WO2018080067A1 - Organic compound and organic electroluminescent device including same - Google Patents

Organic compound and organic electroluminescent device including same Download PDF

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WO2018080067A1
WO2018080067A1 PCT/KR2017/011367 KR2017011367W WO2018080067A1 WO 2018080067 A1 WO2018080067 A1 WO 2018080067A1 KR 2017011367 W KR2017011367 W KR 2017011367W WO 2018080067 A1 WO2018080067 A1 WO 2018080067A1
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synthesis
mat
aryl
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김충한
손효석
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주식회사 두산
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • 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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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB, BCP, Alq 3 and the like are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layer materials, and anthracene derivatives have been reported as emission layer materials.
  • metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
  • the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of an organic material layer material excellent in performance is desired.
  • the present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent holes, electron injection and transport ability, light emitting ability and the like.
  • Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which exhibits low driving voltage and high luminous efficiency and has an improved lifetime.
  • the present invention provides a compound represented by the following formula (1):
  • X is selected from the group consisting of O, S, Se, N (Ar 3 ), C (Ar 4 ) (Ar 5 ) and Si (Ar 6 ) (Ar 7 );
  • L 1 to L 3 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • l and m are each independently an integer from 0 to 4.
  • n and o are each independently an integer from 0 to 3;
  • R 1 to R 4 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and R
  • Ar 1 to Ar 7 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of, or by combining the adjacent tile to form
  • a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphanyl group, a mono or diarylphosphinyl group and an arylsilyl group are each independently deuterium, halogen, cyano group, Nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C Aryloxy group of 6 to C 60 , alkyloxy group of C 1
  • the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .
  • Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
  • Alkenyl in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
  • Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
  • monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom for example, may have 8 to 60 carbon atoms
  • the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity).
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms.
  • R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1-40 alkyl, and is linear, branched or cyclic structure.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • cycloalkyl in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
  • examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms.
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties.
  • an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with improved performance and lifetime can also be manufactured.
  • FIG. 1 illustrates a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • FIG. 2 illustrates a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
  • organic layer 31 hole transport layer
  • the present invention provides a compound represented by the following formula (1):
  • X is selected from the group consisting of O, S, Se, N (Ar 3 ), C (Ar 4 ) (Ar 5 ) and Si (Ar 6 ) (Ar 7 );
  • L 1 to L 3 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • l and m are each independently an integer from 0 to 4.
  • n and o are each independently an integer from 0 to 3;
  • R 1 to R 4 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and R
  • Ar 1 to Ar 7 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of, or by combining the adjacent tile to form
  • a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphanyl group, a mono or diarylphosphinyl group and an arylsilyl group are each independently deuterium, halogen, cyano group, Nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C Aryloxy group of 6 to C 60 , alkyloxy group of C 1
  • novel compounds of the present invention can be represented by the following formula (1):
  • X is selected from the group consisting of O, S, Se, N (Ar 3 ), C (Ar 4 ) (Ar 5 ) and Si (Ar 6 ) (Ar 7 );
  • L 1 to L 3 are each independently a single bond, C 6 ⁇ be an aryl group and a C 18 nuclear atoms of 5 to 18 heteroarylene group is selected from the group consisting of;
  • l and m are each independently an integer from 0 to 4.
  • n and o are each independently an integer from 0 to 3;
  • R 1 to R 4 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and R
  • Ar 1 to Ar 7 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- aryloxy group of C 60, C 3 ⁇ C 40 alkylsilyl group, C group 6 ⁇ C 60 aryl silyl, C 1 ⁇ arylboronic of C 40 group of an alkyl boron, C 6 ⁇ C 60 group, C 6 ⁇ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of, or by combining the adjacent
  • a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphanyl group, a mono or diarylphosphinyl group and an arylsilyl group are each independently deuterium, halogen, cyano group, Nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C Aryloxy group of 6 to C 60 , alkyloxy group of C 1
  • the novel compound provided in the present invention forms a basic skeleton by combining a phenoxazine or phenothiazine moiety to carbazole, and is represented by Chemical Formula 1.
  • the compound represented by the formula (1) has a higher molecular weight than the conventional organic electroluminescent device material (for example, 4,4-dicarbazolylbiphenyl (hereinafter referred to as 'CBP'))
  • the glass transition temperature is high thermally Not only is it excellent in stability, it is also excellent in carrier transport ability, light emission ability, etc. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
  • the host material should have a triplet energy gap of which is higher than the triplet energy gap of the dopant. That is, when the lowest excited state of the host is higher in energy than the lowest emitted state of the dopant, phosphorescence efficiency may be improved.
  • the compound of Formula 1 has a high triplet energy, by introducing a specific substituent on the basic skeleton condensed with a broad singlet energy level and a high triplet energy level, the energy level can be controlled higher than the dopant It can be used as a host material.
  • the compound of the present invention since the compound of the present invention has a high triplet energy as described above, it is possible to prevent the excitons generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. Therefore, when the organic material layer (hereinafter, referred to as a 'light emitting auxiliary layer') is formed between the hole transport layer and the light emitting layer by using the compound of Formula 1, the exciton is prevented from being diffused by the compound, and thus the first exciton is diffused. Unlike conventional organic electroluminescent devices that do not include a barrier layer, the number of excitons that substantially contribute to light emission in the light emitting layer may be increased, thereby improving the luminous efficiency of the device.
  • the organic material layer hereinafter, referred to as a 'light emitting auxiliary layer'
  • the compound represented by Chemical Formula 1 may be used as a light emitting auxiliary layer material or a life improvement layer material other than the host of the light emitting layer.
  • the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, may have a wide bandgap, it may have a high carrier transport.
  • EWG electron-withdrawing electron
  • the compound is bonded to an electron-withdrawing electron (EWG) having a high electron absorption such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.) to the basic skeleton, Since it has a bipolar characteristic, it is possible to increase the bonding force between the hole and the electron.
  • EWG electron-withdrawing electron
  • the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and luminescent properties, and thus, as an electron injection / transport layer material or a life improvement layer material, in addition to the light emitting layer material of the organic EL device Can be used.
  • an electron donor group EWG
  • the hole injection and transport is smooth.
  • it can be usefully used as a hole injection / transport layer or light emitting auxiliary layer material.
  • the compound represented by Chemical Formula 1 may improve the light emission characteristics of the organic EL device, and may also improve the hole injection / transport ability, the electron injection / transport capability, the luminous efficiency, the driving voltage, and the lifespan characteristics.
  • the compound of formula 1 according to the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transport / injection layer material and a hole transport / injection layer It can be used as a material, a light emission auxiliary layer material, a life improvement layer material, more preferably a light emission layer material, an electron injection layer material, a light emission auxiliary layer material, and a life improvement layer material.
  • the compound of Formula 1 has a variety of substituents, particularly aryl groups and / or heteroaryl groups introduced into the basic skeleton significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, thereby the conventional light emission It may have a higher thermal stability than the material (eg CBP).
  • the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.
  • L 1 may be a single bond or a phenylene group, and more preferably, the phenylene group may lower driving voltage and increase luminous efficiency.
  • the compound may be represented by the following formula (2) or (3):
  • X, L 1 to L 3 , R 1 to R 4 , Ar 1 to Ar 2 , l, m, n and o are each as defined in Chemical Formula 1.
  • the compound is particularly connected to the carbazole phenoxazine or phenothiazine moiety as a linker of the phenylene group, as represented by the formula 3, lower driving voltage and high luminous efficiency It is preferable because it can secure.
  • the compound represented by the formula (2) is represented by the following formula (4) or formula (5) can lower the driving voltage and increase the luminous efficiency, more preferably can be represented by the formula (5) have:
  • X, L 2 to L 3 , R 1 to R 4 , Ar 1 to Ar 2 , 1, m, n and o are each as defined in Chemical Formula 1.
  • L 2 and L 3 may be each independently a single bond or a linker represented by any one of the following formula A-1 to A-3:
  • L 2 and L 3 may be each independently a single bond or a linker represented by the formula A-1.
  • Ar 1 and Ar 2 may each independently be a substituent represented by one of the following formulas B-1 to B-10:
  • Z 1 to Z 8 are each independently N or C (R 9 );
  • Any one of Z 1 to Z 4 bonded to L 2 or L 3 in Formula B-2 is C (R 9 ), wherein R 9 is absent;
  • T 1 and T 2 are each independently selected from the group consisting of a single bond, C (R 10 ) (R 11 ), N (R 12 ), O and S, but not both T 1 and T 2 are single bonds;
  • p and q are each independently integers of 0 to 4.
  • R 5 and R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ⁇ C 60, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 ⁇ C 60 mono or diaryl phosphinyl group and a C 6 ⁇ C 60 arylsilyl group, or
  • R 7 to R 12 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting of C 6 ⁇ C 60 mono or diaryl the Phosphinicosuccinic group and a C 6 ⁇ with an aryl silyl group of C 60, or combine tile adjacent to which they are attached may form
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 5 to R 12 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • R 7 and R 8 are each independently from the group consisting of C 1 ⁇ C 30 Alkyl group, C 6 ⁇ C 30 aryl group and 5 to 30 heteroaryl group of nuclear atoms Can be selected.
  • R 7 and R 8 may be each independently selected from the group consisting of phenyl group, biphenyl group and naphthalenyl group, more preferably may be a phenyl group or a biphenyl group.
  • R 9 may be selected from the group consisting of C 1 ⁇ C 30 alkyl group, C 6 ⁇ C 30 aryl group and 5 to 30 heteroaryl groups.
  • R 9 may be selected from the group consisting of phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group and triazinyl group.
  • the substituent represented by Formula B-1 may be a substituent represented by the following Formula 6:
  • R 13 and R 14 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of, or by combining the adjacent tile to form
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group and aryl of R 13 and R 14 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms
  • Z 1 , Z 3 and Z 5 are each as defined in Formula B-1.
  • R 13 and R 14 are each independently selected from the group consisting of C 1 ⁇ C 30 Alkyl group, C 6 ⁇ C 30 aryl group and 5 to 30 heteroaryl group of nuclear atoms Can be selected.
  • R 13 and R 14 may be each independently selected from the group consisting of phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group and triazinyl group.
  • Ar 1 and Ar 2 each may be a substituent represented by the following formula of one of C-1 to C-25 independent, limited to:
  • r is an integer from 0 to 5;
  • p, q and s are each independently integers of 0 to 4.
  • t is an integer from 0 to 3;
  • u is an integer from 0 to 2;
  • R 5 , R 6 and R 15 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 ⁇ C 60 aryl phosphazene group, selected from the group consisting arylsilyl a C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60
  • R 7 to R 12 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from an aryl silyl group the group consisting of or of, by combining groups adjacent to form a conden
  • R 9 and R 15 are each independently a group consisting of an alkyl group of C 1 ⁇ C 30 , an aryl group of C 6 ⁇ C 30 and a heteroaryl group of 5 to 30 nuclear atoms Can be selected.
  • R 9 and R 15 may be each independently selected from the group consisting of phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group and triazinyl group.
  • R 10 and R 11 may be independently selected from the group consisting of hydrogen, C 1 ⁇ C 30 Alkyl group and C 6 ⁇ C 30 An aryl group.
  • R 10 and R 11 may be independently selected from the group consisting of hydrogen, methyl group, ethyl group, butyl group and phenyl group.
  • the substituent represented by Formula C-1 may be represented by any one of the following Formulas D-1 to D-3, but is not limited thereto:
  • Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
  • the compound is selected from the group consisting of the following compounds:
  • organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1).
  • the compound may be used alone or mixed two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by 1.
  • the structure of the organic EL device according to the present invention described above is not particularly limited, but referring to FIG. 1 as an example, for example, the anode 10 and the cathode 20 facing each other, and the anode 10 and the cathode ( 20) and an organic layer 30 positioned between them.
  • the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34.
  • a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32
  • an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.
  • the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, the electron transport layer 34 and the cathode
  • the electron injection layer 36 may be further included between the holes 20.
  • the hole injection layer 37 stacked between the hole transport layer 31 and the anode 10 may not only improve the interface property between the ITO used as the anode and the organic material used as the hole transport layer 31.
  • the surface is applied to the upper surface of the uneven ITO to soften the surface of the ITO, a layer that can be used without particular limitation as long as it is commonly used in the art, for example, may be used an amine compound It is not limited to this.
  • the electron injection layer 36 is stacked on top of the electron transport layer to facilitate the injection of electrons from the cathode to perform a function that ultimately improves the power efficiency, which is specially used in the art It can be used without limitation, and materials such as LiF, Liq, NaCl, CsF, Li 2 O, BaO and the like can be used.
  • a light emitting auxiliary layer may be further included between the hole transport auxiliary layer 33 and the light emitting layer 32.
  • the emission auxiliary layer may serve to transport holes to the emission layer 32 and to adjust the thickness of the organic layer 30.
  • the emission auxiliary layer may include a hole transport material, and may be made of the same material as the hole transport layer 31.
  • a life improvement layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32. Holes traveling through the ionization potential level in the organic light emitting device to the light emitting layer 32 are blocked by the high energy barrier of the lifespan improvement layer, and thus do not diffuse or move to the electron transport layer, and consequently, the holes are limited to the light emitting layer. .
  • Such a function of limiting holes to the light emitting layer prevents holes from diffusing into the electron transporting layer that moves electrons by reduction, thereby suppressing the lifespan phenomenon through irreversible decomposition reaction by oxidation and contributing to improving the life of the organic light emitting device. Can be.
  • the novel compound provided in the present invention forms a basic skeleton by combining a phenoxazine or phenothiazine moiety to carbazole, and is specifically represented by Chemical Formula 1.
  • the compound represented by the formula (1) has a higher molecular weight than the conventional organic electroluminescent device material (for example, 4,4-dicarbazolylbiphenyl (hereinafter referred to as 'CBP'))
  • the glass transition temperature is high thermally Not only is it excellent in stability, it is also excellent in carrier transport ability, light emission ability, etc. Therefore, when the compound of Formula 1 is used in the manufacture of the organic EL device, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
  • the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, may have a wide bandgap, it may have a high carrier transport.
  • the compound has a high electron-absorbing electron withdrawing group (EWG) such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.) to the basic skeleton, the entire molecule is Since it has a bipolar characteristic, it is possible to increase the bonding force between the hole and the electron.
  • EWG electron-absorbing electron withdrawing group
  • the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and luminescent properties, and thus, as an electron injection / transport layer material or a life improvement layer material, in addition to the light emitting layer material of the organic EL device. Can be used.
  • an electron donor group EWG
  • the hole injection and transport is smooth.
  • it can be usefully used as a hole injection / transport layer or a light emitting auxiliary layer material.
  • the compound represented by Chemical Formula 1 may improve the light emission characteristics of the organic EL device, and may also improve the hole injection / transport ability, the electron injection / transport capability, the luminous efficiency, the driving voltage, and the lifespan characteristics.
  • the organic material layer including the compound represented by Formula 1 is preferably selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, an electron transport layer and an electron injection layer, more preferably a light emitting layer, electron It may be a transport layer or a hole transport layer.
  • the compound represented by Formula 1 may be used as a phosphorescent host, a fluorescent host or a dopant material of the light emitting layer, preferably a phosphorescent host (blue, green). And / or red phosphorescent host materials).
  • the organic electroluminescent device may not only sequentially stack an anode, at least one organic material layer, and a cathode as described above, but may further include an insulating layer or an adhesive layer at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic material layers (for example, an electron transport auxiliary layer) is formed to include the compound represented by Chemical Formula 1. It can be prepared by forming other organic material layer and electrode using.
  • the organic material layers for example, an electron transport auxiliary layer
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • the positive electrode material may be made of a high work function conductor, for example, to facilitate hole injection, and may 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), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • the cathode material may be made of a low work function conductor, for example, to facilitate electron injection, and may include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. The same metal or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • a target compound of 8.5g was obtained in the same manner as in [Preparation Example 1], except that 2-bromonaphthalene was used as a reactant .; HRMS [M] +: 435.33
  • Target compound 5.3 was carried out in the same manner as in Synthesis Example 1, except that 3-bromo-9- (9,9-dimethyl-9H-fluoren-3-yl) -9H-carbazole was used as the reactant. g was obtained; HRMS [M] +: 616.76

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Abstract

The present invention relates to a novel compound and an organic electroluminescent device including the same, and according to the present invention, the compound is used in an organic layer of an organic electroluminescent device, preferably, for a light-emitting layer such that light-emitting efficiency, driving voltage, lifespan, and the like of the organic electroluminescent device can be improved.

Description

유기 화합물 및 이를 포함하는 유기 전계 발광 소자Organic compound and organic electroluminescent device comprising the same
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
1950년대 베르나노스(Bernanose)의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 소자에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층 구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.From the observation of Bernanose organic thin film emission in the 1950s, the study of organic electroluminescent (EL) devices led to blue electroluminescence using anthracene single crystal in 1965, followed by Tang in 1987 The organic electroluminescent device of the laminated structure divided into the functional layer of a positive hole layer and a light emitting layer was proposed. Since then, in order to make a high efficiency, high-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다.In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과, 보다 나은 천연색을 구현하기 위한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다.The light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
도펀트 물질은 유기 물질을 사용하는 형광 도펀트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도펀트로 나눌 수 있다. 이때, 인광 재료의 개발은 이론적으로 형광에 비해 4배까지 발광 효율을 향상시킬 수 있기 때문에, 인광 도펀트 뿐만 아니라 인광 호스트 재료들에 대한 연구도 많이 진행되고 있다.The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.
현재까지 정공 주입층, 정공 수송층, 정공 차단층, 전자 수송층 재료로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광층 재료로는 안트라센 유도체들이 보고되고 있다. 특히, 발광층 재료 중 효율 향상 측면에서 장점을 가지고 있는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red)의 인광 도판트 재료로 사용되고 있으며, 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)은 인광 호스트 재료로 사용되고 있다.To date, NPB, BCP, Alq 3 and the like are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layer materials, and anthracene derivatives have been reported as emission layer materials. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
Figure PCTKR2017011367-appb-I000001
Figure PCTKR2017011367-appb-I000001
그러나 종래의 유기물층 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of an organic material layer material excellent in performance is desired.
본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 정공, 전자 주입 및 수송능, 발광능 등이 모두 우수한 신규 유기 화합물을 제공하는 것을 목적으로 한다. The present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent holes, electron injection and transport ability, light emitting ability and the like.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동 전압과 높은 발광 효율을 나타내며 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which exhibits low driving voltage and high luminous efficiency and has an improved lifetime.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following formula (1):
[화학식 1][Formula 1]
Figure PCTKR2017011367-appb-I000002
Figure PCTKR2017011367-appb-I000002
상기 화학식 1에서,In Chemical Formula 1,
X는 O, S, Se, N(Ar3), C(Ar4)(Ar5) 및 Si(Ar6)(Ar7)로 구성된 군으로부터 선택되며;X is selected from the group consisting of O, S, Se, N (Ar 3 ), C (Ar 4 ) (Ar 5 ) and Si (Ar 6 ) (Ar 7 );
L1 내지 L3는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고;L 1 to L 3 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
l 및 m은 각각 독립적으로 0 내지 4의 정수이며;l and m are each independently an integer from 0 to 4;
n 및 o는 각각 독립적으로 0 내지 3의 정수이며;n and o are each independently an integer from 0 to 3;
R1 내지 R4는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R1 내지 R4 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 1 to R 4 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and R 1 to When each of R 4 's is plural, they are the same as or different from each other;
Ar1 내지 Ar7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; Ar 1 to Ar 7 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining the adjacent tile to form a condensed ring;
상기 L1 내지 L3의 아릴렌기 및 헤테로아릴렌기와, 상기 R1 내지 R4 및 Ar1 내지 Ar7의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다. The arylene group and heteroarylene group of L 1 to L 3 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group of R 1 to R 4 and Ar 1 to Ar 7 , A cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphanyl group, a mono or diarylphosphinyl group and an arylsilyl group are each independently deuterium, halogen, cyano group, Nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C Aryloxy group of 6 to C 60 , alkyloxy group of C 1 to C 40 , arylamine group of C 6 to C 60 , cycloalkyl group of C 3 to C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, C C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 An aryl boron group, C 6 ~ C 60 An arylphosphanyl group, C 6 ~ C 60 Mono or di When substituted or unsubstituted with one or more substituents selected from the group consisting of an arylphosphinyl group and a C 6 -C 60 arylsilyl group, they may be the same or different from each other.
본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .
본 발명에서의 “알킬”은 탄소수 1 내지 40개의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지 않는다."Alkyl" in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
본 발명에서의 “알케닐(alkenyl)”은 탄소-탄소 이중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지 않는다."Alkenyl" in the present invention is a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
본 발명에서의 “알키닐(alkynyl)”은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지 않는다."Alkynyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
본 발명에서의 “아릴”은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60개의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 축합되어 있고, 고리 형성 원자로서 탄소만을 포함(예를 들어, 탄소수는 8 내지 60개일 수 있음)하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 치환기도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴, 플루오레닐 등이 있는데, 이에 한정되지 않는다."Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom (for example, may have 8 to 60 carbon atoms), and the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
본 발명에서의 “헤테로아릴”은 핵원자수 5 내지 60개의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, P, S 및 Se 중에서 선택된 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합되어 있고, 고리 형성 원자로서 탄소 외에 N, O, P, S 및 Se 중에서 선택된 헤테로 원자를 포함하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 그룹도 포함하는 것으로 해석된다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리; 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지 않는다."Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity). Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서의 “아릴옥시”는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 60개의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서의 “알킬옥시”는 R’O-로 표시되는 1가의 치환기로, 상기 R’는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1-40 alkyl, and is linear, branched or cyclic structure. Interpret as including. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서의 “아릴아민”은 탄소수 6 내지 60개의 아릴로 치환된 아민을 의미한다."Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서의 “시클로알킬”은 탄소수 3 내지 40개의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지 않는다.By "cycloalkyl" in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서의 “헤테로시클로알킬”은 핵원자수 3 내지 40개의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지 않는다.“Heterocycloalkyl” in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서의 “알킬실릴”은 탄소수 1 내지 40개의 알킬로 치환된 실릴이고, “아릴실릴”은 탄소수 5 내지 60개의 아릴로 치환된 실릴을 의미한다.In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms.
본 발명에서의 “축합 고리”는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.“Condensed ring” in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
본 발명의 화학식 1로 표시되는 화합물은 열적 안정성 및 발광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다. 특히, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트 재료로 사용할 경우, 종래의 호스트 재료에 비해 우수한 발광 성능, 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.The compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with improved performance and lifetime can also be manufactured.
도 1은 본 발명의 일 실시예에 따른 유기 전계 발광 소자의 단면도를 나타낸 것이다.1 illustrates a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
도 2는 본 발명의 일 실시예에 따른 유기 전계 발광 소자의 단면도를 나타낸 것이다. 2 illustrates a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
10: 양극 20: 음극10: anode 20: cathode
30: 유기층 31: 정공 수송층30: organic layer 31: hole transport layer
32: 발광층 33: 정공 수송 보조층32: light emitting layer 33: hole transport auxiliary layer
34: 전자 수송층 35: 전자 수송 보조층34: electron transport layer 35: electron transport auxiliary layer
36: 전자 주입층 37: 정공 주입층36: electron injection layer 37: hole injection layer
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following formula (1):
[화학식 1][Formula 1]
Figure PCTKR2017011367-appb-I000003
Figure PCTKR2017011367-appb-I000003
상기 화학식 1에서,In Chemical Formula 1,
X는 O, S, Se, N(Ar3), C(Ar4)(Ar5) 및 Si(Ar6)(Ar7)로 구성된 군으로부터 선택되며;X is selected from the group consisting of O, S, Se, N (Ar 3 ), C (Ar 4 ) (Ar 5 ) and Si (Ar 6 ) (Ar 7 );
L1 내지 L3는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고;L 1 to L 3 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
l 및 m은 각각 독립적으로 0 내지 4의 정수이며;l and m are each independently an integer from 0 to 4;
n 및 o는 각각 독립적으로 0 내지 3의 정수이며;n and o are each independently an integer from 0 to 3;
R1 내지 R4는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R1 내지 R4 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 1 to R 4 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and R 1 to When each of R 4 's is plural, they are the same as or different from each other;
Ar1 내지 Ar7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; Ar 1 to Ar 7 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining the adjacent tile to form a condensed ring;
상기 L1 내지 L3의 아릴렌기 및 헤테로아릴렌기와, 상기 R1 내지 R4 및 Ar1 내지 Ar7의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다. The arylene group and heteroarylene group of L 1 to L 3 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group of R 1 to R 4 and Ar 1 to Ar 7 , A cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphanyl group, a mono or diarylphosphinyl group and an arylsilyl group are each independently deuterium, halogen, cyano group, Nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C Aryloxy group of 6 to C 60 , alkyloxy group of C 1 to C 40 , arylamine group of C 6 to C 60 , cycloalkyl group of C 3 to C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, C C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 An aryl boron group, C 6 ~ C 60 An arylphosphanyl group, C 6 ~ C 60 Mono or di When substituted or unsubstituted with one or more substituents selected from the group consisting of an arylphosphinyl group and a C 6 -C 60 arylsilyl group, they may be the same or different from each other.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 신규 유기 화합물1. New Organic Compounds
본 발명의 신규 화합물은 하기 화학식 1로 표시될 수 있다:The novel compounds of the present invention can be represented by the following formula (1):
[화학식 1][Formula 1]
Figure PCTKR2017011367-appb-I000004
Figure PCTKR2017011367-appb-I000004
상기 화학식 1에서,In Chemical Formula 1,
X는 O, S, Se, N(Ar3), C(Ar4)(Ar5) 및 Si(Ar6)(Ar7)로 구성된 군으로부터 선택되며;X is selected from the group consisting of O, S, Se, N (Ar 3 ), C (Ar 4 ) (Ar 5 ) and Si (Ar 6 ) (Ar 7 );
L1 내지 L3는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고;L 1 to L 3 are each independently a single bond, C 6 ~ be an aryl group and a C 18 nuclear atoms of 5 to 18 heteroarylene group is selected from the group consisting of;
l 및 m은 각각 독립적으로 0 내지 4의 정수이며;l and m are each independently an integer from 0 to 4;
n 및 o는 각각 독립적으로 0 내지 3의 정수이며;n and o are each independently an integer from 0 to 3;
R1 내지 R4는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R1 내지 R4 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 1 to R 4 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and R 1 to When each of R 4 's is plural, they are the same as or different from each other;
Ar1 내지 Ar7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; Ar 1 to Ar 7 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- aryloxy group of C 60, C 3 ~ C 40 alkylsilyl group, C group 6 ~ C 60 aryl silyl, C 1 ~ arylboronic of C 40 group of an alkyl boron, C 6 ~ C 60 group, C 6 ~ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining the adjacent tile to form a condensed ring;
상기 L1 내지 L3의 아릴렌기 및 헤테로아릴렌기와, 상기 R1 내지 R4 및 Ar1 내지 Ar7의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다. The arylene group and heteroarylene group of L 1 to L 3 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group of R 1 to R 4 and Ar 1 to Ar 7 , A cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphanyl group, a mono or diarylphosphinyl group and an arylsilyl group are each independently deuterium, halogen, cyano group, Nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C Aryloxy group of 6 to C 60 , alkyloxy group of C 1 to C 40 , arylamine group of C 6 to C 60 , cycloalkyl group of C 3 to C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, C C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 An aryl boron group, C 6 ~ C 60 An arylphosphanyl group, C 6 ~ C 60 Mono or di When substituted or unsubstituted with one or more substituents selected from the group consisting of an arylphosphinyl group and a C 6 -C 60 arylsilyl group, they may be the same or different from each other.
본 발명에서 제공하는 신규 화합물은 카바졸에 페녹사진 또는 페노티아진 모이어티가 결합되어 기본 골격을 이루며, 상기 화학식 1로 표시되는 것을 특징으로 한다. 이러한 화학식 1로 표시되는 화합물은 종래 유기 전계 발광 소자용 재료[예: 4,4-디카바졸릴비페닐(이하, 'CBP'라 함)]보다 높은 분자량을 갖기 때문에, 유리전이온도가 높아 열적 안정성이 우수할 뿐만 아니라, 캐리어 수송능, 발광능 등이 우수하다. 따라서, 상기 화학식 1의 화합물을 유기 전계 발광 소자가 포함할 경우, 소자의 구동전압, 효율, 수명 등이 향상될 수 있다.The novel compound provided in the present invention forms a basic skeleton by combining a phenoxazine or phenothiazine moiety to carbazole, and is represented by Chemical Formula 1. Since the compound represented by the formula (1) has a higher molecular weight than the conventional organic electroluminescent device material (for example, 4,4-dicarbazolylbiphenyl (hereinafter referred to as 'CBP')), the glass transition temperature is high thermally Not only is it excellent in stability, it is also excellent in carrier transport ability, light emission ability, etc. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
일반적으로 유기 전계 발광 소자의 인광 발광층에서, 호스트 물질은 이의 삼중항 에너지 갭이 도펀트의 삼중항 에너지 갭보다 높아야 한다. 즉, 호스트의 가장 낮은 여기 상태가 도펀트의 가장 낮은 방출 상태보다 에너지가 더 높은 경우, 인광 발광 효율이 향상될 수 있다. 상기 화학식 1의 화합물은 삼중항 에너지가 높고, 넓은 일중항 에너지 준위와 높은 삼중항 에너지 준위를 가지는 인돌 유도체가 축합되어 있는 기본 골격에 특정의 치환기가 도입됨으로써, 에너지 준위가 도펀트보다 높게 조절될 수 있어 호스트 물질로 사용될 수 있다.In general, in the phosphorescent layer of an organic electroluminescent device, the host material should have a triplet energy gap of which is higher than the triplet energy gap of the dopant. That is, when the lowest excited state of the host is higher in energy than the lowest emitted state of the dopant, phosphorescence efficiency may be improved. The compound of Formula 1 has a high triplet energy, by introducing a specific substituent on the basic skeleton condensed with a broad singlet energy level and a high triplet energy level, the energy level can be controlled higher than the dopant It can be used as a host material.
또한, 본 발명의 화합물은 전술한 바와 같이 높은 삼중항 에너지를 갖기 때문에, 발광층에서 생성된 엑시톤이 발광층에 인접하는 전자 수송층 또는 정공 수송층으로 확산되는 것을 방지할 수 있다. 따라서, 상기 화학식 1의 화합물을 이용하여 정공 수송층과 발광층 사이에 유기물층(이하, '발광 보조층'이라 함)을 형성할 경우, 상기 화합물에 의해서 엑시톤의 확산이 방지되기 때문에, 상기 제1 엑시톤 확산 방지층을 포함하지 않은 종래의 유기 전계 발광 소자와 달리, 실질적으로 발광층 내에서 발광에 기여하는 엑시톤의 수가 증가되어 소자의 발광 효율이 개선될 수 있다. 또한, 상기 화학식 1의 화합물을 이용하여 발광층과 전자 수송층 사이에 유기물층(이하, '수명 개선층'이라 함)을 형성할 경우에도, 상기 화학식 1의 화합물에 의해 엑시톤의 확산이 방지됨으로써, 유기 전계 발광 소자의 내구성 및 안정성이 향상될 수 있고, 이로 인해 소자의 반감 수명이 효율적으로 증가될 수 있다. 이와 같이, 상기 화학식 1로 표시되는 화합물은 발광층의 호스트 이외, 발광 보조층 재료 또는 수명 개선층 재료로 사용될 수 있다.In addition, since the compound of the present invention has a high triplet energy as described above, it is possible to prevent the excitons generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. Therefore, when the organic material layer (hereinafter, referred to as a 'light emitting auxiliary layer') is formed between the hole transport layer and the light emitting layer by using the compound of Formula 1, the exciton is prevented from being diffused by the compound, and thus the first exciton is diffused. Unlike conventional organic electroluminescent devices that do not include a barrier layer, the number of excitons that substantially contribute to light emission in the light emitting layer may be increased, thereby improving the luminous efficiency of the device. In addition, even when an organic material layer (hereinafter, referred to as a "life improvement layer") is formed between the light emitting layer and the electron transport layer by using the compound of Formula 1, the diffusion of excitons by the compound of Formula 1 prevents the organic electric field Durability and stability of the light emitting device can be improved, thereby effectively increasing the half life of the device. As such, the compound represented by Chemical Formula 1 may be used as a light emitting auxiliary layer material or a life improvement layer material other than the host of the light emitting layer.
또한, 상기 화학식 1의 화합물은 상기 기본 골격에 도입되는 치환기의 종류에 따라 HOMO 및 LUMO 에너지 레벨을 조절할 수 있어, 넓은 밴드갭을 가질 수 있고, 높은 캐리어 수송성을 가질 수 있다. 예를 들어, 상기 화합물은 상기 기본 골격에 질소-함유 헤테로환(예컨대, 피리딘기, 피리미딘기, 트리아진기등)과 같이 전자 흡수성이 큰 전자 끌개기(EWG)가 결합될 경우, 분자 전체가 양극성(bipolar) 특성을 갖기 때문에, 정공과 전자의 결합력을 높일 수 있다. 이와 같이, 상기 기본 골격에 EWG가 도입된 상기 화학식 1의 화합물은 우수한 캐리어 수송성 및 발광 특성이 우수하기 때문에, 유기 전계 발광 소자의 발광층 재료 이외, 전자 주입/수송층 재료, 또는 수명 개선층 재료로도 사용될 수 있다. 한편, 상기 화학식 1의 화합물이 상기 기본 골격에 아릴아민기, 카바졸기, 터페닐기, 트리페닐렌기 등과 같이 전자 공여성이 큰 전자 주게기(EDG)가 결합될 경우, 정공의 주입 및 수송이 원활하게 이루어지기 때문에, 발광층 재료 이외, 정공 주입/수송층 또는 발광 보조층 재료로도 유용하게 사용될 수 있다.In addition, the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, may have a wide bandgap, it may have a high carrier transport. For example, when the compound is bonded to an electron-withdrawing electron (EWG) having a high electron absorption such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.) to the basic skeleton, Since it has a bipolar characteristic, it is possible to increase the bonding force between the hole and the electron. As such, the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and luminescent properties, and thus, as an electron injection / transport layer material or a life improvement layer material, in addition to the light emitting layer material of the organic EL device Can be used. On the other hand, when the compound of Formula 1 is combined with an electron donor group (EDG) having a large electron donor such as an arylamine group, carbazole group, terphenyl group, triphenylene group, etc., the hole injection and transport is smooth. In addition to the light emitting layer material, it can be usefully used as a hole injection / transport layer or light emitting auxiliary layer material.
이와 같이, 상기 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 발광 특성을 향상시킴과 동시에, 정공 주입/수송 능력, 전자 주입/수송 능력, 발광 효율, 구동 전압, 수명 특성 등을 향상시킬 수 있다. 따라서, 본 발명에 따른 화학식 1의 화합물은 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 발광층 재료(청색, 녹색 및/또는 적색의 인광 호스트 재료), 전자 수송/주입층 재료 및 정공 수송/주입층 재료, 발광 보조층 재료, 수명 개선층 재료, 더 바람직하게는 발광층 재료, 전자 주입층 재료, 발광 보조층 재료, 수명 개선층 재료로 사용될 수 있다.As described above, the compound represented by Chemical Formula 1 may improve the light emission characteristics of the organic EL device, and may also improve the hole injection / transport ability, the electron injection / transport capability, the luminous efficiency, the driving voltage, and the lifespan characteristics. . Accordingly, the compound of formula 1 according to the present invention is an organic material layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transport / injection layer material and a hole transport / injection layer It can be used as a material, a light emission auxiliary layer material, a life improvement layer material, more preferably a light emission layer material, an electron injection layer material, a light emission auxiliary layer material, and a life improvement layer material.
또한, 상기 화학식 1의 화합물은 상기 기본 골격에 다양한 치환기, 특히 아릴기 및/또는 헤테로아릴기가 도입되어 화합물의 분자량이 유의적으로 증대됨으로써, 유리 전이 온도가 향상될 수 있고, 이로 인해 종래의 발광 재료(예를 들어, CBP)보다 높은 열적 안정성을 가질 수 있다. 또한, 상기 화학식 1로 표시되는 화합물은 유기물층의 결정화 억제에도 효과가 있다. 따라서, 본 발명에 따른 화학식 1의 화합물을 포함하는 유기 전계 발광 소자는 성능 및 수명 특성이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.In addition, the compound of Formula 1 has a variety of substituents, particularly aryl groups and / or heteroaryl groups introduced into the basic skeleton significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, thereby the conventional light emission It may have a higher thermal stability than the material (eg CBP). In addition, the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L1은 단일결합 또는 페닐렌기일 수 있고, 보다 바람직하게는 페닐렌기인 것이 구동전압을 낮추고 발광 효율은 높일 수 있다. According to a preferred embodiment of the present invention, L 1 may be a single bond or a phenylene group, and more preferably, the phenylene group may lower driving voltage and increase luminous efficiency.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화합물은 하기 화학식 2 또는 3으로 표시될 수 있다: According to one preferred embodiment of the invention, the compound may be represented by the following formula (2) or (3):
[화학식 2][Formula 2]
Figure PCTKR2017011367-appb-I000005
Figure PCTKR2017011367-appb-I000005
[화학식 3][Formula 3]
Figure PCTKR2017011367-appb-I000006
Figure PCTKR2017011367-appb-I000006
상기 화학식 2 및 3에서, In Chemical Formulas 2 and 3,
X, L1 내지 L3, R1 내지 R4, Ar1 내지 Ar2, l, m, n 및 o 각각은 상기 화학식 1에서 정의된 바와 같다. X, L 1 to L 3 , R 1 to R 4 , Ar 1 to Ar 2 , l, m, n and o are each as defined in Chemical Formula 1.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화합물은 특히 상기 화학식 3으로 표시되는 바와 같이 카바졸에 페녹사진 또는 페노티아진 모이어티가 페닐렌기의 링커로 연결된 것이, 보다 낮은 구동 전압과 높은 발광 효율을 확보할 수 있어 바람직하다. According to a preferred embodiment of the present invention, the compound is particularly connected to the carbazole phenoxazine or phenothiazine moiety as a linker of the phenylene group, as represented by the formula 3, lower driving voltage and high luminous efficiency It is preferable because it can secure.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 2로 표시되는 화합물은 하기 화학식 4 또는 화학식 5로 표시되는 것이 구동 전압은 낮추고 발광 효율을 높일 수 있으며, 보다 바람직하게는 하기 화학식 5로 표시될 수 있다:According to a preferred embodiment of the present invention, the compound represented by the formula (2) is represented by the following formula (4) or formula (5) can lower the driving voltage and increase the luminous efficiency, more preferably can be represented by the formula (5) have:
[화학식 4][Formula 4]
Figure PCTKR2017011367-appb-I000007
Figure PCTKR2017011367-appb-I000007
[화학식 5][Formula 5]
Figure PCTKR2017011367-appb-I000008
Figure PCTKR2017011367-appb-I000008
상기 화학식 4 및 5에서, In Chemical Formulas 4 and 5,
X, L2 내지 L3, R1 내지 R4, Ar1 내지 Ar2, l, m, n 및 o 각각은 상기 화학식 1에서 정의된 바와 같다. X, L 2 to L 3 , R 1 to R 4 , Ar 1 to Ar 2 , 1, m, n and o are each as defined in Chemical Formula 1.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L2 및 L3는 각각 독립적으로 단일결합이거나, 하기 화학식 A-1 내지 화학식 A-3 중 어느 하나로 표시되는 링커일 수 있다:According to one preferred embodiment of the present invention, L 2 and L 3 may be each independently a single bond or a linker represented by any one of the following formula A-1 to A-3:
Figure PCTKR2017011367-appb-I000009
Figure PCTKR2017011367-appb-I000009
상기 화학식 A-1 내지 A-3에서,In Chemical Formulas A-1 to A-3,
*는 결합이 이루어지는 부분을 의미한다.* Means the part where the coupling is made.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L2 및 L3는 각각 독립적으로 단일결합이거나, 상기 화학식 A-1로 표시되는 링커일 수 있다. According to one preferred embodiment of the present invention, L 2 and L 3 may be each independently a single bond or a linker represented by the formula A-1.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1 및 Ar2는 각각 독립적으로 하기 화학식 B-1 내지 B-10 중 어느 하나로 표시되는 치환기일 수 있다:According to one preferred embodiment of the present invention, Ar 1 and Ar 2 may each independently be a substituent represented by one of the following formulas B-1 to B-10:
Figure PCTKR2017011367-appb-I000010
Figure PCTKR2017011367-appb-I000010
상기 화학식 B-1 내지 B-10에서,In Chemical Formulas B-1 to B-10,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
Z1 내지 Z8은 각각 독립적으로 N 또는 C(R9)이며;Z 1 to Z 8 are each independently N or C (R 9 );
상기 화학식 B-2에서 L2 또는 L3에 결합되는 Z1 내지 Z4 중 어느 하나는 C(R9)이고, 이때 상기 R9는 부재이며;Any one of Z 1 to Z 4 bonded to L 2 or L 3 in Formula B-2 is C (R 9 ), wherein R 9 is absent;
T1 및 T2는 각각 독립적으로 단일결합, C(R10)(R11), N(R12), O 및 S로 이루어진 군에서 선택되나, T1 및 T2 모두가 단일결합은 아니며;T 1 and T 2 are each independently selected from the group consisting of a single bond, C (R 10 ) (R 11 ), N (R 12 ), O and S, but not both T 1 and T 2 are single bonds;
p 및 q는 각각 독립적으로 0 내지 4의 정수이며;p and q are each independently integers of 0 to 4;
R5 및 R6은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R5 및 R6 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 5 and R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ~ C 60, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 ~ C 60 mono or diaryl phosphinyl group and a C 6 ~ C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, wherein R When 5 and R 6 are each plural, they are the same as or different from each other;
R7 내지 R12는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R9 내지 R12 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 7 to R 12 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting of C 6 ~ C 60 mono or diaryl the Phosphinicosuccinic group and a C 6 ~ with an aryl silyl group of C 60, or combine tile adjacent to which they are attached may form a fused ring, When each of R 9 to R 12 plural is the same or different from each other;
상기 R5 내지 R12의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 5 to R 12 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R7 및 R8은 각각 독립적으로 C1~C30의 알킬기, C6~C30의 아릴기 및 핵원자수 5 내지 30개의 헤테로아릴기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 7 and R 8 are each independently from the group consisting of C 1 ~ C 30 Alkyl group, C 6 ~ C 30 aryl group and 5 to 30 heteroaryl group of nuclear atoms Can be selected.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R7 및 R8은 각각 독립적으로 페닐기, 비페닐기 및 나프탈레닐기로 이루어진 군에서 선택될 수 있고, 보다 바람직하게는 페닐기 또는 비페닐기일 수 있다.According to one preferred embodiment of the present invention, R 7 and R 8 may be each independently selected from the group consisting of phenyl group, biphenyl group and naphthalenyl group, more preferably may be a phenyl group or a biphenyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R9는 C1~C30의 알킬기, C6~C30의 아릴기 및 핵원자수 5 내지 30개의 헤테로아릴기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 9 may be selected from the group consisting of C 1 ~ C 30 alkyl group, C 6 ~ C 30 aryl group and 5 to 30 heteroaryl groups.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R9는 페닐기, 비페닐기, 나프탈레닐기, 피리디닐기, 피리미디닐기 및 트리아지닐기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 9 may be selected from the group consisting of phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group and triazinyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 B-1으로 표시되는 치환기는 하기 화학식 6으로 표시되는 치환기일 수 있다:According to one preferred embodiment of the present invention, the substituent represented by Formula B-1 may be a substituent represented by the following Formula 6:
[화학식 6][Formula 6]
Figure PCTKR2017011367-appb-I000011
Figure PCTKR2017011367-appb-I000011
상기 화학식 6에서,In Chemical Formula 6,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
R13 및 R14는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; R 13 and R 14 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining the adjacent tile to form a condensed ring;
상기 R13 및 R14의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group and aryl of R 13 and R 14 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group selected from the group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they are the same as or different from each other;
Z1, Z3 및 Z5 각각은 상기 화학식 B-1에서 정의된 바와 같다. Z 1 , Z 3 and Z 5 are each as defined in Formula B-1.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R13 및 R14는 각각 독립적으로 C1~C30의 알킬기, C6~C30의 아릴기 및 핵원자수 5 내지 30개의 헤테로아릴기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 13 and R 14 are each independently selected from the group consisting of C 1 ~ C 30 Alkyl group, C 6 ~ C 30 aryl group and 5 to 30 heteroaryl group of nuclear atoms Can be selected.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R13 및 R14는 각각 독립적으로 페닐기, 비페닐기, 나프탈레닐기, 피리디닐기, 피리미디닐기 및 트리아지닐기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 13 and R 14 may be each independently selected from the group consisting of phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group and triazinyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1 및 Ar2는 각각 독립적으로 하기 화학식 C-1 내지 C-25 중 어느 하나로 표시되는 치환기일 수 있으나, 이에 제한되는 것은 아니다:According to a preferred embodiment of the present invention, it is not the Ar 1 and Ar 2 each may be a substituent represented by the following formula of one of C-1 to C-25 independent, limited to:
Figure PCTKR2017011367-appb-I000012
Figure PCTKR2017011367-appb-I000012
상기 화학식 C-1 내지 C-25에서, In Chemical Formulas C-1 to C-25,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
r은 0 내지 5의 정수이며;r is an integer from 0 to 5;
p, q 및 s는 각각 독립적으로 0 내지 4의 정수이며;p, q and s are each independently integers of 0 to 4;
t는 0 내지 3의 정수이며;t is an integer from 0 to 3;
u는 0 내지 2의 정수이며;u is an integer from 0 to 2;
R5, R6 및 R15는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R5, R6 및 R15 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 5 , R 6 and R 15 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 ~ C 60 aryl phosphazene group, selected from the group consisting arylsilyl a C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining tile adjacent to which they are attached may form a condensed ring , wherein R 5, R 6 and R 15 each, if these are the same or different, and plural individual;
R7 내지 R12는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;R 7 to R 12 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from an aryl silyl group the group consisting of or of, by combining groups adjacent to form a condensed ring;
상기 R5 내지 R12 및 R15의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron of R 5 to R 12 and R 15 Group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60, alkyloxy group of C 1 ~ C 40 of the , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group , the group consisting of C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 aryl group in the silyl When substituted with at least one selected more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R9 및 R15는 각각 독립적으로 C1~C30의 알킬기, C6~C30의 아릴기 및 핵원자수 5 내지 30개의 헤테로아릴기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 9 and R 15 are each independently a group consisting of an alkyl group of C 1 ~ C 30 , an aryl group of C 6 ~ C 30 and a heteroaryl group of 5 to 30 nuclear atoms Can be selected.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R9 및 R15는 각각 독립적으로 페닐기, 비페닐기, 나프탈레닐기, 피리디닐기, 피리미디닐기 및 트리아지닐기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 9 and R 15 may be each independently selected from the group consisting of phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group and triazinyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10 및 R11은 각각 독립적으로 수소, C1~C30의 알킬기 및 C6~C30의 아릴기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 10 and R 11 may be independently selected from the group consisting of hydrogen, C 1 ~ C 30 Alkyl group and C 6 ~ C 30 An aryl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10 및 R11은 각각 독립적으로 수소, 메틸기, 에틸기, 부틸기 및 페닐기로 이루어진 군에서 선택될 수 있다.According to one preferred embodiment of the present invention, R 10 and R 11 may be independently selected from the group consisting of hydrogen, methyl group, ethyl group, butyl group and phenyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화학식 C-1으로 표시되는 치환기는 하기 화학식 D-1 내지 D-3 중 어느 하나로 표시될 수 있으나, 이에 제한되는 것은 아니다:According to one preferred embodiment of the present invention, the substituent represented by Formula C-1 may be represented by any one of the following Formulas D-1 to D-3, but is not limited thereto:
Figure PCTKR2017011367-appb-I000013
Figure PCTKR2017011367-appb-I000013
상기 화학식 D-1 내지 D-3에서,In Chemical Formulas D-1 to D-3,
*은 결합이 이루어지는 부분을 의미한다.* Means the part where the coupling is made.
본 발명의 화학식 1로 표시되는 화합물은 하기 화합물로 나타낼 수 있으나 이에 한정되는 것은 아니다: Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
상기 화합물은 아래의 화합물로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물: The compound is selected from the group consisting of the following compounds:
Figure PCTKR2017011367-appb-I000014
Figure PCTKR2017011367-appb-I000014
Figure PCTKR2017011367-appb-I000015
Figure PCTKR2017011367-appb-I000015
Figure PCTKR2017011367-appb-I000016
Figure PCTKR2017011367-appb-I000016
Figure PCTKR2017011367-appb-I000017
Figure PCTKR2017011367-appb-I000017
Figure PCTKR2017011367-appb-I000018
Figure PCTKR2017011367-appb-I000018
Figure PCTKR2017011367-appb-I000019
Figure PCTKR2017011367-appb-I000019
Figure PCTKR2017011367-appb-I000020
Figure PCTKR2017011367-appb-I000020
Figure PCTKR2017011367-appb-I000021
Figure PCTKR2017011367-appb-I000021
Figure PCTKR2017011367-appb-I000022
Figure PCTKR2017011367-appb-I000022
Figure PCTKR2017011367-appb-I000023
Figure PCTKR2017011367-appb-I000023
Figure PCTKR2017011367-appb-I000024
Figure PCTKR2017011367-appb-I000024
Figure PCTKR2017011367-appb-I000025
Figure PCTKR2017011367-appb-I000025
Figure PCTKR2017011367-appb-I000026
Figure PCTKR2017011367-appb-I000026
Figure PCTKR2017011367-appb-I000027
Figure PCTKR2017011367-appb-I000027
Figure PCTKR2017011367-appb-I000028
Figure PCTKR2017011367-appb-I000028
Figure PCTKR2017011367-appb-I000029
Figure PCTKR2017011367-appb-I000029
Figure PCTKR2017011367-appb-I000030
Figure PCTKR2017011367-appb-I000030
Figure PCTKR2017011367-appb-I000031
Figure PCTKR2017011367-appb-I000031
Figure PCTKR2017011367-appb-I000032
Figure PCTKR2017011367-appb-I000032
Figure PCTKR2017011367-appb-I000033
Figure PCTKR2017011367-appb-I000033
Figure PCTKR2017011367-appb-I000034
Figure PCTKR2017011367-appb-I000034
Figure PCTKR2017011367-appb-I000035
Figure PCTKR2017011367-appb-I000035
Figure PCTKR2017011367-appb-I000036
Figure PCTKR2017011367-appb-I000036
Figure PCTKR2017011367-appb-I000037
Figure PCTKR2017011367-appb-I000037
본 발명의 화학식 1의 화합물은 일반적인 합성방법에 따라 합성될 수 있다(Chem. Rev., 60:313 (1960); J. Chem . SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조). 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다. Compounds of formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ) And so on). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
2. 유기 2. Organic 전계Electric field 발광 소자 Light emitting element
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다.On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.
구체적으로, 본 발명은 양극(anode), 음극(cathode), 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독 또는 2 이상 혼합되어 사용될 수 있다.Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1). In this case, the compound may be used alone or mixed two or more.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 발광 보조층, 수명 개선층, 전자 수송층, 전자 수송 보조층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by 1.
전술한 본 발명에 따른 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 일 예시로 도 1을 참고하면, 예컨대 서로 마주하는 양극(10)과 음극(20), 그리고 상기 양극(10)과 음극(20) 사이에 위치하는 유기층(30)을 포함한다. 여기서, 상기 유기층(30)은 정공 수송층(31), 발광층(32) 및 전자 수송층(34)을 포함할 수 있다. 또한, 상기 정공 수송층(31)과 발광층(32) 사이에는 정공 수송 보조층(33)을 포함할 수 있으며, 상기 전자 수송층(34)과 발광층(32) 사이에는 전자 수송 보조층(35)을 포함할 수 있다. The structure of the organic EL device according to the present invention described above is not particularly limited, but referring to FIG. 1 as an example, for example, the anode 10 and the cathode 20 facing each other, and the anode 10 and the cathode ( 20) and an organic layer 30 positioned between them. The organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. In addition, a hole transport auxiliary layer 33 may be included between the hole transport layer 31 and the light emitting layer 32, and an electron transport auxiliary layer 35 may be included between the electron transport layer 34 and the light emitting layer 32. can do.
본 발명의 다른 예시로 도 2를 참고하면, 상기 유기층(30)은 정공 수송층(31)과 양극(10)사이에 정공 주입층(37)을 더 포함할 수 있으며, 전자 수송층(34)과 음극(20)사이에는 전자 주입층(36)을 추가로 더 포함할 수 있다. Referring to FIG. 2 as another example of the present invention, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, the electron transport layer 34 and the cathode The electron injection layer 36 may be further included between the holes 20.
본 발명에서 상기 정공 수송층(31)과 양극(10) 사이에 적층되는 정공 주입층(37)은 양극으로 사용되는 ITO와, 정공 수송층(31)으로 사용되는 유기물질 사이의 계면 특성을 개선할 뿐만 아니라 그 표면이 평탄하지 않은 ITO의 상부에 도포되어 ITO의 표면을 부드럽게 만들어주는 기능을 하는 층으로, 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예컨대, 아민 화합물을 사용할 수 있으나 이에 한정되는 것은 아니다.In the present invention, the hole injection layer 37 stacked between the hole transport layer 31 and the anode 10 may not only improve the interface property between the ITO used as the anode and the organic material used as the hole transport layer 31. However, the surface is applied to the upper surface of the uneven ITO to soften the surface of the ITO, a layer that can be used without particular limitation as long as it is commonly used in the art, for example, may be used an amine compound It is not limited to this.
또한, 상기 전자 주입층(36)은 전자 수송층의 상부에 적층되어 음극으로부터의 전자 주입을 용이하게 해주어 궁극적으로 전력효율을 개선시키는 기능을 수행하는 층으로, 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예컨대, LiF, Liq, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다. In addition, the electron injection layer 36 is stacked on top of the electron transport layer to facilitate the injection of electrons from the cathode to perform a function that ultimately improves the power efficiency, which is specially used in the art It can be used without limitation, and materials such as LiF, Liq, NaCl, CsF, Li 2 O, BaO and the like can be used.
또한, 본 발명에서 도면에는 도시하지 않았으나, 상기 정공 수송 보조층(33)과 발광층(32) 사이에 발광 보조층을 더 포함할 수 있다. 상기 발광 보조층은 발광층(32)에 정공을 수송하는 역할을 하면서 유기층(30)의 두께를 조정하는 역할을 할 수 있다. 상기 발광 보조층은 정공 수송 물질을 포함할 수 있고, 정공 수송층(31)과 동일한 물질로 만들어질 수 있다.In addition, although not shown in the drawings in the present invention, a light emitting auxiliary layer may be further included between the hole transport auxiliary layer 33 and the light emitting layer 32. The emission auxiliary layer may serve to transport holes to the emission layer 32 and to adjust the thickness of the organic layer 30. The emission auxiliary layer may include a hole transport material, and may be made of the same material as the hole transport layer 31.
또한, 본 발명에서 도면에는 도시하지 않았으나, 상기 전자 수송 보조층 (35)과 발광층(32) 사이에 수명 개선층을 더 포함할 수 있다. 상기 발광층(32)으로 유기 발광 소자 내에서 이온화 포텐셜 레벨을 타고 이동하는 정공이 수명개선층의 높은 에너지 장벽에 막혀 전자 수송층으로 확산, 또는 이동하지 못해, 결과적으로 정공을 발광층에 제한시키는 기능을 한다. 이렇게 정공을 발광층에 제한시키는 기능은 환원에 의해 전자를 이동시키는 전자 수송층으로 정공이 확산되는 것을 막아, 산화에 의한 비가역적 분해반응을 통한 수명저하 현상을 억제하여, 유기 발광 소자의 수명 개선에 기여할 수 있다.In addition, although not shown in the drawings in the present invention, a life improvement layer may be further included between the electron transport auxiliary layer 35 and the light emitting layer 32. Holes traveling through the ionization potential level in the organic light emitting device to the light emitting layer 32 are blocked by the high energy barrier of the lifespan improvement layer, and thus do not diffuse or move to the electron transport layer, and consequently, the holes are limited to the light emitting layer. . Such a function of limiting holes to the light emitting layer prevents holes from diffusing into the electron transporting layer that moves electrons by reduction, thereby suppressing the lifespan phenomenon through irreversible decomposition reaction by oxidation and contributing to improving the life of the organic light emitting device. Can be.
본 발명에서 제공하는 신규 화합물은 카바졸에 페녹사진 또는 페노티아진 모이어티가 결합되어 기본 골격을 이루며, 구체적으로는 상기 화학식 1로 표시되는 것을 특징으로 한다. 이러한 화학식 1로 표시되는 화합물은 종래 유기 전계 발광 소자용 재료[예: 4,4-디카바졸릴비페닐(이하, 'CBP'라 함)]보다 높은 분자량을 갖기 때문에, 유리전이온도가 높아 열적 안정성이 우수할 뿐만 아니라, 캐리어 수송능, 발광능 등이 우수하다. 따라서, 상기 화학식 1의 화합물을 유기 전계 발광 소자의 제조 시 사용할 경우, 소자의 구동전압, 효율, 수명 등이 향상될 수 있다. The novel compound provided in the present invention forms a basic skeleton by combining a phenoxazine or phenothiazine moiety to carbazole, and is specifically represented by Chemical Formula 1. Since the compound represented by the formula (1) has a higher molecular weight than the conventional organic electroluminescent device material (for example, 4,4-dicarbazolylbiphenyl (hereinafter referred to as 'CBP')), the glass transition temperature is high thermally Not only is it excellent in stability, it is also excellent in carrier transport ability, light emission ability, etc. Therefore, when the compound of Formula 1 is used in the manufacture of the organic EL device, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
또한, 상기 화학식 1의 화합물은 상기 기본 골격에 도입되는 치환기의 종류에 따라 HOMO 및 LUMO 에너지 레벨을 조절할 수 있어, 넓은 밴드갭을 가질 수 있고, 높은 캐리어 수송성을 가질 수 있다. 예를 들어, 상기 화합물은 상기 기본 골격에 질소-함유 헤테로환(예컨대, 피리딘기, 피리미딘기, 트리아진기 등)과 같이 전자 흡수성이 큰 전자 끌개기(EWG)가 결합될 경우, 분자 전체가 양극성(bipolar)의 특성을 갖기 때문에, 정공과 전자의 결합력을 높일 수 있다. 이와 같이, 상기 기본 골격에 EWG가 도입된 상기 화학식 1의 화합물은 우수한 캐리어 수송성 및 발광 특성이 우수하기 때문에, 유기 전계 발광 소자의 발광층 재료 이외, 전자주입/수송층 재료, 또는 수명 개선층 재료로도 사용될 수 있다. 한편, 상기 화학식 1의 화합물이 상기 기본 골격에 아릴아민기, 카바졸기, 터페닐기, 트리페닐렌기 등과 같이 전자 공여성이 큰 전자 주게기(EDG)가 결합될 경우, 정공의 주입 및 수송이 원활하게 이루어지기 때문에, 발광층 재료 이외, 정공주입/수송층 또는 발광 보조층 재료로도 유용하게 사용될 수 있다.In addition, the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, may have a wide bandgap, it may have a high carrier transport. For example, when the compound has a high electron-absorbing electron withdrawing group (EWG) such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.) to the basic skeleton, the entire molecule is Since it has a bipolar characteristic, it is possible to increase the bonding force between the hole and the electron. As such, the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and luminescent properties, and thus, as an electron injection / transport layer material or a life improvement layer material, in addition to the light emitting layer material of the organic EL device. Can be used. On the other hand, when the compound of Formula 1 is combined with an electron donor group (EDG) having a large electron donor such as an arylamine group, carbazole group, terphenyl group, triphenylene group, etc., the hole injection and transport is smooth. In addition to the light emitting layer material, it can be usefully used as a hole injection / transport layer or a light emitting auxiliary layer material.
이와 같이, 상기 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 발광 특성을 향상시킴과 동시에, 정공 주입/수송 능력, 전자 주입/수송 능력, 발광 효율, 구동 전압, 수명 특성 등을 향상시킬 수 있다. 따라서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광층, 발광 보조층, 전자 수송층 및 전자 주입층으로 이루어진 군에서 선택되는 것이 바람직하며, 보다 바람직하게는 발광층, 전자 수송층 또는 정공 수송층일 수 있다.As described above, the compound represented by Chemical Formula 1 may improve the light emission characteristics of the organic EL device, and may also improve the hole injection / transport ability, the electron injection / transport capability, the luminous efficiency, the driving voltage, and the lifespan characteristics. . Therefore, the organic material layer including the compound represented by Formula 1 is preferably selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, an electron transport layer and an electron injection layer, more preferably a light emitting layer, electron It may be a transport layer or a hole transport layer.
또한, 본 발명에 따른 화합물을 발광층 재료로 사용하는 경우, 구체적으로는 상기 화학식 1로 표시되는 화합물을 발광층의 인광 호스트, 형광 호스트 또는 도펀트 재료로 사용할 수 있으며, 바람직하게는 인광 호스트(청색, 녹색 및/또는 적색의 인광 호스트 재료)로 사용할 수 있다.In addition, when the compound according to the present invention is used as a light emitting layer material, specifically, the compound represented by Formula 1 may be used as a phosphorescent host, a fluorescent host or a dopant material of the light emitting layer, preferably a phosphorescent host (blue, green). And / or red phosphorescent host materials).
또한, 본 발명에서 상기 유기 전계 발광 소자는 상기한 바와 같이 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층을 추가로 포함할 수 있다. In addition, in the present invention, the organic electroluminescent device may not only sequentially stack an anode, at least one organic material layer, and a cathode as described above, but may further include an insulating layer or an adhesive layer at an interface between the electrode and the organic material layer.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 적어도 하나 이상(예컨대, 전자 수송 보조층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 다른 유기물층 및 전극을 형성하여 제조될 수 있다.The organic electroluminescent device of the present invention uses materials and methods known in the art, except that at least one of the organic material layers (for example, an electron transport auxiliary layer) is formed to include the compound represented by Chemical Formula 1. It can be prepared by forming other organic material layer and electrode using.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명에서 사용 가능한 기판으로는 특별히 한정되지 않으며, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다.The substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
또, 양극 물질로는 예컨대 정공 주입이 원활하도록 일 함수가 높은 도전체로 만들어질 수 있으며, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 있으나, 이에 한정되지는 않는다.Further, the positive electrode material may be made of a high work function conductor, for example, to facilitate hole injection, and may 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), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
또, 음극 물질로는 예컨대 전자 주입이 원활하도록 일 함수가 낮은 도전체로 만들어질 수 있으며, 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이에 한정되지는 않는다.In addition, the cathode material may be made of a low work function conductor, for example, to facilitate electron injection, and may include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead. The same metal or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.
[[ 준비예Preparation 1]  One]
단계 1. a-1(3-Step 1. a-1 (3- 브로모Bromo -10-페닐-10H--10-phenyl-10H- 페녹사진Phenox Photo )의 합성) Synthesis
Figure PCTKR2017011367-appb-I000038
Figure PCTKR2017011367-appb-I000038
3-브로모-10H-페녹사진 10g (38.15mmol)과 요오드벤젠 8.56g (41.96mmol)에 톨루엔 250 mL를 가하였다. Pd2(dba)3 1.73g (1.9mmol), NaOtBu 9.16g (95.37mmol), P(t-Bu)3 0.76g (3.8mmol)을 첨가 후 120℃에서 24시간 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 500 mL로 반응을 종결시켰다. 혼합액을 M.C 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 12.3g(수율 96%)을 얻었다. 250 mL of toluene was added to 10 g (38.15 mmol) of 3-bromo-10H-phenoxazine and 8.56 g (41.96 mmol) of iodinebenzene. Pd 2 (dba) 3 1.73 g (1.9 mmol), NaOtBu 9.16 g (95.37 mmol), and P (t-Bu) 3 0.76 g (3.8 mmol) were added and heated to reflux at 120 ° C. for 24 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 mL of aqueous ammonium chloride solution. The mixture was extracted with 500 mL of MC and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 12.3 g (yield 96%) of the title compound.
1H-NMR: δ 7.30~7.24(m, 3H), 7.10~6.96(m, 9H); 1 H-NMR: δ 7.30 -7.24 (m, 3H), 7.10-6.96 (m, 9H);
GC-Mass (이론치: 337.01 g/mol, 측정치: 338.20 g/mol)GC-Mass (Theoretical value: 337.01 g / mol, Measured value: 338.20 g / mol)
단계 2. a-2(10-페닐-3-(4,4,5,5-Step 2. a-2 (10-phenyl-3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-10H-페녹사진)의 합성2-yl) -10H-phenoxazine)
Figure PCTKR2017011367-appb-I000039
Figure PCTKR2017011367-appb-I000039
4,4,4',4',5,5,5',5'-옥타메틸-2,2'-비(1,3,2-디옥사보로란) 11.08g(43.64mmol)과 3-브로모-10-페닐-10H-페녹사진 12.3g (36.36mmol)에 1,4-디옥산 250 mL를 가하였다. Pd(dppf)Cl2 0.89g (1.09mmol), KOAc 10.7g (109.08mmol)을 첨가 후 120℃에서 24시간 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 500 mL로 반응을 종결시켰다. 혼합액을 M.C 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 9.8g(수율 70%)을 얻었다. 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane) 11.08 g (43.64 mmol) and 3 To 12.3 g (36.36 mmol) of bromo-10-phenyl-10H-phenoxazine was added 250 mL of 1,4-dioxane. Pd (dppf) Cl 2 0.89 g (1.09 mmol) and KOAc 10.7 g (109.08 mmol) were added and heated to reflux at 120 ° C. for 24 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 mL of aqueous ammonium chloride solution. The mixture was extracted with 500 mL of MC and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 9.8 g (yield 70%) of the title compound.
1H-NMR: δ 7.43 (m, 1H), 7.24(m, 2H), 7.24~6.95(m, 9H), 1.20(m, 12H); 1 H-NMR: δ 7.43 (m, 1 H), 7.24 (m, 2 H), 7.24 to 6.95 (m, 9 H), 1.20 (m, 12 H);
GC-Mass (이론치: 385.27 g/mol, 측정치: 385.18 g/mol)GC-Mass (Theoretical value: 385.27 g / mol, Measured value: 385.18 g / mol)
[[ 준비예Preparation 2]  2] 10-([1,1'-비페닐]-4-일)-3-(4,4,5,5-10-([1,1'-biphenyl] -4-yl) -3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-10H-페녹사진의 합성Synthesis of 2-yl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000040
Figure PCTKR2017011367-appb-I000040
반응물로 4-브로모-1,1'-비페닐을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 8.3g을 얻었다.; HRMS [M]+: 461.378.3g of the target compound was obtained in the same manner as the [Preparation Example 1], except that 4-bromo-1,1'-biphenyl was used as a reactant. HRMS [M] +: 461.37
[[ 준비예Preparation 3]  3] 10-([1,1'-비페닐]-3-일)-3-(4,4,5,5-10-([1,1'-biphenyl] -3-yl) -3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-10H-페녹사진의 합성Synthesis of 2-yl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000041
Figure PCTKR2017011367-appb-I000041
반응물로 3-브로모-1,1'-비페닐을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 7.8g을 얻었다.; HRMS [M]+: 461.377.8 g of the target compound were obtained in the same manner as the [Preparation Example 1], except that 3-bromo-1,1'-biphenyl was used as a reaction product. HRMS [M] +: 461.37
[[ 준비예Preparation 4]  4] 10-(10- ( 디벤조[b,d]퓨란Dibenzo [b, d] furan -2-일)-3-(4,4,5,5--2-yl) -3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-10H-페녹사진의 합성Synthesis of 2-yl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000042
Figure PCTKR2017011367-appb-I000042
반응물로 2-브로모디벤조[b,d]퓨란을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 8.1g을 얻었다.; HRMS [M]+: 475.358.1 g of the target compound was obtained in the same manner as the [Preparation Example 1] except that 2-bromodibenzo [b, d] furan was used as a reactant. HRMS [M] +: 475.35
[[ 준비예Preparation 5]  5] 10-(10- ( 디벤조[b,d]퓨란Dibenzo [b, d] furan -4-일)-3-(4,4,5,5--4-yl) -3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사Dioxa 보로란-2-일)-10H-페녹사진의 합성Synthesis of Bororan-2-yl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000043
Figure PCTKR2017011367-appb-I000043
반응물로 4-브로모디벤조[b,d]퓨란을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 475.356.9 g of the target compound was obtained in the same manner as the [Preparation Example 1], except that 4-bromodibenzo [b, d] furan was used as the reactant. HRMS [M] +: 475.35
[[ 준비예Preparation 6]  6] 10-(나프탈렌-2-일)-3-(4,4,5,5-10- (naphthalen-2-yl) -3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-10H-페녹사진의 합성Synthesis of 2-yl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000044
Figure PCTKR2017011367-appb-I000044
반응물로 2-브로모나프탈렌을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 8.5g을 얻었다.; HRMS [M]+: 435.33A target compound of 8.5g was obtained in the same manner as in [Preparation Example 1], except that 2-bromonaphthalene was used as a reactant .; HRMS [M] +: 435.33
[[ 준비예Preparation 7]  7] N,NN, N -디페닐-4-(3-(4,4,5,5--Diphenyl-4- (3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-10H-페녹사진-10-일)아닐린의 합성Synthesis of -2-yl) -10H-phenoxazine-10-yl) aniline
Figure PCTKR2017011367-appb-I000045
Figure PCTKR2017011367-appb-I000045
반응물로 4-브로모-N,N-디페닐아닐린을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 10.3g을 얻었다.; HRMS [M]+: 552.48Except for using 4-bromo-N, N-diphenylaniline as the reaction was carried out the same procedure as in [Preparation Example 1] to give 10.3g of the target compound .; HRMS [M] +: 552.48
[[ 준비예Preparation 8]  8] 10-(4,6-디페닐-1,3,5-트리아진-2-일)-3-(4,4,5,5-10- (4,6-diphenyl-1,3,5-triazin-2-yl) -3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2-디옥사보로란-2-일)-10H-페녹사진의 합성Synthesis of -1,3,2-dioxaborolan-2-yl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000046
Figure PCTKR2017011367-appb-I000046
반응물로 2-클로로-4,6-디페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 9.4g을 얻었다.; HRMS [M]+: 540.439.4 g of the title compound was obtained in the same manner as the [Preparation Example 1], except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used as the reactant. HRMS [M] +: 540.43
[[ 준비예Preparation 9] 9]
단계 1. a-3(3-(4-Step 1.a-3 (3- (4- 브로모페닐Bromophenyl )-10-페닐-10H-) -10-phenyl-10H- 페녹사진Phenox Photo )의 합성) Synthesis
Figure PCTKR2017011367-appb-I000047
Figure PCTKR2017011367-appb-I000047
질소 기류 [준비예 1] 10g (25.95mmol)과 1,4-디브로모벤젠 7.34g (31.14mmol), K2CO3 8.9g (64.87mmol) Pd(PPh3)4 1.49g (1.29mmol)와 80ml/80ml/80ml의 톨루엔/EtOH/H2O를 넣고 100℃에서 8시간 동안 교반하였다. 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 500 mL로 반응을 종결시켰다. 혼합액을 M.C 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 9.4g(수율 88%)을 얻었다. Nitrogen stream [Preparation Example 1] 10 g (25.95 mmol), 1,4-dibromobenzene 7.34 g (31.14 mmol), K 2 CO 3 8.9 g (64.87 mmol) Pd (PPh 3 ) 4 Put 1.49g (1.29mmol) and 80ml / 80ml / 80ml of toluene / EtOH / H 2 O was stirred at 100 ℃ for 8 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 mL of aqueous ammonium chloride solution. The mixture was extracted with 500 mL of MC and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 9.4 g (yield 88%) of the title compound.
1H-NMR: δ 7.65(s, 4H), 7.33~7.24(m, 5H), 7.14~6.96(m, 7H); 1 H-NMR: δ 7.65 (s, 4H), 7.33 to 7.44 (m, 5H), 7.14 to 6.96 (m, 7H);
GC-Mass (이론치: 313.04 g/mol, 측정치: 414.3 g/mol)GC-Mass (Theoretical value: 313.04 g / mol, Measured value: 414.3 g / mol)
단계 2. a-4(10-페닐-3-(4-(4,4,5,5-Step 2. a-4 (10-phenyl-3- (4- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)페닐)-10H-페녹사진)의 합성2-yl) phenyl) -10H-phenoxazine)
Figure PCTKR2017011367-appb-I000048
Figure PCTKR2017011367-appb-I000048
4,4,4',4',5,5,5',5'-옥타메틸-2,2'-비(1,3,2-디옥사보로란) 6.91g(27.22mmol)과 3-(4-브로모페닐)-10-페닐-10H-페녹사진 9.4g (22.68mmol)에 1,4-디옥산 250 mL를 가하였다. Pd(dppf)Cl2 0.55g (0.68mmol), KOAc 6.67g (68.04mmol)을 첨가 후 120℃에서 24시간 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 500 mL로 반응을 종결시켰다. 혼합액을 M.C 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 7.11g(수율 68%)을 얻었다. 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane) 6.91 g (27.22 mmol) and 3 To 9.4 g (22.68 mmol) of-(4-bromophenyl) -10-phenyl-10H-phenoxazine was added 250 mL of 1,4-dioxane. Pd (dppf) Cl 2 0.55 g (0.68 mmol) and KO67 6.67 g (68.04 mmol) were added and refluxed at 120 ° C. for 24 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 mL of aqueous ammonium chloride solution. The mixture was extracted with 500 mL of MC and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 7.11 g (yield 68%) of the title compound.
1H-NMR:δ 7.94 (m, 2H), 7.77 (m, 2H), 7.33~7.24(m, 4H), 7.14~6.96(m, 7H); 1 H-NMR: δ 7.94 (m, 2H), 7.77 (m, 2H), 7.33 to 7.44 (m, 4H), 7.14 to 6.96 (m, 7H);
GC-Mass (이론치: 461.22 g/mol, 측정치: 461.347 g/mol)GC-Mass (Theoretical value: 461.22 g / mol, Measured value: 461.347 g / mol)
[[ 준비예Preparation 10]  10] 10-페닐-3-(3-(4,4,5,5-10-phenyl-3- (3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)페닐)-10H-페녹사진의 합성Synthesis of 2-yl) phenyl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000049
Figure PCTKR2017011367-appb-I000049
반응물로 [준비예 1]을 사용한 것을 제외하고는 [준비예 9]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 461.376.7 g of the target compound was obtained in the same manner as the [Preparation Example 9], except that [Preparation Example 1] was used as the reactant. HRMS [M] +: 461.37
[[ 준비예Preparation 11]  11] 10-([1,1'-비페닐]-3-일)-3-(3-(4,4,5,5-10-([1,1'-biphenyl] -3-yl) -3- (3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)페닐)-10H-페녹사진의 합성Synthesis of 2-yl) phenyl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000050
Figure PCTKR2017011367-appb-I000050
반응물로 [준비예 3]을 사용한 것을 제외하고는 [준비예 10]과 동일한 과정을 수행하여 목적 화합물 7.6g을 얻었다.; HRMS [M]+: 537.477.6 g of the target compound was obtained in the same manner as the [Preparation Example 10], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 537.47
[[ 준비예Preparation 12]  12] 10-(10- ( 디벤조[b,d]퓨란Dibenzo [b, d] furan -4-일)-3-(3-(4,4,5,5--4-yl) -3- (3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)페닐)-10H-페녹사진의 합성Synthesis of 2-yl) phenyl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000051
Figure PCTKR2017011367-appb-I000051
반응물로 [준비예 5]을 사용한 것을 제외하고는 [준비예 10]과 동일한 과정을 수행하여 목적 화합물 7.2g을 얻었다.; HRMS [M]+: 551.457.2g of the target compound was obtained in the same manner as [Preparation Example 10], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 551.45
[[ 준비예Preparation 13]  13] 10-(4,6-디페닐-1,3,5-트리아진-2-일)-3-(3-(4,4,5,5-10- (4,6-diphenyl-1,3,5-triazin-2-yl) -3- (3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2-디옥사보로란-2-일)페닐)-10H-페녹사진의 합성Synthesis of -1,3,2-dioxaborolan-2-yl) phenyl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000052
Figure PCTKR2017011367-appb-I000052
반응물로 [준비예 8]을 사용한 것을 제외하고는 [준비예 10]과 동일한 과정을 수행하여 목적 화합물 7.8g을 얻었다.; HRMS [M]+: 616.53Except that [Preparation Example 8] was used as the reactant, the same procedure as in [Preparation Example 10] was performed to obtain 7.8 g of the target compound. HRMS [M] +: 616.53
[[ 준비예Preparation 14]  14] 10-페닐-3-(4,4,5,5-10-phenyl-3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-10H-페노티아진의 합성Synthesis of 2-yl) -10H-phenothiazine
Figure PCTKR2017011367-appb-I000053
Figure PCTKR2017011367-appb-I000053
반응물로 3-브로모-10H-페노티아진을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 401.336.8 g of the target compound was obtained in the same manner as the [Preparation Example 1], except that 3-bromo-10H-phenothiazine was used as the reaction. HRMS [M] +: 401.33
[[ 준비예Preparation 15]  15] 10-([1,1'-비페닐]-4-일)-3-(4,4,5,5-10-([1,1'-biphenyl] -4-yl) -3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사Dioxa 보로란-2-일)-10H-페노티아진의 합성Synthesis of Bororan-2-yl) -10H-phenothiazine
Figure PCTKR2017011367-appb-I000054
Figure PCTKR2017011367-appb-I000054
반응물로 3-브로모-10H-페노티아진을 사용한 것을 제외하고는 [준비예 2]과 동일한 과정을 수행하여 목적 화합물 8.0g을 얻었다.; HRMS [M]+: 477.43Except that 3-bromo-10H-phenothiazine was used as a reaction, the same procedure as in [Preparation Example 2] was carried out to obtain 8.0 g of the target compound. HRMS [M] +: 477.43
[[ 준비예Preparation 16]  16] 10-([1,1'-비페닐]-3-일)-3-(4,4,5,5-10-([1,1'-biphenyl] -3-yl) -3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-10H-페노티아진의 합성Synthesis of 2-yl) -10H-phenothiazine
Figure PCTKR2017011367-appb-I000055
Figure PCTKR2017011367-appb-I000055
반응물로 3-브로모-10H-페노티아진을 사용한 것을 제외하고는 [준비예 3]과 동일한 과정을 수행하여 목적 화합물 8.2g을 얻었다.; HRMS [M]+: 477.438.2 g of the target compound was obtained in the same manner as the [Preparation Example 3], except that 3-bromo-10H-phenothiazine was used as the reaction. HRMS [M] +: 477.43
[[ 준비예Preparation 17]  17] 10-(10- ( 디벤조[b,d]퓨란Dibenzo [b, d] furan -2-일)-3-(4,4,5,5--2-yl) -3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-10H-페노티아진의 합성Synthesis of 2-yl) -10H-phenothiazine
Figure PCTKR2017011367-appb-I000056
Figure PCTKR2017011367-appb-I000056
반응물로 3-브로모-10H-페노티아진을 사용한 것을 제외하고는 [준비예 4]과 동일한 과정을 수행하여 목적 화합물 7.6g을 얻었다.; HRMS [M]+: 491.417.6 g of the target compound was obtained in the same manner as the [Preparation Example 4], except that 3-bromo-10H-phenothiazine was used as the reaction. HRMS [M] +: 491.41
[[ 준비예Preparation 18]  18] 10-(10- ( 디벤조[b,d]퓨란Dibenzo [b, d] furan -4-일)-3-(4,4,5,5--4-yl) -3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-10H-페노티아진의 합성Synthesis of 2-yl) -10H-phenothiazine
Figure PCTKR2017011367-appb-I000057
Figure PCTKR2017011367-appb-I000057
반응물로 3-브로모-10H-페노티아진을 사용한 것을 제외하고는 [준비예 5]과 동일한 과정을 수행하여 목적 화합물 7.3g을 얻었다.; HRMS [M]+: 491.417.3 g of the target compound were obtained in the same manner as in [Preparation Example 5], except that 3-bromo-10H-phenothiazine was used as the reaction. HRMS [M] +: 491.41
[[ 준비예Preparation 19]  19] 10-(나프탈렌-2-일)-3-(4,4,5,5-10- (naphthalen-2-yl) -3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-10H-페노티아진의 합성Synthesis of 2-yl) -10H-phenothiazine
Figure PCTKR2017011367-appb-I000058
Figure PCTKR2017011367-appb-I000058
반응물로 3-브로모-10H-페노티아진을 사용한 것을 제외하고는 [준비예 6]과 동일한 과정을 수행하여 목적 화합물 8.1 g을 얻었다.; HRMS [M]+: 451.398.1 g of the target compound was obtained in the same manner as the [Preparation Example 6], except that 3-bromo-10H-phenothiazine was used as the reaction. HRMS [M] +: 451.39
[[ 준비예Preparation 20]  20] N,NN, N -디페닐-4-(3-(4,4,5,5--Diphenyl-4- (3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)-10H-페노티아진-10-일)아닐린의 합성Synthesis of 2-yl) -10H-phenothiazin-10-yl) aniline
Figure PCTKR2017011367-appb-I000059
Figure PCTKR2017011367-appb-I000059
반응물로 3-브로모-10H-페노티아진을 사용한 것을 제외하고는 [준비예 7]과 동일한 과정을 수행하여 목적 화합물 9.4g을 얻었다.; HRMS [M]+: 568.549.4 g of the title compound was obtained in the same manner as the [Preparation Example 7] except that 3-bromo-10H-phenothiazine was used as the reaction. HRMS [M] +: 568.54
[[ 준비예Preparation 21]  21] 10-(4,6-디페닐-1,3,5-트리아진-2-일)-3-(4,4,5,5-10- (4,6-diphenyl-1,3,5-triazin-2-yl) -3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2-디옥사보로란-2-일)-10H-페노티아진의 합성Synthesis of -1,3,2-dioxaborolan-2-yl) -10H-phenothiazine
Figure PCTKR2017011367-appb-I000060
Figure PCTKR2017011367-appb-I000060
반응물로 3-브로모-10H-페노티아진을 사용한 것을 제외하고는 [준비예 8]과 동일한 과정을 수행하여 목적 화합물 8.4g을 얻었다.; HRMS [M]+: 556.498.4 g of the target compound was obtained in the same manner as in [Preparation Example 8], except that 3-bromo-10H-phenothiazine was used as the reaction. HRMS [M] +: 556.49
[[ 준비예Preparation 22]  22] 3-(4-3- (4- 브로모페닐Bromophenyl )-10-페닐-10H-) -10-phenyl-10H- 페녹사진의Phenox Photo 합성 synthesis
Figure PCTKR2017011367-appb-I000061
Figure PCTKR2017011367-appb-I000061
반응물로 [준비예 14]을 사용한 것을 제외하고는 [준비예 9]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 551.45Except that [Preparation Example 14] was used as the reactant, the same procedure as in [Preparation Example 9] was performed, to obtain 6.5 g of the target compound. HRMS [M] +: 551.45
[[ 준비예Preparation 23]  23] 10-페닐-3-(3-(4,4,5,5-10-phenyl-3- (3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)페닐)-10H-페녹사진의 합성Synthesis of 2-yl) phenyl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000062
Figure PCTKR2017011367-appb-I000062
반응물로 [준비예 14]을 사용한 것을 제외하고는 [준비예 10]과 동일한 과정을 수행하여 목적 화합물 7.3g을 얻었다.; HRMS [M]+: 461.377.3 g of the title compound was obtained in the same manner as the [Preparation Example 10], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 461.37
[[ 준비예Preparation 24]  24] 10-([1,1'-비페닐]-3-일)-3-(3-(4,4,5,5-10-([1,1'-biphenyl] -3-yl) -3- (3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)페닐)-10H-페녹사진의 합성Synthesis of 2-yl) phenyl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000063
Figure PCTKR2017011367-appb-I000063
반응물로 [준비예 16]을 사용한 것을 제외하고는 [준비예 11]과 동일한 과정을 수행하여 목적 화합물 7.8g을 얻었다.; HRMS [M]+: 537.47A target compound of 7.8g was obtained in the same manner as in [Preparation Example 11], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 537.47
[[ 준비예Preparation 25]  25] 10-(10- ( 디벤조[b,d]퓨란Dibenzo [b, d] furan -4-일)-3-(3-(4,4,5,5--4-yl) -3- (3- (4,4,5,5- 테트라메틸Tetramethyl -1,3,2--1,3,2- 디옥사보로란Dioxaboloran -2-일)페닐)-10H-페녹사진의 합성Synthesis of 2-yl) phenyl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000064
Figure PCTKR2017011367-appb-I000064
반응물로 [준비예 18]을 사용한 것을 제외하고는 [준비예 12]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 551.456.8 g of the target compound was obtained in the same manner as the [Preparation Example 12], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 551.45
[[ 준비예Preparation 26]  26] 10-(4,6-디페닐-1,3,5-트리아진-2-일)-3-(3-(4,4,5,5-10- (4,6-diphenyl-1,3,5-triazin-2-yl) -3- (3- (4,4,5,5- 테트라메Tetrame 틸-1,3,2-디옥사보로란-2-일)페닐)-10H-페녹사진의 합성Synthesis of Thile-1,3,2-dioxaborolan-2-yl) phenyl) -10H-phenoxazine
Figure PCTKR2017011367-appb-I000065
Figure PCTKR2017011367-appb-I000065
반응물로 [준비예 21]을 사용한 것을 제외하고는 [준비예 13]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 616.536.9 g of the target compound was obtained in the same manner as [Preparation Example 13], except that [Preparation Example 21] was used as a reactant. HRMS [M] +: 616.53
[[ 합성예Synthesis Example 1] Mat 1의 합성 1] Synthesis of Mat 1
[준비예 1] 5g (12.97mmol)과 9-([1,1'-비페닐]-3-일)-3-브로모-9H-카바졸 6.2g (15.57mmol), K2CO3 4.48g (32.42mmol) Pd(PPh3)4 0.75g (0.64mol)와 80ml/80ml/80ml의 톨루엔/EtOH/H2O를 넣고 100℃에서 8시간 동안 교반하였다. 상온으로 온도를 냉각하고 반응액에 염화암모늄 수용액 500 mL로 반응을 종결시켰다. 혼합액을 M.C 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 6.4g(수율 86%)을 얻었다. PREPARATION EXAMPLE 1 5g (12.97mmol) and 9-([1,1'-biphenyl] -3-yl) -3-bromo-9H-carbazole 6.2g (15.57mmol), K2CO3 4.48g (32.42 mmol) Pd (PPh3) 4 0.75g (0.64mol) and 80ml / 80ml / 80ml of toluene / EtOH / H2O were added and stirred at 100 ° C for 8 hours. The temperature was cooled to room temperature, and the reaction was terminated with 500 mL of aqueous ammonium chloride solution. The mixture was extracted with 500 mL of MC and washed with distilled water. The resulting organic layer was dried over anhydrous MgSO 4, and was evaporated under reduced pressure and purified by silica gel column chromatography to obtain the title compound 6.4g (yield 86%).
1H-NMR: δ 8.30(m, 1H), 7.21~8.13(m, 3H), 7.89(s, 1H), 7.75~6.96(m, 23H); 1 H-NMR: δ 8.30 (m, 1 H), 7.21-8.13 (m, 3 H), 7.89 (s, 1 H), 7.75-6.96 (m, 23H);
GC-Mass (이론치: 576.21 g/mol, 측정치: 576.70 g/mol)GC-Mass (Theoretical value: 576.21 g / mol, Measured value: 576.70 g / mol)
[[ 합성예Synthesis Example 2] Mat 2의 합성 2] Synthesis of Mat 2
Figure PCTKR2017011367-appb-I000067
Figure PCTKR2017011367-appb-I000067
반응물로 9-([1,1'-비페닐]-4-일)-3-브로모-9H-카바졸을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 576.705.8 g of the target compound was carried out in the same manner as in Synthesis Example 1, except that 9-([1,1'-biphenyl] -4-yl) -3-bromo-9H-carbazole was used as the reactant. To obtain; HRMS [M] +: 576.70
[[ 합성예Synthesis Example 3] Mat 5의 합성 3] Synthesis of Mat 5
Figure PCTKR2017011367-appb-I000068
Figure PCTKR2017011367-appb-I000068
반응물로 3-브로모-9-(트리페닐렌-2-일)-9H-카바졸을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 650.786.3 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that 3-bromo-9- (triphenylen-2-yl) -9H-carbazole was used as the reactant. HRMS [M] +: 650.78
[[ 합성예Synthesis Example 4] Mat 7의 합성 4] Synthesis of Mat 7
Figure PCTKR2017011367-appb-I000069
Figure PCTKR2017011367-appb-I000069
반응물로 3-브로모-9-페닐-9H-카바졸을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 500.605.1 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that 3-bromo-9-phenyl-9H-carbazole was used as the reactant. HRMS [M] +: 500.60
[[ 합성예Synthesis Example 5] Mat 8의 합성 5] Synthesis of Mat 8
Figure PCTKR2017011367-appb-I000070
Figure PCTKR2017011367-appb-I000070
반응물로 3-브로모-9-(디벤조[b,d]퓨란-2-일)-9H-카바졸을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 590.685.7 g of the target compound was obtained in the same manner as in Synthesis Example 1, except that 3-bromo-9- (dibenzo [b, d] furan-2-yl) -9H-carbazole was used as the reactant. Obtained; HRMS [M] +: 590.68
[[ 합성예Synthesis Example 6] Mat 10의 합성 6] Synthesis of Mat 10
Figure PCTKR2017011367-appb-I000071
Figure PCTKR2017011367-appb-I000071
반응물로 3-브로모-9-(9,9-디메틸-9H-플루오렌-3-일)-9H-카바졸을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 616.76Target compound 5.3 was carried out in the same manner as in Synthesis Example 1, except that 3-bromo-9- (9,9-dimethyl-9H-fluoren-3-yl) -9H-carbazole was used as the reactant. g was obtained; HRMS [M] +: 616.76
[[ 합성예Synthesis Example 7] Mat 13의 합성 7] Synthesis of Mat 13
Figure PCTKR2017011367-appb-I000072
Figure PCTKR2017011367-appb-I000072
반응물로 3-브로모-9-(디벤조[b,d]퓨란-4-일)-9H-카바졸을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다.; HRMS [M]+: 590.68Except for using 3-bromo-9- (dibenzo [b, d] furan-4-yl) -9H-carbazole as the reaction product, the same procedure as in Synthesis Example 1 was performed to obtain 6.0 g of the target compound. Obtained; HRMS [M] +: 590.68
[[ 합성예Synthesis Example 8] Mat 14의 합성 8] Synthesis of Mat 14
Figure PCTKR2017011367-appb-I000073
Figure PCTKR2017011367-appb-I000073
반응물로 4-(3-브로모-9H-카바졸-9-일)-N,N-디페닐아닐린을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 667.815.3 g of the target compound was obtained by the same procedure as the Synthesis Example 1, except that 4- (3-bromo-9H-carbazol-9-yl) -N, N-diphenylaniline was used as a reactant. .; HRMS [M] +: 667.81
[[ 합성예Synthesis Example 9] Mat 19의 합성 9] Synthesis of Mat 19
Figure PCTKR2017011367-appb-I000074
Figure PCTKR2017011367-appb-I000074
반응물로 3-브로모-9-(3-(4,6-디페닐-1,3,5-트리아진-2-일)페닐)-9H-카바졸을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 731.86[Synthesis Example 1], except that 3-bromo-9- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -9H-carbazole was used as the reactant. ] 6.4 g of the target compound were obtained by the same procedure as the above. HRMS [M] +: 731.86
[[ 합성예Synthesis Example 10] Mat 20의 합성 10] Synthesis of Mat 20
Figure PCTKR2017011367-appb-I000075
Figure PCTKR2017011367-appb-I000075
반응물로 3-브로모-9-(4,6-디페닐-1,3,5-트리아진-2-일)-9H-카바졸을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다.; HRMS [M]+: 655.76The same procedure as in [Synthesis Example 1] was performed except that 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole was used as the reactant. This gave 6.0 g of the target compound. HRMS [M] +: 655.76
[[ 합성예Synthesis Example 11] Mat 21의 합성 11] Synthesis of Mat 21
Figure PCTKR2017011367-appb-I000076
Figure PCTKR2017011367-appb-I000076
반응물로 9-(4-([1,1'-비페닐]-4-일)-6-페닐-1,3,5-트리아진-2-일)-3-브로모-9H-카바졸을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 731.869- (4-([1,1'-biphenyl] -4-yl) -6-phenyl-1,3,5-triazin-2-yl) -3-bromo-9H-carbazole as reactant Except for using the same procedure as in Synthesis Example 1 to obtain the title compound 5.9g; HRMS [M] +: 731.86
[[ 합성예Synthesis Example 12] Mat 24의 합성 12] Synthesis of Mat 24
Figure PCTKR2017011367-appb-I000077
Figure PCTKR2017011367-appb-I000077
반응물로 3-브로모-9-(4-페닐퀴나졸린-2-일)-9H-카바졸을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 628.745.4 g of the target compound was obtained by the same procedure as the Synthesis Example 1, except that 3-bromo-9- (4-phenylquinazolin-2-yl) -9H-carbazole was used as the reaction. HRMS [M] +: 628.74
[[ 합성예Synthesis Example 13] Mat 26의 합성 13] Synthesis of Mat 26
Figure PCTKR2017011367-appb-I000078
Figure PCTKR2017011367-appb-I000078
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 652.806.3 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 2] was used as a reactant. HRMS [M] +: 652.80
[[ 합성예Synthesis Example 14] Mat 27의 합성 14] Synthesis of Mat 27
Figure PCTKR2017011367-appb-I000079
Figure PCTKR2017011367-appb-I000079
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 652.805.7 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 2] was used as a reactant. HRMS [M] +: 652.80
[[ 합성예Synthesis Example 15] Mat 30의 합성 15] Synthesis of Mat 30
Figure PCTKR2017011367-appb-I000080
Figure PCTKR2017011367-appb-I000080
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 726.886.6 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 2] was used as a reactant. HRMS [M] +: 726.88
[[ 합성예Synthesis Example 16] Mat 32의 합성 16] Synthesis of Mat 32
Figure PCTKR2017011367-appb-I000081
Figure PCTKR2017011367-appb-I000081
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 576.705.8 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 2] was used as a reactant. HRMS [M] +: 576.70
[[ 합성예Synthesis Example 17] Mat 33의 합성 17] Synthesis of Mat 33
Figure PCTKR2017011367-appb-I000082
Figure PCTKR2017011367-appb-I000082
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 666.786.7 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 2] was used as a reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 18] Mat 35의 합성 18] Synthesis of Mat 35
Figure PCTKR2017011367-appb-I000083
Figure PCTKR2017011367-appb-I000083
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 692.866.7 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 2] was used as a reactant. HRMS [M] +: 692.86
[[ 합성예Synthesis Example 19] Mat 38의 합성 19] Synthesis of Mat 38
Figure PCTKR2017011367-appb-I000084
Figure PCTKR2017011367-appb-I000084
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 666.785.9 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 2] was used as a reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 20] Mat 39의 합성 20] Synthesis of Mat 39
Figure PCTKR2017011367-appb-I000085
Figure PCTKR2017011367-appb-I000085
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 743.916.3 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 2] was used as a reactant. HRMS [M] +: 743.91
[[ 합성예Synthesis Example 21]  21] Mat44의Mat44 합성 synthesis
Figure PCTKR2017011367-appb-I000086
Figure PCTKR2017011367-appb-I000086
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 807.966.6 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 2] was used as a reactant. HRMS [M] +: 807.96
[[ 합성예Synthesis Example 22] Mat 45의 합성 22] Synthesis of Mat 45
Figure PCTKR2017011367-appb-I000087
Figure PCTKR2017011367-appb-I000087
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 731.865.8 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 2] was used as a reactant. HRMS [M] +: 731.86
[[ 합성예Synthesis Example 23] Mat 46의 합성 23] Synthesis of Mat 46
Figure PCTKR2017011367-appb-I000088
Figure PCTKR2017011367-appb-I000088
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 807.966.5 g of the target compound was obtained in the same manner as the [Synthesis Example 11], except that [Preparation Example 2] was used as a reactant. HRMS [M] +: 807.96
[[ 합성예Synthesis Example 24] Mat 49의 합성 24] Synthesis of Mat 49
Figure PCTKR2017011367-appb-I000089
Figure PCTKR2017011367-appb-I000089
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 704.836.4 g of the target compound was obtained in the same manner as the [Synthesis Example 12], except that [Preparation Example 2] was used as a reactant. HRMS [M] +: 704.83
[[ 합성예Synthesis Example 25] Mat 51의 합성 25] Synthesis of Mat 51
Figure PCTKR2017011367-appb-I000090
Figure PCTKR2017011367-appb-I000090
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 652.806.3 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 652.80
[[ 합성예Synthesis Example 26] Mat 52의 합성 26] Synthesis of Mat 52
Figure PCTKR2017011367-appb-I000091
Figure PCTKR2017011367-appb-I000091
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 652.805.7 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 652.80
[[ 합성예Synthesis Example 27] Mat 55의 합성 27] Synthesis of Mat 55
Figure PCTKR2017011367-appb-I000092
Figure PCTKR2017011367-appb-I000092
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 726.886.6 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 726.88
[[ 합성예Synthesis Example 28] Mat 57의 합성 28] Synthesis of Mat 57
Figure PCTKR2017011367-appb-I000093
Figure PCTKR2017011367-appb-I000093
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 576.705.8 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 576.70
[[ 합성예Synthesis Example 29] Mat 58의 합성 29] Synthesis of Mat 58
Figure PCTKR2017011367-appb-I000094
Figure PCTKR2017011367-appb-I000094
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 666.786.7 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 30] Mat 60의 합성 30] Synthesis of Mat 60
Figure PCTKR2017011367-appb-I000095
Figure PCTKR2017011367-appb-I000095
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 692.866.7 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 692.86
[[ 합성예Synthesis Example 31] Mat 63의 합성 31] Synthesis of Mat 63
Figure PCTKR2017011367-appb-I000096
Figure PCTKR2017011367-appb-I000096
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 666.785.9 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 32] Mat 64의 합성 32] Synthesis of Mat 64
Figure PCTKR2017011367-appb-I000097
Figure PCTKR2017011367-appb-I000097
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 743.916.3 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 743.91
[[ 합성예Synthesis Example 33] Mat 69의 합성 33] Synthesis of Mat 69
Figure PCTKR2017011367-appb-I000098
Figure PCTKR2017011367-appb-I000098
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 807.966.6 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 807.96
[[ 합성예Synthesis Example 34] Mat 70의 합성 34] Synthesis of Mat 70
Figure PCTKR2017011367-appb-I000099
Figure PCTKR2017011367-appb-I000099
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 6731.865.8 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 6731.86
[[ 합성예Synthesis Example 35] Mat 71의 합성 35] Synthesis of Mat 71
Figure PCTKR2017011367-appb-I000100
Figure PCTKR2017011367-appb-I000100
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 807.966.5 g of the target compound was obtained in the same manner as the [Synthesis Example 11], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 807.96
[[ 합성예Synthesis Example 36] Mat 74의 합성 36] Synthesis of Mat 74
Figure PCTKR2017011367-appb-I000101
Figure PCTKR2017011367-appb-I000101
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 704.836.4 g of the target compound was obtained in the same manner as the [Synthesis Example 12], except that [Preparation Example 3] was used as a reactant. HRMS [M] +: 704.83
[[ 합성예Synthesis Example 37] Mat 76의 합성 37] Synthesis of Mat 76
Figure PCTKR2017011367-appb-I000102
Figure PCTKR2017011367-appb-I000102
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 666.786.7 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 38] Mat 77의 합성 38] Synthesis of Mat 77
Figure PCTKR2017011367-appb-I000103
Figure PCTKR2017011367-appb-I000103
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 666.786.7 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 39] Mat 80의 합성 39] Synthesis of Mat 80
Figure PCTKR2017011367-appb-I000104
Figure PCTKR2017011367-appb-I000104
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 740.866.5 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 740.86
[[ 합성예Synthesis Example 40] Mat 82의 합성 40] Synthesis of Mat 82
Figure PCTKR2017011367-appb-I000105
Figure PCTKR2017011367-appb-I000105
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 6.2g을 얻었다.; HRMS [M]+: 590.686.2 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 590.68
[[ 합성예Synthesis Example 41] Mat 83의 합성 41] Synthesis of Mat 83
Figure PCTKR2017011367-appb-I000106
Figure PCTKR2017011367-appb-I000106
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 680.766.8 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 680.76
[[ 합성예Synthesis Example 42] Mat 85의 합성 42] Synthesis of Mat 85
Figure PCTKR2017011367-appb-I000107
Figure PCTKR2017011367-appb-I000107
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 706.856.4 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 706.85
[[ 합성예Synthesis Example 43] Mat 88의 합성 43] Synthesis of Mat 88
Figure PCTKR2017011367-appb-I000108
Figure PCTKR2017011367-appb-I000108
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 680.766.7 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 680.76
[[ 합성예Synthesis Example 44] Mat 89의 합성 44] Synthesis of Mat 89
Figure PCTKR2017011367-appb-I000109
Figure PCTKR2017011367-appb-I000109
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 757.896.9 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 757.89
[[ 합성예Synthesis Example 45] Mat 94의 합성 45] Synthesis of Mat 94
Figure PCTKR2017011367-appb-I000110
Figure PCTKR2017011367-appb-I000110
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 821.946.6 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 821.94
[[ 합성예Synthesis Example 46] Mat 95의 합성 46] Synthesis of Mat 95
Figure PCTKR2017011367-appb-I000111
Figure PCTKR2017011367-appb-I000111
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 745.846.8 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 745.84
[[ 합성예Synthesis Example 47] Mat 96의 합성 47] Synthesis of Mat 96
Figure PCTKR2017011367-appb-I000112
Figure PCTKR2017011367-appb-I000112
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 821.946.4 g of the target compound was obtained in the same manner as the [Synthesis Example 11], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 821.94
[[ 합성예Synthesis Example 48] Mat 99의 합성 48] Synthesis of Mat 99
Figure PCTKR2017011367-appb-I000113
Figure PCTKR2017011367-appb-I000113
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 718.826.8 g of the target compound was obtained in the same manner as the [Synthesis Example 12], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 718.82
[[ 합성예Synthesis Example 49] Mat 101의 합성 49] Synthesis of Mat 101
Figure PCTKR2017011367-appb-I000114
Figure PCTKR2017011367-appb-I000114
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 666.786.4 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation 5] was used as a reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 50] Mat 102의 합성 50] Synthesis of Mat 102
Figure PCTKR2017011367-appb-I000115
Figure PCTKR2017011367-appb-I000115
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 666.786.5 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 51] Mat 105의 합성 51] Synthesis of Mat 105
Figure PCTKR2017011367-appb-I000116
Figure PCTKR2017011367-appb-I000116
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 740.866.3 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 740.86
[[ 합성예Synthesis Example 52] Mat 107의 합성 52] Synthesis of Mat 107
Figure PCTKR2017011367-appb-I000117
Figure PCTKR2017011367-appb-I000117
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 590.686.9 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 590.68
[[ 합성예Synthesis Example 53] Mat 108의 합성 53] Synthesis of Mat 108
Figure PCTKR2017011367-appb-I000118
Figure PCTKR2017011367-appb-I000118
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 680.766.1 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 680.76
[[ 합성예Synthesis Example 54] Mat 110의 합성 54] Synthesis of Mat 110
Figure PCTKR2017011367-appb-I000119
Figure PCTKR2017011367-appb-I000119
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 706.856.9 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 706.85
[[ 합성예Synthesis Example 55] Mat 113의 합성 55] Synthesis of Mat 113
Figure PCTKR2017011367-appb-I000120
Figure PCTKR2017011367-appb-I000120
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 680.766.4 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 680.76
[[ 합성예Synthesis Example 56] Mat 114의 합성 56] Synthesis of Mat 114
Figure PCTKR2017011367-appb-I000121
Figure PCTKR2017011367-appb-I000121
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 757.896.3 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 757.89
[[ 합성예Synthesis Example 57] Mat 119의 합성 57] Synthesis of Mat 119
Figure PCTKR2017011367-appb-I000122
Figure PCTKR2017011367-appb-I000122
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 821.946.1 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 821.94
[[ 합성예Synthesis Example 58] Mat 120의 합성 58] Synthesis of Mat 120
Figure PCTKR2017011367-appb-I000123
Figure PCTKR2017011367-appb-I000123
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 745.846.4 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 745.84
[[ 합성예Synthesis Example 59] Mat 121의 합성 59] Synthesis of Mat 121
Figure PCTKR2017011367-appb-I000124
Figure PCTKR2017011367-appb-I000124
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 821.946.9 g of the target compound was obtained in the same manner as the [Synthesis Example 11], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 821.94
[[ 합성예Synthesis Example 60] Mat 124의 합성 60] Synthesis of Mat 124
Figure PCTKR2017011367-appb-I000125
Figure PCTKR2017011367-appb-I000125
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 718.826.7 g of the target compound was obtained in the same manner as the [Synthesis Example 12], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 718.82
[[ 합성예Synthesis Example 61] Mat 126의 합성 61] Synthesis of Mat 126
Figure PCTKR2017011367-appb-I000126
Figure PCTKR2017011367-appb-I000126
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 626.765.9 g of the title compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 626.76
[[ 합성예Synthesis Example 62] Mat 127의 합성 62] Synthesis of Mat 127
Figure PCTKR2017011367-appb-I000127
Figure PCTKR2017011367-appb-I000127
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 626.765.5 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 626.76
[[ 합성예Synthesis Example 63] Mat 130의 합성 63] Synthesis of Mat 130
Figure PCTKR2017011367-appb-I000128
Figure PCTKR2017011367-appb-I000128
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 700.845.3 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 700.84
[[ 합성예Synthesis Example 64] Mat 132의 합성 64] Synthesis of Mat 132
Figure PCTKR2017011367-appb-I000129
Figure PCTKR2017011367-appb-I000129
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 550.665.9 g of the title compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 550.66
[[ 합성예Synthesis Example 65] Mat 133의 합성 65] Synthesis of Mat 133
Figure PCTKR2017011367-appb-I000130
Figure PCTKR2017011367-appb-I000130
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 640.745.1 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 6] was used as the reactant. HRMS [M] +: 640.74
[[ 합성예Synthesis Example 66] Mat 135의 합성 66] Synthesis of Mat 135
Figure PCTKR2017011367-appb-I000131
Figure PCTKR2017011367-appb-I000131
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 666.825.9 g of the title compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 666.82
[[ 합성예Synthesis Example 67] Mat 138의 합성 67] Synthesis of Mat 138
Figure PCTKR2017011367-appb-I000132
Figure PCTKR2017011367-appb-I000132
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 640.745.4 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 640.74
[[ 합성예Synthesis Example 68] Mat 139의 합성 68] Synthesis of Mat 139
Figure PCTKR2017011367-appb-I000133
Figure PCTKR2017011367-appb-I000133
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 717.875.3 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 717.87
[[ 합성예Synthesis Example 69] Mat 144의 합성 69] Synthesis of Mat 144
Figure PCTKR2017011367-appb-I000134
Figure PCTKR2017011367-appb-I000134
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 781.925.1 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 781.92
[[ 합성예Synthesis Example 70] Mat 145의 합성 70] Synthesis of Mat 145
Figure PCTKR2017011367-appb-I000135
Figure PCTKR2017011367-appb-I000135
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 705.825.4 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 705.82
[[ 합성예Synthesis Example 71] Mat 146의 합성 71] Synthesis of Mat 146
Figure PCTKR2017011367-appb-I000136
Figure PCTKR2017011367-appb-I000136
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 781.925.9 g of the title compound was obtained in the same manner as the [Synthesis Example 11], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 781.92
[[ 합성예Synthesis Example 72] Mat 149의 합성 72] Synthesis of Mat 149
Figure PCTKR2017011367-appb-I000137
Figure PCTKR2017011367-appb-I000137
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 678.805.7 g of the target compound was obtained in the same manner as the [Synthesis Example 12], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 678.80
[[ 합성예Synthesis Example 73] Mat 151의 합성 73] Synthesis of Mat 151
Figure PCTKR2017011367-appb-I000138
Figure PCTKR2017011367-appb-I000138
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 743.916.9 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 743.91
[[ 합성예Synthesis Example 74] Mat 152의 합성 74] Synthesis of Mat 152
Figure PCTKR2017011367-appb-I000139
Figure PCTKR2017011367-appb-I000139
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 743.916.5 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 743.91
[[ 합성예Synthesis Example 75] Mat 155의 합성 75] Synthesis of Mat 155
Figure PCTKR2017011367-appb-I000140
Figure PCTKR2017011367-appb-I000140
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 817.996.8 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 817.99
[[ 합성예Synthesis Example 76] Mat 157의 합성 76] Synthesis of Mat 157
Figure PCTKR2017011367-appb-I000141
Figure PCTKR2017011367-appb-I000141
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 667.817.1 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 9] was used as the reactant. HRMS [M] +: 667.81
[[ 합성예Synthesis Example 77] Mat 158의 합성 77] Synthesis of Mat 158
Figure PCTKR2017011367-appb-I000142
Figure PCTKR2017011367-appb-I000142
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 757.896.1 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 9] was used as the reactant. HRMS [M] +: 757.89
[[ 합성예Synthesis Example 78] Mat 160의 합성 78] Synthesis of Mat 160
Figure PCTKR2017011367-appb-I000143
Figure PCTKR2017011367-appb-I000143
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 783.986.9 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 9] was used as the reactant. HRMS [M] +: 783.98
[[ 합성예Synthesis Example 79] Mat 163의 합성 79] Synthesis of Mat 163
Figure PCTKR2017011367-appb-I000144
Figure PCTKR2017011367-appb-I000144
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 757.896.3 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 9] was used as the reactant. HRMS [M] +: 757.89
[[ 합성예Synthesis Example 80] Mat 164의 합성 80] Synthesis of Mat 164
Figure PCTKR2017011367-appb-I000145
Figure PCTKR2017011367-appb-I000145
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 835.026.9 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 9] was used as the reactant. HRMS [M] +: 835.02
[[ 합성예Synthesis Example 81] Mat 169의 합성 81] Synthesis of Mat 169
Figure PCTKR2017011367-appb-I000146
Figure PCTKR2017011367-appb-I000146
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 899.07Except that [Preparation Example 9] was used as the reactant, the same procedure as in [Synthesis Example 9] was performed to obtain 7.0 g of the target compound. HRMS [M] +: 899.07
[[ 합성예Synthesis Example 82] Mat 170의 합성 82] Synthesis of Mat 170
Figure PCTKR2017011367-appb-I000147
Figure PCTKR2017011367-appb-I000147
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 7.3g을 얻었다.; HRMS [M]+: 822.977.3 g of the title compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 822.97
[[ 합성예Synthesis Example 83] Mat 171의 합성 83] Synthesis of Mat 171
Figure PCTKR2017011367-appb-I000148
Figure PCTKR2017011367-appb-I000148
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 899.077.1 g of the target compound was obtained in the same manner as the [Synthesis Example 11], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 899.07
[[ 합성예Synthesis Example 84] Mat 174의 합성 84] Synthesis of Mat 174
Figure PCTKR2017011367-appb-I000149
Figure PCTKR2017011367-appb-I000149
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 795.956.7 g of the target compound was obtained in the same manner as the [Synthesis Example 12], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 795.95
[[ 합성예Synthesis Example 85] Mat 176의 합성 85] Synthesis of Mat 176
Figure PCTKR2017011367-appb-I000150
Figure PCTKR2017011367-appb-I000150
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 652.806.5 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 652.80
[[ 합성예Synthesis Example 86] Mat 177의 합성 86] Synthesis of Mat 177
Figure PCTKR2017011367-appb-I000151
Figure PCTKR2017011367-appb-I000151
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 652.806.9 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 652.80
[[ 합성예Synthesis Example 87] Mat 180의 합성 87] Synthesis of Mat 180
Figure PCTKR2017011367-appb-I000152
Figure PCTKR2017011367-appb-I000152
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.2g을 얻었다.; HRMS [M]+: 726.886.2 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 726.88
[[ 합성예Synthesis Example 88] Mat 182의 합성 88] Synthesis of Mat 182
Figure PCTKR2017011367-appb-I000153
Figure PCTKR2017011367-appb-I000153
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 576.705.9 g of the title compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 576.70
[[ 합성예Synthesis Example 89] Mat 183의 합성 89] Synthesis of Mat 183
Figure PCTKR2017011367-appb-I000154
Figure PCTKR2017011367-appb-I000154
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 666.785.3 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 9] was used as the reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 90] Mat 185의 합성 90] Synthesis of Mat 185
Figure PCTKR2017011367-appb-I000155
Figure PCTKR2017011367-appb-I000155
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 692.866.8 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 692.86
[[ 합성예Synthesis Example 91] Mat 188의 합성 91] Synthesis of Mat 188
Figure PCTKR2017011367-appb-I000156
Figure PCTKR2017011367-appb-I000156
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 666.785.7 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 92] Mat 189의 합성 92] Synthesis of Mat 189
Figure PCTKR2017011367-appb-I000157
Figure PCTKR2017011367-appb-I000157
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 743.915.9 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 743.91
[[ 합성예Synthesis Example 93] Mat 194의 합성 93] Synthesis of Mat 194
Figure PCTKR2017011367-appb-I000158
Figure PCTKR2017011367-appb-I000158
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다.; HRMS [M]+: 807.966.0 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 807.96
[[ 합성예Synthesis Example 94] Mat 195의 합성 94] Synthesis of Mat 195
Figure PCTKR2017011367-appb-I000159
Figure PCTKR2017011367-appb-I000159
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 731.866.3 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 731.86
[[ 합성예Synthesis Example 95] Mat 196의 합성 95] Synthesis of Mat 196
Figure PCTKR2017011367-appb-I000160
Figure PCTKR2017011367-appb-I000160
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 807.966.1 g of the target compound was obtained in the same manner as the [Synthesis Example 11], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 807.96
[[ 합성예Synthesis Example 96] Mat 199의 합성 96] Synthesis of Mat 199
Figure PCTKR2017011367-appb-I000161
Figure PCTKR2017011367-appb-I000161
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 704.835.7 g of the target compound was obtained in the same manner as the [Synthesis Example 12], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 704.83
[[ 합성예Synthesis Example 97] Mat 201의 합성 97] Synthesis of Mat 201
Figure PCTKR2017011367-appb-I000162
Figure PCTKR2017011367-appb-I000162
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 652.806.9 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 652.80
[[ 합성예Synthesis Example 98] Mat 202의 합성 98] Synthesis of Mat 202
Figure PCTKR2017011367-appb-I000163
Figure PCTKR2017011367-appb-I000163
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 652.805.4 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 652.80
[[ 합성예Synthesis Example 99] Mat 205의 합성 99] Synthesis of Mat 205
Figure PCTKR2017011367-appb-I000164
Figure PCTKR2017011367-appb-I000164
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 726.885.8 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 726.88
[[ 합성예Synthesis Example 100] Mat 207의 합성 100] Synthesis of Mat 207
Figure PCTKR2017011367-appb-I000165
Figure PCTKR2017011367-appb-I000165
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 576.705.6 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 576.70
[[ 합성예Synthesis Example 101] Mat 208의 합성 101] Synthesis of Mat 208
Figure PCTKR2017011367-appb-I000166
Figure PCTKR2017011367-appb-I000166
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 666.786.3 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 102] Mat 210의 합성 102] Synthesis of Mat 210
Figure PCTKR2017011367-appb-I000167
Figure PCTKR2017011367-appb-I000167
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화물 5.8g을 얻었다.; HRMS [M]+: 692.86A target cargo of 5.8 g was obtained in the same manner as in [Synthesis Example 6], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 692.86
[[ 합성예Synthesis Example 103] Mat 213의 합성 103] Synthesis of Mat 213
Figure PCTKR2017011367-appb-I000168
Figure PCTKR2017011367-appb-I000168
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 666.785.3 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 104] Mat 214의 합성 104] Synthesis of Mat 214
Figure PCTKR2017011367-appb-I000169
Figure PCTKR2017011367-appb-I000169
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 743.915.7 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 743.91
[[ 합성예Synthesis Example 105] Mat 219의 합성 105] Synthesis of Mat 219
Figure PCTKR2017011367-appb-I000170
Figure PCTKR2017011367-appb-I000170
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 807.965.8 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 807.96
[[ 합성예Synthesis Example 106] Mat 220의 합성 106] Synthesis of Mat 220
Figure PCTKR2017011367-appb-I000171
Figure PCTKR2017011367-appb-I000171
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 731.865.3 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 731.86
[[ 합성예Synthesis Example 107] Mat 221의 합성 107] Synthesis of Mat 221
Figure PCTKR2017011367-appb-I000172
Figure PCTKR2017011367-appb-I000172
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 807.965.7 g of the target compound was obtained in the same manner as the [Synthesis Example 11], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 807.96
[[ 합성예Synthesis Example 108] Mat 224의 합성 108] Synthesis of Mat 224
Figure PCTKR2017011367-appb-I000173
Figure PCTKR2017011367-appb-I000173
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 704.835.3 g of the target compound was obtained in the same manner as the [Synthesis Example 12], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 704.83
[[ 합성예Synthesis Example 109] Mat 226의 합성 109] Synthesis of Mat 226
Figure PCTKR2017011367-appb-I000174
Figure PCTKR2017011367-appb-I000174
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 7.2g을 얻었다.; HRMS [M]+: 728.907.2g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation 11] was used as a reactant. HRMS [M] +: 728.90
[[ 합성예Synthesis Example 110] Mat 227의 합성 110] Synthesis of Mat 227
Figure PCTKR2017011367-appb-I000175
Figure PCTKR2017011367-appb-I000175
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 728.906.4 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 11] was used as a reactant. HRMS [M] +: 728.90
[[ 합성예Synthesis Example 111] Mat 230의 합성 111] Synthesis of Mat 230
Figure PCTKR2017011367-appb-I000176
Figure PCTKR2017011367-appb-I000176
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 802.986.8 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation 11] was used as a reactant. HRMS [M] +: 802.98
[[ 합성예Synthesis Example 112] Mat 232의 합성 112] Synthesis of Mat 232
Figure PCTKR2017011367-appb-I000177
Figure PCTKR2017011367-appb-I000177
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 652.806.5 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 11] was used as a reactant. HRMS [M] +: 652.80
[[ 합성예Synthesis Example 113] Mat 233의 합성 113] Synthesis of Mat 233
Figure PCTKR2017011367-appb-I000178
Figure PCTKR2017011367-appb-I000178
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 742.886.8 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation 11] was used as a reactant. HRMS [M] +: 742.88
[[ 합성예Synthesis Example 114] Mat 235의 합성 114] Synthesis of Mat 235
Figure PCTKR2017011367-appb-I000179
Figure PCTKR2017011367-appb-I000179
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 768.966.8 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation 11] was used as a reactant. HRMS [M] +: 768.96
[[ 합성예Synthesis Example 115] Mat 238의 합성 115] Synthesis of Mat 238
Figure PCTKR2017011367-appb-I000180
Figure PCTKR2017011367-appb-I000180
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 742.886.3 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation 11] was used as a reactant. HRMS [M] +: 742.88
[[ 합성예Synthesis Example 116] Mat 239의 합 116] Sum of Mat 239
Figure PCTKR2017011367-appb-I000181
Figure PCTKR2017011367-appb-I000181
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 820.016.7 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation 11] was used as a reactant. HRMS [M] +: 820.01
[[ 합성예Synthesis Example 117] Mat 244의 합성 117] Synthesis of Mat 244
Figure PCTKR2017011367-appb-I000182
Figure PCTKR2017011367-appb-I000182
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 884.066.3 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation 11] was used as a reactant. HRMS [M] +: 884.06
[[ 합성예Synthesis Example 118] Mat 245의 합성 118] Synthesis of Mat 245
Figure PCTKR2017011367-appb-I000183
Figure PCTKR2017011367-appb-I000183
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 807.966.9 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation 11] was used as a reactant. HRMS [M] +: 807.96
[[ 합성예Synthesis Example 119] Mat 246의 합성 119] Synthesis of Mat 246
Figure PCTKR2017011367-appb-I000184
Figure PCTKR2017011367-appb-I000184
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 884.066.7 g of the target compound was obtained in the same manner as the [Synthesis Example 11], except that [Preparation 11] was used as a reactant. HRMS [M] +: 884.06
[[ 합성예Synthesis Example 120] Mat 249의 합성 120] Synthesis of Mat 249
Figure PCTKR2017011367-appb-I000185
Figure PCTKR2017011367-appb-I000185
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 780.936.3 g of the target compound was obtained in the same manner as the [Synthesis Example 12], except that [Preparation 11] was used as a reactant. HRMS [M] +: 780.93
[[ 합성예Synthesis Example 121] Mat 251의 합성 121] Synthesis of Mat 251
Figure PCTKR2017011367-appb-I000186
Figure PCTKR2017011367-appb-I000186
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 7.6g을 얻었다.; HRMS [M]+: 742.887.6 g of the title compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 742.88
[[ 합성예Synthesis Example 122] Mat 252의 합성 122] Synthesis of Mat 252
Figure PCTKR2017011367-appb-I000187
Figure PCTKR2017011367-appb-I000187
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 7.4g을 얻었다.; HRMS [M]+: 742.887.4 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 742.88
[[ 합성예Synthesis Example 123] Mat 255의 합성 123] Synthesis of Mat 255
Figure PCTKR2017011367-appb-I000188
Figure PCTKR2017011367-appb-I000188
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 816.967.1 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 816.96
[[ 합성예Synthesis Example 124] Mat 257의 합성 124] Synthesis of Mat 257
Figure PCTKR2017011367-appb-I000189
Figure PCTKR2017011367-appb-I000189
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 666.786.9 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 666.78
[[ 합성예Synthesis Example 125] Mat 258의 합성 125] Synthesis of Mat 258
Figure PCTKR2017011367-appb-I000190
Figure PCTKR2017011367-appb-I000190
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 756.86Except that [Preparation Example 12] was used as a reaction product, the same procedure as in Synthesis Example 5 was performed, to obtain 7.0 g of the title compound; HRMS [M] +: 756.86
[[ 합성예Synthesis Example 126] Mat 260의 합성 126] Synthesis of Mat 260
Figure PCTKR2017011367-appb-I000191
Figure PCTKR2017011367-appb-I000191
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 7.2g을 얻었다.; HRMS [M]+: 782.947.2g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 782.94
[[ 합성예Synthesis Example 127] Mat 263의 합성 127] Synthesis of Mat 263
Figure PCTKR2017011367-appb-I000192
Figure PCTKR2017011367-appb-I000192
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 7.3g을 얻었다.; HRMS [M]+: 756.867.3 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 756.86
[[ 합성예Synthesis Example 128] Mat 264의 합성 128] Synthesis of Mat 264
Figure PCTKR2017011367-appb-I000193
Figure PCTKR2017011367-appb-I000193
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 833.99Except that [Preparation Example 12] was used as a reaction product, the same procedure as in Synthesis Example 8 was performed, to obtain 7.0 g of the title compound; HRMS [M] +: 833.99
[[ 합성예Synthesis Example 129] Mat 269의 합성 129] Synthesis of Mat 269
Figure PCTKR2017011367-appb-I000194
Figure PCTKR2017011367-appb-I000194
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 898.047.1 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 898.04
[[ 합성예Synthesis Example 130] Mat 270의 합성 130] Synthesis of Mat 270
Figure PCTKR2017011367-appb-I000195
Figure PCTKR2017011367-appb-I000195
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 7.4g을 얻었다.; HRMS [M]+: 821.947.4 g of the title compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 821.94
[[ 합성예Synthesis Example 131] Mat 271의 합성 131] Synthesis of Mat 271
Figure PCTKR2017011367-appb-I000196
Figure PCTKR2017011367-appb-I000196
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 7.5g을 얻었다.; HRMS [M]+: 898.047.5 g of the target compound was obtained in the same manner as the [Synthesis Example 11], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 898.04
[[ 합성예Synthesis Example 132] Mat 274의 합성 132] Synthesis of Mat 274
Figure PCTKR2017011367-appb-I000197
Figure PCTKR2017011367-appb-I000197
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 794.91Except that [Preparation Example 12] was used as a reaction product, the same procedure as in Synthesis Example 12 was performed, to obtain 7.0 g of the title compound; HRMS [M] +: 794.91
[[ 합성예Synthesis Example 133] Mat 276의 합성 133] Synthesis of Mat 276
Figure PCTKR2017011367-appb-I000198
Figure PCTKR2017011367-appb-I000198
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 7.8g을 얻었다.; HRMS [M]+: 807.96Except that [Preparation Example 13] was used as the reactant, the same procedure as in [Synthesis Example 1] was performed, to obtain 7.8 g of the target compound; HRMS [M] +: 807.96
[[ 합성예Synthesis Example 134] Mat 277의 합성 134] Synthesis of Mat 277
Figure PCTKR2017011367-appb-I000199
Figure PCTKR2017011367-appb-I000199
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 8.3g을 얻었다.; HRMS [M]+: 807.968.3 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 807.96
[[ 합성예Synthesis Example 135] Mat 280의 합성 135] Synthesis of Mat 280
Figure PCTKR2017011367-appb-I000200
Figure PCTKR2017011367-appb-I000200
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 7.5g을 얻었다.; HRMS [M]+: 882.047.5 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 882.04
[[ 합성예Synthesis Example 136] Mat 282의 합성 136] Synthesis of Mat 282
Figure PCTKR2017011367-appb-I000201
Figure PCTKR2017011367-appb-I000201
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 7.7g을 얻었다.; HRMS [M]+: 731.867.7 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 731.86
[[ 합성예Synthesis Example 137] Mat 283의 합성 137] Synthesis of Mat 283
Figure PCTKR2017011367-appb-I000202
Figure PCTKR2017011367-appb-I000202
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 7.2g을 얻었다.; HRMS [M]+: 821.947.2g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 821.94
[[ 합성예Synthesis Example 138] Mat 285의 합성 138] Synthesis of Mat 285
Figure PCTKR2017011367-appb-I000203
Figure PCTKR2017011367-appb-I000203
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 7.6g을 얻었다.; HRMS [M]+: 848.027.6 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 848.02
[[ 합성예Synthesis Example 139] Mat 288의 합성 139] Synthesis of Mat 288
Figure PCTKR2017011367-appb-I000204
Figure PCTKR2017011367-appb-I000204
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 7.9g을 얻었다.; HRMS [M]+: 821.947.9 g of the target compound was obtained in the same manner as the [Synthesis Example 7] except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 821.94
[[ 합성예Synthesis Example 140] Mat 289의 합성 140] Synthesis of Mat 289
Figure PCTKR2017011367-appb-I000205
Figure PCTKR2017011367-appb-I000205
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 899.077.1 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 899.07
[[ 합성예Synthesis Example 141] Mat 294의 합성 141] Synthesis of Mat 294
Figure PCTKR2017011367-appb-I000206
Figure PCTKR2017011367-appb-I000206
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 7.4g을 얻었다.; HRMS [M]+: 963.127.4 g of the title compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 963.12
[[ 합성예Synthesis Example 142] Mat 295의 합성 142] Synthesis of Mat 295
Figure PCTKR2017011367-appb-I000207
Figure PCTKR2017011367-appb-I000207
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 7.8g을 얻었다.; HRMS [M]+: 887.02Except for using [Preparation Example 13] as a reactant to the same procedure as in [Synthesis Example 10] to obtain the target compound 7.8g; HRMS [M] +: 887.02
[[ 합성예Synthesis Example 143] Mat 296의 합성 143] Synthesis of Mat 296
Figure PCTKR2017011367-appb-I000208
Figure PCTKR2017011367-appb-I000208
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 7.3g을 얻었다.; HRMS [M]+: 963.127.3 g of the target compound was obtained in the same manner as the [Synthesis Example 11], except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 963.12
[[ 합성예Synthesis Example 144] Mat 299의 합성 144] Synthesis of Mat 299
Figure PCTKR2017011367-appb-I000209
Figure PCTKR2017011367-appb-I000209
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 7.2g을 얻었다.; HRMS [M]+: 859.997.2g of the target compound was obtained in the same manner as the [Synthesis Example 12], except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 859.99
[[ 합성예Synthesis Example 145] Mat 301의 합성 145] Synthesis of Mat 301
Figure PCTKR2017011367-appb-I000210
Figure PCTKR2017011367-appb-I000210
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 592.765.8 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 592.76
[[ 합성예Synthesis Example 146] Mat 302의 합성 146] Synthesis of Mat 302
Figure PCTKR2017011367-appb-I000211
Figure PCTKR2017011367-appb-I000211
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 592.765.8 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 592.76
[[ 합성예Synthesis Example 147] Mat 305의 합성 147] Synthesis of Mat 305
Figure PCTKR2017011367-appb-I000212
Figure PCTKR2017011367-appb-I000212
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 666.846.3 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 666.84
[[ 합성예Synthesis Example 148] Mat 307의 합성 148] Synthesis of Mat 307
Figure PCTKR2017011367-appb-I000213
Figure PCTKR2017011367-appb-I000213
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 516.665.1 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 516.66
[[ 합성예Synthesis Example 149] Mat 308의 합성 149] Synthesis of Mat 308
Figure PCTKR2017011367-appb-I000214
Figure PCTKR2017011367-appb-I000214
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 606.745.7 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 606.74
[[ 합성예Synthesis Example 150] Mat 310의 합성 150] Synthesis of Mat 310
Figure PCTKR2017011367-appb-I000215
Figure PCTKR2017011367-appb-I000215
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 632.835.3 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 632.83
[[ 합성예Synthesis Example 151] Mat 313의 합성 151] Synthesis of Mat 313
Figure PCTKR2017011367-appb-I000216
Figure PCTKR2017011367-appb-I000216
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다.; HRMS [M]+: 606.746.0 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 606.74
[[ 합성예Synthesis Example 152] Mat 314의 합성 152] Synthesis of Mat 314
Figure PCTKR2017011367-appb-I000217
Figure PCTKR2017011367-appb-I000217
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 683.875.3 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 683.87
[[ 합성예Synthesis Example 153] Mat 319의 합성 153] Synthesis of Mat 319
Figure PCTKR2017011367-appb-I000218
Figure PCTKR2017011367-appb-I000218
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 747.926.4 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 747.92
[[ 합성예Synthesis Example 154] Mat 320의 합성 154] Synthesis of Mat 320
Figure PCTKR2017011367-appb-I000219
Figure PCTKR2017011367-appb-I000219
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다.; HRMS [M]+: 671.826.0 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 671.82
[[ 합성예Synthesis Example 155] Mat 321의 합성 155] Synthesis of Mat 321
Figure PCTKR2017011367-appb-I000220
Figure PCTKR2017011367-appb-I000220
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 747.925.9 g of the title compound was obtained in the same manner as the [Synthesis Example 11], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 747.92
[[ 합성예Synthesis Example 156] Mat 324의 합성 156] Synthesis of Mat 324
Figure PCTKR2017011367-appb-I000221
Figure PCTKR2017011367-appb-I000221
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 644.805.4 g of the target compound was obtained in the same manner as the [Synthesis Example 12], except that [Preparation Example 14] was used as a reactant. HRMS [M] +: 644.80
[[ 합성예Synthesis Example 157] Mat 326의 합성 157] Synthesis of Mat 326
Figure PCTKR2017011367-appb-I000222
Figure PCTKR2017011367-appb-I000222
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 13]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 668.866.3 g of the title compound was obtained in the same manner as the [Synthesis Example 13], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 668.86
[[ 합성예Synthesis Example 158] Mat 327의 합성 158] Synthesis of Mat 327
Figure PCTKR2017011367-appb-I000223
Figure PCTKR2017011367-appb-I000223
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 14]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 668.865.7 g of the target compound was obtained in the same manner as the [Synthesis Example 14], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 668.86
[[ 합성예Synthesis Example 159] Mat 330의 합성 159] Synthesis of Mat 330
Figure PCTKR2017011367-appb-I000224
Figure PCTKR2017011367-appb-I000224
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 15]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 742.946.6 g of the target compound was obtained in the same manner as the [Synthesis Example 15], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 742.94
[[ 합성예Synthesis Example 160] Mat 332의 합성 160] Synthesis of Mat 332
Figure PCTKR2017011367-appb-I000225
Figure PCTKR2017011367-appb-I000225
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 16]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 592.765.8 g of the target compound was obtained in the same manner as the [Synthesis Example 16], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 592.76
[[ 합성예Synthesis Example 161] Mat 333의 합성 161] Synthesis of Mat 333
Figure PCTKR2017011367-appb-I000226
Figure PCTKR2017011367-appb-I000226
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 17]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 682.846.7 g of the target compound was obtained in the same manner as the [Synthesis Example 17], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 162] Mat 335의 합성 162] Synthesis of Mat 335
Figure PCTKR2017011367-appb-I000227
Figure PCTKR2017011367-appb-I000227
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 18]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 708.926.7 g of the target compound was obtained in the same manner as the [Synthesis Example 18], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 708.92
[[ 합성예Synthesis Example 163] Mat 338의 합성 163] Synthesis of Mat 338
Figure PCTKR2017011367-appb-I000228
Figure PCTKR2017011367-appb-I000228
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 19]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 682.845.9 g of the target compound was obtained in the same manner as the [Synthesis Example 19], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 164] Mat 339의 합성 164] Synthesis of Mat 339
Figure PCTKR2017011367-appb-I000229
Figure PCTKR2017011367-appb-I000229
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 20]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 759.976.3 g of the title compound was obtained in the same manner as the [Synthesis Example 20], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 759.97
[[ 합성예Synthesis Example 165] Mat 344의 합성 165] Synthesis of Mat 344
Figure PCTKR2017011367-appb-I000230
Figure PCTKR2017011367-appb-I000230
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 21]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 824.026.6 g of the target compound was obtained in the same manner as the [Synthesis Example 21], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 824.02
[[ 합성예Synthesis Example 166] Mat 345의 합성 166] Synthesis of Mat 345
Figure PCTKR2017011367-appb-I000231
Figure PCTKR2017011367-appb-I000231
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 22]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 747.925.8 g of the target compound was obtained in the same manner as the [Synthesis Example 22], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 747.92
[[ 합성예Synthesis Example 167] Mat 346의 합성 167] Synthesis of Mat 346
Figure PCTKR2017011367-appb-I000232
Figure PCTKR2017011367-appb-I000232
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 23]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 824.026.5 g of the target compound was obtained in the same manner as the [Synthesis Example 23], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 824.02
[[ 합성예Synthesis Example 168] Mat 349의 합성 168] Synthesis of Mat 349
Figure PCTKR2017011367-appb-I000233
Figure PCTKR2017011367-appb-I000233
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 24]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 720.896.4 g of the target compound was obtained in the same manner as the [Synthesis Example 24], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 720.89
[[ 합성예Synthesis Example 169] Mat 351의 합성 169] Synthesis of Mat 351
Figure PCTKR2017011367-appb-I000234
Figure PCTKR2017011367-appb-I000234
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 25]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 668.866.3 g of the target compound was obtained in the same manner as the [Synthesis Example 25], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 668.86
[[ 합성예Synthesis Example 170] Mat 352의 합성 170] Synthesis of Mat 352
Figure PCTKR2017011367-appb-I000235
Figure PCTKR2017011367-appb-I000235
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 26]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 668.865.7 g of the target compound was obtained in the same manner as the [Synthesis Example 26], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 668.86
[[ 합성예Synthesis Example 171] Mat 355의 합성 171] Synthesis of Mat 355
Figure PCTKR2017011367-appb-I000236
Figure PCTKR2017011367-appb-I000236
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 27]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 742.946.6 g of the target compound was obtained in the same manner as the [Synthesis Example 27], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 742.94
[[ 합성예Synthesis Example 172] Mat 357의 합성 172] Synthesis of Mat 357
Figure PCTKR2017011367-appb-I000237
Figure PCTKR2017011367-appb-I000237
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 28]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 592.765.8 g of the target compound was obtained in the same manner as the [Synthesis Example 28], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 592.76
[[ 합성예Synthesis Example 173] Mat 358의 합성 173] Synthesis of Mat 358
Figure PCTKR2017011367-appb-I000238
Figure PCTKR2017011367-appb-I000238
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 29]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 682.846.7 g of the target compound was obtained in the same manner as the [Synthesis Example 29], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 174] Mat 360의 합성 174] Synthesis of Mat 360
Figure PCTKR2017011367-appb-I000239
Figure PCTKR2017011367-appb-I000239
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 30]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 708.926.7 g of the target compound was obtained in the same manner as the [Synthesis Example 30], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 708.92
[[ 합성예Synthesis Example 175] Mat 363의 합성 175] Synthesis of Mat 363
Figure PCTKR2017011367-appb-I000240
Figure PCTKR2017011367-appb-I000240
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 31]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 682.845.9 g of the title compound was obtained in the same manner as the [Synthesis Example 31], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 176] Mat 364의 합성 176] Synthesis of Mat 364
Figure PCTKR2017011367-appb-I000241
Figure PCTKR2017011367-appb-I000241
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 32]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 759.976.3 g of the title compound was obtained in the same manner as the [Synthesis Example 32], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 759.97
[[ 합성예Synthesis Example 177] Mat 369의 합성 177] Synthesis of Mat 369
Figure PCTKR2017011367-appb-I000242
Figure PCTKR2017011367-appb-I000242
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 33]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 824.026.6 g of the target compound was obtained in the same manner as the [Synthesis Example 33], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 824.02
[[ 합성예Synthesis Example 178] Mat 370의 합성 178] Synthesis of Mat 370
Figure PCTKR2017011367-appb-I000243
Figure PCTKR2017011367-appb-I000243
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 34]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 747.925.8 g of the target compound was obtained in the same manner as the [Synthesis Example 34], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 747.92
[[ 합성예Synthesis Example 179] Mat 371의 합성 179] Synthesis of Mat 371
Figure PCTKR2017011367-appb-I000244
Figure PCTKR2017011367-appb-I000244
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 35]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 824.026.5 g of the target compound was obtained in the same manner as the [Synthesis Example 35], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 824.02
[[ 합성예Synthesis Example 180] Mat 374의 합성 180] Synthesis of Mat 374
Figure PCTKR2017011367-appb-I000245
Figure PCTKR2017011367-appb-I000245
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 36]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 720.896.4 g of the target compound was obtained in the same manner as the [Synthesis Example 36], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 720.89
[[ 합성예Synthesis Example 181] Mat 376의 합성 181] Synthesis of Mat 376
Figure PCTKR2017011367-appb-I000246
Figure PCTKR2017011367-appb-I000246
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 37]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 682.846.7 g of the target compound was obtained in the same manner as the [Synthesis Example 37], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 182] Mat 377의 합성 182] Synthesis of Mat 377
Figure PCTKR2017011367-appb-I000247
Figure PCTKR2017011367-appb-I000247
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 38]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 682.846.7 g of the target compound was obtained in the same manner as the [Synthesis Example 38], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 183] Mat 380의 합성 183] Synthesis of Mat 380
Figure PCTKR2017011367-appb-I000248
Figure PCTKR2017011367-appb-I000248
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 39]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 756.926.5 g of the target compound was obtained in the same manner as the [Synthesis Example 39], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 756.92
[[ 합성예Synthesis Example 184] Mat 382의 합성 184] Synthesis of Mat 382
Figure PCTKR2017011367-appb-I000249
Figure PCTKR2017011367-appb-I000249
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 40]과 동일한 과정을 수행하여 목적 화합물 6.2g을 얻었다.; HRMS [M]+: 606.746.2 g of the target compound was obtained in the same manner as the [Synthesis Example 40], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 606.74
[[ 합성예Synthesis Example 185] Mat 383의 합성 185] Synthesis of Mat 383
Figure PCTKR2017011367-appb-I000250
Figure PCTKR2017011367-appb-I000250
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 41]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 696.826.8 g of the target compound was obtained in the same manner as the [Synthesis Example 41], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 696.82
[[ 합성예Synthesis Example 186] Mat 385의 합성 186] Synthesis of Mat 385
Figure PCTKR2017011367-appb-I000251
Figure PCTKR2017011367-appb-I000251
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 42]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 722.916.4 g of the target compound was obtained in the same manner as the [Synthesis Example 42], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 722.91
[[ 합성예Synthesis Example 187] Mat 388의 합성 187] Synthesis of Mat 388
Figure PCTKR2017011367-appb-I000252
Figure PCTKR2017011367-appb-I000252
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 43]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 696.826.7 g of the target compound was obtained in the same manner as the [Synthesis Example 43], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 696.82
[[ 합성예Synthesis Example 188] Mat 389의 합성 188] Synthesis of Mat 389
Figure PCTKR2017011367-appb-I000253
Figure PCTKR2017011367-appb-I000253
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 44]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 773.956.9 g of the target compound was obtained in the same manner as the [Synthesis Example 44], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 773.95
[[ 합성예Synthesis Example 189] Mat 394의 합성 189] Synthesis of Mat 394
Figure PCTKR2017011367-appb-I000254
Figure PCTKR2017011367-appb-I000254
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 45]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 838.006.6 g of the target compound was obtained in the same manner as the [Synthesis Example 45], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 838.00
[[ 합성예Synthesis Example 190] Mat 395의 합성 190] Synthesis of Mat 395
Figure PCTKR2017011367-appb-I000255
Figure PCTKR2017011367-appb-I000255
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 46]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 761.906.8 g of the target compound was obtained in the same manner as the [Synthesis Example 46], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 761.90
[[ 합성예Synthesis Example 191] Mat 396의 합성 191] Synthesis of Mat 396
Figure PCTKR2017011367-appb-I000256
Figure PCTKR2017011367-appb-I000256
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 47]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 838.006.4 g of the target compound was obtained in the same manner as the [Synthesis Example 47], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 838.00
[[ 합성예Synthesis Example 192] Mat 399의 합성 192] Synthesis of Mat 399
Figure PCTKR2017011367-appb-I000257
Figure PCTKR2017011367-appb-I000257
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 48]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 734.886.8 g of the target compound was obtained in the same manner as the [Synthesis Example 48], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 734.88
[[ 합성예Synthesis Example 193] Mat 401의 합성 193] Synthesis of Mat 401
Figure PCTKR2017011367-appb-I000258
Figure PCTKR2017011367-appb-I000258
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 49]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 682.846.4 g of the target compound was obtained in the same manner as the [Synthesis Example 49], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 194] Mat 402의 합성 194] Synthesis of Mat 402
Figure PCTKR2017011367-appb-I000259
Figure PCTKR2017011367-appb-I000259
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 50]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 682.846.5 g of the target compound was obtained in the same manner as the [Synthesis Example 50], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 195] Mat 405의 합성 195] Synthesis of Mat 405
Figure PCTKR2017011367-appb-I000260
Figure PCTKR2017011367-appb-I000260
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 51]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 756.926.3 g of the target compound was obtained in the same manner as the [Synthesis Example 51], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 756.92
[[ 합성예Synthesis Example 196] Mat 407의 합성 196] Synthesis of Mat 407
Figure PCTKR2017011367-appb-I000261
Figure PCTKR2017011367-appb-I000261
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 52]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 606.746.9 g of the target compound was obtained in the same manner as the [Synthesis Example 52], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 606.74
[[ 합성예Synthesis Example 197] Mat 408의 합성 197] Synthesis of Mat 408
Figure PCTKR2017011367-appb-I000262
Figure PCTKR2017011367-appb-I000262
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 53]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 696.826.1 g of the target compound was obtained in the same manner as the [Synthesis Example 53], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 696.82
[[ 합성예Synthesis Example 198] Mat 410의 합성 198] Synthesis of Mat 410
Figure PCTKR2017011367-appb-I000263
Figure PCTKR2017011367-appb-I000263
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 54]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 722.916.9 g of the target compound was obtained in the same manner as the [Synthesis Example 54], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 722.91
[[ 합성예Synthesis Example 199] Mat 413의 합성 199] Synthesis of Mat 413
Figure PCTKR2017011367-appb-I000264
Figure PCTKR2017011367-appb-I000264
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 55]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 696.826.4 g of the target compound was obtained in the same manner as the [Synthesis Example 55], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 696.82
[[ 합성예Synthesis Example 200] Mat 414의 합성 200] Synthesis of Mat 414
Figure PCTKR2017011367-appb-I000265
Figure PCTKR2017011367-appb-I000265
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 56]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 773.956.3 g of the target compound was obtained in the same manner as the [Synthesis Example 56], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 773.95
[[ 합성예Synthesis Example 201] Mat 419의 합성 201] Synthesis of Mat 419
Figure PCTKR2017011367-appb-I000266
Figure PCTKR2017011367-appb-I000266
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 57]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 838.006.1 g of the target compound was obtained in the same manner as the [Synthesis Example 57], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 838.00
[[ 합성예Synthesis Example 202] Mat 420의 합성 202] Synthesis of Mat 420
Figure PCTKR2017011367-appb-I000267
Figure PCTKR2017011367-appb-I000267
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 58]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 761.906.4 g of the target compound was obtained in the same manner as the [Synthesis Example 58], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 761.90
[[ 합성예Synthesis Example 203] Mat 421의 합성 203] Synthesis of Mat 421
Figure PCTKR2017011367-appb-I000268
Figure PCTKR2017011367-appb-I000268
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 59]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 838.006.9 g of the target compound was obtained in the same manner as the [Synthesis Example 59], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 838.00
[[ 합성예Synthesis Example 204] Mat 424의 합성 204] Synthesis of Mat 424
Figure PCTKR2017011367-appb-I000269
Figure PCTKR2017011367-appb-I000269
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 60]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 734.886.7 g of the target compound was obtained in the same manner as the [Synthesis Example 60], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 734.88
[[ 합성예Synthesis Example 205] Mat 426의 합성 205] Synthesis of Mat 426
Figure PCTKR2017011367-appb-I000270
Figure PCTKR2017011367-appb-I000270
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 61]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 642.825.9 g of the target compound was obtained in the same manner as the [Synthesis Example 61], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 642.82
[[ 합성예Synthesis Example 206] Mat 427의 합성 206] Synthesis of Mat 427
Figure PCTKR2017011367-appb-I000271
Figure PCTKR2017011367-appb-I000271
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 62]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 642.825.5 g of the target compound was obtained in the same manner as the [Synthesis Example 62], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 642.82
[[ 합성예Synthesis Example 207] Mat 430의 합성 207] Synthesis of Mat 430
Figure PCTKR2017011367-appb-I000272
Figure PCTKR2017011367-appb-I000272
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 63]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 716.905.3 g of the target compound was obtained in the same manner as the [Synthesis Example 63], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 716.90
[[ 합성예Synthesis Example 208] Mat 432의 합성 208] Synthesis of Mat 432
Figure PCTKR2017011367-appb-I000273
Figure PCTKR2017011367-appb-I000273
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 64]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 566.725.9 g of the target compound was obtained in the same manner as the [Synthesis Example 64], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 566.72
[[ 합성예Synthesis Example 209] Mat 433의 합성 209] Synthesis of Mat 433
Figure PCTKR2017011367-appb-I000274
Figure PCTKR2017011367-appb-I000274
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 65]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 656.805.1 g of the target compound was obtained in the same manner as the [Synthesis Example 65], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 656.80
[[ 합성예Synthesis Example 210] Mat 435의 합성 210] Synthesis of Mat 435
Figure PCTKR2017011367-appb-I000275
Figure PCTKR2017011367-appb-I000275
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 66]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 682.895.9 g of the target compound was obtained in the same manner as the [Synthesis Example 66], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 682.89
[[ 합성예Synthesis Example 211] Mat 438의 합성 211] Synthesis of Mat 438
Figure PCTKR2017011367-appb-I000276
Figure PCTKR2017011367-appb-I000276
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 67]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 656.805.4 g of the title compound was obtained in the same manner as the [Synthesis Example 67], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 656.80
[[ 합성예Synthesis Example 212] Mat 439의 합성 212] Synthesis of Mat 439
Figure PCTKR2017011367-appb-I000277
Figure PCTKR2017011367-appb-I000277
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 68]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 733.935.3 g of the target compound was obtained in the same manner as the [Synthesis Example 68], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 733.93
[[ 합성예Synthesis Example 213] Mat 444의 합성 213] Synthesis of Mat 444
Figure PCTKR2017011367-appb-I000278
Figure PCTKR2017011367-appb-I000278
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 69]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 797.985.1 g of the target compound was obtained in the same manner as the [Synthesis Example 69], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 797.98
[[ 합성예Synthesis Example 214] Mat 445의 합성 214] Synthesis of Mat 445
Figure PCTKR2017011367-appb-I000279
Figure PCTKR2017011367-appb-I000279
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 70]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 721.885.4 g of the title compound was obtained in the same manner as the [Synthesis Example 70], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 721.88
[[ 합성예Synthesis Example 215] Mat 446의 합성 215] Synthesis of Mat 446
Figure PCTKR2017011367-appb-I000280
Figure PCTKR2017011367-appb-I000280
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 71]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 797.985.9 g of the title compound was obtained in the same manner as the [Synthesis Example 71], except that [Preparation 19] was used as a reactant. HRMS [M] +: 797.98
[[ 합성예Synthesis Example 216] Mat 449의 합성 216] Synthesis of Mat 449
Figure PCTKR2017011367-appb-I000281
Figure PCTKR2017011367-appb-I000281
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 72]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 694.865.7 g of the target compound was obtained in the same manner as the [Synthesis Example 72], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 694.86
[[ 합성예Synthesis Example 217] Mat 451의 합성 217] Synthesis of Mat 451
Figure PCTKR2017011367-appb-I000282
Figure PCTKR2017011367-appb-I000282
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 73]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 759.976.9 g of the target compound was obtained in the same manner as the [Synthesis Example 73], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 759.97
[[ 합성예Synthesis Example 218] Mat 452의 합 218] Sum of Mat 452
Figure PCTKR2017011367-appb-I000283
Figure PCTKR2017011367-appb-I000283
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 74]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 759.976.5 g of the target compound was obtained in the same manner as the [Synthesis Example 74], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 759.97
[[ 합성예Synthesis Example 219] Mat 455의 합성 219] Synthesis of Mat 455
Figure PCTKR2017011367-appb-I000284
Figure PCTKR2017011367-appb-I000284
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 75]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 834.056.8 g of the target compound was obtained in the same manner as the [Synthesis Example 75], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 834.05
[[ 합성예Synthesis Example 220] Mat 457의 합성 220] Synthesis of Mat 457
Figure PCTKR2017011367-appb-I000285
Figure PCTKR2017011367-appb-I000285
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 76]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 683.877.1 g of the target compound was obtained in the same manner as the [Synthesis Example 76], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 683.87
[[ 합성예Synthesis Example 221] Mat 458의 합성 221] Synthesis of Mat 458
Figure PCTKR2017011367-appb-I000286
Figure PCTKR2017011367-appb-I000286
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 77]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 773.956.1 g of the target compound was obtained in the same manner as the [Synthesis Example 77], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 773.95
[[ 합성예Synthesis Example 222] Mat 460의 합성 222] Synthesis of Mat 460
Figure PCTKR2017011367-appb-I000287
Figure PCTKR2017011367-appb-I000287
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 78]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 800.046.9 g of the target compound was obtained in the same manner as the [Synthesis Example 78], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 800.04
[[ 합성예Synthesis Example 223] Mat 463의 합성 223] Synthesis of Mat 463
Figure PCTKR2017011367-appb-I000288
Figure PCTKR2017011367-appb-I000288
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 79]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 773.956.3 g of the target compound was obtained in the same manner as the [Synthesis Example 79], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 773.95
[[ 합성예Synthesis Example 224] Mat 464의 합성 224] Synthesis of Mat 464
Figure PCTKR2017011367-appb-I000289
Figure PCTKR2017011367-appb-I000289
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 80]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 851.086.9 g of the target compound was obtained in the same manner as the [Synthesis Example 80], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 851.08
[[ 합성예Synthesis Example 225] Mat 469의 합성 225] Synthesis of Mat 469
Figure PCTKR2017011367-appb-I000290
Figure PCTKR2017011367-appb-I000290
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 81]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 915.137.0 g of the target compound was obtained in the same manner as the [Synthesis Example 81], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 915.13
[[ 합성예Synthesis Example 226] Mat 470의 합성 226] Synthesis of Mat 470
Figure PCTKR2017011367-appb-I000291
Figure PCTKR2017011367-appb-I000291
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 82]과 동일한 과정을 수행하여 목적 화합물 7.3g을 얻었다.; HRMS [M]+: 839.037.3 g of the target compound was obtained in the same manner as the [Synthesis Example 82], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 839.03
[[ 합성예Synthesis Example 227] Mat 471의 합성 227] Synthesis of Mat 471
Figure PCTKR2017011367-appb-I000292
Figure PCTKR2017011367-appb-I000292
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 83]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 915.137.1 g of the target compound was obtained in the same manner as the [Synthesis Example 83], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 915.13
[[ 합성예Synthesis Example 228] Mat 474의 합성 228] Synthesis of Mat 474
Figure PCTKR2017011367-appb-I000293
Figure PCTKR2017011367-appb-I000293
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 84]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 812.016.7 g of the target compound was obtained in the same manner as the [Synthesis Example 84], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 812.01
[[ 합성예Synthesis Example 229] Mat 476의 합성 229] Synthesis of Mat 476
Figure PCTKR2017011367-appb-I000294
Figure PCTKR2017011367-appb-I000294
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 85]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 668.866.5 g of the target compound was obtained in the same manner as the [Synthesis Example 85], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 668.86
[[ 합성예Synthesis Example 230] Mat 477의 합성 230] Synthesis of Mat 477
Figure PCTKR2017011367-appb-I000295
Figure PCTKR2017011367-appb-I000295
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 86]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 668.866.9 g of the target compound was obtained in the same manner as the [Synthesis Example 86], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 668.86
[[ 합성예Synthesis Example 231] Mat 480의 합성 231] Synthesis of Mat 480
Figure PCTKR2017011367-appb-I000296
Figure PCTKR2017011367-appb-I000296
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 87]과 동일한 과정을 수행하여 목적 화합물 6.2g을 얻었다.; HRMS [M]+: 742.946.2 g of the target compound was obtained in the same manner as the [Synthesis Example 87], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 742.94
[[ 합성예Synthesis Example 232] Mat 482의 합성 232] Synthesis of Mat 482
Figure PCTKR2017011367-appb-I000297
Figure PCTKR2017011367-appb-I000297
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 88]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 592.765.9 g of the target compound was obtained in the same manner as the [Synthesis Example 88], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 592.76
[[ 합성예Synthesis Example 233] Mat 483의 합성 233] Synthesis of Mat 483
Figure PCTKR2017011367-appb-I000298
Figure PCTKR2017011367-appb-I000298
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 89]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 682.845.3 g of the target compound was obtained in the same manner as the [Synthesis Example 89], except that [Preparation 22] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 234] Mat 485의 합성 234] Synthesis of Mat 485
Figure PCTKR2017011367-appb-I000299
Figure PCTKR2017011367-appb-I000299
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 90]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 708.926.8 g of the target compound was obtained in the same manner as the [Synthesis Example 90], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 708.92
[[ 합성예Synthesis Example 235] Mat 488의 합성 235] Synthesis of Mat 488
Figure PCTKR2017011367-appb-I000300
Figure PCTKR2017011367-appb-I000300
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 91]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 682.845.7 g of the target compound was obtained in the same manner as the [Synthesis Example 91], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 236] Mat 489의 합성 236] Synthesis of Mat 489
Figure PCTKR2017011367-appb-I000301
Figure PCTKR2017011367-appb-I000301
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 92]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 759.975.9 g of the title compound was obtained in the same manner as the [Synthesis Example 92], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 759.97
[[ 합성예Synthesis Example 237] Mat 494의 합성 237] Synthesis of Mat 494
Figure PCTKR2017011367-appb-I000302
Figure PCTKR2017011367-appb-I000302
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 93]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다.; HRMS [M]+: 824.026.0 g of the target compound was obtained in the same manner as the [Synthesis Example 93], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 824.02
[[ 합성예Synthesis Example 238] Mat 495의 합성 238] Synthesis of Mat 495
Figure PCTKR2017011367-appb-I000303
Figure PCTKR2017011367-appb-I000303
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 94]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 747.926.3 g of the target compound was obtained in the same manner as the [Synthesis Example 94] except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 747.92
[[ 합성예Synthesis Example 239] Mat 496의 합성 239] Synthesis of Mat 496
Figure PCTKR2017011367-appb-I000304
Figure PCTKR2017011367-appb-I000304
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 95]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 824.026.1 g of the target compound was obtained in the same manner as the [Synthesis Example 95], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 824.02
[[ 합성예Synthesis Example 240] Mat 499의 합성 240] Synthesis of Mat 499
Figure PCTKR2017011367-appb-I000305
Figure PCTKR2017011367-appb-I000305
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 96]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 720.895.7 g of the target compound was obtained in the same manner as the [Synthesis Example 96], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 720.89
[[ 합성예Synthesis Example 241] Mat 501의 합성 241] Synthesis of Mat 501
Figure PCTKR2017011367-appb-I000306
Figure PCTKR2017011367-appb-I000306
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 97]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 668.866.9 g of the target compound was obtained in the same manner as the [Synthesis Example 97], except that [Preparation 23] was used as a reactant. HRMS [M] +: 668.86
[[ 합성예Synthesis Example 242] Mat 502의 합성 242] Synthesis of Mat 502
Figure PCTKR2017011367-appb-I000307
Figure PCTKR2017011367-appb-I000307
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 98]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 668.865.4 g of the target compound was obtained in the same manner as the [Synthesis Example 98], except that [Preparation 23] was used as a reactant. HRMS [M] +: 668.86
[[ 합성예Synthesis Example 243] Mat 505의 합성 243] Synthesis of Mat 505
Figure PCTKR2017011367-appb-I000308
Figure PCTKR2017011367-appb-I000308
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 99]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 742.945.8 g of the target compound was obtained in the same manner as the [Synthesis Example 99], except that [Preparation 23] was used as a reactant. HRMS [M] +: 742.94
[[ 합성예Synthesis Example 244] Mat 507의 합성 244] Synthesis of Mat 507
Figure PCTKR2017011367-appb-I000309
Figure PCTKR2017011367-appb-I000309
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 100]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 592.765.6 g of the target compound was obtained in the same manner as the [Synthesis Example 100], except that [Preparation Example 23] was used as a reactant. HRMS [M] +: 592.76
[[ 합성예Synthesis Example 245] Mat 508의 합성 245] Synthesis of Mat 508
Figure PCTKR2017011367-appb-I000310
Figure PCTKR2017011367-appb-I000310
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 101]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 682.846.3 g of the target compound was obtained in the same manner as the [Synthesis Example 101], except that [Preparation 23] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 246] Mat 510의 합성 246] Synthesis of Mat 510
Figure PCTKR2017011367-appb-I000311
Figure PCTKR2017011367-appb-I000311
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 102]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 708.925.8 g of the target compound was obtained in the same manner as the [Synthesis Example 102], except that [Preparation 23] was used as a reactant. HRMS [M] +: 708.92
[[ 합성예Synthesis Example 247] Mat 513의 합성 247] Synthesis of Mat 513
Figure PCTKR2017011367-appb-I000312
Figure PCTKR2017011367-appb-I000312
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 103]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 682.845.3 g of the target compound was obtained in the same manner as the [Synthesis Example 103], except that [Preparation 23] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 248] Mat 514의 합성 248] Synthesis of Mat 514
Figure PCTKR2017011367-appb-I000313
Figure PCTKR2017011367-appb-I000313
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 104]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 759.975.7 g of the target compound was obtained in the same manner as the [Synthesis Example 104], except that [Preparation 23] was used as a reactant. HRMS [M] +: 759.97
[[ 합성예Synthesis Example 249] Mat 519의 합성 249] Synthesis of Mat 519
Figure PCTKR2017011367-appb-I000314
Figure PCTKR2017011367-appb-I000314
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 105]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 824.025.8 g of the target compound was obtained in the same manner as the [Synthesis Example 105], except that [Preparation Example 23] was used as a reactant. HRMS [M] +: 824.02
[[ 합성예Synthesis Example 250] Mat 520의 합성 250] Synthesis of Mat 520
Figure PCTKR2017011367-appb-I000315
Figure PCTKR2017011367-appb-I000315
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 747.925.3 g of the target compound was obtained in the same manner as the [Synthesis Example 106], except that [Preparation 23] was used as a reactant. HRMS [M] +: 747.92
[[ 합성예Synthesis Example 251] Mat 521의 합성 251] Synthesis of Mat 521
Figure PCTKR2017011367-appb-I000316
Figure PCTKR2017011367-appb-I000316
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 107]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 824.025.7 g of the target compound was obtained in the same manner as the [Synthesis Example 107], except that [Preparation 23] was used as a reactant. HRMS [M] +: 824.02
[[ 합성예Synthesis Example 252] Mat 524의 합성 252] Synthesis of Mat 524
Figure PCTKR2017011367-appb-I000317
Figure PCTKR2017011367-appb-I000317
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 108]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 720.895.3 g of the target compound was obtained in the same manner as the [Synthesis Example 108], except that [Preparation 23] was used as a reactant. HRMS [M] +: 720.89
[[ 합성예Synthesis Example 253] Mat 526의 합성 253] Synthesis of Mat 526
Figure PCTKR2017011367-appb-I000318
Figure PCTKR2017011367-appb-I000318
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 109]과 동일한 과정을 수행하여 목적 화합물 7.2g을 얻었다.; HRMS [M]+: 744.967.2g of the target compound was obtained in the same manner as the [Synthesis Example 109], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 744.96
[[ 합성예Synthesis Example 254] Mat 527의 합성 254] Synthesis of Mat 527
Figure PCTKR2017011367-appb-I000319
Figure PCTKR2017011367-appb-I000319
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 110]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 744.966.4 g of the target compound was obtained in the same manner as the [Synthesis Example 110], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 744.96
[[ 합성예Synthesis Example 255] Mat 530의 합성 255] Synthesis of Mat 530
Figure PCTKR2017011367-appb-I000320
Figure PCTKR2017011367-appb-I000320
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 111]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 819.046.8 g of the target compound was obtained in the same manner as the [Synthesis Example 111], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 819.04
[[ 합성예Synthesis Example 256] Mat 532의 합성 256] Synthesis of Mat 532
Figure PCTKR2017011367-appb-I000321
Figure PCTKR2017011367-appb-I000321
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 112]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 668.866.5 g of the target compound was obtained in the same manner as the [Synthesis Example 112], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 668.86
[[ 합성예Synthesis Example 257] Mat 533의 합성 257] Synthesis of Mat 533
Figure PCTKR2017011367-appb-I000322
Figure PCTKR2017011367-appb-I000322
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 113]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 758.946.8 g of the target compound was obtained in the same manner as the [Synthesis Example 113], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 758.94
[[ 합성예Synthesis Example 258] Mat 535의 합성 258] Synthesis of Mat 535
Figure PCTKR2017011367-appb-I000323
Figure PCTKR2017011367-appb-I000323
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 114]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 785.026.8 g of the target compound was obtained in the same manner as the [Synthesis Example 114], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 785.02
[[ 합성예Synthesis Example 259] Mat 538의 합성 259] Synthesis of Mat 538
Figure PCTKR2017011367-appb-I000324
Figure PCTKR2017011367-appb-I000324
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 115]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 758.946.3 g of the target compound was obtained in the same manner as the [Synthesis Example 115], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 758.94
[[ 합성예Synthesis Example 260] Mat 539의 합성 260] Synthesis of Mat 539
Figure PCTKR2017011367-appb-I000325
Figure PCTKR2017011367-appb-I000325
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 116]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 836.076.7 g of the target compound was obtained in the same manner as the [Synthesis Example 116], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 836.07
[[ 합성예Synthesis Example 261] Mat 544의 합성 261] Synthesis of Mat 544
Figure PCTKR2017011367-appb-I000326
Figure PCTKR2017011367-appb-I000326
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 117]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 900.126.3 g of the title compound was obtained in the same manner as the [Synthesis Example 117], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 900.12
[[ 합성예Synthesis Example 262] Mat 545의 합성 262] Synthesis of Mat 545
Figure PCTKR2017011367-appb-I000327
Figure PCTKR2017011367-appb-I000327
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 118]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 824.026.9 g of the target compound was obtained in the same manner as the [Synthesis Example 118], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 824.02
[[ 합성예Synthesis Example 263] Mat 546의 합성 263] Synthesis of Mat 546
Figure PCTKR2017011367-appb-I000328
Figure PCTKR2017011367-appb-I000328
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 119]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 900.126.7 g of the target compound was obtained in the same manner as the [Synthesis Example 119], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 900.12
[[ 합성예Synthesis Example 264] Mat 549의 합성 264] Synthesis of Mat 549
Figure PCTKR2017011367-appb-I000329
Figure PCTKR2017011367-appb-I000329
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 120]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 796.996.3 g of the target compound was obtained in the same manner as the [Synthesis Example 120], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 796.99
[[ 합성예Synthesis Example 265] Mat 551의 합성 265] Synthesis of Mat 551
Figure PCTKR2017011367-appb-I000330
Figure PCTKR2017011367-appb-I000330
반응물로 [준비예 25]을 사용한 것을 제외하고는 [합성예 121]과 동일한 과정을 수행하여 목적 화합물 7.6g을 얻었다.; HRMS [M]+: 758.947.6 g of the target compound was obtained in the same manner as the [Synthesis Example 121], except that [Preparation Example 25] was used as a reactant. HRMS [M] +: 758.94
[[ 합성예Synthesis Example 266] Mat 552의 합성 266] Synthesis of Mat 552
Figure PCTKR2017011367-appb-I000331
Figure PCTKR2017011367-appb-I000331
반응물로 [준비예 25]을 사용한 것을 제외하고는 [합성예 122]과 동일한 과정을 수행하여 목적 화합물 7.4g을 얻었다.; HRMS [M]+: 758.947.4 g of the target compound was obtained in the same manner as the [Synthesis Example 122], except that [Preparation Example 25] was used as a reactant. HRMS [M] +: 758.94
[[ 합성예Synthesis Example 267] Mat 555의 합성 267] Synthesis of Mat 555
Figure PCTKR2017011367-appb-I000332
Figure PCTKR2017011367-appb-I000332
반응물로 [준비예 25]을 사용한 것을 제외하고는 [합성예 123]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 833.027.1 g of the target compound was obtained in the same manner as the [Synthesis Example 123], except that [Preparation Example 25] was used as a reactant. HRMS [M] +: 833.02
[[ 합성예Synthesis Example 268] Mat 557의 합성 268] Synthesis of Mat 557
Figure PCTKR2017011367-appb-I000333
Figure PCTKR2017011367-appb-I000333
반응물로 [준비예 25]을 사용한 것을 제외하고는 [합성예 124]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 682.846.9 g of the target compound was obtained in the same manner as the [Synthesis Example 124], except that [Preparation Example 25] was used as a reactant. HRMS [M] +: 682.84
[[ 합성예Synthesis Example 269] Mat 558의 합성 269] Synthesis of Mat 558
Figure PCTKR2017011367-appb-I000334
Figure PCTKR2017011367-appb-I000334
반응물로 [준비예 25]을 사용한 것을 제외하고는 [합성예 125]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 772.92Except for using [Preparation Example 25] as a reactant to the same procedure as in [Synthesis Example 125] to give the target compound 7.0g; HRMS [M] +: 772.92
[[ 합성예Synthesis Example 270] Mat 560의 합성 270] Synthesis of Mat 560
Figure PCTKR2017011367-appb-I000335
Figure PCTKR2017011367-appb-I000335
반응물로 [준비예 25]을 사용한 것을 제외하고는 [합성예 126]과 동일한 과정을 수행하여 목적 화합물 7.2g을 얻었다.; HRMS [M]+: 799.007.2g of the target compound was obtained in the same manner as the [Synthesis Example 126], except that [Preparation Example 25] was used as a reactant. HRMS [M] +: 799.00
[[ 합성예Synthesis Example 271] Mat 563의 합성 271] Synthesis of Mat 563
Figure PCTKR2017011367-appb-I000336
Figure PCTKR2017011367-appb-I000336
반응물로 [준비예 25]을 사용한 것을 제외하고는 [합성예 127]과 동일한 과정을 수행하여 목적 화합물 7.3g을 얻었다.; HRMS [M]+: 772.927.3 g of the title compound was obtained in the same manner as the [Synthesis Example 127], except that [Preparation Example 25] was used as a reactant. HRMS [M] +: 772.92
[[ 합성예Synthesis Example 272] Mat 564의 합성 272] Synthesis of Mat 564
Figure PCTKR2017011367-appb-I000337
Figure PCTKR2017011367-appb-I000337
반응물로 [준비예 25]을 사용한 것을 제외하고는 [합성예 128]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 850.05Except for using [Preparation Example 25] as a reactant to the same procedure as in [Synthesis Example 128] to give the target compound 7.0g; HRMS [M] +: 850.05
[[ 합성예Synthesis Example 273] Mat 569의 합성 273] Synthesis of Mat 569
Figure PCTKR2017011367-appb-I000338
Figure PCTKR2017011367-appb-I000338
반응물로 [준비예 25]을 사용한 것을 제외하고는 [합성예 129]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 914.107.1 g of the target compound was obtained in the same manner as the [Synthesis Example 129], except that [Preparation Example 25] was used as a reactant. HRMS [M] +: 914.10
[[ 합성예Synthesis Example 274] Mat 570의 합성 274] Synthesis of Mat 570
Figure PCTKR2017011367-appb-I000339
Figure PCTKR2017011367-appb-I000339
반응물로 [준비예 25]을 사용한 것을 제외하고는 [합성예 130]과 동일한 과정을 수행하여 목적 화합물 7.4g을 얻었다.; HRMS [M]+: 838.007.4 g of the target compound was obtained in the same manner as the [Synthesis Example 130], except that [Preparation Example 25] was used as a reactant. HRMS [M] +: 838.00
[[ 합성예Synthesis Example 275] Mat 571의 합성 275] Synthesis of Mat 571
Figure PCTKR2017011367-appb-I000340
Figure PCTKR2017011367-appb-I000340
반응물로 [준비예 25]을 사용한 것을 제외하고는 [합성예 131]과 동일한 과정을 수행하여 목적 화합물 7.5g을 얻었다.; HRMS [M]+: 914.107.5 g of the target compound was obtained in the same manner as the [Synthesis Example 131], except that [Preparation Example 25] was used as a reactant. HRMS [M] +: 914.10
[[ 합성예Synthesis Example 276] Mat 574의 합성 276] Synthesis of Mat 574
Figure PCTKR2017011367-appb-I000341
Figure PCTKR2017011367-appb-I000341
반응물로 [준비예 25]을 사용한 것을 제외하고는 [합성예 132]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 810.98Except for using [Preparation Example 25] as a reactant to the same procedure as in [Synthesis Example 132] to obtain the target compound 7.0g; HRMS [M] +: 810.98
[[ 합성예Synthesis Example 277] Mat 576의 합성 277] Synthesis of Mat 576
Figure PCTKR2017011367-appb-I000342
Figure PCTKR2017011367-appb-I000342
반응물로 [준비예 26]을 사용한 것을 제외하고는 [합성예 133]과 동일한 과정을 수행하여 목적 화합물 7.8g을 얻었다.; HRMS [M]+: 824.02Except for using [Preparation Example 26] as a reactant to the same procedure as in [Synthesis Example 133] to give the target compound 7.8g; HRMS [M] +: 824.02
[[ 합성예Synthesis Example 278] Mat 577의 합성 278] Synthesis of Mat 577
Figure PCTKR2017011367-appb-I000343
Figure PCTKR2017011367-appb-I000343
반응물로 [준비예 26]을 사용한 것을 제외하고는 [합성예 134]과 동일한 과정을 수행하여 목적 화합물 8.3g을 얻었다.; HRMS [M]+: 824.028.3 g of the target compound was obtained in the same manner as the [Synthesis Example 134], except that [Preparation Example 26] was used as a reactant. HRMS [M] +: 824.02
[[ 합성예Synthesis Example 279] Mat 580의 합성 279] Synthesis of Mat 580
Figure PCTKR2017011367-appb-I000344
Figure PCTKR2017011367-appb-I000344
반응물로 [준비예 26]을 사용한 것을 제외하고는 [합성예 135]과 동일한 과정을 수행하여 목적 화합물 7.5g을 얻었다.; HRMS [M]+: 898.107.5 g of the target compound was obtained in the same manner as the [Synthesis Example 135], except that [Preparation Example 26] was used as a reactant. HRMS [M] +: 898.10
[[ 합성예Synthesis Example 280] Mat 582의 합성 280] Synthesis of Mat 582
Figure PCTKR2017011367-appb-I000345
Figure PCTKR2017011367-appb-I000345
반응물로 [준비예 26]을 사용한 것을 제외하고는 [합성예 136]과 동일한 과정을 수행하여 목적 화합물 7.7g을 얻었다.; HRMS [M]+: 747.927.7 g of the target compound was obtained in the same manner as the [Synthesis Example 136], except that [Preparation Example 26] was used as a reactant. HRMS [M] +: 747.92
[[ 합성예Synthesis Example 281] Mat 583의 합성 281] Synthesis of Mat 583
Figure PCTKR2017011367-appb-I000346
Figure PCTKR2017011367-appb-I000346
반응물로 [준비예 26]을 사용한 것을 제외하고는 [합성예 137]과 동일한 과정을 수행하여 목적 화합물 7.2g을 얻었다.; HRMS [M]+: 838.007.2g of the target compound was obtained in the same manner as the [Synthesis Example 137], except that [Preparation Example 26] was used as a reactant. HRMS [M] +: 838.00
[[ 합성예Synthesis Example 282] Mat 585의 합성 282] Synthesis of Mat 585
Figure PCTKR2017011367-appb-I000347
Figure PCTKR2017011367-appb-I000347
반응물로 [준비예 26]을 사용한 것을 제외하고는 [합성예 138]과 동일한 과정을 수행하여 목적 화합물 7.6g을 얻었다.; HRMS [M]+: 864.087.6 g of the title compound was obtained in the same manner as the [Synthesis Example 138], except that [Preparation Example 26] was used as a reactant. HRMS [M] +: 864.08
[[ 합성예Synthesis Example 283] Mat 588의 합성 283] Synthesis of Mat 588
Figure PCTKR2017011367-appb-I000348
Figure PCTKR2017011367-appb-I000348
반응물로 [준비예 26]을 사용한 것을 제외하고는 [합성예 139]과 동일한 과정을 수행하여 목적 화합물 7.9g을 얻었다.; HRMS [M]+: 838.007.9 g of the title compound was obtained in the same manner as the [Synthesis Example 139], except that [Preparation Example 26] was used as a reactant. HRMS [M] +: 838.00
[[ 합성예Synthesis Example 284] Mat 589의 합성 284] Synthesis of Mat 589
Figure PCTKR2017011367-appb-I000349
Figure PCTKR2017011367-appb-I000349
반응물로 [준비예 26]을 사용한 것을 제외하고는 [합성예 140]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 915.137.1 g of the target compound was obtained in the same manner as the [Synthesis Example 140], except that [Preparation Example 26] was used as a reactant. HRMS [M] +: 915.13
[[ 합성예Synthesis Example 285] Mat 594의 합성 285] Synthesis of Mat 594
Figure PCTKR2017011367-appb-I000350
Figure PCTKR2017011367-appb-I000350
반응물로 [준비예 26]을 사용한 것을 제외하고는 [합성예 141]과 동일한 과정을 수행하여 목적 화합물 7.4g을 얻었다.; HRMS [M]+: 979.18Except for using [Preparation Example 26] as a reactant to the same procedure as in [Synthesis Example 141] to obtain the title compound 7.4g; HRMS [M] +: 979.18
[[ 합성예Synthesis Example 286] Mat 595의 합성 286] Synthesis of Mat 595
Figure PCTKR2017011367-appb-I000351
Figure PCTKR2017011367-appb-I000351
반응물로 [준비예 26]을 사용한 것을 제외하고는 [합성예 142]과 동일한 과정을 수행하여 목적 화합물 7.8g을 얻었다.; HRMS [M]+: 903.08Except for using [Preparation Example 26] as a reactant to the same procedure as in [Synthesis Example 142] to obtain the target compound 7.8g; HRMS [M] +: 903.08
[[ 합성예Synthesis Example 287] Mat 596의 합성 287] Synthesis of Mat 596
Figure PCTKR2017011367-appb-I000352
Figure PCTKR2017011367-appb-I000352
반응물로 [준비예 26]을 사용한 것을 제외하고는 [합성예 143]과 동일한 과정을 수행하여 목적 화합물 7.3g을 얻었다.; HRMS [M]+: 979.187.3 g of the target compound was obtained in the same manner as the [Synthesis Example 143], except that [Preparation Example 26] was used as a reactant. HRMS [M] +: 979.18
[[ 합성예Synthesis Example 288] Mat 599의 합성 288] Synthesis of Mat 599
Figure PCTKR2017011367-appb-I000353
Figure PCTKR2017011367-appb-I000353
반응물로 [준비예 26]을 사용한 것을 제외하고는 [합성예 144]과 동일한 과정을 수행하여 목적 화합물 7.2g을 얻었다.; HRMS [M]+: 876.057.2g of the target compound was obtained in the same manner as the [Synthesis Example 144], except that [Preparation Example 26] was used as a reactant. HRMS [M] +: 876.05
[[ 실시예Example 1 ~ 40] 녹색 유기  1 to 40] green organic 전계Electric field 발광 소자의 제조 Manufacture of light emitting device
합성예 1~277에서 합성한 화합물 Mat 1 ~ Mat 576를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.Compounds 1 to 277 synthesized in Synthesis Examples 1 to 277 were subjected to high purity sublimation purification by a conventionally known method, and then green organic EL devices were manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ Mat 1 ~ Mat 576의 각각의 화합물 + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. M-MTDATA (60 nm) / TCTA (80 nm) / Mat 1 to Mat 576 each compound + 10% Ir (ppy) 3 (30nm) / BCP (10 nm) / Alq 3 ( 30 nm) / LiF (1 nm) / Al (200 nm) was laminated to fabricate an organic EL device.
m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP are as follows.
Figure PCTKR2017011367-appb-I000354
Figure PCTKR2017011367-appb-I000354
Figure PCTKR2017011367-appb-I000355
Figure PCTKR2017011367-appb-I000355
[비교예 1] 녹색 유기 전계 발광 소자의 제조Comparative Example 1 Fabrication of Green Organic Electroluminescent Device
발광층 형성시 발광 호스트 물질로서 화합물 Mat 1 대신 CBP를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Mat 1 as a light emitting host material.
[평가예 1][Evaluation Example 1]
실시예 1 ~ 40 및 비교예 1에서 제작한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 (10) mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.For each of the green organic electroluminescent devices fabricated in Examples 1 to 40 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at current density (10) mA / cm 2 were measured, and the results are shown in Table 1 below. Indicated.
샘플Sample 호스트Host 구동 전압(V)Drive voltage (V) EL 피크(nm)EL peak (nm) 전류효율(cd/A)Current efficiency (cd / A)
실시예 1Example 1 Mat 1Mat 1 6.86.8 516516 3838
실시예 2Example 2 Mat 2Mat 2 5.95.9 516516 3838
실시예 3Example 3 Mat 5Mat 5 6.36.3 516516 4343
실시예 4Example 4 Mat 8Mat 8 5.895.89 516516 4242
실시예 5Example 5 Mat 10Mat 10 5.85.8 516516 4141
실시예 6Example 6 Mat 13Mat 13 5.775.77 516516 3939
실시예 7Example 7 Mat 20Mat 20 5.85.8 516516 38.538.5
실시예 8Example 8 Mat 26Mat 26 5.865.86 517517 3939
실시예 9Example 9 Mat 30Mat 30 5.875.87 516516 4040
실시예 10Example 10 Mat 33Mat 33 6.46.4 516516 4141
실시예 11Example 11 Mat 45Mat 45 5.85.8 516516 4242
실시예 12Example 12 Mat 51Mat 51 6.26.2 516516 4444
실시예 13Example 13 Mat 58Mat 58 5.95.9 516516 4343
실시예 14Example 14 Mat 63Mat 63 5.915.91 516516 4040
실시예 15Example 15 Mat 70Mat 70 6.06.0 516516 39.839.8
실시예 16Example 16 Mat 76Mat 76 5.95.9 516516 4141
실시예 17Example 17 Mat 83Mat 83 6.86.8 516516 3838
실시예 18Example 18 Mat 95Mat 95 6.26.2 516516 4343
실시예 19Example 19 Mat 101Mat 101 5.85.8 516516 4040
실시예 20Example 20 Mat 113Mat 113 6.66.6 517517 4141
실시예 21Example 21 Mat 120Mat 120 5.95.9 516516 4242
실시예 22Example 22 Mat 126Mat 126 6.46.4 516516 4444
실시예 23Example 23 Mat 151Mat 151 6.56.5 516516 4343
실시예 24Example 24 Mat 176Mat 176 5.95.9 516516 5151
실시예 25Example 25 Mat 201Mat 201 5.45.4 516516 48.948.9
실시예 26Example 26 Mat 226Mat 226 5.35.3 516516 4949
실시예 27Example 27 Mat 251Mat 251 5.45.4 516516 5252
실시예 28Example 28 Mat 276Mat 276 6.876.87 516516 5151
실시예 29Example 29 Mat 301Mat 301 6.26.2 516516 4343
실시예 30Example 30 Mat 326Mat 326 5.85.8 516516 4444
실시예 31Example 31 Mat 351Mat 351 6.66.6 516516 4343
실시예 32Example 32 Mat 376Mat 376 6.66.6 516516 4040
실시예 33Example 33 Mat 401Mat 401 5.95.9 516516 39.839.8
실시예 34Example 34 Mat 426Mat 426 6.66.6 516516 4141
실시예 35Example 35 Mat 451Mat 451 5.95.9 516516 4242
실시예 36Example 36 Mat 476Mat 476 5.55.5 516516 5050
실시예 37Example 37 Mat 501Mat 501 6.36.3 516516 5555
실시예 38Example 38 Mat 526Mat 526 5.85.8 516516 5353
실시예 39Example 39 Mat 551Mat 551 5.25.2 516516 4848
실시예 40Example 40 Mat 576Mat 576 5.35.3 517517 50.150.1
비교예 1Comparative Example 1 CBPCBP 6.93 6.93 516 516 38.2 38.2
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물 (Mat 1 ~ Mat 576)을 녹색 유기 전계 발광 소자의 발광층으로 사용하였을 경우(실시예 1 내지 40) 종래 CBP를 사용한 녹색 유기 전계 발광 소자(비교예1)와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 1 above, when the compounds (Mat 1 to Mat 576) according to the present invention were used as the light emitting layer of the green organic electroluminescent device (Examples 1 to 40), the green organic electroluminescent device using the conventional CBP (compared to Compared with Example 1, it can be seen that it shows better performance in terms of efficiency and driving voltage.
[실시예 41 ~ 70] 적색 유기 전계 발광 소자의 제조Examples 41 to 70 Fabrication of Red Organic Electroluminescent Devices
합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ Mat 20 ~ Mat 599의 화합물 + 10 % (piq)2Ir(acac) (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다.M-MTDATA (60 nm) / TCTA (80 nm) / Mat 20 ~ Mat 599 + 10% (piq) 2 Ir (acac) (30 nm) / BCP (10 nm) / Alq 3 on the prepared ITO transparent electrode (30 nm) / LiF (1 nm) / Al (200 nm) were stacked to fabricate an organic EL device.
[비교예 2]Comparative Example 2 적색 유기 전계 발광 소자의 제조Fabrication of Red Organic Electroluminescent Devices
발광층 형성시 발광 호스트 물질로서 상기 Mat 20의 화합물 대신 CBP를 사용하는 것을 제외하고는 상기 실시예 36와 동일한 과정으로 적색 유기 전계 발광 소자를 제작하였다.A red organic electroluminescent device was manufactured in the same manner as in Example 36, except that CBP was used instead of the compound of Mat 20 as a light emitting host material when forming the light emitting layer.
상기 실시예 41 ~ 70 및 비교예 2에서 사용된 m-MTDATA, (piq)2Ir(acac), CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, (piq) 2 Ir (acac), CBP and BCP used in Examples 41 to 70 and Comparative Example 2 are as follows.
Figure PCTKR2017011367-appb-I000356
Figure PCTKR2017011367-appb-I000356
[[ 평가예Evaluation example 2] 2]
실시예 41 ~ 70 및 비교예 2에서 제작한 각각의 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 2에 나타내었다.For each organic electroluminescent device manufactured in Examples 41 to 70 and Comparative Example 2, the driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.
샘플Sample 호스트Host 구동 전압(V)Drive voltage (V) 전류효율(cd/A)Current efficiency (cd / A)
실시예 41Example 41 Mat 20 Mat 20 5.15.1 8.98.9
실시예 42Example 42 Mat 21Mat 21 5.05.0 8.38.3
실시예 43Example 43 Mat 24Mat 24 4.84.8 9.19.1
실시예 44Example 44 Mat 45Mat 45 4.84.8 9.09.0
실시예 45Example 45 Mat 49Mat 49 4.784.78 8.68.6
실시예 46Example 46 Mat 70Mat 70 5.05.0 9.09.0
실시예 47Example 47 Mat 74Mat 74 4.94.9 8.88.8
실시예 48Example 48 Mat 95Mat 95 5.05.0 8.68.6
실시예 49Example 49 Mat 99Mat 99 5.15.1 8.68.6
실시예 50Example 50 Mat 120Mat 120 4.84.8 9.59.5
실시예 51Example 51 Mat 124Mat 124 5.25.2 8.128.12
실시예 52Example 52 Mat 149Mat 149 4.94.9 8.68.6
실시예 53Example 53 Mat 174Mat 174 4.94.9 8.68.6
실시예 54Example 54 Mat 199Mat 199 4.54.5 10.110.1
실시예 55Example 55 Mat 224Mat 224 4.24.2 10.5610.56
실시예 56Example 56 Mat 249Mat 249 4.04.0 9.89.8
실시예 57Example 57 Mat 274Mat 274 4.24.2 10.6410.64
실시예 58Example 58 Mat 299Mat 299 4.34.3 10.4810.48
실시예 59Example 59 Mat 324Mat 324 5.05.0 9.09.0
실시예 60Example 60 Mat 349Mat 349 4.94.9 8.68.6
실시예 61Example 61 Mat 374Mat 374 4.94.9 9.09.0
실시예 62Example 62 Mat 399Mat 399 5.25.2 8.568.56
실시예 63Example 63 Mat 424Mat 424 5.05.0 8.58.5
실시예 64Example 64 Mat 449Mat 449 4.84.8 8.628.62
실시예 65Example 65 Mat 474Mat 474 5.25.2 8.68.6
실시예 66Example 66 Mat 499Mat 499 4.24.2 10.5610.56
실시예 67Example 67 Mat 524Mat 524 4.34.3 10.610.6
실시예 68Example 68 Mat 549Mat 549 4.14.1 10.8810.88
실시예 69Example 69 Mat 574Mat 574 4.74.7 10.610.6
실시예 70Example 70 Mat 599Mat 599 4.44.4 9.799.79
비교예 2Comparative Example 2 CBPCBP 5.255.25 8.28.2
상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화합물을 적색 유기 전계 발광 소자의 발광층의 재료로 사용하였을 경우(실시예 36 내지 57) 종래 CBP를 발광층의 재료로 사용한 적색 유기 전계 발광 소자(비교예 2)와 비교해 볼 때 효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 2 above, when the compound according to the present invention was used as a material of the light emitting layer of the red organic electroluminescent device (Examples 36 to 57), a red organic electroluminescent device using a conventional CBP as a material of the light emitting layer (comparative example) Compared with 2), it shows excellent performance in terms of efficiency and driving voltage.
[[ 실시예Example 71 ~ 94] 유기  71 ~ 94] Organic 전계Electric field 발광 소자의 제조 Manufacture of light emitting device
합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.
ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5 분간 세정한 후 진공 층착기로 기판을 이송하였다.A glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out. The substrate was then transferred to a vacuum depositor.
상기와 같이 준비된 ITO 투명 전극 위에 m-MTDATA(60nm)/ Mat 10 ~ Mat 589의 화합물 (80nm)/DS-H522 + 5% DS-501(30nm)/BCP(10nm)/Alq3(30 nm)/LiF(1nm)/Al(200nm) 순서로 유기 전계 발광 소자를 제조하였다.  M-MTDATA (60nm) / Mat 10 ~ Mat 589 compound (80nm) / DS-H522 + 5% DS-501 (30nm) / BCP (10nm) / Alq3 (30 nm) / on the prepared ITO transparent electrode as described above An organic EL device was manufactured in the order of LiF (1 nm) / Al (200 nm).
소자 제작에 사용된 DS-H522 및 DS-501은 ㈜두산 전자 BG의 제품이며, m-MTDATA, TCTA, CBP, Ir(ppy)3, 및 BCP의 구조는 하기와 같다.DS-H522 and DS-501 used in device fabrication are products of Doosan Electronics BG, and the structures of m-MTDATA, TCTA, CBP, Ir (ppy) 3 , and BCP are as follows.
Figure PCTKR2017011367-appb-I000357
Figure PCTKR2017011367-appb-I000357
Figure PCTKR2017011367-appb-I000358
Figure PCTKR2017011367-appb-I000358
[비교예 3] 유기 전계 발광 소자의 제조Comparative Example 3 Fabrication of Organic Electroluminescent Device
실시예 71에서 정공 수송층 형성시 정공 수송층 물질로 사용된 화합물 Mat 10 대신 NPB를 정공수송층 물질로 사용한 것을 제외하고는, 상기 실시예 71과 동일한 방법으로 유기 전계 발광 소자를 제조하였다. 사용된 NPB의 구조는 하기와 같다.An organic electroluminescent device was manufactured in the same manner as in Example 71, except that NPB was used as the hole transport layer material instead of the compound Mat 10 used as the hole transport layer material when forming the hole transport layer. The structure of the NPB used is as follows.
Figure PCTKR2017011367-appb-I000359
Figure PCTKR2017011367-appb-I000359
[평가예 3][Evaluation Example 3]
실시예 71 ~ 97 및 비교예 3에서 각각 제조된 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율를 측정하였고, 그 결과를 하기 표 1에 나타내었다.The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 71 to 97 and Comparative Example 3, and the results are shown in Table 1 below.
샘플Sample 정공수송층Hole transport layer 구동 전압 (V)Driving voltage (V) 전류효율 (cd/A)Current efficiency (cd / A)
실시예 71Example 71 Mat 10 Mat 10 4.64.6 19.419.4
실시예 72Example 72 Mat 14Mat 14 4.84.8 18.918.9
실시예 73Example 73 Mat 35 Mat 35 4.54.5 18.818.8
실시예 74Example 74 Mat 39Mat 39 4.74.7 19.419.4
실시예 75Example 75 Mat 60Mat 60 4.64.6 18.818.8
실시예 76Example 76 Mat 64Mat 64 4.54.5 19.419.4
실시예 77Example 77 Mat 89Mat 89 4.74.7 18.818.8
실시예 78Example 78 Mat 114Mat 114 4.64.6 19.419.4
실시예 79Example 79 Mat 139Mat 139 4.84.8 18.918.9
실시예 80Example 80 Mat 164Mat 164 4.54.5 18.818.8
실시예 81Example 81 Mat 189Mat 189 4.14.1 21.421.4
실시예 82Example 82 Mat 214Mat 214 4.24.2 20.920.9
실시예 83Example 83 Mat 239Mat 239 4.04.0 20.820.8
실시예 84Example 84 Mat 264Mat 264 4.24.2 20.820.8
실시예 85Example 85 Mat 289Mat 289 4.14.1 21.421.4
실시예 86Example 86 Mat 314Mat 314 4.54.5 18.918.9
실시예 87Example 87 Mat 339Mat 339 4.74.7 18.818.8
실시예 88Example 88 Mat 364Mat 364 4.64.6 19.419.4
실시예 89Example 89 Mat 389Mat 389 4.94.9 19.219.2
실시예 90Example 90 Mat 414Mat 414 4.64.6 18.818.8
실시예 91Example 91 Mat 439Mat 439 4.74.7 18.618.6
실시예 92Example 92 Mat 464Mat 464 4.64.6 18.518.5
실시예 93Example 93 Mat 489Mat 489 4.14.1 21.821.8
실시예 94Example 94 Mat 514Mat 514 4.14.1 21.021.0
실시예 95Example 95 Mat 539Mat 539 4.04.0 21.521.5
실시예 96Example 96 Mat 564Mat 564 4.24.2 20.620.6
실시예 97Example 97 Mat 589Mat 589 4.14.1 21.221.2
비교예 3Comparative Example 3 NPBNPB 5.25.2 18.118.1
상기 표 3에 나타낸 바와 같이, 본 발명에 따른 화합물(Mat 10 ~ Mat 589)을 정공 수송층으로 사용한 유기 전계 발광 소자(실시예 71 내지 97)는, 종래 NPB를 사용한 유기 전계 발광 소자(비교예 3)에 비해 전류효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 3 above, the organic electroluminescent devices (Examples 71 to 97) using the compounds (Mat 10 to Mat 589) according to the present invention as the hole transporting layer are organic electroluminescent devices using the conventional NPB (Comparative Example 3 Compared with), it shows better performance in terms of current efficiency and driving voltage.
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

Claims (13)

  1. 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2017011367-appb-I000360
    Figure PCTKR2017011367-appb-I000360
    상기 화학식 1에서,In Chemical Formula 1,
    X는 O, S, Se, N(Ar3), C(Ar4)(Ar5) 및 Si(Ar6)(Ar7)로 구성된 군으로부터 선택되며;X is selected from the group consisting of O, S, Se, N (Ar 3 ), C (Ar 4 ) (Ar 5 ) and Si (Ar 6 ) (Ar 7 );
    L1 내지 L3는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고;L 1 to L 3 are each independently a single bond, C 6 ~ be an aryl group and a C 18 nuclear atoms of 5 to 18 heteroarylene group is selected from the group consisting of;
    l 및 m은 각각 독립적으로 0 내지 4의 정수이며;l and m are each independently an integer from 0 to 4;
    n 및 o는 각각 독립적으로 0 내지 3의 정수이며;n and o are each independently an integer from 0 to 3;
    R1 내지 R4는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하고, 상기 R1 내지 R4 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 1 to R 4 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring, and R 1 to When each of R 4 's is plural, they are the same as or different from each other;
    Ar1 내지 Ar7은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; Ar 1 to Ar 7 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- aryloxy group of C 60, C 3 ~ C 40 alkylsilyl group, C group 6 ~ C 60 aryl silyl, C 1 ~ arylboronic of C 40 group of an alkyl boron, C 6 ~ C 60 group, C 6 ~ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining the adjacent tile to form a condensed ring;
    상기 L1 내지 L3의 아릴렌기 및 헤테로아릴렌기와, 상기 R1 내지 R4 및 Ar1 내지 Ar7의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다. The arylene group and heteroarylene group of L 1 to L 3 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group of R 1 to R 4 and Ar 1 to Ar 7 , A cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl boron group, an arylphosphanyl group, a mono or diarylphosphinyl group and an arylsilyl group are each independently deuterium, halogen, cyano group, Nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C Aryloxy group of 6 to C 60 , alkyloxy group of C 1 to C 40 , arylamine group of C 6 to C 60 , cycloalkyl group of C 3 to C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, C C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 An aryl boron group, C 6 ~ C 60 An arylphosphanyl group, C 6 ~ C 60 Mono or di When substituted or unsubstituted with one or more substituents selected from the group consisting of an arylphosphinyl group and a C 6 -C 60 arylsilyl group, they may be the same or different from each other.
  2. 제1항에 있어서,The method of claim 1,
    상기 화합물은 하기 화학식 2 또는 3으로 표시되는, 화합물: The compound is represented by the formula 2 or 3, the compound:
    [화학식 2][Formula 2]
    Figure PCTKR2017011367-appb-I000361
    Figure PCTKR2017011367-appb-I000361
    [화학식 3][Formula 3]
    Figure PCTKR2017011367-appb-I000362
    Figure PCTKR2017011367-appb-I000362
    상기 화학식 2 및 3에서, In Chemical Formulas 2 and 3,
    X, L2 내지 L3, R1 내지 R4, Ar1 내지 Ar2, l, m, n 및 o 각각은 제1항에서 정의된 바와 같다. X, L 2 to L 3 , R 1 to R 4 , Ar 1 to Ar 2 , l, m, n and o are each as defined in claim 1.
  3. 제1항에 있어서,The method of claim 1,
    상기 화합물은 하기 화학식 4 또는 화학식 5로 표시되는, 화합물:The compound is represented by the following formula (4) or (5), compound:
    [화학식 4][Formula 4]
    Figure PCTKR2017011367-appb-I000363
    Figure PCTKR2017011367-appb-I000363
    [화학식 5][Formula 5]
    Figure PCTKR2017011367-appb-I000364
    Figure PCTKR2017011367-appb-I000364
    상기 화학식 4 및 5에서, In Chemical Formulas 4 and 5,
    X, L2 내지 L3, R1 내지 R4, Ar1 내지 Ar2, l, m, n 및 o 각각은 제1항에서 정의된 바와 같다. X, L 2 to L 3 , R 1 to R 4 , Ar 1 to Ar 2 , l, m, n and o are each as defined in claim 1.
  4. 제1항에 있어서,The method of claim 1,
    상기 L2 및 L3는 각각 독립적으로 단일결합이거나, 하기 화학식 A-1 내지 화학식 A-3 중 어느 하나로 표시되는 링커인, 화합물:Wherein L 2 and L 3 are each independently a single bond or a linker represented by any one of the following Formulas A-1 to A-3:
    Figure PCTKR2017011367-appb-I000365
    Figure PCTKR2017011367-appb-I000365
    상기 화학식 A-1 내지 A-3에서,In Chemical Formulas A-1 to A-3,
    *는 결합이 이루어지는 부분을 의미한다.* Means the part where the coupling is made.
  5. 제1항에 있어서,The method of claim 1,
    상기 Ar1 및 Ar2는 각각 독립적으로 하기 화학식 B-1 내지 B-10 중 어느 하나로 표시되는 치환기인, 화합물:Ar 1 and Ar 2 are each independently a substituent represented by any one of the following formulas B-1 to B-10:
    Figure PCTKR2017011367-appb-I000366
    Figure PCTKR2017011367-appb-I000366
    상기 화학식 B-1 내지 B-10에서,In Chemical Formulas B-1 to B-10,
    *은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    Z1 내지 Z8은 각각 독립적으로 N 또는 C(R9)이며;Z 1 to Z 8 are each independently N or C (R 9 );
    상기 화학식 B-2에서 L2 또는 L3에 결합되는 Z1 내지 Z4 중 어느 하나는 C(R9)이고, 이때 상기 R9는 부재이며;Any one of Z 1 to Z 4 bonded to L 2 or L 3 in Formula B-2 is C (R 9 ), wherein R 9 is absent;
    T1 및 T2는 각각 독립적으로 단일결합, C(R10)(R11), N(R12), O 및 S로 이루어진 군에서 선택되나, T1 및 T2 모두가 단일결합은 아니며;T 1 and T 2 are each independently selected from the group consisting of a single bond, C (R 10 ) (R 11 ), N (R 12 ), O and S, but not both T 1 and T 2 are single bonds;
    p 및 q는 각각 독립적으로 0 내지 4의 정수이며;p and q are each independently integers of 0 to 4;
    R5 및 R6은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R5 및 R6 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 5 and R 6 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ~ C 60, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 ~ C 60 mono or diaryl phosphinyl group and a C 6 ~ C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, wherein R When 5 and R 6 are each plural, they are the same as or different from each other;
    R7 내지 R12는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R9 내지 R12 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 7 to R 12 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting of C 6 ~ C 60 mono or diaryl the Phosphinicosuccinic group and a C 6 ~ with an aryl silyl group of C 60, or combine tile adjacent to which they are attached may form a fused ring, When each of R 9 to R 12 plural is the same or different from each other;
    상기 R5 내지 R12의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 5 to R 12 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ selected from the group consisting of C 60 aryl silyl When substituted by one or more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.
  6. 제5항에 있어서,The method of claim 5,
    상기 R7 및 R8은 각각 독립적으로 C1~C30의 알킬기, C6~C30의 아릴기 및 핵원자수 5 내지 30개의 헤테로아릴기로 이루어진 군에서 선택되는, 화합물. Wherein R 7 and R 8 are, each independently represent a compound C 1 ~ C 30 alkyl group, C 6 ~ C 30 aryl group and the number of nuclear atoms of 5 to 30 heteroaryl group selected from the group consisting of.
  7. 제5항에 있어서,The method of claim 5,
    상기 R9는 C1~C30의 알킬기, C6~C30의 아릴기 및 핵원자수 5 내지 30개의 헤테로아릴기로 이루어진 군에서 선택되는, 화합물.Wherein R 9 is A compound selected from the group consisting of C 1 ~ C 30 alkyl group, C 6 ~ C 30 aryl group and the number of nuclear atoms of 5 to 30 heteroaryl group for.
  8. 제5항에 있어서,The method of claim 5,
    상기 화학식 B-1으로 표시되는 치환기는 하기 화학식 6으로 표시되는 치환기인, 화합물:The substituent represented by Formula B-1 is a substituent represented by Formula 6 below:
    [화학식 6][Formula 6]
    Figure PCTKR2017011367-appb-I000367
    Figure PCTKR2017011367-appb-I000367
    상기 화학식 6에서,In Chemical Formula 6,
    *은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    R13 및 R14는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; R 13 and R 14 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, selected from the group consisting of an arylamine C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining the adjacent tile to form a condensed ring;
    상기 R13 및 R14의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하며;The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group and aryl of R 13 and R 14 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group selected from the group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they are the same as or different from each other;
    Z1, Z3 및 Z5 각각은 제5항에서 정의된 바와 같다. Z 1 , Z 3 and Z 5 are each as defined in claim 5.
  9. 제1항에 있어서,The method of claim 1,
    상기 Ar1 및 Ar2는 각각 독립적으로 하기 화학식 C-1 내지 C-25 중 어느 하나로 표시되는 치환기인, 화합물:Ar 1 and Ar 2 are each independently a substituent represented by any one of Formulas C-1 to C-25:
    Figure PCTKR2017011367-appb-I000368
    Figure PCTKR2017011367-appb-I000368
    상기 화학식 C-1 내지 C-25에서, In Chemical Formulas C-1 to C-25,
    *은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    r은 0 내지 5의 정수이며;r is an integer from 0 to 5;
    p, q 및 s는 각각 독립적으로 0 내지 4의 정수이며;p, q and s are each independently integers of 0 to 4;
    t는 0 내지 3의 정수이며;t is an integer from 0 to 3;
    u는 0 내지 2의 정수이며;u is an integer from 0 to 2;
    R5, R6 및 R15는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R5, R6 및 R15 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 5 , R 6 and R 15 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 ~ C 60 aryl phosphazene group, selected from the group consisting arylsilyl a C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining tile adjacent to which they are attached may form a condensed ring , wherein R 5, R 6 and R 15 each, if these are the same or different, and plural individual;
    R7 내지 R12는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;R 7 to R 12 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from an aryl silyl group the group consisting of or of, by combining groups adjacent to form a condensed ring;
    상기 R5 내지 R12 및 R15의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron of R 5 to R 12 and R 15 Group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60, alkyloxy group of C 1 ~ C 40 of the , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group , the group consisting of C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 aryl group in the silyl When substituted with at least one selected more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.
  10. 제9항에 있어서,The method of claim 9,
    상기 화학식 C-1으로 표시되는 치환기는 하기 화학식 D-1 내지 D-3 중 어느 하나로 표시되는, 화합물:The substituent represented by Formula C-1 is represented by any one of the following Formulas D-1 to D-3:
    Figure PCTKR2017011367-appb-I000369
    Figure PCTKR2017011367-appb-I000369
    상기 화학식 D-1 내지 D-3에서, In Chemical Formulas D-1 to D-3,
    *은 결합이 이루어지는 부분을 의미한다* Means part of the combination
  11. 제1항에 있어서,The method of claim 1,
    상기 화합물은 아래의 화합물로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물: The compound is selected from the group consisting of the following compounds:
    Figure PCTKR2017011367-appb-I000370
    Figure PCTKR2017011367-appb-I000370
    Figure PCTKR2017011367-appb-I000371
    Figure PCTKR2017011367-appb-I000371
    Figure PCTKR2017011367-appb-I000372
    Figure PCTKR2017011367-appb-I000372
    Figure PCTKR2017011367-appb-I000373
    Figure PCTKR2017011367-appb-I000373
    Figure PCTKR2017011367-appb-I000374
    Figure PCTKR2017011367-appb-I000374
    Figure PCTKR2017011367-appb-I000375
    Figure PCTKR2017011367-appb-I000375
    Figure PCTKR2017011367-appb-I000376
    Figure PCTKR2017011367-appb-I000376
    Figure PCTKR2017011367-appb-I000377
    Figure PCTKR2017011367-appb-I000377
    Figure PCTKR2017011367-appb-I000378
    Figure PCTKR2017011367-appb-I000378
    Figure PCTKR2017011367-appb-I000379
    Figure PCTKR2017011367-appb-I000379
    Figure PCTKR2017011367-appb-I000380
    Figure PCTKR2017011367-appb-I000380
    Figure PCTKR2017011367-appb-I000381
    Figure PCTKR2017011367-appb-I000381
    Figure PCTKR2017011367-appb-I000382
    Figure PCTKR2017011367-appb-I000382
    Figure PCTKR2017011367-appb-I000383
    Figure PCTKR2017011367-appb-I000383
    Figure PCTKR2017011367-appb-I000384
    Figure PCTKR2017011367-appb-I000384
    Figure PCTKR2017011367-appb-I000385
    Figure PCTKR2017011367-appb-I000385
    Figure PCTKR2017011367-appb-I000386
    Figure PCTKR2017011367-appb-I000386
    Figure PCTKR2017011367-appb-I000387
    Figure PCTKR2017011367-appb-I000387
    Figure PCTKR2017011367-appb-I000388
    Figure PCTKR2017011367-appb-I000388
    Figure PCTKR2017011367-appb-I000389
    Figure PCTKR2017011367-appb-I000389
    Figure PCTKR2017011367-appb-I000390
    Figure PCTKR2017011367-appb-I000390
    Figure PCTKR2017011367-appb-I000391
    Figure PCTKR2017011367-appb-I000391
    Figure PCTKR2017011367-appb-I000392
    Figure PCTKR2017011367-appb-I000392
    Figure PCTKR2017011367-appb-I000393
    Figure PCTKR2017011367-appb-I000393
  12. (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode,
    상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항의 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.At least one of the one or more organic material layer is an organic electroluminescent device, characterized in that it comprises a compound represented by the formula (1) of claim 1.
  13. 제12항에 있어서,The method of claim 12,
    상기 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 전자 수송층, 전자 수송 보조층, 전자 주입층, 수명 개선층, 발광층 및 발광 보조층으로 이루어진 군에서 선택되는 유기 전계 발광 소자.The organic material layer including the compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a life improvement layer, a light emitting layer and a light emitting auxiliary layer.
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