌기, 2가의 비페닐기, 2가의 터페닐기, 2가의 나프틸기, 2가의 안트라센기, 2가의 페난트렌기, 2가의 파이렌기, 2가의 카바졸기, 2가의 피리딘기, 2가의 피리미딘기, 2가의 트리아진기, 2가의 디벤조퓨란기, 2가의 디벤조티오펜기, 2가의 퓨란기, 2가의 티오펜기, 2가의 벤즈이미다졸기, 또는 2가의 벤즈옥사졸기이다.벤즈옥사졸기이다.벤즈옥사졸기이다.따르면, 상기 L3은 직접결합, 페닐렌기, 2가의 비페닐기, 2가의 나프틸기, 또는 2가의 터페닐기이다.According to an exemplary embodiment of the present specification, L3 is a direct bond, a phenylene group, a divalent biphenyl group, a divalent terphenyl group, a divalent naphthyl group, a divalent anthracene group, a divalent phenanthrene group, a divalent pyrene group, 2 divalent carbazole group, divalent pyridine group, divalent pyrimidine group, divalent triazine group, dibenzofuran group, dibenzothiophene group, divalent furan group, divalent thiophene group, divalent benzimi It is a polyazole group, or a divalent benzoxazole group. It is a benzoxazole group. It is a benzoxazole group. Accordingly, L3 is a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, or a divalent terphenyl group.
본 명세서의 일 실시상태에 따르면, 상기 L3은 직접결합, 페닐렌기, 또는 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L3 is a direct bond, a phenylene group, or a divalent naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 L3은 직접결합이다.According to an exemplary embodiment of the present specification, L3 is a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 L3은 페닐렌기, 2가의 나프틸기, 2가의 비페닐기, 또는 2가의 터페닐기이다.According to an exemplary embodiment of the present specification, L3 is a phenylene group, a divalent naphthyl group, a divalent biphenyl group, or a divalent terphenyl group.
본 명세서의 일 실시상태에 따르면, 상기 L3은 페닐렌기, 또는 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L3 is a phenylene group or a divalent naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 L3은 직접결합이다.According to an exemplary embodiment of the present specification, L3 is a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 L3은 페닐렌기이다.According to an exemplary embodiment of the present specification, L3 is a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 L3은 2가의 나프틸기이다.According to an exemplary embodiment of the present specification, L3 is a divalent naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. .
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기 또는 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms. .
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 30의 아릴기, 또는 탄소수 3 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 20의 아릴기, 또는 탄소수 6 내지 30의 아릴기로 치환된 탄소수 3 내지 20의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group of 6 to 20 carbon atoms, or a heteroaryl group of 3 to 20 carbon atoms substituted with an aryl group of 6 to 30 carbon atoms. .
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 30의 아릴기, 탄소수 1 내지 10의 알킬기, 또는 탄소수 3 내지 30의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently substituted or provided with an aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms. a ringed aryl group having 6 to 20 carbon atoms; Or it is a heteroaryl group having 3 to 20 carbon atoms that is substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 20의 아릴기, 탄소수 1 내지 10의 알킬기, 또는 탄소수 3 내지 20의 헤테로아릴기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently substituted or provided with an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. a ringed aryl group having 6 to 20 carbon atoms; Or it is a heteroaryl group having 3 to 20 carbon atoms that is substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 페닐기, 비페닐기, 나프틸기, 터페닐기, 플루오란텐기, 페난트렌기, 트리페닐렌기, 디벤조퓨란기, 디벤조티오펜기, 벤조퓨로피리딘기, 벤조티오피리딘기, 벤조나프토퓨란기, 또는 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 카바졸기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluoranthene group, a phenanthrene group, a triphenylene group, and a dibenzofuran group. , a dibenzothiophene group, a benzofuropyridine group, a benzothiopyridine group, a benzonaphthofuran group, or a carbazole group substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2 중 적어도 하나는 치환 또는 비치환된 3환 이상의 아릴기이거나, 치환 또는 비치환된 2환 이상의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a substituted or unsubstituted aryl group with three or more rings, or a substituted or unsubstituted heteroaryl group with two or more rings.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 페닐기, 비페닐기, 나프틸기, 터페닐기, 플루오란텐기, 페난트렌기, 트리페닐렌기, 디벤조퓨란기, 디벤조티오펜기, 벤조퓨로피리딘기, 벤조티오피리딘기, 벤조나프토퓨란기, 또는 페닐기로 치환 또는 비치환된 카바졸기이다.According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluoranthene group, a phenanthrene group, a triphenylene group, and a dibenzofuran group. , a dibenzothiophene group, a benzofuropyridine group, a benzothiopyridine group, a benzonaphthofuran group, or a carbazole group substituted or unsubstituted by a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 X9 또는 X10가 N일 때, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기이고, According to an exemplary embodiment of the present specification, when X9 or It is a heteroarylene group of 3 to 30,
L3은 직접결합, 치환 또는 비치환된 탄소수 10 내지 30의 다환의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기이고, L3 is a direct bond, a substituted or unsubstituted polycyclic arylene group having 10 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms,
Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 10 내지 30의 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기이다. Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 X9 또는 X10가 N일 때, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 30의 아릴렌기 또는 탄소수 3 내지 30의 헤테로아릴렌기이고, L3은 직접결합, 탄소수 10 내지 30의 다환의 아릴렌기, 또는 탄소수 3 내지 30의 헤테로아릴렌기이고, According to an exemplary embodiment of the present specification, when X9 or is a direct bond, a polycyclic arylene group having 10 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms,
Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 10 내지 30의 다환의 아릴기; 또는 탄소수 6 내지 30의 아릴기로 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기이다. Ar1 and Ar2 are the same or different from each other, and are each independently a polycyclic aryl group having 10 to 30 carbon atoms; Or it is a heteroaryl group having 3 to 30 carbon atoms that is substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 X9 또는 X10가 N일 때, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 30의 아릴렌기 또는 탄소수 3 내지 30의 헤테로아릴렌기이고, L3은 직접결합, 탄소수 10 내지 30의 다환의 아릴렌기, 또는 탄소수 3 내지 30의 헤테로아릴렌기이고, According to an exemplary embodiment of the present specification, when X9 or is a direct bond, a polycyclic arylene group having 10 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms,
Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 탄소수 10 내지 30의 다환의 아릴기; 또는 페닐기 또는 나프틸기로 탄소수 3 내지 30의 헤테로아릴기이다. Ar1 and Ar2 are the same or different from each other, and are each independently a polycyclic aryl group having 10 to 30 carbon atoms; Or it is a phenyl group or a naphthyl group, a heteroaryl group having 3 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 X9 또는 X10가 N일 때, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 페닐렌기, 또는 2가의 나프틸기이고, L3은 직접결합, 또는 2가의 나프틸기이고, According to an exemplary embodiment of the present specification, when X9 or It is til group,
Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 비페닐기, 나프틸기, 터페닐기, 플루오란텐기, 페난트렌기, 트리페닐렌기, 디벤조퓨란기, 디벤조티오펜기, 벤조퓨로피리딘기, 벤조티오피리딘기, 벤조나프토퓨란기, 또는 페닐기로 치환 또는 비치환된 카바졸기이다.Ar1 and Ar2 are the same or different from each other, and are each independently a biphenyl group, naphthyl group, terphenyl group, fluoranthene group, phenanthrene group, triphenylene group, dibenzofuran group, dibenzothiophene group, and benzofuropyridine group. , a benzothiopyridine group, a benzonaphthofuran group, or a carbazole group substituted or unsubstituted with a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R은 수소, 또는 중수소이다.According to an exemplary embodiment of the present specification, R is hydrogen or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R은 수소이다.According to an exemplary embodiment of the present specification, R is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R은 중수소이다.According to an exemplary embodiment of the present specification, R is deuterium.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 아래 구조식 중 어느 하나이다. According to an exemplary embodiment of the present specification, Formula 1 is one of the structural formulas below.
Figure PCTKR2023007638-appb-img-000011
Figure PCTKR2023007638-appb-img-000011
Figure PCTKR2023007638-appb-img-000012
Figure PCTKR2023007638-appb-img-000012
Figure PCTKR2023007638-appb-img-000013
Figure PCTKR2023007638-appb-img-000013
Figure PCTKR2023007638-appb-img-000014
Figure PCTKR2023007638-appb-img-000014
Figure PCTKR2023007638-appb-img-000015
Figure PCTKR2023007638-appb-img-000015
Figure PCTKR2023007638-appb-img-000016
Figure PCTKR2023007638-appb-img-000016
Figure PCTKR2023007638-appb-img-000017
Figure PCTKR2023007638-appb-img-000017
Figure PCTKR2023007638-appb-img-000018
Figure PCTKR2023007638-appb-img-000018
Figure PCTKR2023007638-appb-img-000019
Figure PCTKR2023007638-appb-img-000019
Figure PCTKR2023007638-appb-img-000020
Figure PCTKR2023007638-appb-img-000020
Figure PCTKR2023007638-appb-img-000021
Figure PCTKR2023007638-appb-img-000021
Figure PCTKR2023007638-appb-img-000022
Figure PCTKR2023007638-appb-img-000022
Figure PCTKR2023007638-appb-img-000023
Figure PCTKR2023007638-appb-img-000023
Figure PCTKR2023007638-appb-img-000024
Figure PCTKR2023007638-appb-img-000024
Figure PCTKR2023007638-appb-img-000025
Figure PCTKR2023007638-appb-img-000025
상기 화학식 1의 화합물의 치환기는 당 기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 또는 개수는 당 기술분야에 알려져 있는 기술에 따라 변경될 수 있다.Substituents of the compound of Formula 1 may be combined by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.
또한, 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 도입된 치환기의 고유 특성을 갖는 화합물을 합성할 수 있다. 예컨대, 유기 발광 소자 제조시 사용되는 정공 주입층 물질, 정공 수송용 물질, 발광층 물질 및 전자 수송층 물질에 주로 사용되는 치환기를 상기 코어 구조에 도입함으로써 각 유기물층에서 요구하는 조건들을 충족시키는 물질을 합성할 수 있다.In addition, by introducing various substituents into the core structure of the above structure, it is possible to synthesize compounds having the unique properties of the introduced substituents. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the core structure, a material that satisfies the conditions required for each organic material layer can be synthesized. You can.
또한, 본 발명에 따른 유기 발광 소자는 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 전술한 화합물을 포함하는 것을 특징으로 한다.Additionally, the organic light emitting device according to the present invention includes a first electrode; a second electrode provided opposite the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the above-described compound.
본 발명의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.
상기 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥 코팅, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The compound may be formed into 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 application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
본 발명의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공주입층, 정공수송층, 정공주입 및 정공수송을 동시에 하는 층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나, 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기물층 또는 더 많은 수의 유기물층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this and may include fewer or more organic material layers.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함한다.In one embodiment of the present invention, the organic material layer includes a light-emitting layer.
본 발명의 일 실시상태에 있어서, 상기 발광층은 상기 화학식 1의 화합물을 호스트로 포함한다. In one embodiment of the present invention, the light-emitting layer includes the compound of Formula 1 as a host.
본 발명의 일 실시상태에 있어서, 상기 발광층은 도펀트와 호스트를 포함한다.In one embodiment of the present invention, the light emitting layer includes a dopant and a host.
본 발명의 일 실시상태에 있어서, 상기 발광층은 도펀트와 호스트를 1:99 내지 30:70의 질량비로 포함한다. In one embodiment of the present invention, the light-emitting layer includes a dopant and a host at a mass ratio of 1:99 to 30:70.
본 발명의 일 실시상태에 있어서, 상기 발광층은 도펀트와 호스트를 1:99 내지 25:75의 질량비로 포함한다. In one embodiment of the present invention, the light-emitting layer includes a dopant and a host at a mass ratio of 1:99 to 25:75.
본 발명의 일 실시상태에 있어서, 상기 발광층은 도펀트와 호스트를 1:99 내지 20:80의 질량비로 포함한다. In one embodiment of the present invention, the light-emitting layer includes a dopant and a host at a mass ratio of 1:99 to 20:80.
본 발명의 일 실시상태에 있어서, 상기 발광층은 도펀트와 호스트를 1:99 내지 15:85의 질량비로 포함한다. In one embodiment of the present invention, the light-emitting layer includes a dopant and a host at a mass ratio of 1:99 to 15:85.
본 발명의 일 실시상태에 있어서, 상기 발광층은 도펀트와 호스트를 1:99 내지 5:95의 질량비로 포함한다. In one embodiment of the present invention, the light-emitting layer includes a dopant and a host at a mass ratio of 1:99 to 5:95.
본 발명의 유기 발광 소자에서, 상기 유기물층은 전자수송층, 전자주입층, 및 전자주입 및 수송 층 중 1층 이상을 포함할 수 있고, 상기 층들 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, the organic material layer may include one or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more of the layers includes the compound represented by Formula 1 can do.
또 하나의 유기 발광 소자에서, 상기 유기물층은 전자수송층 또는 전자주입층을 포함할 수 있고, 상기 전자수송층 또는 전자주입층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In another organic light emitting device, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Formula 1.
본 발명의 유기 발광 소자에서, 상기 전자주입 및 수송층은 상기 화학식 1의 화합물과 금속 착체를 포함한다.In the organic light emitting device of the present invention, the electron injection and transport layer includes the compound of Formula 1 and a metal complex.
본 발명의 유기 발광 소자에서, 상기 전자주입 및 수송층은 상기 화학식 1의 화합물과 리튬퀴놀레이트를 포함한다.In the organic light emitting device of the present invention, the electron injection and transport layer includes the compound of Formula 1 and lithium quinolate.
본 발명의 유기 발광 소자에서, 상기 전자주입 및 수송층은 상기 화학식 1의 화합물과 금속착체를 1:10 내지 10:1의 중량비로 포함할 수 있다.In the organic light emitting device of the present invention, the electron injection and transport layer may include the compound of Formula 1 and the metal complex at a weight ratio of 1:10 to 10:1.
본 발명의 유기 발광 소자에서, 상기 전자주입 및 수송층은 상기 화학식 1의 화합물과 금속착체를 1:5 내지 5:1의 중량비로 포함할 수 있다.In the organic light emitting device of the present invention, the electron injection and transport layer may include the compound of Formula 1 and the metal complex at a weight ratio of 1:5 to 5:1.
본 발명의 유기 발광 소자에서, 상기 전자주입 및 수송층은 상기 화학식 1의 화합물과 금속착체를 1:3 내지 3:1의 중량비로 포함할 수 있다.In the organic light emitting device of the present invention, the electron injection and transport layer may include the compound of Formula 1 and the metal complex at a weight ratio of 1:3 to 3:1.
본 발명의 유기 발광 소자에서, 상기 전자주입 및 수송층은 상기 화학식 1의 화합물과 리튬퀴놀레이트를 1:10 내지 10:1의 중량비로 포함할 수 있다.In the organic light emitting device of the present invention, the electron injection and transport layer may include the compound of Formula 1 and lithium quinolate at a weight ratio of 1:10 to 10:1.
본 발명의 유기 발광 소자에서, 상기 전자주입 및 수송층은 상기 화학식 1의 화합물과 리튬퀴놀레이트를 1:5 내지 5:1의 중량비로 포함할 수 있다.In the organic light emitting device of the present invention, the electron injection and transport layer may include the compound of Formula 1 and lithium quinolate in a weight ratio of 1:5 to 5:1.
본 발명의 유기 발광 소자에서, 상기 전자주입 및 수송층은 상기 화학식 1의 화합물과 리튬퀴놀레이트를 1:3 내지 3:1의 중량비로 포함할 수 있다.In the organic light emitting device of the present invention, the electron injection and transport layer may include the compound of Formula 1 and lithium quinolate at a weight ratio of 1:3 to 3:1.
본 발명의 유기 발광 소자에서, 상기 유기물층은 정공차단층을 포함하고, 상기 정공차단층은 상기 화학식 1의 화합물을 포함한다.In the organic light emitting device of the present invention, the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound of Formula 1.
본 발명의 유기 발광 소자에서, 상기 유기물층은 정공주입층, 정공수송층 및 정공주입과 정공수송을 동시에 하는 층 중 1층 이상을 포함할 수 있고, 상기 층들 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present invention, the organic material layer may include one or more layers among a hole injection layer, a hole transport layer, and a layer that performs both hole injection and hole transport, and one or more of the layers is represented by the formula (1) It may contain compounds.
또 하나의 유기 발광 소자에서, 상기 유기물층은 정공주입층 또는 정공수송층을 포함할 수 있고, 상기 정공수송층 또는 정공주입층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In another organic light emitting device, the organic material layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include the compound represented by Formula 1.
본 발명의 유기 발광 소자에서, 상기 발광층 및 유기물 사이에 정공주입층 또는 정공수송층이 추가로 구비된다.In the organic light emitting device of the present invention, a hole injection layer or a hole transport layer is additionally provided between the light emitting layer and the organic material.
본 발명의 유기 발광 소자에서, 상기 발광층 및 유기물 사이에 정공주입층 또는 정공수송층이 추가로 구비된다.In the organic light emitting device of the present invention, a hole injection layer or a hole transport layer is additionally provided between the light emitting layer and the organic material.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 제2 전극은 음극이다.In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.
또 하나의 일 실시상태에 따르면, 상기 제1 전극은 음극이고, 제2 전극은 양극이다.According to another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.
(1) 양극/정공수송층/발광층/음극(1) Anode/hole transport layer/light emitting layer/cathode
(2) 양극/정공주입층/정공수송층/발광층/음극(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) 양극/정공주입층/정공버퍼층/정공수송층/발광층/음극(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode
(4) 양극/정공수송층/발광층/전자수송층/음극(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) 양극/정공수송층/발광층/전자수송층/전자주입층/음극(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(6) 양극/정공주입층/정공수송층/발광층/전자수송층/음극(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(7) 양극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/음극(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(8) 양극/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/음극(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode
(9) 양극/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/전자주입층 /음극(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(10) 양극/ 정공수송층/전자억제층/발광층/전자수송층/음극(10) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(11) 양극/ 정공수송층/전자억제층/발광층/전자수송층/전자주입층/음극(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) 양극/정공주입층/정공수송층/전자억제층/발광층/전자수송층/음극(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(13)양극/정공주입층/정공수송층/전자억제층/발광층/전자수송층/전자주입 층/음극(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(14) 양극/정공수송층/발광층/정공억제층/전자수송층/음극(14) Anode/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode
(15) 양극/정공수송층/발광층/ 정공억제층/전자수송층/전자주입층/음극(15) Anode/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode
(16) 양극/정공주입층/정공수송층/발광층/정공억제층/전자수송층/음극(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode
(17)양극/정공주입층/정공수송층/발광층/정공억제층/전자수송층/전자주입 층/음극(17) Anode/hole injection layer/hole transport layer/light-emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode
(18)양극/정공주입층/정공수송층/전자억제층/발광층/정공저지층/전자주입및 수송층/음극(18) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/hole blocking layer/electron injection and transport layer/cathode
본 발명의 유기 발광 소자의 구조는 도 1에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.The structure of the organic light emitting device of the present invention may have the same structure as shown in FIG. 1, but is not limited thereto.
도 1에는 기판(1) 위에 양극(2), 유기물층(3) 및 음극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 유기물층(3)에 포함될 수 있다.Figure 1 illustrates the structure of an organic light-emitting device in which an anode 2, an organic material layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In this structure, the compound represented by Formula 1 may be included in the organic layer 3.
도 2에는 기판(1) 위에 양극(2), 정공주입층(5), 정공수송층(6), 전자차단층(7), 발광층(8), 정공저지층(9), 전자주입 및 수송층(10) 및 음극(4)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층(8)에 포함될 수 있다.In Figure 2, an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), a hole blocking layer (9), an electron injection and transport layer ( The structure of an organic light emitting device in which the cathode 10) and the cathode 4 are sequentially stacked is illustrated. In this structure, the compound represented by Formula 1 may be included in the light-emitting layer 8.
예컨대, 본 발명에 따른 유기 발광 소자는 스퍼터링(sputtering)이나 전자빔 증발(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 정공주입층, 정공수송층, 정공수송 및 정공주입을 동시에 하는 층, 발광층, 전자수송층, 전자주입층, 및 전자수송 및 전자주입을 동시에하는 층으로 이루어진 군으로부터 선택된 1층 이상을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다.For example, the organic light emitting device according to the present invention deposits a metal, a conductive metal oxide, or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. An anode is formed by depositing a layer on which a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, a light emitting layer, an electron transport layer, an electron injection layer, and a layer that performs both electron transport and electron injection are selected from the group consisting of It can be manufactured by forming an organic material layer containing one or more selected layers and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
상기 유기물층은 정공주입층, 정공수송층, 발광층 및 전자수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용매 공정(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, but is not limited to this and may have a single-layer structure. In addition, the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.
상기 양극은 정공을 주입하는 전극으로, 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO, Indium Tin Oxide), 인듐아연 산화물(IZO, Indium Zinc Oxide)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, 이들에만 한정되는 것은 아니다.The anode is an electrode that injects holes, and the anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combination of metal and 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 are included, but are not limited to these.
상기 음극은 전자를 주입하는 전극으로, 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 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, 이들에만 한정되는 것은 아니다.The cathode is an electrode that injects electrons, and the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are multi-layer structure materials such as LiF/Al or LiO 2 /Al, but they are not limited to these.
상기 정공주입층은 양극으로부터 발광층으로 정공의 주입을 원활하게 하는 역할을 하는 층이며, 정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입 받을 수 있는 물질로서, 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(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. 정공주입층의 두께는 1 내지 150nm일 수 있다. 상기 정공주입층의 두께가 1nm 이상이면, 정공 주입 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 150nm 이하이면, 정공주입층의 두께가 너무 두꺼워 정공의 이동을 향상시키기 위해 구동전압이 상승되는것을 방지할 수 있는 이점이 있다.The hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage. HOMO (highest occupied) of the hole injection material It is preferable that the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. organic substances, anthraquinone, polyaniline, and polythiophene series conductive polymers, etc., but are not limited to these. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage to preventing this.
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 하기 화학식 HI-1 로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following formula HI-1.
[화학식 HI-1][Formula HI-1]
Figure PCTKR2023007638-appb-img-000026
Figure PCTKR2023007638-appb-img-000026
상기 화학식 HI-1에 있어서,In the formula HI-1,
R400 내지 R402는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R400 to R402 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with adjacent groups to form a substituted or unsubstituted ring,
L402는 치환 또는 비치환된 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이다.L402 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
본 명세서의 일 실시상태에 따르면, 상기 R400 내지 R402는 서로 같거나 상이하고, 각가 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, R400 to R402 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 R402는 카바졸기 또는 아릴아민기로 치환된 페닐기; 카바졸기 또는 아릴아민기로 치환된 바이페닐기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, R402 is a phenyl group substituted with a carbazole group or an arylamine group; Biphenyl group substituted with carbazole group or arylamine group; and any one selected from the group consisting of combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 R400 및 R401는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이거나, 인접한 기와 서로 결합하여 알킬기로 치환된 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R400 and R401 are the same or different from each other and are each independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 R400 및 R401는 서로 같거나 상이하고, 각각 독립적으로 알킬기로 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, R400 and R401 are the same or different from each other, and each independently represents an aryl group substituted or unsubstituted by an alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 R400 및 R401는 서로 같거나 상이하고, 각각 독립적으로 페닐기 또는 디메틸플루오렌기이다.According to an exemplary embodiment of the present specification, R400 and R401 are the same or different from each other, and are each independently a phenyl group or a dimethylfluorene group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HI-1은 하기 화합물들 선택된다.According to an exemplary embodiment of the present specification, the formula HI-1 is selected from the following compounds.
Figure PCTKR2023007638-appb-img-000027
Figure PCTKR2023007638-appb-img-000027
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 하기 화학식 HI-2 로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole injection layer includes a compound represented by the following formula HI-2, but is not limited thereto.
[화학식 HI-2][Formula HI-2]
Figure PCTKR2023007638-appb-img-000028
Figure PCTKR2023007638-appb-img-000028
상기 화학식 HI-2에 있어서,In the formula HI-2,
X'1 내지 X'3은 서로 같거나 상이하고, 각각 독립적으로 수소, 중수소, 또는 할로겐기이며,X'1 to X'3 are the same or different from each other and are each independently hydrogen, deuterium, or halogen group,
R309 내지 R314는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,R309 to R314 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
x1' 내지 x3'은 각각 1 내지 4의 정수이고, 이들이 2 이상일 때 괄호안의 치환기는 서로 같거나 상이하다.x1' to x3' are each integers from 1 to 4, and when they are 2 or more, the substituents in parentheses are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 X'1 내지 X'3는 할로겐기이다.According to an exemplary embodiment of the present specification, X'1 to X'3 are halogen groups.
본 명세서의 일 실시상태에 따르면, 상기 X'1 내지 X'3는 F 또는 Cl이다.According to an exemplary embodiment of the present specification, X'1 to X'3 are F or Cl.
본 명세서의 일 실시상태에 따르면, 상기 X'1 내지 X'3는 F이다.According to an exemplary embodiment of the present specification, X'1 to X'3 are F.
본 명세서의 일 실시상태에 따르면, 상기 R309 내지 R314는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 니트릴기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아민기이다.According to an exemplary embodiment of the present specification, R309 to R314 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted amine group.
본 명세서의 일 실시상태에 따르면, 상기 R309 내지 R314는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 니트릴이다.According to an exemplary embodiment of the present specification, R309 to R314 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or nitrile.
본 명세서의 일 실시상태에 따르면, 상기 R309 내지 R314는 니트릴기다.According to an exemplary embodiment of the present specification, R309 to R314 are nitrile groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HI-2은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula HI-2 is represented by the following compound.
Figure PCTKR2023007638-appb-img-000029
Figure PCTKR2023007638-appb-img-000029
상기 정공수송층은 정공의 수송을 원활하게 하는 역할을 할 수 있다. 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer may play a role in facilitating the transport of holes. The hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.
본 명세서의 일 실시상태에 따르면, 상기 정공수송층은 하기 화학식 HT-2로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HT-2, but is not limited thereto.
[화학식 HT-2][Formula HT-2]
Figure PCTKR2023007638-appb-img-000030
Figure PCTKR2023007638-appb-img-000030
상기 화학식 HT-2에 있어서,In the formula HT-2,
R403 내지 R406는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R403 to R406 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with adjacent groups to form a substituted or unsubstituted ring,
L403는 치환 또는 비치환된 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이고,L403 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
l403은 1 내지 3의 정수이고, l403이 2 이상이면, L403은 서로 같거나 상이하다.l403 is an integer from 1 to 3, and if l403 is 2 or more, L403 is the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 R403 내지 R406는 서로 같거나 상이하고, 각가 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 R403 내지 R406는 서로 같거나 상이하고, 각가 독립적으로 탄소수 6 내지 30의 아릴기이다.According to an exemplary embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R403 내지 R406는 서로 같거나 상이하고, 각가 독립적으로 페닐기, 비페닐기, 또는 나프틸기이다According to an exemplary embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents a phenyl group, a biphenyl group, or a naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 R403 내지 R406는 서로 같거나 상이하고, 각가 독립적으로 페닐기 이다. According to an exemplary embodiment of the present specification, R403 to R406 are the same or different from each other, and each independently represents a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 L403은 탄소수 6 내지 30의 아릴렌기, 또는 아릴렌기로 치환된 탄소수 3 내지 30의 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L403 is an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms substituted with an arylene group.
본 명세서의 일 실시상태에 따르면, 상기 L403은 페닐렌기, 2가의 비페닐기, 또는 아릴기로 치환 또는 비치환된 2가의 카바졸기이다.According to an exemplary embodiment of the present specification, L403 is a divalent carbazole group unsubstituted or substituted with a phenylene group, a divalent biphenyl group, or an aryl group.
본 명세서의 일 실시상태에 따르면, 상기 L403은 나프틸기로 치환된 2가의 카바졸기이다.According to an exemplary embodiment of the present specification, L403 is a divalent carbazole group substituted with a naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HT-2는 하기 화합물들 선택된다.According to an exemplary embodiment of the present specification, the formula HT-2 is selected from the following compounds.
Figure PCTKR2023007638-appb-img-000031
Figure PCTKR2023007638-appb-img-000031
정공수송층과 발광층 사이에 전자차단층이 구비될 수 있다. 상기 전자차단층은 전술한 스피로 화합물 또는 당 기술분야에 알려져 있는 재료가 사용될 수 있다.An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be made of the spiro compound described above or a material known in the art.
본 명세서의 일 실시상태에 따르면, 상기 전자차단층은 하기 화학식 EB-1로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the electron blocking layer includes, but is not limited to, a compound represented by the following formula EB-1.
[화학식 EB-1][Formula EB-1]
Figure PCTKR2023007638-appb-img-000032
Figure PCTKR2023007638-appb-img-000032
상기 화학식 EB-1에 있어서,In the formula EB-1,
L311 내지 L313은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L311 to L313 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R311 내지 R313는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.R311 to R313 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and combinations thereof, or is combined with adjacent groups to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 따르면, 상기 R311 내지 R313는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 치환 또는 비치환된 헤테로아릴기; 및 이들의 조합으로 이루어진 군에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, R311 to R313 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
본 명세서의 일 실시상태에 따르면, 상기 R311 내지 R313는 서로 같거나 상이하고, 각각 독립적으로 바이페닐기; 또는 페난트렌기이다.According to an exemplary embodiment of the present specification, R311 to R313 are the same as or different from each other, and are each independently a biphenyl group; Or it is a phenanthrene group.
본 명세서의 일 실시상태에 따르면, 상기 L311 내지 L313은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 아릴렌기; 또는 헤테로아릴렌기이다.According to an exemplary embodiment of the present specification, L311 to L313 are the same or different from each other and are each independently directly bonded; Arylene group; Or it is a heteroarylene group.
본 명세서의 일 실시상태에 따르면, 상기 L311 내지 L313은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 페닐렌기이다.According to an exemplary embodiment of the present specification, L311 to L313 are the same or different from each other and are each independently directly bonded; Or it is a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 EB-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula EB-1 is represented by the following compound.
Figure PCTKR2023007638-appb-img-000033
Figure PCTKR2023007638-appb-img-000033
상기 발광층은 적색, 녹색 또는 청색을 발광할 수 있으며, 인광 물질 또는 형광 물질로 이루어질 수 있다. 상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light-emitting layer may emit red, green, or blue light and may be made of a phosphorescent material or a fluorescent material. The light-emitting material is a material capable of emitting light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.
발광층의 호스트 재료로는 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 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다.Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-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 carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
발광층이 적색 발광을 하는 경우, 발광 도펀트로는 PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum)와 같은 인광 물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. 발광층이 녹색 발광을 하는 경우, 발광 도펀트로는 Ir(ppy)3(fac tris(2-phenylpyridine)iridium)와 같은 인광물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. 발광층이 청색 발광을 하는 경우, 발광 도펀트로는 (4,6-F2ppy)2Irpic와 같은 인광 물질이나, spiro-DPVBi, spiro-6P, 디스틸벤젠(DSB), 디스트릴아릴렌(DSA), PFO계 고분자, PPV계 고분자와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다.When the light-emitting layer emits red light, the light-emitting dopants include PIQIr(acac)(bis(1-phenylsoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), and PQIr(tris(1-phenylquinoline)iridium). ), phosphorescent materials such as PtOEP (octaethylporphyrin platinum), or fluorescent materials such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but are not limited to these. If the light-emitting layer emits green light, a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used as the light-emitting dopant. However, it is not limited to this. If the light-emitting layer emits blue light, the light-emitting dopant may be a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited to these.
본 명세서의 일 실시상태에 따르면, 상기 도펀트는 금속착체가 사용될 수 있다. According to an exemplary embodiment of the present specification, a metal complex may be used as the dopant.
본 명세서의 일 실시상태에 따르면, 상기 도펀트는 이리듐 착체가 사용될 수 있다. According to an exemplary embodiment of the present specification, the dopant may be an iridium complex.
본 명세서의 일 실시상태에 따르면, 상기 도펀트에 사용되는 이리듐 착체는 아래의 구조 중 어느 하나일 수 있으나, 이에 한정하는 것은 아니다.According to an exemplary embodiment of the present specification, the iridium complex used as the dopant may have any one of the structures below, but is not limited thereto.
Figure PCTKR2023007638-appb-img-000034
Figure PCTKR2023007638-appb-img-000034
Figure PCTKR2023007638-appb-img-000035
Figure PCTKR2023007638-appb-img-000035
Figure PCTKR2023007638-appb-img-000036
Figure PCTKR2023007638-appb-img-000036
Figure PCTKR2023007638-appb-img-000037
Figure PCTKR2023007638-appb-img-000037
상기 명시된 구조는 도판트 화합물로 이에 한정하는 것은 아니다.The structure specified above is not limited to the dopant compound.
전자수송층과 발광층 사이에 정공억제층이 구비될 수 있으며, 당 기술분야에 알려져 있는 재료가 사용될 수 있다.A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
상기 전자수송층은 전자의 수송을 원활하게 하는 역할을 할 수 있다. 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자수송층의 두께는 1 내지 50nm일 수 있다. 전자수송층의 두께가 1nm 이상이면, 전자 수송 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 50nm 이하이면, 전자수송층의 두께가 너무 두꺼워 전자의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다.The electron transport layer may play a role in facilitating the transport of electrons. The electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There are benefits to this.
상기 전자주입층은 전자의 주입을 원활하게 하는 역할을 할 수 있다. 전자 주입 물질로는 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 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 한정되지 않는다. The electron injection layer may serve to facilitate injection of electrons. The electron injection material has the ability to transport electrons, has an excellent electron injection effect from the cathode, a light emitting layer or a light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also has an excellent electron injection effect from the cathode to the light emitting layer or light emitting material. , Compounds with excellent thin film forming ability are preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[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 한정되지 않는다.Examples of the metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, Tris(2-methyl-8-hydroxyquinolinato)aluminum, Tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.
본 명세서의 일 실시상태에 따르면, 상기 전자주입 및 수송층은 하기 화학식 ET-1의 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the electron injection and transport layer includes, but is not limited to, a compound of the following formula ET-1.
[화학식 ET-1][Formula ET-1]
Figure PCTKR2023007638-appb-img-000038
Figure PCTKR2023007638-appb-img-000038
상기 화학식 ET-1에 있어서,In the formula ET-1,
Z11 내지 Z13 중 적어도 하나는 N이고, 나머지는 CH이고,At least one of Z11 to Z13 is N, the others are CH,
L601는 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L601 is directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar601 내지 Ar603은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,Ar601 to Ar603 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
l601은 1 내지 5의 정수이며, 상기 l601이 2 이상인 경우, 상기 2 이상의 L601은 서로 같거나 상이하다.l601 is an integer from 1 to 5, and when l601 is 2 or more, the 2 or more L601s are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 L601은 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L601은 페닐렌기; 바이페닐릴렌기; 또는 나프틸렌기이다.According to an exemplary embodiment of the present specification, L601 is a phenylene group; Biphenylylene group; Or it is a naphthylene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar601 및 Ar602는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar601 and Ar602 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar601 및 Ar602는 페닐기이다.According to an exemplary embodiment of the present specification, Ar601 and Ar602 are phenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 Ar603은 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar603 is a heteroaryl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar603은 페닐기로 치환 또는 비치환된 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar603 is a heteroaryl group substituted or unsubstituted with a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar603은 페닐기로 치환 또는 비치환된 트리아진기이다.According to an exemplary embodiment of the present specification, Ar603 is a triazine group substituted or unsubstituted by a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 ET-1은 하기 화합물로 표시된다According to an exemplary embodiment of the present specification, the formula ET-1 is represented by the following compound
Figure PCTKR2023007638-appb-img-000039
Figure PCTKR2023007638-appb-img-000039
본 명세서의 상기 정공저지층은 정공의 음극 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 구체적으로 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되지 않는다.The hole blocking layer of this specification is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 정공저지층은 하기 화학식 HB-1의 화합물을 포함한다.According to an exemplary embodiment of the present specification, the hole blocking layer includes a compound of the following formula HB-1.
[화학식 HB-1][Formula HB-1]
Figure PCTKR2023007638-appb-img-000040
Figure PCTKR2023007638-appb-img-000040
상기 화학식 HB-1에 있어서,In the formula HB-1,
Z1 내지 Z3 중 적어도 하나는 N이고, 나머지는 CH이고,At least one of Z1 to Z3 is N, the others are CH,
L601 및 L602는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L601 and L602 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar601 내지 Ar603은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar601 to Ar603 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 L601은 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L601 및 L602는 서로 같거나 상이하고, 각각 독립적으로 페닐렌기; 바이페닐릴렌기; 또는 나프틸렌기이다.According to an exemplary embodiment of the present specification, L601 and L602 are the same as or different from each other, and are each independently a phenylene group; Biphenylylene group; Or it is a naphthylene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar601 내지 Ar603은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기, 또는 탄소수 3 내지 30의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar601 to Ar603 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms. .
본 명세서의 일 실시상태에 따르면, 상기 Ar601 내지 Ar603은 페닐기, 또는 트리페닐렌기이다.According to an exemplary embodiment of the present specification, Ar601 to Ar603 are phenyl groups or triphenylene groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HB-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula HB-1 is represented by the following compound.
Figure PCTKR2023007638-appb-img-000041
Figure PCTKR2023007638-appb-img-000041
본 발명에 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 invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
본 발명의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.
상기 화학식 1의 화합물의 제조방법 및 이들을 이용한 유기 발광 소자의 제조는 이하의 실시예에서 구체적으로 설명한다. 그러나, 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.The method for producing the compound of Formula 1 and the production of organic light-emitting devices using the same will be described in detail in the examples below. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.
하기 반응식에 있어서, 치환기의 종류 및 개수는 당업자가 공지된 출발물질을 적절히 선택함에 따라 다양한 종류의 중간체를 합성할 수 있다. 반응 종류 및 반응 조건은 당기술분야에 알려져 있는 것들이 이용될 수 있다. In the following reaction formula, various types of intermediates can be synthesized by appropriately selecting starting materials known to those skilled in the art regarding the type and number of substituents. Reaction types and reaction conditions known in the art can be used.
본 명세서의 실시예에 기재된 제조식과 상기 중간체들을 통상의 기술상식을 바탕으로 적절히 조합하면, 본 명세서에 기재되어 있는 상기 화학식 1의 화합물들을 모두 제조할 수 있다. By appropriately combining the production formulas described in the Examples of this specification and the intermediates based on common technical knowledge, all of the compounds of Formula 1 described in this specification can be prepared.
합성예 1Synthesis Example 1
Figure PCTKR2023007638-appb-img-000042
Figure PCTKR2023007638-appb-img-000042
Trz1 (15g, 33.5mmol)와 sub1 (12.5g, 35.2mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.9g, 100.5mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1를 14.6g 제조하였다. (수율 68%, MS: [M+H]+= 642)Trz1 (15g, 33.5mmol) and sub1 (12.5g, 35.2mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.9g, 100.5mmol) was dissolved in 100ml of water and stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.6 g of Compound 1. (Yield 68%, MS: [M+H]+= 642)
합성예 2Synthesis Example 2
Figure PCTKR2023007638-appb-img-000043
Figure PCTKR2023007638-appb-img-000043
Trz2 (15g, 35.9mmol)와 sub2 (13.4g, 37.7mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14.9g, 107.7mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 2를 14.5g 제조하였다. (수율 66%, MS: [M+H]+= 612)Trz2 (15g, 35.9mmol) and sub2 (13.4g, 37.7mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.9g, 107.7mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.5 g of Compound 2. (Yield 66%, MS: [M+H]+= 612)
합성예 3Synthesis Example 3
Figure PCTKR2023007638-appb-img-000044
Figure PCTKR2023007638-appb-img-000044
Trz3 (15g, 33.3mmol)와 sub1 (12.4g, 35mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.8g, 100mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 3를 17.1g 제조하였다. (수율 80%, MS: [M+H]+= 644)Trz3 (15g, 33.3mmol) and sub1 (12.4g, 35mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.8g, 100mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.1 g of Compound 3. (Yield 80%, MS: [M+H]+= 644)
합성예 4Synthesis Example 4
Figure PCTKR2023007638-appb-img-000045
Figure PCTKR2023007638-appb-img-000045
Trz4 (15g, 36.8mmol)와 sub3 (16.7g, 38.6mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.2g, 110.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 4를 18.2g 제조하였다. (수율 73%, MS: [M+H]+= 678)Trz4 (15g, 36.8mmol) and sub3 (16.7g, 38.6mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.2g, 110.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.2 g of Compound 4. (Yield 73%, MS: [M+H]+= 678)
합성예 5Synthesis Example 5
Figure PCTKR2023007638-appb-img-000046
Figure PCTKR2023007638-appb-img-000046
Trz5 (15g, 41.9mmol)와 sub4 (15.6g, 44mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(17.4g, 125.8mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 5를 17.1g 제조하였다. (수율 74%, MS: [M+H]+= 552)Trz5 (15g, 41.9mmol) and sub4 (15.6g, 44mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (17.4g, 125.8mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.1 g of Compound 5. (Yield 74%, MS: [M+H]+= 552)
합성예 6Synthesis Example 6
Figure PCTKR2023007638-appb-img-000047
Figure PCTKR2023007638-appb-img-000047
Trz6 (15g, 38.1mmol)와 sub5 (14.2g, 40mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.8g, 114.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 6를 15.2g 제조하였다. (수율 68%, MS: [M+H]+= 588)Trz6 (15g, 38.1mmol) and sub5 (14.2g, 40mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.8g, 114.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.2 g of Compound 6. (Yield 68%, MS: [M+H]+= 588)
합성예 7Synthesis Example 7
Figure PCTKR2023007638-appb-img-000048
Figure PCTKR2023007638-appb-img-000048
Trz5 (15g, 41.9mmol)와 sub6 (19g, 44mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(17.4g, 125.8mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 7를 18.7g 제조하였다. (수율 71%, MS: [M+H]+= 628)Trz5 (15g, 41.9mmol) and sub6 (19g, 44mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (17.4g, 125.8mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.7 g of Compound 7. (Yield 71%, MS: [M+H]+= 628)
합성예 8Synthesis Example 8
Figure PCTKR2023007638-appb-img-000049
Figure PCTKR2023007638-appb-img-000049
Trz7 (15g, 34.6mmol)와 sub7 (15.7g, 36.4mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14.4g, 103.9mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 8를 17.3g 제조하였다. (수율 71%, MS: [M+H]+= 703)Trz7 (15g, 34.6mmol) and sub7 (15.7g, 36.4mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.4g, 103.9mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.3 g of Compound 8. (Yield 71%, MS: [M+H]+= 703)
합성예 9Synthesis Example 9
Figure PCTKR2023007638-appb-img-000050
Figure PCTKR2023007638-appb-img-000050
Trz8 (15g, 38.1mmol)와 sub8 (17.2g, 40mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.8g, 114.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 9를 18.2g 제조하였다. (수율 72%, MS: [M+H]+= 664)Trz8 (15g, 38.1mmol) and sub8 (17.2g, 40mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.8g, 114.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.2 g of compound 9. (Yield 72%, MS: [M+H]+= 664)
합성예 10Synthesis Example 10
Figure PCTKR2023007638-appb-img-000051
Figure PCTKR2023007638-appb-img-000051
Trz9 (15g, 33.8mmol)와 sub9 (15.3g, 35.5mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14g, 101.4mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 10를 17.1g 제조하였다. (수율 71%, MS: [M+H]+= 714)Trz9 (15g, 33.8mmol) and sub9 (15.3g, 35.5mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14g, 101.4mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.1 g of compound 10. (Yield 71%, MS: [M+H]+= 714)
합성예 11Synthesis Example 11
Figure PCTKR2023007638-appb-img-000052
Figure PCTKR2023007638-appb-img-000052
Trz10 (15g, 33.6mmol)와 sub10 (12.5g, 35.2mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.9g, 100.7mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 11를 14g 제조하였다. (수율 65%, MS: [M+H]+= 641)Trz10 (15g, 33.6mmol) and sub10 (12.5g, 35.2mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.9g, 100.7mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14g of compound 11. (Yield 65%, MS: [M+H]+= 641)
합성예 12Synthesis Example 12
Figure PCTKR2023007638-appb-img-000053
Figure PCTKR2023007638-appb-img-000053
Trz11 (15g, 31.9mmol)와 sub11 (11.9g, 33.5mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.2g, 95.8mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 12를 13.1g 제조하였다. (수율 62%, MS: [M+H]+= 664)Trz11 (15g, 31.9mmol) and sub11 (11.9g, 33.5mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.2g, 95.8mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.1 g of Compound 12. (Yield 62%, MS: [M+H]+= 664)
합성예 13Synthesis Example 13
Figure PCTKR2023007638-appb-img-000054
Figure PCTKR2023007638-appb-img-000054
Trz12 (15g, 42mmol)와 sub4 (15.7g, 44.1mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(17.4g, 126.1mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 13를 16.2g 제조하였다. (수율 70%, MS: [M+H]+= 551)Trz12 (15g, 42mmol) and sub4 (15.7g, 44.1mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (17.4g, 126.1mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.2 g of Compound 13. (Yield 70%, MS: [M+H]+= 551)
합성예 14Synthesis Example 14
Figure PCTKR2023007638-appb-img-000055
Figure PCTKR2023007638-appb-img-000055
Trz13 (15g, 40.8mmol)와 sub12 (15.2g, 42.8mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(16.9g, 122.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 14를 15.1g 제조하였다. (수율 66%, MS: [M+H]+= 562)Trz13 (15g, 40.8mmol) and sub12 (15.2g, 42.8mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (16.9g, 122.3mmol) was dissolved in 100ml of water, stirred sufficiently, and bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.1 g of compound 14. (Yield 66%, MS: [M+H]+= 562)
합성예 15Synthesis Example 15
Figure PCTKR2023007638-appb-img-000056
Figure PCTKR2023007638-appb-img-000056
Trz5 (15g, 41.9mmol)와 sub13 (15.6g, 44mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(17.4g, 125.8mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 15를 15.9g 제조하였다. (수율 69%, MS: [M+H]+= 552)Trz5 (15g, 41.9mmol) and sub13 (15.6g, 44mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (17.4g, 125.8mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.9 g of Compound 15. (Yield 69%, MS: [M+H]+= 552)
합성예 16Synthesis Example 16
Figure PCTKR2023007638-appb-img-000057
Figure PCTKR2023007638-appb-img-000057
Trz14 (15g, 38.1mmol)와 sub14 (17.2g, 40mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.8g, 114.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 16를 18.2g 제조하였다. (수율 72%, MS: [M+H]+= 664)Trz14 (15g, 38.1mmol) and sub14 (17.2g, 40mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.8g, 114.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.2 g of Compound 16. (Yield 72%, MS: [M+H]+= 664)
합성예 17Synthesis Example 17
Figure PCTKR2023007638-appb-img-000058
Figure PCTKR2023007638-appb-img-000058
Trz15 (15g, 40.8mmol)와 sub15 (18.5g, 42.8mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(16.9g, 122.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 17를 19.5g 제조하였다. (수율 75%, MS: [M+H]+= 638)Trz15 (15g, 40.8mmol) and sub15 (18.5g, 42.8mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (16.9g, 122.3mmol) was dissolved in 100ml of water, stirred sufficiently, and bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 19.5 g of compound 17. (Yield 75%, MS: [M+H]+= 638)
합성예 18Synthesis Example 18
Figure PCTKR2023007638-appb-img-000059
Figure PCTKR2023007638-appb-img-000059
Trz16 (15g, 35.9mmol)와 sub16 (16.3g, 37.7mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14.9g, 107.7mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 18를 19.5g 제조하였다. (수율 79%, MS: [M+H]+= 688)Trz16 (15g, 35.9mmol) and sub16 (16.3g, 37.7mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.9g, 107.7mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 19.5 g of compound 18. (Yield 79%, MS: [M+H]+= 688)
합성예 19Synthesis Example 19
Figure PCTKR2023007638-appb-img-000060
Figure PCTKR2023007638-appb-img-000060
Trz17 (15g, 36.8mmol)와 sub17 (13.7g, 38.6mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.2g, 110.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 19를 15g 제조하였다. (수율 68%, MS: [M+H]+= 602)Trz17 (15g, 36.8mmol) and sub17 (13.7g, 38.6mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.2g, 110.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15 g of compound 19. (Yield 68%, MS: [M+H]+= 602)
합성예 20Synthesis Example 20
Figure PCTKR2023007638-appb-img-000061
Figure PCTKR2023007638-appb-img-000061
Trz18 (15g, 38.1mmol)와 sub18 (14.2g, 40mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.8g, 114.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 20를 14.7g 제조하였다. (수율 66%, MS: [M+H]+= 587)Trz18 (15g, 38.1mmol) and sub18 (14.2g, 40mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.8g, 114.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.7 g of compound 20. (Yield 66%, MS: [M+H]+= 587)
합성예 21Synthesis Example 21
Figure PCTKR2023007638-appb-img-000062
Figure PCTKR2023007638-appb-img-000062
Trz19 (15g, 41.8mmol)와 sub19 (15.6g, 43.9mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(17.3g, 125.4mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 21를 15.7g 제조하였다. (수율 68%, MS: [M+H]+= 552)Trz19 (15g, 41.8mmol) and sub19 (15.6g, 43.9mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (17.3g, 125.4mmol) was dissolved in 100ml of water and stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.7 g of Compound 21. (Yield 68%, MS: [M+H]+= 552)
합성예 22Synthesis Example 22
Figure PCTKR2023007638-appb-img-000063
Figure PCTKR2023007638-appb-img-000063
Trz20 (15g, 32.8mmol)와 sub19 (12.2g, 34.4mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.6g, 98.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 4시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 22를 14.1g 제조하였다. (수율 66%, MS: [M+H]+= 651)Trz20 (15g, 32.8mmol) and sub19 (12.2g, 34.4mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.6g, 98.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 4 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.1 g of Compound 22. (Yield 66%, MS: [M+H]+= 651)
합성예 23Synthesis Example 23
Figure PCTKR2023007638-appb-img-000064
Figure PCTKR2023007638-appb-img-000064
Trz5 (15g, 41.9mmol)와 sub20 (19g, 44mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(17.4g, 125.8mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 23를 16g 제조하였다. (수율 61%, MS: [M+H]+= 627)Trz5 (15g, 41.9mmol) and sub20 (19g, 44mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (17.4g, 125.8mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16g of Compound 23. (Yield 61%, MS: [M+H]+= 627)
합성예 24Synthesis Example 24
Figure PCTKR2023007638-appb-img-000065
Figure PCTKR2023007638-appb-img-000065
Trz21 (15g, 36.8mmol)와 sub19 (13.7g, 38.6mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.2g, 110.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 24를 16.6g 제조하였다. (수율 75%, MS: [M+H]+= 601)Trz21 (15g, 36.8mmol) and sub19 (13.7g, 38.6mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.2g, 110.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.6 g of compound 24. (Yield 75%, MS: [M+H]+= 601)
합성예 25Synthesis Example 25
Figure PCTKR2023007638-appb-img-000066
Figure PCTKR2023007638-appb-img-000066
Trz22 (15g, 35.7mmol)와 sub19 (13.3g, 37.5mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14.8g, 107.2mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 25를 17.1g 제조하였다. (수율 78%, MS: [M+H]+= 613)Trz22 (15g, 35.7mmol) and sub19 (13.3g, 37.5mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.8g, 107.2mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.1 g of Compound 25. (Yield 78%, MS: [M+H]+= 613)
합성예 26Synthesis Example 26
Figure PCTKR2023007638-appb-img-000067
Figure PCTKR2023007638-appb-img-000067
Trz23 (15g, 34.6mmol)와 sub19 (12.9g, 36.4mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14.4g, 103.9mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 26를 16.9g 제조하였다. (수율 78%, MS: [M+H]+= 626)Trz23 (15g, 34.6mmol) and sub19 (12.9g, 36.4mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.4g, 103.9mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.9 g of Compound 26. (Yield 78%, MS: [M+H]+= 626)
합성예 27Synthesis Example 27
Figure PCTKR2023007638-appb-img-000068
Figure PCTKR2023007638-appb-img-000068
Trz19 (15g, 41.8mmol)와 sub21 (18.9g, 43.9mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(17.3g, 125.4mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 27를 16g 제조하였다. (수율 61%, MS: [M+H]+= 628)Trz19 (15g, 41.8mmol) and sub21 (18.9g, 43.9mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (17.3g, 125.4mmol) was dissolved in 100ml of water and stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16g of compound 27. (Yield 61%, MS: [M+H]+= 628)
합성예 28Synthesis Example 28
Figure PCTKR2023007638-appb-img-000069
Figure PCTKR2023007638-appb-img-000069
Trz24 (15g, 33.5mmol)와 sub22 (12.5g, 35.2mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.9g, 100.5mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 28를 15g 제조하였다. (수율 70%, MS: [M+H]+= 641)Trz24 (15g, 33.5mmol) and sub22 (12.5g, 35.2mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.9g, 100.5mmol) was dissolved in 100ml of water and stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15 g of compound 28. (Yield 70%, MS: [M+H]+= 641)
합성예 29Synthesis Example 29
Figure PCTKR2023007638-appb-img-000070
Figure PCTKR2023007638-appb-img-000070
Trz25 (15g, 36.8mmol)와 sub23 (13.7g, 38.6mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.2g, 110.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 29를 17.2g 제조하였다. (수율 78%, MS: [M+H]+= 601)Trz25 (15g, 36.8mmol) and sub23 (13.7g, 38.6mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.2g, 110.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.2 g of compound 29. (Yield 78%, MS: [M+H]+= 601)
합성예 30Synthesis Example 30
Figure PCTKR2023007638-appb-img-000071
Figure PCTKR2023007638-appb-img-000071
Trz26 (15g, 32.8mmol)와 sub23 (12.2g, 34.4mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.6g, 98.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 30를 15.8g 제조하였다. (수율 74%, MS: [M+H]+= 651)Trz26 (15g, 32.8mmol) and sub23 (12.2g, 34.4mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.6g, 98.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.8 g of Compound 30. (Yield 74%, MS: [M+H]+= 651)
합성예 31Synthesis Example 31
Figure PCTKR2023007638-appb-img-000072
Figure PCTKR2023007638-appb-img-000072
Trz27 (15g, 34.5mmol)와 sub24 (12.9g, 36.2mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14.3g, 103.5mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 31를 16.2g 제조하였다. (수율 75%, MS: [M+H]+= 628)Trz27 (15g, 34.5mmol) and sub24 (12.9g, 36.2mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.3g, 103.5mmol) was dissolved in 100ml of water and stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.2 g of compound 31. (Yield 75%, MS: [M+H]+= 628)
합성예 32Synthesis Example 32
Figure PCTKR2023007638-appb-img-000073
Figure PCTKR2023007638-appb-img-000073
Trz28 (15g, 30.1mmol)와 sub25 (11.2g, 31.6mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(12.5g, 90.4mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 32를 13.5g 제조하였다. (수율 65%, MS: [M+H]+= 691)Trz28 (15g, 30.1mmol) and sub25 (11.2g, 31.6mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (12.5g, 90.4mmol) was dissolved in 100ml of water and stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.5 g of Compound 32. (Yield 65%, MS: [M+H]+= 691)
합성예 33Synthesis Example 33
Figure PCTKR2023007638-appb-img-000074
Figure PCTKR2023007638-appb-img-000074
Trz29 (15g, 32.3mmol)와 sub26 (12g, 33.9mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.4g, 96.8mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 33를 15.9g 제조하였다. (수율 75%, MS: [M+H]+= 658)Trz29 (15g, 32.3mmol) and sub26 (12g, 33.9mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.4g, 96.8mmol) was dissolved in 100ml of water, stirred sufficiently, and bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.9 g of compound 33. (Yield 75%, MS: [M+H]+= 658)
합성예 34Synthesis Example 34
Figure PCTKR2023007638-appb-img-000075
Figure PCTKR2023007638-appb-img-000075
Trz30 (15g, 32.8mmol)와 sub27 (12.2g, 34.4mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.6g, 98.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 34를 16g 제조하였다. (수율 75%, MS: [M+H]+= 651)Trz30 (15g, 32.8mmol) and sub27 (12.2g, 34.4mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.6g, 98.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16g of compound 34. (Yield 75%, MS: [M+H]+= 651)
합성예 35Synthesis Example 35
Figure PCTKR2023007638-appb-img-000076
Figure PCTKR2023007638-appb-img-000076
Trz31 (15g, 33.8mmol)와 sub26 (12.6g, 35.5mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14g, 101.4mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 4시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 35를 15.9g 제조하였다. (수율 74%, MS: [M+H]+= 637)Trz31 (15g, 33.8mmol) and sub26 (12.6g, 35.5mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14g, 101.4mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 4 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.9 g of Compound 35. (Yield 74%, MS: [M+H]+= 637)
합성예 36Synthesis Example 36
Figure PCTKR2023007638-appb-img-000077
Figure PCTKR2023007638-appb-img-000077
Trz32 (15g, 36.8mmol)와 sub28 (13.7g, 38.6mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.2g, 110.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 4시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 36를 17g 제조하였다. (수율 77%, MS: [M+H]+= 601)Trz32 (15g, 36.8mmol) and sub28 (13.7g, 38.6mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.2g, 110.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 4 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17g of compound 36. (Yield 77%, MS: [M+H]+= 601)
합성예 37Synthesis Example 37
Figure PCTKR2023007638-appb-img-000078
Figure PCTKR2023007638-appb-img-000078
Trz33 (15g, 36.8mmol)와 sub29 (16.7g, 38.6mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.2g, 110.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 37를 16.7g 제조하였다. (수율 67%, MS: [M+H]+= 677)Trz33 (15g, 36.8mmol) and sub29 (16.7g, 38.6mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.2g, 110.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.7 g of compound 37. (Yield 67%, MS: [M+H]+= 677)
합성예 38Synthesis Example 38
Figure PCTKR2023007638-appb-img-000079
Figure PCTKR2023007638-appb-img-000079
Trz15 (15g, 40.8mmol)와 sub30 (18.5g, 42.8mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(16.9g, 122.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 38를 17.6g 제조하였다. (수율 68%, MS: [M+H]+= 637)Trz15 (15g, 40.8mmol) and sub30 (18.5g, 42.8mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (16.9g, 122.3mmol) was dissolved in 100ml of water, stirred sufficiently, and bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.6 g of compound 38. (Yield 68%, MS: [M+H]+= 637)
합성예 39Synthesis Example 39
Figure PCTKR2023007638-appb-img-000080
Figure PCTKR2023007638-appb-img-000080
Trz34 (15g, 36.8mmol)와 sub31 (13.7g, 38.6mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.2g, 110.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 39를 17g 제조하였다. (수율 77%, MS: [M+H]+= 601)Trz34 (15g, 36.8mmol) and sub31 (13.7g, 38.6mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.2g, 110.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17g of compound 39. (Yield 77%, MS: [M+H]+= 601)
합성예 40Synthesis Example 40
Figure PCTKR2023007638-appb-img-000081
Figure PCTKR2023007638-appb-img-000081
Trz7 (15g, 34.6mmol)와 sub32 (15.7g, 36.4mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14.4g, 103.9mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 40를 19.2g 제조하였다. (수율 79%, MS: [M+H]+= 702)Trz7 (15g, 34.6mmol) and sub32 (15.7g, 36.4mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.4g, 103.9mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 19.2 g of compound 40. (Yield 79%, MS: [M+H]+= 702)
합성예 41Synthesis Example 41
Figure PCTKR2023007638-appb-img-000082
Figure PCTKR2023007638-appb-img-000082
Trz35 (15g, 35.4mmol)와 sub33 (16g, 37.2mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14.7g, 106.2mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 41를 18.1g 제조하였다. (수율 74%, MS: [M+H]+= 693)Trz35 (15g, 35.4mmol) and sub33 (16g, 37.2mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.7g, 106.2mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 18.1 g of compound 41. (Yield 74%, MS: [M+H]+= 693)
합성예 42Synthesis Example 42
Figure PCTKR2023007638-appb-img-000083
Figure PCTKR2023007638-appb-img-000083
Trz36 (15g, 41.8mmol)와 sub34 (15.6g, 43.9mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(17.3g, 125.4mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 42를 13.8g 제조하였다. (수율 60%, MS: [M+H]+= 552)Trz36 (15g, 41.8mmol) and sub34 (15.6g, 43.9mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (17.3g, 125.4mmol) was dissolved in 100ml of water and stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.8 g of compound 42. (Yield 60%, MS: [M+H]+= 552)
합성예 43Synthesis Example 43
Figure PCTKR2023007638-appb-img-000084
Figure PCTKR2023007638-appb-img-000084
Trz37 (15g, 33.3mmol)와 sub35 (12.4g, 35mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.8g, 100mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 43를 14.6g 제조하였다. (수율 68%, MS: [M+H]+= 643)Trz37 (15g, 33.3mmol) and sub35 (12.4g, 35mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.8g, 100mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.6 g of compound 43. (Yield 68%, MS: [M+H]+= 643)
합성예 44Synthesis Example 44
Figure PCTKR2023007638-appb-img-000085
Figure PCTKR2023007638-appb-img-000085
Trz38 (15g, 34.6mmol)와 sub36 (12.9g, 36.4mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14.4g, 103.9mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 44를 15.6g 제조하였다. (수율 72%, MS: [M+H]+= 626)Trz38 (15g, 34.6mmol) and sub36 (12.9g, 36.4mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.4g, 103.9mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.6 g of compound 44. (Yield 72%, MS: [M+H]+= 626)
합성예 45Synthesis Example 45
Figure PCTKR2023007638-appb-img-000086
Figure PCTKR2023007638-appb-img-000086
Trz39 (15g, 36.8mmol)와 sub37 (16.7g, 38.6mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.2g, 110.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 4시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 45를 19.4g 제조하였다. (수율 78%, MS: [M+H]+= 677)Trz39 (15g, 36.8mmol) and sub37 (16.7g, 38.6mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.2g, 110.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 4 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 19.4 g of compound 45. (Yield 78%, MS: [M+H]+= 677)
합성예 46Synthesis Example 46
Figure PCTKR2023007638-appb-img-000087
Figure PCTKR2023007638-appb-img-000087
Trz40 (15g, 38.3mmol)와 sub38 (14.3g, 40.2mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.9g, 114.8mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 46를 15.7g 제조하였다. (수율 70%, MS: [M+H]+= 585)Trz40 (15g, 38.3mmol) and sub38 (14.3g, 40.2mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.9g, 114.8mmol) was dissolved in 100ml of water and stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.7 g of compound 46. (Yield 70%, MS: [M+H]+= 585)
합성예 47Synthesis Example 47
Figure PCTKR2023007638-appb-img-000088
Figure PCTKR2023007638-appb-img-000088
Trz41 (15g, 31.9mmol)와 sub39 (11.9g, 33.5mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.2g, 95.8mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 47를 15g 제조하였다. (수율 71%, MS: [M+H]+= 663)Trz41 (15g, 31.9mmol) and sub39 (11.9g, 33.5mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.2g, 95.8mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15 g of compound 47. (Yield 71%, MS: [M+H]+= 663)
합성예 48Synthesis Example 48
Figure PCTKR2023007638-appb-img-000089
Figure PCTKR2023007638-appb-img-000089
Trz42 (15g, 34.6mmol)와 sub40 (15.7g, 36.3mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(14.3g, 103.7mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 48를 17.5g 제조하였다. (수율 72%, MS: [M+H]+= 703)Trz42 (15g, 34.6mmol) and sub40 (15.7g, 36.3mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (14.3g, 103.7mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 17.5 g of compound 48. (Yield 72%, MS: [M+H]+= 703)
합성예 49Synthesis Example 49
Figure PCTKR2023007638-appb-img-000090
Figure PCTKR2023007638-appb-img-000090
Trz43 (15g, 32.8mmol)와 sub41 (12.2g, 34.4mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.6g, 98.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 2시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 49를 14.1g 제조하였다. (수율 66%, MS: [M+H]+= 651)Trz43 (15g, 32.8mmol) and sub41 (12.2g, 34.4mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.6g, 98.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.1 g of compound 49. (Yield 66%, MS: [M+H]+= 651)
합성예 50Synthesis Example 50
Figure PCTKR2023007638-appb-img-000091
Figure PCTKR2023007638-appb-img-000091
Trz12 (15g, 42mmol)와 sub42 (15.7g, 44.1mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(17.4g, 126.1mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 50를 14.5g 제조하였다. (수율 63%, MS: [M+H]+= 550)Trz12 (15g, 42mmol) and sub42 (15.7g, 44.1mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (17.4g, 126.1mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.5 g of compound 50. (Yield 63%, MS: [M+H]+= 550)
합성예 51Synthesis Example 51
Figure PCTKR2023007638-appb-img-000092
Figure PCTKR2023007638-appb-img-000092
Trz44 (15g, 31.9mmol)와 sub43 (11.9g, 33.5mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.2g, 95.8mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 5시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 51를 14.2g 제조하였다. (수율 67%, MS: [M+H]+= 663)Trz44 (15g, 31.9mmol) and sub43 (11.9g, 33.5mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.2g, 95.8mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After 5 hours of reaction, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.2 g of compound 51. (Yield 67%, MS: [M+H]+= 663)
합성예 52Synthesis Example 52
Figure PCTKR2023007638-appb-img-000093
Figure PCTKR2023007638-appb-img-000093
Trz45 (15g, 31.9mmol)와 sub44 (11.9g, 33.5mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(13.2g, 95.8mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol)을 투입하였다. 4시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 52를 13.3g 제조하였다. (수율 63%, MS: [M+H]+= 663)Trz45 (15g, 31.9mmol) and sub44 (11.9g, 33.5mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (13.2g, 95.8mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.3mmol) was added. After reaction for 4 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.3 g of compound 52. (Yield 63%, MS: [M+H]+= 663)
합성예 53Synthesis Example 53
Figure PCTKR2023007638-appb-img-000094
Figure PCTKR2023007638-appb-img-000094
Trz46 (15g, 36.8mmol)와 sub43 (13.7g, 38.6mmol)를 THF 300ml에 넣고 교반 및 환류하였다. 이 후 potassium carbonate(15.2g, 110.3mmol)를 물 100ml에 녹여 투입하고 충분히 교반한 후 bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol)을 투입하였다. 3시간 반응 후 상온으로 식히고 유기층과 물층을 분리 후 유기층을 증류하였다. 이를 다시 클로로포름에 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 53를 16.8g 제조하였다. (수율 76%, MS: [M+H]+= 601)Trz46 (15g, 36.8mmol) and sub43 (13.7g, 38.6mmol) were added to 300ml of THF, stirred and refluxed. Afterwards, potassium carbonate (15.2g, 110.3mmol) was dissolved in 100ml of water, stirred sufficiently, and then bis(tri-tert-butylphosphine)palladium(0) (0.2g, 0.4mmol) was added. After reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 16.8 g of compound 53. (Yield 76%, MS: [M+H]+= 601)
실시예 1Example 1
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척했다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용했다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행했다. 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) with a thickness of 1,000 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 정공주입층으로 하기 HI-1 화합물을 1150Å의 두께로 형성하되 하기 A-1 화합물을 1.5% 농도로 p-doping 했다. 상기 정공주입층 위에 하기 HT-1 화합물을 진공 증착하여 막 두께 800Å 의 정공수송층을 형성했다. 이어서, 상기 정공수송층 위에 막 두께 150Å으로 하기 EB-1 화합물을 진공 증착하여 전자차단층을 형성했다. 이어서, 상기 EB-1 증착막 위에 하기 호스트로 화합물 1과 도판트로 Dp-7 화합물을 98:2의 중량비로 진공 증착하여 400Å 두께의 적색 발광층을 형성했다. 상기 발광층 위에 막 두께 30Å으로 하기 HB-1 화합물을 진공 증착하여 정공저지층을 형성했다. 이어서, 상기 정공저지층 위에 하기 ET-1 화합물과 하기 LiQ 화합물을 2:1의 중량비로 진공 증착하여 300Å의 두께로 전자 주입 및 수송층을 형성했다. 상기 전자 주입 및 수송층 위에 순차적으로 12Å 두께로 리튬플로라이드(LiF)와 1,000Å 두께로 알루미늄을 증착하여 음극을 형성했다. On the ITO transparent electrode prepared in this way, the following HI-1 compound was formed as a hole injection layer to a thickness of 1150 Å, and the following A-1 compound was p-doped at a concentration of 1.5%. The following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer with a film thickness of 800 Å. Subsequently, the following EB-1 compound was vacuum deposited to a film thickness of 150 Å on the hole transport layer to form an electron blocking layer. Next, Compound 1 as a host and Compound Dp-7 as a dopant were vacuum deposited on the EB-1 deposition film at a weight ratio of 98:2 to form a red light-emitting layer with a thickness of 400 Å. The following HB-1 compound was vacuum deposited to a film thickness of 30 Å on the light emitting layer to form a hole blocking layer. Next, the following ET-1 compound and the following LiQ compound were vacuum deposited on the hole blocking layer at a weight ratio of 2:1 to form an electron injection and transport layer with a thickness of 300 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.
Figure PCTKR2023007638-appb-img-000095
Figure PCTKR2023007638-appb-img-000095
Figure PCTKR2023007638-appb-img-000096
Figure PCTKR2023007638-appb-img-000096
상기의 과정에서 유기물의 증착속도는 0.4~0.7Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2ⅹ10-7 ~ 5ⅹ10-6 torr를 유지하여, 유기 발광 소자를 제작했다.In the above process, the deposition rate of organic matter was maintained at 0.4~0.7Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3Å/sec, and the deposition rate of aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2×10 -7 ~ An organic light emitting device was manufactured by maintaining 5×10 -6 torr.
실시예 2 내지 실시예 53Examples 2 to 53
실시예 1의 유기 발광 소자에서 표 1에 기재된 호스트로 화학식 1의 화합물을 사용하는 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 유기 발광 소자를 제조했다. An organic light-emitting device was manufactured in the same manner as Example 1, except that the compound of Formula 1 was used as the host shown in Table 1 in the organic light-emitting device of Example 1.
비교예 1 내지 비교예 6Comparative Examples 1 to 6
실시예 1의 유기 발광 소자에서 표 2에 기재된 호스트로 비교예 화합물을 사용하는 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 유기 발광 소자를 제조했다. An organic light-emitting device was manufactured in the same manner as Example 1, except that the comparative example compound was used as the host shown in Table 2 in the organic light-emitting device of Example 1.
상기 실시예 1 내지 실시예 53 및 비교예 1 내지 비교예 6에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율을 측정(15mA/cm2 기준)하고 그 결과를 하기 표 1 내지 표 2에 나타냈다. 수명 T95는 휘도가 초기 휘도(6,000 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When current was applied to the organic light emitting devices manufactured in Examples 1 to 53 and Comparative Examples 1 to 6, the voltage and efficiency were measured (based on 15 mA/cm 2 ), and the results are shown in Tables 1 to 6 below. Shown in 2. Lifespan T95 refers to the time it takes for luminance to decrease from the initial luminance (6,000 nits) to 95%.
구분division 호스트host 구동전압(V)Driving voltage (V) 효율(cd/A)Efficiency (cd/A) 수명 T95(hr)Life T95(hr) 발광색Luminous color
실시예 1Example 1 화합물1Compound 1 3.36 3.36 23.6823.68 240240 적색Red
실시예 2Example 2 화합물2Compound 2 3.37 3.37 24.7024.70 221221 적색Red
실시예 3Example 3 화합물3Compound 3 3.41 3.41 24.5624.56 238238 적색Red
실시예 4Example 4 화합물4Compound 4 3.34 3.34 23.5223.52 240240 적색Red
실시예 5Example 5 화합물5Compound 5 3.31 3.31 23.0823.08 256256 적색Red
실시예 6Example 6 화합물6Compound 6 3.33 3.33 22.8722.87 259259 적색Red
실시예 7Example 7 화합물7Compound 7 3.35 3.35 23.5123.51 233233 적색Red
실시예 8Example 8 화합물8Compound 8 3.37 3.37 24.6424.64 225225 적색Red
실시예 9Example 9 화합물9Compound 9 3.45 3.45 22.9222.92 203203 적색Red
실시예 10Example 10 화합물10Compound 10 3.43 3.43 23.6223.62 223223 적색Red
실시예 11Example 11 화합물11Compound 11 3.44 3.44 23.0223.02 218218 적색Red
실시예 12Example 12 화합물12Compound 12 3.49 3.49 22.9722.97 211211 적색Red
실시예 13Example 13 화합물13Compound 13 3.35 3.35 23.0523.05 263263 적색Red
실시예 14Example 14 화합물14Compound 14 3.43 3.43 22.9622.96 208208 적색Red
실시예 15Example 15 화합물15Compound 15 3.47 3.47 24.5024.50 221221 적색Red
실시예 16Example 16 화합물16Compound 16 3.43 3.43 22.8122.81 215215 적색Red
실시예 17Example 17 화합물17Compound 17 3.51 3.51 22.6222.62 201201 적색Red
실시예 18Example 18 화합물18Compound 18 3.47 3.47 23.1823.18 209209 적색Red
실시예 19Example 19 화합물19Compound 19 3.46 3.46 24.0324.03 210210 적색Red
실시예 20Example 20 화합물20Compound 20 3.63 3.63 21.7521.75 257257 적색Red
실시예 21Example 21 화합물21Compound 21 3.64 3.64 22.4122.41 263263 적색Red
실시예 22Example 22 화합물22Compound 22 3.66 3.66 21.8721.87 256256 적색Red
실시예 23Example 23 화합물23Compound 23 3.68 3.68 22.3822.38 250250 적색Red
실시예 24Example 24 화합물24Compound 24 3.60 3.60 22.4822.48 261261 적색Red
실시예 25Example 25 화합물25Compound 25 3.71 3.71 21.7321.73 253253 적색Red
실시예 26Example 26 화합물26Compound 26 3.68 3.68 22.4722.47 259259 적색Red
실시예 27Example 27 화합물27Compound 27 3.71 3.71 21.9421.94 251251 적색Red
실시예 28Example 28 화합물28Compound 28 3.38 3.38 22.4422.44 242242 적색Red
실시예 29Example 29 화합물29Compound 29 3.33 3.33 23.1323.13 258258 적색Red
실시예 30Example 30 화합물30Compound 30 3.40 3.40 24.5124.51 249249 적색Red
실시예 31Example 31 화합물31Compound 31 3.39 3.39 22.6422.64 259259 적색Red
실시예 32Example 32 화합물32Compound 32 3.32 3.32 22.4022.40 255255 적색Red
실시예 33Example 33 화합물33Compound 33 3.64 3.64 22.4922.49 252252 적색Red
실시예 34Example 34 화합물34Compound 34 3.54 3.54 21.4221.42 255255 적색Red
실시예 35Example 35 화합물35Compound 35 3.61 3.61 22.5722.57 244244 적색Red
실시예 36Example 36 화합물36Compound 36 3.64 3.64 23.0323.03 256256 적색Red
실시예 37Example 37 화합물37Compound 37 3.54 3.54 22.4822.48 253253 적색Red
실시예 38Example 38 화합물38Compound 38 3.49 3.49 24.9224.92 213213 적색Red
실시예 39Example 39 화합물39Compound 39 3.43 3.43 21.6521.65 209209 적색Red
실시예 40Example 40 화합물40Compound 40 3.52 3.52 24.4024.40 209209 적색Red
실시예 41Example 41 화합물41Compound 41 3.34 3.34 21.6121.61 234234 적색Red
실시예 42Example 42 화합물42Compound 42 3.39 3.39 23.9323.93 222222 적색Red
실시예 43Example 43 화합물43Compound 43 3.34 3.34 22.7822.78 242242 적색Red
실시예 44Example 44 화합물44Compound 44 3.32 3.32 22.9322.93 242242 적색Red
실시예 45Example 45 화합물45Compound 45 3.39 3.39 22.5722.57 222222 적색Red
실시예 46Example 46 화합물46Compound 46 3.33 3.33 24.6524.65 250250 적색Red
실시예 47Example 47 화합물47Compound 47 3.41 3.41 24.2024.20 252252 적색Red
실시예 48Example 48 화합물48Compound 48 3.34 3.34 23.8123.81 262262 적색Red
실시예 49Example 49 화합물49Compound 49 3.32 3.32 24.1624.16 252252 적색Red
실시예 50Example 50 화합물50Compound 50 3.39 3.39 23.6123.61 263263 적색Red
실시예 51Example 51 화합물51Compound 51 3.39 3.39 22.7222.72 252252 적색Red
실시예 52Example 52 화합물52Compound 52 3.38 3.38 21.5121.51 246246 적색Red
실시예 53Example 53 화합물53Compound 53 3.36 3.36 22.7022.70 256256 적색Red
구분division 호스트host 구동전압(V)Driving voltage (V) 효율(cd/A)Efficiency (cd/A) 수명 T95(hr)Life T95(hr) 발광색Luminous color
비교예 1Comparative Example 1 화합물B-1Compound B-1 3.86 3.86 19.8719.87 156156 적색Red
비교예 2Comparative Example 2 화합물B-2Compound B-2 3.98 3.98 19.3219.32 142142 적색Red
비교예 3Comparative Example 3 화합물B-3Compound B-3 4.12 4.12 16.2116.21 3636 적색Red
비교예 4Comparative Example 4 화합물B-4Compound B-4 3.96 3.96 19.2619.26 104104 적색Red
비교예 5Comparative Example 5 화합물B-5Compound B-5 3.94 3.94 18.7018.70 163163 적색Red
비교예 6Comparative Example 6 화합물B-6Compound B-6 4.03 4.03 18.2418.24 185185 적색Red
화합물 B-3 및 B-4는 본원 X1 내지 X10 중 2개가 N이다. 본원 실시예의 화합물들은 X1 내지 X10 중 어느 하나만 N이다. 화합물 B-3 및 B-4를 사용한 비교예 3 및 4는 실시예 1 내지 53과 비교하여, 저수명, 저효율, 고전압의 특성을 보인다. 이로서, X1 내지 X10 중 어느 하나만 N인 것이 유기 발광 소자 내에서 더 좋은 효과를 얻을 수 있음을 알 수 있다. In compounds B-3 and B-4, two of X1 to X10 in the present application are N. In the compounds of the examples herein, only one of X1 to X10 is N. Comparative Examples 3 and 4 using compounds B-3 and B-4 show the characteristics of low lifespan, low efficiency, and high voltage compared to Examples 1 to 53. As a result, it can be seen that better effects can be obtained in the organic light-emitting device when only one of X1 to X10 is N.
화합물 B-1 및 B-2는 본원 화학식 1의 화합물들과 다르게, X11 또는 X12가 N이다. 실시예 1 내지 53은 비교예 1 및 2와 비교하여, 고효율, 장수명의 특성을 보인다. Compounds B-1 and B-2 differ from the compounds of Formula 1 herein, where X11 or X12 is N. Examples 1 to 53 show characteristics of high efficiency and long life compared to Comparative Examples 1 and 2.
화합물 B-5는 R이 수소나 중수소가 아니라 페닐기인데, 이 경우, 전압, 효율, 수명면에서 실시예 1 내지 53보다 좋지 않음을 알 수 있다. In compound B-5, R is a phenyl group rather than hydrogen or deuterium, and in this case, it can be seen that it is not better than Examples 1 to 53 in terms of voltage, efficiency, and lifespan.
화합물 B-6은 트리아진 대신 피리미딘을 사용했는데, 실시예 1 내지 53은 비교예 6에 비해 저전압, 고효율, 장수명의 특성을 보인다.Compound B-6 used pyrimidine instead of triazine, and Examples 1 to 53 showed the characteristics of low voltage, high efficiency, and long life compared to Comparative Example 6.
실시예 1 내지 53 및 비교예 1 내지 6에 의해 제작된 유기 발광 소자에 전류를 인가하였을 때, 상기 표 1 내지 표 2의 결과를 얻었다. 상기 실시예 1의 적색 유기 발광 소자는 종래 널리 사용되고 있는 물질을 사용하였으며, 전자 차단층으로 화합물 [EB-1], 적색 도판트로 Dp-7을 사용하는 구조이다. When current was applied to the organic light emitting devices manufactured in Examples 1 to 53 and Comparative Examples 1 to 6, the results shown in Tables 1 to 2 were obtained. The red organic light emitting device of Example 1 used widely used materials and had a structure using compound [EB-1] as an electron blocking layer and Dp-7 as a red dopant.
본 발명의 화합물을 적색 발광층으로 사용했을 때 표 1과 같이 표 2의 비교예 대비 구동 전압이 감소하고 효율 및 수명이 증가하는 것을 볼 수 있다. 이러한 결과들로 유추했을 때 구동 전압이 개선되고 효율 및 수명이 상승하는 이유는 본 발명의 화합물을 호스트로 사용했을 때 비교예 화합물 대비 적색 발광층 내의 적색 도판트로의 에너지 전달이 잘 이뤄진다는 것을 알 수 있었다.When the compound of the present invention is used as a red light emitting layer, as shown in Table 1, it can be seen that the driving voltage is reduced and the efficiency and lifespan are increased compared to the comparative example in Table 2. Inferred from these results, the reason why the driving voltage is improved and the efficiency and lifespan are increased is that when the compound of the present invention is used as a host, energy is better transferred to the red dopant in the red emitting layer compared to the comparative example compound. there was.
이것은 결국 비교예 화합물 대비 발광층에서 더 안정적인 균형을 통해 전자와 정공이 결합하여 엑시톤을 형성하여 효율과 수명이 많이 상승 하는 것을 확인할 수 있었다. 결론적으로 본 발명의 화합물을 적색 발광층의 호스트로 사용하였을 때 유기 발광 소자의 구동전압, 발광 효율 및 수명 특성을 개선할 수 있다는 것을 확인할 수 있다. In the end, it was confirmed that electrons and holes combined to form exciton through a more stable balance in the light emitting layer compared to the comparative example compound, greatly increasing efficiency and lifespan. In conclusion, it can be confirmed that the driving voltage, luminous efficiency, and lifespan characteristics of organic light-emitting devices can be improved when the compound of the present invention is used as a host for a red light-emitting layer.

Claims (18)

  1. 하기 화학식 1의 화합물: Compound of formula 1:
    [화학식 1][Formula 1]
    Figure PCTKR2023007638-appb-img-000097
    Figure PCTKR2023007638-appb-img-000097
    상기 화학식 1에 있어서, In Formula 1,
    L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로 직접결합, 치환 또는 비치환된 아릴렌기 또는 치환 또는 비치환된 헤테로아릴렌기이고, L1 to L3 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
    Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기이고, Ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
    Ar3은 하기 화학식 2이고,Ar3 is of the formula 2 below,
    [화학식 2][Formula 2]
    Figure PCTKR2023007638-appb-img-000098
    Figure PCTKR2023007638-appb-img-000098
    상기 화학식 2에 있어서,In Formula 2,
    X1 내지 X10 중 어느 하나는 N이고, 나머지는 서로 같거나 상이하고 각각 독립적으로 N 또는 CR이고, Any one of X1 to
    X11 및 X12은 서로 같거나 상이하고, 각각 독립적으로 CR이고, X11 and X12 are the same or different from each other and are each independently CR,
    X11, X12 및 X1 내지 X10 중 N이 아닌 나머지 중 하나는 L3과 결합하는 C이고, Among X11, X12, and X1 to
    R은 수소, 또는 중수소이고,R is hydrogen or deuterium,
    X9 또는 X10가 N일 때, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴렌기 또는 치환 또는 비치환된 헤테로아릴렌기이고, L3은 직접결합, 치환 또는 비치환된 다환의 아릴렌기, 또는 치환 또는 비치환된 헤테로아릴렌기이고, Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 다환의 아릴기 또는 치환 또는 비치환된 헤테로아릴기이다. When X9 or It is a cyclic arylene group, or a substituted or unsubstituted heteroarylene group, and Ar1 and Ar2 are the same or different from each other, and each independently represents a substituted or unsubstituted polycyclic aryl group or a substituted or unsubstituted heteroaryl group.
  2. 청구항 1에 있어서, 상기 L1 내지 L3은 서로 같거나 상이하고, 각각 독립적으로, 직접결합, 탄소수 6 내지 20의 아릴렌기, 또는 탄소수 3 내지 20의 헤테로아릴렌기인 것인 화합물.The compound according to claim 1, wherein L1 to L3 are the same as or different from each other, and are each independently a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
  3. 청구항 1에 있어서, 상기 L1 및 L2는 서로 같고, 직접결합, 탄소수 6 내지 20의 아릴렌기, 또는 탄소수 3 내지 20의 헤테로아릴렌기인 것인 화합물.The compound according to claim 1, wherein L1 and L2 are the same and are a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
  4. 청구항 1에 있어서, 상기 L1 및 L2는 서로 상이하고, 각각 독립적으로, 직접결합, 탄소수 6 내지 20의 아릴렌기, 또는 탄소수 3 내지 20의 헤테로아릴렌기인 것인 화합물.The compound according to claim 1, wherein L1 and L2 are different from each other and are each independently a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
  5. 청구항 1에 있어서, 상기 L3은 직접결합, 탄소수 6 내지 20의 아릴렌기, 또는 탄소수 3 내지 20의 헤테로아릴렌기인 것인 화합물.The compound according to claim 1, wherein L3 is a direct bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 3 to 20 carbon atoms.
  6. 청구항 1에 있어서, 상기 X1 내지 X4 중 하나는 N인 것인 화합물.The compound according to claim 1, wherein one of X1 to X4 is N.
  7. 청구항 1에 있어서, 상기 X9 또는 X10은 N인 것인 화합물.The compound according to claim 1, wherein X9 or X10 is N.
  8. 청구항 1에 있어서, 상기 Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기, 또는 치환 또는 비치환된 탄소수 3 내지 20의 헤테로아릴기인 것인 화합물.The compound according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.
  9. 청구항 1에 있어서, 상기 R은 수소인 것인 화합물.The compound according to claim 1, wherein R is hydrogen.
  10. 청구항 1에 있어서, 상기 X9 또는 X10가 N일 때, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기이고, The method of claim 1, when X9 or It is a heteroarylene group,
    L3은 직접결합, 치환 또는 비치환된 탄소수 10 내지 30의 다환의 아릴렌기, 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴렌기이고, L3 is a direct bond, a substituted or unsubstituted polycyclic arylene group having 10 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms,
    Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 10 내지 30의 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기인 것인 화합물.Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms; Or a compound that is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
  11. 청구항 1에 있어서, 상기 화학식 2은 아래 구조 중 어느 하나인 것인 화합물:The compound according to claim 1, wherein Formula 2 has any one of the following structures:
    Figure PCTKR2023007638-appb-img-000099
    Figure PCTKR2023007638-appb-img-000099
    예컨대, 상기 각 구조에 포함된 탄소 중 어느 하나는 상기 화학식 1의 L3에 결합한다.For example, one of the carbons included in each structure is bonded to L3 in Chemical Formula 1.
  12. 청구항 1에 있어서, 상기 화학식 2은 아래 구조 중 어느 하나인 것인 화합물:The compound according to claim 1, wherein Formula 2 has any one of the following structures:
    Figure PCTKR2023007638-appb-img-000100
    Figure PCTKR2023007638-appb-img-000100
    예컨대, 상기 각 구조에 포함된 탄소 중 어느 하나는 상기 화학식 1의 L3에 결합한다.For example, one of the carbons included in each structure is bonded to L3 in Chemical Formula 1.
  13. 청구항 1에 있어서, 상기 화학식 1은 아래 화합물 중 어느 하나인 것인 화합물: The method according to claim 1, wherein Formula 1 is any one of the following compounds:
    Figure PCTKR2023007638-appb-img-000101
    Figure PCTKR2023007638-appb-img-000101
    Figure PCTKR2023007638-appb-img-000102
    Figure PCTKR2023007638-appb-img-000102
    Figure PCTKR2023007638-appb-img-000103
    Figure PCTKR2023007638-appb-img-000103
    Figure PCTKR2023007638-appb-img-000104
    Figure PCTKR2023007638-appb-img-000104
    Figure PCTKR2023007638-appb-img-000105
    Figure PCTKR2023007638-appb-img-000105
    Figure PCTKR2023007638-appb-img-000106
    Figure PCTKR2023007638-appb-img-000106
    Figure PCTKR2023007638-appb-img-000107
    Figure PCTKR2023007638-appb-img-000107
    Figure PCTKR2023007638-appb-img-000108
    Figure PCTKR2023007638-appb-img-000108
    Figure PCTKR2023007638-appb-img-000109
    Figure PCTKR2023007638-appb-img-000109
    Figure PCTKR2023007638-appb-img-000110
    Figure PCTKR2023007638-appb-img-000110
    Figure PCTKR2023007638-appb-img-000111
    Figure PCTKR2023007638-appb-img-000111
    Figure PCTKR2023007638-appb-img-000112
    Figure PCTKR2023007638-appb-img-000112
    Figure PCTKR2023007638-appb-img-000113
    Figure PCTKR2023007638-appb-img-000113
    Figure PCTKR2023007638-appb-img-000114
    Figure PCTKR2023007638-appb-img-000114
    Figure PCTKR2023007638-appb-img-000115
    Figure PCTKR2023007638-appb-img-000115
  14. 제1 전극; 상기 제1 전극과 대향하여 구비되는 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비되는 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상이 청구항 1 내지 13 중 어느 한 항에 따른 화합물을 포함하는 유기 발광 소자.first electrode; a second electrode provided opposite the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 13. .
  15. 청구항 14에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층이 상기 화합물을 포함하는 유기 발광 소자.The organic light-emitting device of claim 14, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound.
  16. 청구항 15에 있어서, 상기 발광층은 상기 화합물을 호스트로 포함하는 유기 발광 소자.The organic light-emitting device of claim 15, wherein the light-emitting layer includes the compound as a host.
  17. 청구항 15에 있어서, 상기 발광층 및 유기물층 사이에 정공주입층 또는 정공수송층이 추가로 구비되는 유기 발광 소자.The organic light-emitting device of claim 15, wherein a hole injection layer or a hole transport layer is further provided between the light-emitting layer and the organic material layer.
  18. 청구항 1에 있어서, 상기 Ar1 및 Ar2 중 적어도 하나는 치환 또는 비치환된 3환 이상의 아릴기이거나, 치환 또는 비치환된 2환 이상의 헤테로아릴기인 것인 화합물.The compound according to claim 1, wherein at least one of Ar1 and Ar2 is a substituted or unsubstituted aryl group having 3 or more rings, or a substituted or unsubstituted heteroaryl group having 2 or more rings.
PCT/KR2023/007638 2022-06-03 2023-06-02 Compound and organic light-emitting device comprising same WO2023234749A1 (en)

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