WO2018080066A1 - Organic compound and organic electroluminescent device comprising same - Google Patents

Organic compound and organic electroluminescent device comprising same Download PDF

Info

Publication number
WO2018080066A1
WO2018080066A1 PCT/KR2017/011366 KR2017011366W WO2018080066A1 WO 2018080066 A1 WO2018080066 A1 WO 2018080066A1 KR 2017011366 W KR2017011366 W KR 2017011366W WO 2018080066 A1 WO2018080066 A1 WO 2018080066A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
aryl
synthesis
alkyl
synthesis example
Prior art date
Application number
PCT/KR2017/011366
Other languages
French (fr)
Korean (ko)
Inventor
김충한
손효석
Original Assignee
주식회사 두산
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 두산 filed Critical 주식회사 두산
Publication of WO2018080066A1 publication Critical patent/WO2018080066A1/en

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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 2 ), C (Ar 3 ) (Ar 4 ) and Si (Ar 5 ) (Ar 6 );
  • Rings A and B are each independently selected from the group consisting of C 6 ⁇ C 30 arene and 5 to 30 heteroarenes of nuclear atoms;
  • L 1 is 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 o are each independently an integer from 0 to 4.
  • n are each independently an integer from 0 to 2;
  • 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 6 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 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
  • 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 2 ), C (Ar 3 ) (Ar 4 ) and Si (Ar 5 ) (Ar 6 );
  • Rings A and B are each independently selected from the group consisting of C 6 ⁇ C 30 arene and 5 to 30 heteroarenes of nuclear atoms;
  • L 1 is 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 o are each independently an integer from 0 to 4.
  • n are each independently an integer from 0 to 2;
  • 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 6 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 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
  • 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 2 ), C (Ar 3 ) (Ar 4 ) and Si (Ar 5 ) (Ar 6 );
  • Rings A and B are each independently selected from the group consisting of C 6 ⁇ C 30 arene and 5 to 30 heteroarenes of nuclear atoms;
  • L 1 is 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 o are each independently an integer from 0 to 4.
  • n are each independently an integer from 0 to 2;
  • 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 6 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 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
  • the novel compound provided in the present invention forms a basic skeleton by combining xanthene moiety with 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.
  • the conventional organic electroluminescent device material for example, 4,4-dicarbazolylbiphenyl (hereinafter referred to as 'CBP')
  • 'CBP' 4,4-dicarbazolylbiphenyl
  • 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 of the present invention has a higher triplet energy, a specific substituent is introduced into the basic skeleton condensed with a broad singlet energy level and a high triplet energy level, the energy level is higher than the dopant It can be adjusted and 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.
  • 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 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 the formula 1 of the present invention is introduced into the various skeleton, especially the aryl group and / or heteroaryl group in the basic skeleton significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, thereby It may have higher thermal stability than conventional light emitting materials (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.
  • the ring A and B may be independently represented by any one of the following Formulas 2 to 4:
  • the dotted line means the part where condensation takes place.
  • At least one of the rings A and B is represented by the formula (3) or 4, it is preferable to lower the driving voltage and increase the luminous efficiency.
  • the compound may be represented by any one of the following Formulas 5 to 12.
  • X, Ar 1 , L 1 , R 1 , R 4 , l and o are each as defined in Chemical Formula 1.
  • the compound is particularly preferably a compound represented by any one of Formulas 7 to 12, it is preferable to lower the driving voltage and increase the luminous efficiency.
  • L 1 may be a single bond or a linker represented by any one of the following Formulas A-1 to A-3:
  • Ar 1 may be a substituent represented by the following formula (13):
  • Z 1 to Z 5 are each independently N or C (R 5 );
  • R 5 is 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, nuclear atom 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C An alkylsilyl group of 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkyl boron group of C 1 to C 40, an aryl boron group of C 6 to C 60 , an arylphosphanyl group of C 6 to C 60 , C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 arylamine group selected from the group consisting of, or combine with adjacent groups to form a condensed
  • R 5 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 5 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 13 may be a substituent represented by the following Formula 14:
  • R 6 and R 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
  • 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 R 6 and R 7 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 Chemical Formula 13.
  • Ar 1 may be a substituent represented by Formula 15:
  • R 8 and R 9 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
  • R 8 and R 9 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 8 and R 9 may be independently selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group and a fluorenyl group.
  • Ar 1 may be a substituent represented by any one of the following Formulas B-1 to B-8:
  • Z 5 to Z 12 are each independently N or C (R 12 );
  • Any one of Z 5 to Z 8 bonded to L 1 in Formula B-1 is C (R 12 ), wherein R 12 is absent;
  • T 1 and T 2 are each independently selected from the group consisting of a single bond, C (R 13 ) (R 14 ), N (R 15 ), O and S, but not both T 1 and T 2 are single bonds;
  • q and r are each independently integers of 0 to 4.
  • R 10 and R 11 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 12 to R 15 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 10 to R 15 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
  • Ar 1 may be a substituent represented by any one of the following Formulas C-1 to C-14:
  • q, r and s are each independently integers of 0 to 4.
  • R 10 , R 11 and R 16 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 12 to R 15 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
  • 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 10 to R 16 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 10 to R 16 are each independently selected from a C 1 to C 30 alkyl group, C 6 to C 30 aryl group and a nuclear atom of 5 to 30 heteroaryl group in the group Can be selected.
  • R 10 to R 16 may be each independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.
  • R 13 and R 14 may be each independently selected from the group consisting of hydrogen, C 1 ⁇ C 30 Alkyl group and C 6 ⁇ C 30 An aryl group.
  • R 13 and R 14 may be each independently selected from the group consisting of hydrogen, methyl group, ethyl group, butyl group and phenyl group.
  • Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
  • 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 xanthene moiety with 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.
  • the conventional organic electroluminescent device material for example, 4,4-dicarbazolylbiphenyl (hereinafter referred to as 'CBP')
  • 'CBP' 4,4-dicarbazolylbiphenyl
  • 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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Optics & Photonics (AREA)

Abstract

The present invention relates to a new compound and an organic electroluminescent device comprising the same. As the compound according to the present invention is used for an organic layer of an organic electroluminescent device, and preferably for a luminescent layer, an electron transfer layer, or a hole transfer layer, it is possible to improve the luminous efficiency, driving voltage, lifespan, etc. of the organic electroluminescent device.

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 PCTKR2017011366-appb-I000001
Figure PCTKR2017011366-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 구동전압과 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 PCTKR2017011366-appb-I000002
Figure PCTKR2017011366-appb-I000002
상기 화학식 1에서, In Chemical Formula 1,
X는 O, S, Se, N(Ar2), C(Ar3)(Ar4) 및 Si(Ar5)(Ar6)로 구성된 군으로부터 선택되고;X is selected from the group consisting of O, S, Se, N (Ar 2 ), C (Ar 3 ) (Ar 4 ) and Si (Ar 5 ) (Ar 6 );
환 A 및 B는 각각 독립적으로 각각 독립적으로 C6~C30의 아렌 및 핵원자수 5 내지 30개의 헤테로아렌으로 이루어진 군에서 선택되며;Rings A and B are each independently selected from the group consisting of C 6 ~ C 30 arene and 5 to 30 heteroarenes of nuclear atoms;
L1은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고;L 1 is 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 o는 각각 독립적으로 0 내지 4의 정수이며;l and o are each independently an integer from 0 to 4;
m 및 n은 각각 독립적으로 0 내지 2의 정수이며;m and n are each independently an integer from 0 to 2;
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 Ar6는 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 6 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 의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 내지 Ar6 및 R1 내지 R4의 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 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group and cycloalkyl group of Ar 1 to Ar 6 and R 1 to R 4 , 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 An aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atoms 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono- or dia rilpo of If blood group and a C 6 ~ substituted by one or more substituents selected from the group consisting of C 60 or silyl aryl is unsubstituted, substituted by a plurality of substituents, 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 PCTKR2017011366-appb-I000003
Figure PCTKR2017011366-appb-I000003
상기 화학식 1에서, In Chemical Formula 1,
X는 O, S, Se, N(Ar2), C(Ar3)(Ar4) 및 Si(Ar5)(Ar6)로 구성된 군으로부터 선택되고;X is selected from the group consisting of O, S, Se, N (Ar 2 ), C (Ar 3 ) (Ar 4 ) and Si (Ar 5 ) (Ar 6 );
환 A 및 B는 각각 독립적으로 각각 독립적으로 C6~C30의 아렌 및 핵원자수 5 내지 30개의 헤테로아렌으로 이루어진 군에서 선택되며;Rings A and B are each independently selected from the group consisting of C 6 ~ C 30 arene and 5 to 30 heteroarenes of nuclear atoms;
L1은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고;L 1 is 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 o는 각각 독립적으로 0 내지 4의 정수이며;l and o are each independently an integer from 0 to 4;
m 및 n은 각각 독립적으로 0 내지 2의 정수이며;m and n are each independently an integer from 0 to 2;
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 Ar6는 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 6 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 의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 내지 Ar6 및 R1 내지 R4의 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 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group and cycloalkyl group of Ar 1 to Ar 6 and R 1 to R 4 , 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 An aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atoms 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono- or dia rilpo of If blood group and a C 6 ~ substituted by one or more substituents selected from the group consisting of C 60 or silyl aryl is unsubstituted, substituted by a plurality of substituents, 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 PCTKR2017011366-appb-I000004
Figure PCTKR2017011366-appb-I000004
상기 화학식 1에서, In Chemical Formula 1,
X는 O, S, Se, N(Ar2), C(Ar3)(Ar4) 및 Si(Ar5)(Ar6)로 구성된 군으로부터 선택되고;X is selected from the group consisting of O, S, Se, N (Ar 2 ), C (Ar 3 ) (Ar 4 ) and Si (Ar 5 ) (Ar 6 );
환 A 및 B는 각각 독립적으로 각각 독립적으로 C6~C30의 아렌 및 핵원자수 5 내지 30개의 헤테로아렌으로 이루어진 군에서 선택되며;Rings A and B are each independently selected from the group consisting of C 6 ~ C 30 arene and 5 to 30 heteroarenes of nuclear atoms;
L1은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고;L 1 is 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 o는 각각 독립적으로 0 내지 4의 정수이며;l and o are each independently an integer from 0 to 4;
m 및 n은 각각 독립적으로 0 내지 2의 정수이며;m and n are each independently an integer from 0 to 2;
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 Ar6는 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 6 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 의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 내지 Ar6 및 R1 내지 R4의 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 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group and cycloalkyl group of Ar 1 to Ar 6 and R 1 to R 4 , 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 An aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atoms 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono- or dia rilpo of If blood group and a C 6 ~ substituted by one or more substituents selected from the group consisting of C 60 or silyl aryl is unsubstituted, substituted by a plurality of substituents, they may be the same or different from each other.
본 발명에서 제공하는 신규 화합물은 카바졸에 크산텐 모이어티(Xanthene moiety)가 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 xanthene moiety with 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.
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. 본 발명의 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 of the present invention has a higher triplet energy, a specific substituent is introduced into the basic skeleton condensed with a broad singlet energy level and a high triplet energy level, the energy level is higher than the dopant It can be adjusted and 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, 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, 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, 본 발명의 상기 화학식 1의 화합물은 상기 기본 골격에 다양한 치환기, 특히 아릴기 및/또는 헤테로아릴기가 도입되어 화합물의 분자량이 유의적으로 증대됨으로써, 유리 전이온도가 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 the formula 1 of the present invention is introduced into the various skeleton, especially the aryl group and / or heteroaryl group in the basic skeleton significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, thereby It may have higher thermal stability than conventional light emitting materials (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 환 A 및 B는 각각 독립적으로 하기 화학식 2 내지 4 중 어느 하나로 표시될 수 있다:According to a preferred embodiment of the present invention, the ring A and B may be independently represented by any one of the following Formulas 2 to 4:
[화학식 2][Formula 2]
Figure PCTKR2017011366-appb-I000005
Figure PCTKR2017011366-appb-I000005
[화학식 3][Formula 3]
Figure PCTKR2017011366-appb-I000006
Figure PCTKR2017011366-appb-I000006
[화학식 4][Formula 4]
Figure PCTKR2017011366-appb-I000007
Figure PCTKR2017011366-appb-I000007
상기 화학식 2 내지 4에서,In Chemical Formulas 2 to 4,
점선은 축합이 이루어지는 부분을 의미한다.The dotted line means the part where condensation takes place.
본 발명의 바람직한 한 구현 예에 따르면, 상기 환 A 및 B 중 적어도 하나는 상기 화학식 3 또는 4로 표시되는 것이, 구동 전압을 낮추고 발광 효율을 높일 수 있어 바람직하다. According to one preferred embodiment of the present invention, at least one of the rings A and B is represented by the formula (3) or 4, it is preferable to lower the driving voltage and increase the luminous efficiency.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화합물은 하기 화학식 5 내지 12 중 어느 하나로 표시될 수 있다. According to one preferred embodiment of the present invention, the compound may be represented by any one of the following Formulas 5 to 12.
[화학식 5][Formula 5]
Figure PCTKR2017011366-appb-I000008
Figure PCTKR2017011366-appb-I000008
[화학식 6][Formula 6]
Figure PCTKR2017011366-appb-I000009
Figure PCTKR2017011366-appb-I000009
[화학식 7][Formula 7]
Figure PCTKR2017011366-appb-I000010
Figure PCTKR2017011366-appb-I000010
[화학식 8][Formula 8]
Figure PCTKR2017011366-appb-I000011
Figure PCTKR2017011366-appb-I000011
[화학식 9][Formula 9]
Figure PCTKR2017011366-appb-I000012
Figure PCTKR2017011366-appb-I000012
[화학식 10][Formula 10]
Figure PCTKR2017011366-appb-I000013
Figure PCTKR2017011366-appb-I000013
[화학식 11][Formula 11]
Figure PCTKR2017011366-appb-I000014
Figure PCTKR2017011366-appb-I000014
[화학식 12][Formula 12]
Figure PCTKR2017011366-appb-I000015
Figure PCTKR2017011366-appb-I000015
상기 화학식 5 내지 12에서, In Chemical Formulas 5 to 12,
X, Ar1, L1, R1, R4, l 및 o 각각은 상기 화학식 1에서 정의된 바와 같다. X, Ar 1 , L 1 , R 1 , R 4 , l and o are each as defined in Chemical Formula 1.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화합물은 특히 상기 화학식 7 내지 12 중 어느 하나로 표시되는 화합물인 것이, 구동 전압을 낮추고 발광 효율을 높일 수 있어 바람직하다. According to one preferred embodiment of the present invention, the compound is particularly preferably a compound represented by any one of Formulas 7 to 12, it is preferable to lower the driving voltage and increase the luminous efficiency.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L1은 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 1 may be a single bond or a linker represented by any one of the following Formulas A-1 to A-3:
Figure PCTKR2017011366-appb-I000016
Figure PCTKR2017011366-appb-I000016
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 Ar1은 하기 화학식 13으로 표시되는 치환기일 수 있다:According to one preferred embodiment of the present invention, Ar 1 may be a substituent represented by the following formula (13):
[화학식 13][Formula 13]
Figure PCTKR2017011366-appb-I000017
Figure PCTKR2017011366-appb-I000017
상기 화학식 13에서,In Chemical Formula 13,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
Z1 내지 Z5는 각각 독립적으로 N 또는 C(R5)이며;Z 1 to Z 5 are each independently N or C (R 5 );
R5는 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 R5가 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 5 is 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, nuclear atom 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C An alkylsilyl group of 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkyl boron group of C 1 to C 40, an aryl boron group of C 6 to C 60 , an arylphosphanyl group of C 6 to C 60 , C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylamine group selected from the group consisting of, or combine with adjacent groups to form a condensed ring, when there are a plurality of R 5 They are the same as each other Or different;
상기 R5의 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 상이하다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R 5 , heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group and 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, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, 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, C 6 ~ C 60 the arylboronic group, one member selected from the group consisting of C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl group in the silyl Substituted with a substituent being unsubstituted or, if substituted by a plurality of substituents, they are same as or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R5는 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 5 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 R5는 페닐기, 비페닐기, 나프탈레닐기, 피리디닐기, 피리미디닐기 및 트리아지닐기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 5 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 13으로 표시되는 치환기는 하기 화학식 14로 표시되는 치환기일 수 있다:According to one preferred embodiment of the present invention, the substituent represented by Formula 13 may be a substituent represented by the following Formula 14:
[화학식 14][Formula 14]
Figure PCTKR2017011366-appb-I000018
Figure PCTKR2017011366-appb-I000018
상기 화학식 14에서,In Chemical Formula 14,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
R6 및 R7은 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 6 and R 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 R6 및 R7의 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;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 R 6 and R 7 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 blood group and a C 6 ~ C 60 aryl silyl group selected from the group consisting of 1 When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other;
Z1, Z3 및 Z5 각각은 상기 화학식 13에서 정의된 바와 같다. Z 1 , Z 3 and Z 5 are each as defined in Chemical Formula 13.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1은 하기 화학식 15로 표시되는 치환기일 수 있다:According to one preferred embodiment of the present invention, Ar 1 may be a substituent represented by Formula 15:
[화학식 15][Formula 15]
Figure PCTKR2017011366-appb-I000019
Figure PCTKR2017011366-appb-I000019
상기 화학식 15에서, In Chemical Formula 15,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
R8 및 R9는 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 8 and R 9 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 R8 및 R9의 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 상이하다. 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 R 8 and R 9 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 blood group and a C 6 ~ C 60 aryl silyl group selected from the group consisting of 1 When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R8 및 R9는 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 8 and R 9 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 R8 및 R9는 각각 독립적으로 페닐기, 비페닐기, 나프탈레닐기 및 플루오레닐기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 8 and R 9 may be independently selected from the group consisting of a phenyl group, a biphenyl group, a naphthalenyl group and a fluorenyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1은 하기 화학식 B-1 내지 B-8 중 어느 하나로 표시되는 치환기일 수 있다:According to one preferred embodiment of the present invention, Ar 1 may be a substituent represented by any one of the following Formulas B-1 to B-8:
Figure PCTKR2017011366-appb-I000020
Figure PCTKR2017011366-appb-I000020
상기 화학식 B-1 내지 B-8에서, In Chemical Formulas B-1 to B-8,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
Z5 내지 Z12는 각각 독립적으로 N 또는 C(R12)이며;Z 5 to Z 12 are each independently N or C (R 12 );
상기 화학식 B-1에서 L1에 결합되는 Z5 내지 Z8 중 어느 하나는 C(R12)이고, 이때 상기 R12는 부재이며;Any one of Z 5 to Z 8 bonded to L 1 in Formula B-1 is C (R 12 ), wherein R 12 is absent;
T1 및 T2는 각각 독립적으로 단일결합, C(R13)(R14), N(R15), 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 13 ) (R 14 ), N (R 15 ), O and S, but not both T 1 and T 2 are single bonds;
q 및 r은 각각 독립적으로 0 내지 4의 정수이며;q and r are each independently integers of 0 to 4;
R10 및 R11은 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 R10 및 R11 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 10 and R 11 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 there are a plurality of each of 10 and R 11 , they are the same as or different from each other;
R12 내지 R15는 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 R12 내지 R15 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 12 to R 15 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 12 to R 15 is plural, they are the same as or different from each other;
상기 R10 내지 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 group, aryl of the above R 10 to R 15 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 When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1은 하기 화학식 C-1 내지 C-14 중 어느 하나로 표시되는 치환기일 수 있다:According to one preferred embodiment of the present invention, Ar 1 may be a substituent represented by any one of the following Formulas C-1 to C-14:
Figure PCTKR2017011366-appb-I000021
Figure PCTKR2017011366-appb-I000021
상기 화학식 C-1 내지 C-14에서, In Chemical Formulas C-1 to C-14,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
q, r 및 s는 각각 독립적으로 0 내지 4의 정수이며;q, r and s are each independently integers of 0 to 4;
R10, R11 및 R16은 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 R10, R11 및 R18 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 10 , R 11 and R 16 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 When R 10 , R 11 and R 18 are each plural, they are the same as or different from each other;
R12 내지 R15는 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 12 to R 15 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 R10 내지 R16의 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 10 to R 16 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 When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10 내지 R16은 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 10 to R 16 are each independently selected from a C 1 to C 30 alkyl group, C 6 to C 30 aryl group and a nuclear atom of 5 to 30 heteroaryl group in the group Can be selected.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10 내지 R16은 각각 독립적으로 페닐기, 비페닐기 및 나프탈레닐기로 이루어진 군에서 선택될 수 있다.According to one preferred embodiment of the present invention, R 10 to R 16 may be each independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R13 및 R14는 각각 독립적으로 수소, C1~C30의 알킬기 및 C6~C30의 아릴기로 이루어진 군에서 선택될 수 있다.According to one preferred embodiment of the present invention, R 13 and R 14 may be each 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 R13 및 R14는 각각 독립적으로 수소, 메틸기, 에틸기, 부틸기 및 페닐기로 이루어진 군에서 선택될 수 있다.According to one preferred embodiment of the present invention, R 13 and R 14 may be each independently selected from the group consisting of hydrogen, methyl group, ethyl group, butyl group and phenyl group.
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:
Figure PCTKR2017011366-appb-I000022
Figure PCTKR2017011366-appb-I000022
Figure PCTKR2017011366-appb-I000023
Figure PCTKR2017011366-appb-I000023
Figure PCTKR2017011366-appb-I000024
Figure PCTKR2017011366-appb-I000024
Figure PCTKR2017011366-appb-I000025
Figure PCTKR2017011366-appb-I000025
Figure PCTKR2017011366-appb-I000026
Figure PCTKR2017011366-appb-I000026
Figure PCTKR2017011366-appb-I000027
Figure PCTKR2017011366-appb-I000027
Figure PCTKR2017011366-appb-I000028
Figure PCTKR2017011366-appb-I000028
Figure PCTKR2017011366-appb-I000029
Figure PCTKR2017011366-appb-I000029
Figure PCTKR2017011366-appb-I000030
Figure PCTKR2017011366-appb-I000030
Figure PCTKR2017011366-appb-I000031
Figure PCTKR2017011366-appb-I000031
Figure PCTKR2017011366-appb-I000032
Figure PCTKR2017011366-appb-I000032
Figure PCTKR2017011366-appb-I000033
Figure PCTKR2017011366-appb-I000033
Figure PCTKR2017011366-appb-I000034
Figure PCTKR2017011366-appb-I000034
Figure PCTKR2017011366-appb-I000035
Figure PCTKR2017011366-appb-I000035
Figure PCTKR2017011366-appb-I000036
Figure PCTKR2017011366-appb-I000036
Figure PCTKR2017011366-appb-I000037
Figure PCTKR2017011366-appb-I000037
Figure PCTKR2017011366-appb-I000038
Figure PCTKR2017011366-appb-I000038
Figure PCTKR2017011366-appb-I000039
Figure PCTKR2017011366-appb-I000039
Figure PCTKR2017011366-appb-I000040
Figure PCTKR2017011366-appb-I000040
Figure PCTKR2017011366-appb-I000041
Figure PCTKR2017011366-appb-I000041
Figure PCTKR2017011366-appb-I000042
Figure PCTKR2017011366-appb-I000042
Figure PCTKR2017011366-appb-I000043
Figure PCTKR2017011366-appb-I000043
Figure PCTKR2017011366-appb-I000044
Figure PCTKR2017011366-appb-I000044
Figure PCTKR2017011366-appb-I000045
Figure PCTKR2017011366-appb-I000045
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 전계 발광 소자2. Organic electroluminescent device
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 크산텐 모이어티(Xanthene moiety)가 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 xanthene moiety with 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]
3-(3- ( 스피로Spiro [[ 플루오렌Fluorene -9,9'-크산텐]-3-일)-9H--9,9'-xanthene] -3-yl) -9H- 카바졸의Carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000046
Figure PCTKR2017011366-appb-I000046
14,4,5,5-테트라메틸-2-(스피로[플루오렌-9,9'-크산텐]-3-일)-1,3,2-디옥사보로란 10g(21.8mmol)과 3-브로모-9H-카바졸 4.47g (18.18mmol)에 자일렌 250 mL를 가하였다. Pd(PPh3)4 1.25g (1.09mmol), K2CO3 7.53g (54.5mmol)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 7.4g(수율 82%)을 얻었다. 10 g (21.8 mmol) of 14,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-xanthene] -3-yl) -1,3,2-dioxaborolane and To 4.47 g (18.18 mmol) of 3-bromo-9H-carbazole was added 250 mL of xylene. Pd (PPh 3 ) 4 1.25 g (1.09 mmol) and 7.53 g (54.5 mmol) K 2 CO 3 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 7.4 g (yield 82%) of the title compound.
1H-NMR: δ 11.66 (br, 1H), 8.19~8.18(m, 2H), 7.99~7.90(m, 3H), 7.77~7.5(m, 5H), 7.31~7.17(m, 9H), 7.01(m, 2H); 1 H-NMR: δ 11.66 (br, 1H), 8.19-8.18 (m, 2H), 7.99-7.90 (m, 3H), 7.77-7.5 (m, 5H), 7.31-7.17 (m, 9H), 7.01 (m, 2H);
GC-Mass (이론치: 497.60 g/mol, 측정치: 497.18 g/mol)GC-Mass (Theoretical value: 497.60 g / mol, Measured value: 497.18 g / mol)
[[ 준비예Preparation 2] 2]
3-(3- ( 스피로Spiro [[ 플루오렌Fluorene -9,9'-크산텐]-2-일)-9H--9,9'-xanthene] -2-yl) -9H- 카바졸의Carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000047
Figure PCTKR2017011366-appb-I000047
반응물로 14,4,5,5-테트라메틸-2-(스피로[플루오렌-9,9'-크산텐]-2-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 497.18Except for using 14,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-xanthene] -2-yl) -1,3,2-dioxaborolane as reactant Then, the same procedure as in [Preparation Example 1], to obtain 6.9 g of the target compound. HRMS [M] +: 497.18
[[ 준비예Preparation 3] 3]
3-(3- ( 스피로Spiro [[ 플루오렌Fluorene -9,9'--9,9'- 티오크산텐Thioxanthene ]-3-일)-9H-] -3-yl) -9H- 카바졸의Carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000048
Figure PCTKR2017011366-appb-I000048
반응물로 4,4,5,5-테트라메틸-2-(스피로[플루오렌-9,9'-티오크산텐]-3-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 513.66 4,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-thioxanthene] -3-yl) -1,3,2-dioxaborolane as the reactant Except for [Preparation Example 1], to give the target compound 6.5g; HRMS [M] +: 513.66
[[ 준비예Preparation 4] 4]
3-(3- ( 스피로Spiro [[ 플루오렌Fluorene -9,9'--9,9'- 티오크산텐Thioxanthene ]-2-일)-9H-] -2-yl) -9H- 카바졸의Carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000049
Figure PCTKR2017011366-appb-I000049
반응물로 4,4,5,5-테트라메틸-2-(스피로[플루오렌-9,9'-티오크산텐]-2-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 513.66 4,4,5,5-tetramethyl-2- (spiro [fluorene-9,9'-thioxanthene] -2-yl) -1,3,2-dioxaborolane as the reactant Except for the same procedure as in [Preparation Example 1], 7.1g of the target compound was obtained. HRMS [M] +: 513.66
[[ 준비예Preparation 5] 5]
3'-(9H-3 '-(9H- 카바졸Carbazole -3-일)-10-페닐-10H--3-yl) -10-phenyl-10H- 스피로[아크리딘-9,9'-플루오렌]의Of spiro [acridin-9,9'-fluorene] 합성 synthesis
Figure PCTKR2017011366-appb-I000050
Figure PCTKR2017011366-appb-I000050
반응물로 10-페닐-3'-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-10H-스피로[아크리딘-9,9'-플루오렌]을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 7.7g을 얻었다.; HRMS [M]+: 572.7110-phenyl-3 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -10H-spiro [acridin-9,9' as reactant 7.7 g of the target compound was obtained by the same procedure as the [Preparation Example 1] except that [Fluorene] was used .; HRMS [M] +: 572.71
[[ 준비예Preparation 6] 6]
3'-(9H-3 '-(9H- 카바졸Carbazole -3-일)-10-페닐-10H--3-yl) -10-phenyl-10H- 스피로[아크리딘-9,9'-플루오렌]의Of spiro [acridin-9,9'-fluorene] 합성 synthesis
Figure PCTKR2017011366-appb-I000051
Figure PCTKR2017011366-appb-I000051
반응물로 10-페닐-2'-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-10H-스피로[아크리딘-9,9'-플루오렌]을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 572.7110-phenyl-2 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -10H-spiro [acridin-9,9' as reactant 7.0 g of the target compound was obtained by the same procedure as in [Preparation Example 1], except that -fluorene] was used; HRMS [M] +: 572.71
[[ 준비예Preparation 7] 7]
10-(10- ( 스피로Spiro [[ 플루오렌Fluorene -9,9'-크산텐]-3-일)-7H--9,9'-xanthene] -3-yl) -7H- 벤조[c]카바졸의Of benzo [c] carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000052
Figure PCTKR2017011366-appb-I000052
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 547.66Except that 10-bromo-7H-benzo [c] carbazole was used as a reaction, the same procedure as in [Preparation Example 1] was carried out to obtain 7.0 g of the target compound. HRMS [M] +: 547.66
[[ 준비예Preparation 8] 8]
10-(10- ( 스피로Spiro [[ 플루오렌Fluorene -9,9'-크산텐]-2-일)-7H--9,9'-xanthene] -2-yl) -7H- 벤조[c]카바졸의Of benzo [c] carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000053
Figure PCTKR2017011366-appb-I000053
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 2]과 동일한 과정을 수행하여 목적 화합물 7.2g을 얻었다.; HRMS [M]+: 547.667.2 g of the target compound were obtained in the same manner as in [Preparation Example 2], except that 10-bromo-7H-benzo [c] carbazole was used as the reactant. HRMS [M] +: 547.66
[[ 준비예Preparation 9] 9]
3-(3- ( 스피로Spiro [[ 플루오렌Fluorene -9,9'--9,9'- 티오크산텐Thioxanthene ]-3-일)-9H-] -3-yl) -9H- 벤조[c]카바졸의Of benzo [c] carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000054
Figure PCTKR2017011366-appb-I000054
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 3]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 563.727.1 g of the target compound was obtained in the same manner as the [Preparation Example 3], except that 10-bromo-7H-benzo [c] carbazole was used as the reactant. HRMS [M] +: 563.72
[[ 준비예Preparation 10] 10]
3-(3- ( 스피로Spiro [[ 플루오렌Fluorene -9,9'--9,9'- 티오크산텐Thioxanthene ]-2-일)-9H-] -2-yl) -9H- 벤조[c]카바졸의Of benzo [c] carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000055
Figure PCTKR2017011366-appb-I000055
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 4]과 동일한 과정을 수행하여 목적 화합물 7.0g을 얻었다.; HRMS [M]+: 563.72Except that 10-bromo-7H-benzo [c] carbazole was used as a reaction, the same procedure as in [Preparation Example 4] was carried out to obtain 7.0 g of the target compound. HRMS [M] +: 563.72
[준비예 11]Preparation Example 11
3'-(7H-3 '-(7H- 벤조[c]카바졸Benzo [c] carbazole -10-일)-10-페닐-10H--10-yl) -10-phenyl-10H- 스피로[아크리딘-9,9'-플루오렌]Spiro [Acridin-9,9'-fluorene] 의 합성Synthesis of
Figure PCTKR2017011366-appb-I000056
Figure PCTKR2017011366-appb-I000056
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 5]과 동일한 과정을 수행하여 목적 화합물 7.8g을 얻었다.; HRMS [M]+: 622.77 Except that 10-bromo-7H-benzo [c] carbazole was used as a reaction, the same procedure as in [Preparation Example 5] was carried out to obtain 7.8 g of the target compound. HRMS [M] +: 622.77
[준비예 12]Preparation Example 12
3'-(9H-3 '-(9H- 벤조[c]카바졸Benzo [c] carbazole -3-일)-10-페닐-10H--3-yl) -10-phenyl-10H- 스피로[아크리딘-9,9'-플루오렌]의Of spiro [acridin-9,9'-fluorene] 합성 synthesis
Figure PCTKR2017011366-appb-I000057
Figure PCTKR2017011366-appb-I000057
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 6]과 동일한 과정을 수행하여 목적 화합물 7.5g을 얻었다.; HRMS [M]+: 622.777.5 g of the target compound was obtained in the same manner as the [Preparation Example 6], except that 10-bromo-7H-benzo [c] carbazole was used as the reactant. HRMS [M] +: 622.77
[[ 준비예Preparation 13] 13]
3-(3- ( 스피로Spiro [[ 벤조[c]플루오렌Benzo [c] fluorene -7,9'-크산텐]-10-일)-9H--7,9'-xanthene] -10-yl) -9H- 카바졸의Carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000058
Figure PCTKR2017011366-appb-I000058
반응물로 4,4,5,5-테트라메틸-2-(스피로[벤조[c]플루오렌-7,9'-크산텐]-10-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 547.664,4,5,5-tetramethyl-2- (spiro [benzo [c] fluorene-7,9'-xanthene] -10-yl) -1,3,2-dioxaborolane as reactant Except for using the same procedure as in [Preparation Example 1] to obtain the target compound 6.6g; HRMS [M] +: 547.66
[[ 준비예Preparation 14] 14]
3-(3- ( 스피로Spiro [[ 벤조[c]플루오렌Benzo [c] fluorene -7,9'-크산텐]-9-일)-9H--7,9'-xanthene] -9-yl) -9H- 카바졸의Carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000059
Figure PCTKR2017011366-appb-I000059
반응물로 4,4,5,5-테트라메틸-2-(스피로[벤조[c]플루오렌-7,9'-크산텐]-9-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 2]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 547.664,4,5,5-tetramethyl-2- (spiro [benzo [c] fluorene-7,9'-xanthene] -9-yl) -1,3,2-dioxaborolane as reactant Except for using the same procedure as in [Preparation Example 2] to give the desired compound 6.4g; HRMS [M] +: 547.66
[[ 준비예Preparation 15] 15]
3-(3- ( 스피로Spiro [[ 벤조[c]플루오렌Benzo [c] fluorene -7,9'--7,9'- 티오크산텐Thioxanthene ]-10-일)-9H-] -10-Sun) -9H- 카바졸의Carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000060
Figure PCTKR2017011366-appb-I000060
반응물로 4,4,5,5-테트라메틸-2-(스피로[벤조[c]플루오렌-7,9'-티오크산텐]-10-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 3]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 563.72 4,4,5,5-tetramethyl-2- (spiro [benzo [c] fluorene-7,9'-thioxanthene] -10-yl) -1,3,2-dioxaboro as reactant Except for using the column, the same procedure as in [Preparation Example 3], to obtain 6.9 g of the target compound; HRMS [M] +: 563.72
[[ 준비예Preparation 16] 16]
3-(3- ( 스피로Spiro [[ 벤조[c]플루오렌Benzo [c] fluorene -7,9'--7,9'- 티오크산텐Thioxanthene ]-9-일)-9H-] -9-Sun) -9H- 카바졸의Carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000061
Figure PCTKR2017011366-appb-I000061
반응물로 4,4,5,5-테트라메틸-2-(스피로[벤조[c]플루오렌-7,9'-티오크산텐]-9-일)-1,3,2-디옥사보로란을 사용한 것을 제외하고는 [준비예 4]과 동일한 과정을 수행하여 목적 화합물 7.5g을 얻었다.; HRMS [M]+: 563.72 4,4,5,5-tetramethyl-2- (spiro [benzo [c] fluorene-7,9'-thioxanthene] -9-yl) -1,3,2-dioxaboro as reactant Except for using the column, the same procedure as in [Preparation 4] was carried out to obtain 7.5 g of the target compound. HRMS [M] +: 563.72
[준비예 17]Preparation 17
10'-(9H-10 '-(9H- 카바졸Carbazole -3-일)-10-페닐-10H--3-yl) -10-phenyl-10H- 스피로[아크리딘-9,7'-벤조[c]플루오렌]의Of spiro [acridin-9,7'-benzo [c] fluorene] 합성 synthesis
Figure PCTKR2017011366-appb-I000062
Figure PCTKR2017011366-appb-I000062
반응물로 10-페닐-10'-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-10H-스피로[아크리딘-9,7'-벤조[c]플루오렌]을 사용한 것을 제외하고는 [준비예 5]과 동일한 과정을 수행하여 목적 화합물 7.8g을 얻었다.; HRMS [M]+: 622.77 10-phenyl-10 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -10H-spiro [acridin-9,7' as reactant 7.8 g of the target compound were obtained in the same manner as the [Preparation Example 5] except that -benzo [c] fluorene] was used; HRMS [M] +: 622.77
[준비예 18]Preparation 18
9'-(9H-9 '-(9H- 카바졸Carbazole -3-일)-10-페닐-10H--3-yl) -10-phenyl-10H- 스피로[아크리딘-9,7'-벤조[c]플루오렌]의Of spiro [acridin-9,7'-benzo [c] fluorene] 합성 synthesis
Figure PCTKR2017011366-appb-I000063
Figure PCTKR2017011366-appb-I000063
반응물로 10-페닐-9'-(4,4,5,5-테트라메틸-1,3,2-디옥사보로란-2-일)-10H-스피로[아크리딘-9,7'-벤조[c]플루오렌]을 사용한 것을 제외하고는 [준비예 6]과 동일한 과정을 수행하여 목적 화합물 7.5g을 얻었다.; HRMS [M]+: 622.7710-phenyl-9 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -10H-spiro [acridin-9,7' as reactant 7.5 g of the target compound were obtained in the same manner as in [Preparation Example 6], except that -benzo [c] fluorene] was used; HRMS [M] +: 622.77
[[ 준비예Preparation 19] 19]
10-(10- ( 스피로Spiro [[ 벤조[c]플루오렌Benzo [c] fluorene -7,9'-크산텐]-10-일)-7H--7,9'-xanthene] -10-yl) -7H- 벤조[c]카바졸의Of benzo [c] carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000064
Figure PCTKR2017011366-appb-I000064
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 13]과 동일한 과정을 수행하여 목적 화합물 7.59g을 얻었다.; HRMS [M]+: 597.727.59 g of the target compound was obtained in the same manner as the [Preparation Example 13], except that 10-bromo-7H-benzo [c] carbazole was used as the reactant. HRMS [M] +: 597.72
[[ 준비예Preparation 20] 20]
10-(10- ( 스피로Spiro [[ 벤조[c]플루오렌Benzo [c] fluorene -7,9'-크산텐]-9-일)-7H--7,9'-xanthene] -9-yl) -7H- 벤조[c]카바졸의Of benzo [c] carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000065
Figure PCTKR2017011366-appb-I000065
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 14]과 동일한 과정을 수행하여 목적 화합물 7.9g을 얻었다.; HRMS [M]+: 597.727.9 g of the title compound was obtained in the same manner as the [Preparation Example 14], except that 10-bromo-7H-benzo [c] carbazole was used as the reactant. HRMS [M] +: 597.72
[준비예 21]Preparation Example 21
10-(10- ( 스피로Spiro [[ 벤조[c]플루오렌Benzo [c] fluorene -7,9'--7,9'- 티오크산텐Thioxanthene ]-10-일)-7H-] -10-Sun) -7H- 벤조[c]카바졸의Of benzo [c] carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000066
Figure PCTKR2017011366-appb-I000066
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 15]과 동일한 과정을 수행하여 목적 화합물 8.0g을 얻었다.; HRMS [M]+: 613.78 Except that 10-bromo-7H-benzo [c] carbazole was used as a reaction, the same procedure as in [Preparation Example 15] was carried out to obtain 8.0 g of the target compound. HRMS [M] +: 613.78
[준비예 22]Preparation Example 22
10-(10- ( 스피로Spiro [[ 벤조[c]플루오렌Benzo [c] fluorene -7,9'--7,9'- 티오크산텐Thioxanthene ]-9-일)-7H-] -9-Sun) -7H- 벤조[c]카바졸의Of benzo [c] carbazole 합성 synthesis
Figure PCTKR2017011366-appb-I000067
Figure PCTKR2017011366-appb-I000067
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 16]과 동일한 과정을 수행하여 목적 화합물 7.6g을 얻었다.; HRMS [M]+: 613.787.6 g of the title compound was obtained in the same manner as the [Preparation Example 16], except that 10-bromo-7H-benzo [c] carbazole was used as the reactant. HRMS [M] +: 613.78
[준비예 23]Preparation 23
10'-(7H-10 '-(7H- 벤조[c]카바졸Benzo [c] carbazole -10-일)-10-페닐-10H--10-yl) -10-phenyl-10H- 스피로[아크리딘-9,7'-벤조[c]플Spiro [acridin-9,7'-benzo [c] ple 루오렌]의 합성Luorene] Synthesis
Figure PCTKR2017011366-appb-I000068
Figure PCTKR2017011366-appb-I000068
10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 17]과 동일한 과정을 수행하여 목적 화합물 7.9g을 얻었다.; HRMS [M]+: 672.837.9 g of the title compound was obtained in the same manner as [Preparation 17], except that 10-bromo-7H-benzo [c] carbazole was used; HRMS [M] +: 672.83
[준비예 24]Preparation 24
9'-(7H-9 '-(7H- 벤조[c]카바졸Benzo [c] carbazole -10-일)-10-페닐-10H--10-yl) -10-phenyl-10H- 스피로[아크리딘-9,7'-벤조[c]플루오렌]의Of spiro [acridin-9,7'-benzo [c] fluorene] 합성 synthesis
Figure PCTKR2017011366-appb-I000069
Figure PCTKR2017011366-appb-I000069
반응물로 10-브로모-7H-벤조[c]카바졸을 사용한 것을 제외하고는 [준비예 18]과 동일한 과정을 수행하여 목적 화합물 7.5g을 얻었다.; HRMS [M]+: 672.837.5 g of the target compound was obtained in the same manner as in [Preparation Example 18], except that 10-bromo-7H-benzo [c] carbazole was used as the reactant. HRMS [M] +: 672.83
[[ 합성예Synthesis Example 1] Mat 1의 합성 1] Synthesis of Mat 1
Figure PCTKR2017011366-appb-I000070
Figure PCTKR2017011366-appb-I000070
준비예 1 5g (10.04mmol)과 3-요오드-1,1'-비페닐 3.37g (12.04mmol)에 자일렌 250 mL를 가하였다. Pd2(dba)3 0.45g (0.5mmol), Xphos 0.47g (1mmol), NaOtBu 2.4g (25.1mol)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 5.6g (수율 86%)을 얻었다. Preparation Example 1 250 mL of xylene was added to 5 g (10.04 mmol) and 3.37 g (12.04 mmol) of 3-iodine-1,1'-biphenyl. 0.45 g (0.5 mmol) of Pd 2 (dba) 3 , 0.47 g (1 mmol) of Xphos, and 2.4 g (25.1 mol) of NaOtBu were heated 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 5.6 g (yield 86%) of the title compound.
1H-NMR: δ 8.3 (d, 1H), 8.21~8.13(m, 4H), 7.90~7.89(m, 2H), 7.68~7.17(m, 22H), 7.01(m, 2H); HRMS [M]+: 649.79 1 H-NMR: δ 8.3 (d, 1H), 8.21-8.13 (m, 4H), 7.90-7.89 (m, 2H), 7.68-7.17 (m, 22H), 7.01 (m, 2H); HRMS [M] + : 649.79
[[ 합성예Synthesis Example 2] Mat 2의 합성 2] Synthesis of Mat 2
Figure PCTKR2017011366-appb-I000071
Figure PCTKR2017011366-appb-I000071
반응물로 4-요오드-1,1'-비페닐을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 649.795.8 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that 4-iodine-1,1'-biphenyl was used as a reactant. HRMS [M] +: 649.79
[[ 합성예Synthesis Example 3] Mat 5의 합성 3] Synthesis of Mat 5
Figure PCTKR2017011366-appb-I000072
Figure PCTKR2017011366-appb-I000072
반응물로 2-브로모트리페닐렌을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 723.886.7 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that 2-bromotriphenylene was used as a reactant. HRMS [M] +: 723.88
[[ 합성예Synthesis Example 4] Mat 7의 합성 4] Synthesis of Mat 7
Figure PCTKR2017011366-appb-I000073
Figure PCTKR2017011366-appb-I000073
반응물로 요오드벤젠을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 573.704.9 g of the target compound was obtained by the same procedure as the [Synthesis Example 1], except that iodinebenzene was used as a reactant. HRMS [M] +: 573.70
[[ 합성예Synthesis Example 5] Mat 8의 합성 5] Synthesis of Mat 8
Figure PCTKR2017011366-appb-I000074
Figure PCTKR2017011366-appb-I000074
반응물로 2-브로모디벤조[b,d]퓨란을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 663.785.4 g of the title compound was obtained in the same manner as the [Synthesis Example 1], except that 2-bromodibenzo [b, d] furan was used as the reactant. HRMS [M] +: 663.78
[[ 합성예Synthesis Example 6] Mat 13의 합성 6] Synthesis of Mat 13
Figure PCTKR2017011366-appb-I000075
Figure PCTKR2017011366-appb-I000075
반응물로 4-브로모디벤조[b,d]퓨란을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 663.785.0 g of the target compound was obtained in the same manner as the Synthesis Example 1, except that 4-bromodibenzo [b, d] furan was used as the reactant. HRMS [M] +: 663.78
[[ 합성예Synthesis Example 7] Mat 20의 합성 7] Synthesis of Mat 20
Figure PCTKR2017011366-appb-I000076
Figure PCTKR2017011366-appb-I000076
반응물로 2-클로로-4,6-디페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 728.864.5 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used as the reactant. HRMS [M] +: 728.86
[[ 합성예Synthesis Example 8] Mat 21의 합성 8] Synthesis of Mat 21
Figure PCTKR2017011366-appb-I000077
Figure PCTKR2017011366-appb-I000077
반응물로 2-([1,1'-비페닐]-4-일)-4-클로로-6-페닐-1,3,5-트리아진을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 804.95Same procedure as in [Synthesis Example 1], except that 2-([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine was used as the reactant. This was carried out to give 5.7 g of the target compound. HRMS [M] +: 804.95
[[ 합성예Synthesis Example 9] Mat 23의 합성 9] Synthesis of Mat 23
Figure PCTKR2017011366-appb-I000078
Figure PCTKR2017011366-appb-I000078
반응물로 4-([1,1'-비페닐]-4-일)-6-클로로-2-페닐피리미딘을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 803.974.8 g of the target compound was carried out in the same manner as in [Synthesis Example 1], except that 4-([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine was used as a reactant. To obtain; HRMS [M] +: 803.97
[[ 합성예Synthesis Example 10] Mat 24의 합성 10] Synthesis of Mat 24
Figure PCTKR2017011366-appb-I000079
Figure PCTKR2017011366-appb-I000079
반응물로 2-클로로-4-페닐퀴나졸린을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 701.834.2 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that 2-chloro-4-phenylquinazoline was used as the reactant. HRMS [M] +: 701.83
[[ 합성예Synthesis Example 11] Mat 26의 합성 11] Synthesis of Mat 26
Figure PCTKR2017011366-appb-I000080
Figure PCTKR2017011366-appb-I000080
반응물로 [준비예 2] 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 701.834.2 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] +: 701.83
[[ 합성예Synthesis Example 12] Mat 27의 합성 12] Synthesis of Mat 27
Figure PCTKR2017011366-appb-I000081
Figure PCTKR2017011366-appb-I000081
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 649.795.8 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] +: 649.79
[[ 합성예Synthesis Example 13] Mat 30의 합성 13] Synthesis of Mat 30
Figure PCTKR2017011366-appb-I000082
Figure PCTKR2017011366-appb-I000082
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 723.886.7 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] +: 723.88
[[ 합성예Synthesis Example 14] Mat 32의 합성 14] Synthesis of Mat 32
Figure PCTKR2017011366-appb-I000083
Figure PCTKR2017011366-appb-I000083
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 573.704.9 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] +: 573.70
[[ 합성예Synthesis Example 15] Mat 33의 합성 15] Synthesis of Mat 33
Figure PCTKR2017011366-appb-I000084
Figure PCTKR2017011366-appb-I000084
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 663.785.4 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] +: 663.78
[[ 합성예Synthesis Example 16] Mat 38의 합성 16] Synthesis of Mat 38
Figure PCTKR2017011366-appb-I000085
Figure PCTKR2017011366-appb-I000085
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 663.785.0 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] +: 663.78
[[ 합성예Synthesis Example 17] Mat 45의 합성 17] Synthesis of Mat 45
Figure PCTKR2017011366-appb-I000086
Figure PCTKR2017011366-appb-I000086
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 728.864.5 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] +: 728.86
[[ 합성예Synthesis Example 18] Mat 46의 합성 18] Synthesis of Mat 46
Figure PCTKR2017011366-appb-I000087
Figure PCTKR2017011366-appb-I000087
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 804.955.7 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] +: 804.95
[[ 합성예Synthesis Example 19] Mat 48의 합성 19] Synthesis of Mat 48
Figure PCTKR2017011366-appb-I000088
Figure PCTKR2017011366-appb-I000088
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 803.974.8 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] +: 803.97
[[ 합성예Synthesis Example 20] Mat 49의 합성 20] Synthesis of Mat 49
Figure PCTKR2017011366-appb-I000089
Figure PCTKR2017011366-appb-I000089
반응물로 [준비예 2]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 701.834.2 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] +: 701.83
[[ 합성예Synthesis Example 21] Mat 51의 합성 21] Synthesis of Mat 51
Figure PCTKR2017011366-appb-I000090
Figure PCTKR2017011366-appb-I000090
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 665.855.3 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] +: 665.85
[[ 합성예Synthesis Example 22] Mat 52의 합성 22] Synthesis of Mat 52
Figure PCTKR2017011366-appb-I000091
Figure PCTKR2017011366-appb-I000091
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 665.855.4 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] +: 665.85
[[ 합성예Synthesis Example 23] Mat 55의 합성 23] Synthesis of Mat 55
Figure PCTKR2017011366-appb-I000092
Figure PCTKR2017011366-appb-I000092
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 739.946.4 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] +: 739.94
[[ 합성예Synthesis Example 24] Mat 57의 합성 24] Synthesis of Mat 57
Figure PCTKR2017011366-appb-I000093
Figure PCTKR2017011366-appb-I000093
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 589.764.4 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] +: 589.76
[[ 합성예Synthesis Example 25] Mat 58의 합성 25] Synthesis of Mat 58
Figure PCTKR2017011366-appb-I000094
Figure PCTKR2017011366-appb-I000094
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 679.845.1 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] +: 679.84
[[ 합성예Synthesis Example 26] Mat 63의 합성 26] Synthesis of Mat 63
Figure PCTKR2017011366-appb-I000095
Figure PCTKR2017011366-appb-I000095
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 679.845.6 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] +: 679.84
[[ 합성예Synthesis Example 27] Mat 70의 합성 27] Synthesis of Mat 70
Figure PCTKR2017011366-appb-I000096
Figure PCTKR2017011366-appb-I000096
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 744.924.8 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] +: 744.92
[[ 합성예Synthesis Example 28] Mat 71의 합성 28] Synthesis of Mat 71
Figure PCTKR2017011366-appb-I000097
Figure PCTKR2017011366-appb-I000097
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 821.015.4 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] +: 821.01
[[ 합성예Synthesis Example 29] Mat 73의 합성 29] Synthesis of Mat 73
Figure PCTKR2017011366-appb-I000098
Figure PCTKR2017011366-appb-I000098
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 820.034.1 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] +: 820.03
[[ 합성예Synthesis Example 30] Mat 74의 합성 30] Synthesis of Mat 74
Figure PCTKR2017011366-appb-I000099
Figure PCTKR2017011366-appb-I000099
반응물로 [준비예 3]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 717.894.9 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] +: 717.89
[[ 합성예Synthesis Example 31] Mat 76의 합성 31] Synthesis of Mat 76
Figure PCTKR2017011366-appb-I000100
Figure PCTKR2017011366-appb-I000100
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 665.855.3 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] +: 665.85
[[ 합성예Synthesis Example 32] Mat 77의 합성 32] Synthesis of Mat 77
Figure PCTKR2017011366-appb-I000101
Figure PCTKR2017011366-appb-I000101
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 665.855.4 g of the title compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 665.85
[[ 합성예Synthesis Example 33] Mat 80의 합성 33] Synthesis of Mat 80
Figure PCTKR2017011366-appb-I000102
Figure PCTKR2017011366-appb-I000102
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 739.946.4 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] +: 739.94
[[ 합성예Synthesis Example 34] Mat 82의 합성 34] Synthesis of Mat 82
Figure PCTKR2017011366-appb-I000103
Figure PCTKR2017011366-appb-I000103
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 589.764.4 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] +: 589.76
[[ 합성예Synthesis Example 35] Mat 83의 합성 35] Synthesis of Mat 83
Figure PCTKR2017011366-appb-I000104
Figure PCTKR2017011366-appb-I000104
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 679.845.1 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] +: 679.84
[[ 합성예Synthesis Example 36] Mat 88의 합성 36] Synthesis of Mat 88
Figure PCTKR2017011366-appb-I000105
Figure PCTKR2017011366-appb-I000105
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 679.845.6 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] +: 679.84
[[ 합성예Synthesis Example 37] Mat 95의 합성 37] Synthesis of Mat 95
Figure PCTKR2017011366-appb-I000106
Figure PCTKR2017011366-appb-I000106
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 744.924.8 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] +: 744.92
[[ 합성예Synthesis Example 38] Mat 96의 합성 38] Synthesis of Mat 96
Figure PCTKR2017011366-appb-I000107
Figure PCTKR2017011366-appb-I000107
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 821.015.4 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] +: 821.01
[[ 합성예Synthesis Example 39] Mat 98의 합성 39] Synthesis of Mat 98
Figure PCTKR2017011366-appb-I000108
Figure PCTKR2017011366-appb-I000108
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 820.034.1 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] +: 820.03
[[ 합성예Synthesis Example 40] Mat 99의 합성 40] Synthesis of Mat 99
Figure PCTKR2017011366-appb-I000109
Figure PCTKR2017011366-appb-I000109
반응물로 [준비예 4]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 717.894.9 g of the title compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 4] was used as a reactant. HRMS [M] +: 717.89
[[ 합성예Synthesis Example 41] Mat 51의 합성 41] Synthesis of Mat 51
Figure PCTKR2017011366-appb-I000110
Figure PCTKR2017011366-appb-I000110
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 724.915.9 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 724.91
[[ 합성예Synthesis Example 42] Mat 52의 합성 42] Synthesis of Mat 52
Figure PCTKR2017011366-appb-I000111
Figure PCTKR2017011366-appb-I000111
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 724.915.4 g of the target compound was obtained in the same manner as [Synthesis Example 2], except that [Preparation Example 5] was used as a reactant. HRMS [M] +: 724.91
[[ 합성예Synthesis Example 43] Mat 55의 합성 43] Synthesis of Mat 55
Figure PCTKR2017011366-appb-I000112
Figure PCTKR2017011366-appb-I000112
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 798.996.5 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] +: 798.99
[[ 합성예Synthesis Example 44] Mat 57의 합성 44] Synthesis of Mat 57
Figure PCTKR2017011366-appb-I000113
Figure PCTKR2017011366-appb-I000113
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 648.814.1 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] +: 648.81
[[ 합성예Synthesis Example 45] Mat 58의 합성 45] Synthesis of Mat 58
Figure PCTKR2017011366-appb-I000114
Figure PCTKR2017011366-appb-I000114
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 738.895.7 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] +: 738.89
[[ 합성예Synthesis Example 46] Mat 63의 합성 46] Synthesis of Mat 63
Figure PCTKR2017011366-appb-I000115
Figure PCTKR2017011366-appb-I000115
반응물로 [준비예 5]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 738.895.6 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] +: 738.89
[[ 합성예Synthesis Example 47] Mat 101의 합성 47] Synthesis of Mat 101
Figure PCTKR2017011366-appb-I000116
Figure PCTKR2017011366-appb-I000116
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 724.915.4 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 724.91
[[ 합성예Synthesis Example 48] Mat 102의 합성 48] Synthesis of Mat 102
Figure PCTKR2017011366-appb-I000117
Figure PCTKR2017011366-appb-I000117
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 724.915.7 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] +: 724.91
[[ 합성예Synthesis Example 49] Mat 105의 합성 49] Synthesis of Mat 105
Figure PCTKR2017011366-appb-I000118
Figure PCTKR2017011366-appb-I000118
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 798.996.3 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] +: 798.99
[[ 합성예Synthesis Example 50] Mat 107의 합성 50] Synthesis of Mat 107
Figure PCTKR2017011366-appb-I000119
Figure PCTKR2017011366-appb-I000119
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 648.814.9 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 648.81
[[ 합성예Synthesis Example 51] Mat 108의 합성 51] Synthesis of Mat 108
Figure PCTKR2017011366-appb-I000120
Figure PCTKR2017011366-appb-I000120
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 738.895.8 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 738.89
[[ 합성예Synthesis Example 52] Mat 113의 합성 52] Synthesis of Mat 113
Figure PCTKR2017011366-appb-I000121
Figure PCTKR2017011366-appb-I000121
반응물로 [준비예 6]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 738.895.6 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 6] was used as a reactant. HRMS [M] +: 738.89
[[ 합성예Synthesis Example 53] Mat 131의 합성 53] Synthesis of Mat 131
Figure PCTKR2017011366-appb-I000122
Figure PCTKR2017011366-appb-I000122
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 699.855.8 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 7] was used as a reactant. HRMS [M] +: 699.85
[[ 합성예Synthesis Example 54] Mat 132의 합성 54] Synthesis of Mat 132
Figure PCTKR2017011366-appb-I000123
Figure PCTKR2017011366-appb-I000123
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 699.854.8 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 7] was used as a reactant. HRMS [M] +: 699.85
[[ 합성예Synthesis Example 55] Mat 134의 합성 55] Synthesis of Mat 134
Figure PCTKR2017011366-appb-I000124
Figure PCTKR2017011366-appb-I000124
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 773.945.7 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 7] was used as a reactant. HRMS [M] +: 773.94
[[ 합성예Synthesis Example 56] Mat 135의 합성 56] Synthesis of Mat 135
Figure PCTKR2017011366-appb-I000125
Figure PCTKR2017011366-appb-I000125
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 629.764.2 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 7] was used as a reactant. HRMS [M] +: 629.76
[[ 합성예Synthesis Example 57] Mat 136의 합성 57] Synthesis of Mat 136
Figure PCTKR2017011366-appb-I000126
Figure PCTKR2017011366-appb-I000126
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 713.844.4 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 7] was used as a reactant. HRMS [M] +: 713.84
[[ 합성예Synthesis Example 58] Mat 141의 합성 58] Synthesis of Mat 141
Figure PCTKR2017011366-appb-I000127
Figure PCTKR2017011366-appb-I000127
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 713.845.8 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 7] was used as a reactant. HRMS [M] +: 713.84
[[ 합성예Synthesis Example 59] Mat 145의 합성 59] Synthesis of Mat 145
Figure PCTKR2017011366-appb-I000128
Figure PCTKR2017011366-appb-I000128
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 778.924.4 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 7] was used as a reactant. HRMS [M] +: 778.92
[[ 합성예Synthesis Example 60] Mat 146의 합성 60] Synthesis of Mat 146
Figure PCTKR2017011366-appb-I000129
Figure PCTKR2017011366-appb-I000129
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 855.015.0 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 7] was used as a reactant. HRMS [M] +: 855.01
[[ 합성예Synthesis Example 61] Mat 148의 합성 61] Synthesis of Mat 148
Figure PCTKR2017011366-appb-I000130
Figure PCTKR2017011366-appb-I000130
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 854.034.5 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 7] was used as a reactant. HRMS [M] +: 854.03
[[ 합성예Synthesis Example 62] Mat 149의 합성 62] Synthesis of Mat 149
Figure PCTKR2017011366-appb-I000131
Figure PCTKR2017011366-appb-I000131
반응물로 [준비예 7]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 751.894.9 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 7] was used as a reactant. HRMS [M] +: 751.89
[[ 합성예Synthesis Example 63] Mat 151의 합성 63] Synthesis of Mat 151
Figure PCTKR2017011366-appb-I000132
Figure PCTKR2017011366-appb-I000132
반응물로 [준비예 8] 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 699.855.2 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 8] was used as a reactant. HRMS [M] +: 699.85
[[ 합성예Synthesis Example 64] Mat 152의 합성 64] Synthesis of Mat 152
Figure PCTKR2017011366-appb-I000133
Figure PCTKR2017011366-appb-I000133
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 699.855.3 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 8] was used as a reactant. HRMS [M] +: 699.85
[[ 합성예Synthesis Example 65] Mat 155의 합성 65] Synthesis of Mat 155
Figure PCTKR2017011366-appb-I000134
Figure PCTKR2017011366-appb-I000134
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 773.945.7 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 8] was used as a reactant. HRMS [M] +: 773.94
[[ 합성예Synthesis Example 66] Mat 157의 합성 66] Synthesis of Mat 157
Figure PCTKR2017011366-appb-I000135
Figure PCTKR2017011366-appb-I000135
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 623.764.1 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 8] was used as the reactant. HRMS [M] +: 623.76
[[ 합성예Synthesis Example 67] Mat 158의 합성 67] Synthesis of Mat 158
Figure PCTKR2017011366-appb-I000136
Figure PCTKR2017011366-appb-I000136
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 713.844.4 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 8] was used as a reactant. HRMS [M] +: 713.84
[[ 합성예Synthesis Example 68] Mat 163의 합성 68] Synthesis of Mat 163
Figure PCTKR2017011366-appb-I000137
Figure PCTKR2017011366-appb-I000137
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 713.845.0 g of the target compound was obtained in the same manner as the Synthesis Example 6, except that [Preparation Example 8] was used as the reactant. HRMS [M] +: 713.84
[[ 합성예Synthesis Example 69] Mat 170의 합성 69] Synthesis of Mat 170
Figure PCTKR2017011366-appb-I000138
Figure PCTKR2017011366-appb-I000138
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 778.925.5 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 8] was used as a reactant. HRMS [M] +: 778.92
[[ 합성예Synthesis Example 70] Mat 171의 합성 70] Synthesis of Mat 171
Figure PCTKR2017011366-appb-I000139
Figure PCTKR2017011366-appb-I000139
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 855.014.7 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 8] was used as the reactant. HRMS [M] +: 855.01
[[ 합성예Synthesis Example 71] Mat 173의 합성 71] Synthesis of Mat 173
Figure PCTKR2017011366-appb-I000140
Figure PCTKR2017011366-appb-I000140
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 854.035.8 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 8] was used as a reactant. HRMS [M] +: 854.03
[[ 합성예Synthesis Example 72] Mat 174의 합성 72] Synthesis of Mat 174
Figure PCTKR2017011366-appb-I000141
Figure PCTKR2017011366-appb-I000141
반응물로 [준비예 8]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 751.895.2 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 8] was used as a reactant. HRMS [M] +: 751.89
[[ 합성예Synthesis Example 73] Mat 176의 합성 73] Synthesis of Mat 176
Figure PCTKR2017011366-appb-I000142
Figure PCTKR2017011366-appb-I000142
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.3g을 얻었다.; HRMS [M]+: 715.916.3 g of the title compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 715.91
[[ 합성예Synthesis Example 74] Mat 177의 합성 74] Synthesis of Mat 177
Figure PCTKR2017011366-appb-I000143
Figure PCTKR2017011366-appb-I000143
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 715.914.4 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] +: 715.91
[[ 합성예Synthesis Example 75] Mat 179의 합성 75] Synthesis of Mat 179
Figure PCTKR2017011366-appb-I000144
Figure PCTKR2017011366-appb-I000144
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 790.006.1 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] +: 790.00
[[ 합성예Synthesis Example 76] Mat 180의 합성 76] Synthesis of Mat 180
Figure PCTKR2017011366-appb-I000145
Figure PCTKR2017011366-appb-I000145
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 639.824.5 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 9] was used as a reactant. HRMS [M] +: 639.82
[[ 합성예Synthesis Example 77] Mat 181의 합성 77] Synthesis of Mat 181
Figure PCTKR2017011366-appb-I000146
Figure PCTKR2017011366-appb-I000146
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 729.904.1 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] +: 729.90
[[ 합성예Synthesis Example 78] Mat 186의 합성 78] Synthesis of Mat 186
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 729.905.0 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] +: 729.90
[[ 합성예Synthesis Example 79] Mat 190의 합성 79] Synthesis of Mat 190
Figure PCTKR2017011366-appb-I000148
Figure PCTKR2017011366-appb-I000148
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 794.984.4 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] +: 794.98
[[ 합성예Synthesis Example 80] Mat 191의 합성 80] Synthesis of Mat 191
Figure PCTKR2017011366-appb-I000149
Figure PCTKR2017011366-appb-I000149
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 871.075.5 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] +: 871.07
[[ 합성예Synthesis Example 81] Mat 193의 합성 81] Synthesis of Mat 193
Figure PCTKR2017011366-appb-I000150
Figure PCTKR2017011366-appb-I000150
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 합물 6.1g을 얻었다.; HRMS [M]+: 870.096.1 g of the target compound was obtained in the same manner as in [Synthesis Example 9], except that [Preparation Example 9] was used as the reactant. HRMS [M] +: 870.09
[[ 합성예Synthesis Example 82] Mat 194의 합성 82] Synthesis of Mat 194
Figure PCTKR2017011366-appb-I000151
Figure PCTKR2017011366-appb-I000151
반응물로 [준비예 9]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 767.954.7 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] +: 767.95
[[ 합성예Synthesis Example 83] Mat 196의 합성 83] Synthesis of Mat 196
Figure PCTKR2017011366-appb-I000152
Figure PCTKR2017011366-appb-I000152
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다.; HRMS [M]+: 715.914.3 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] +: 715.91
[[ 합성예Synthesis Example 84] Mat 197의 합성 84] Synthesis of Mat 197
Figure PCTKR2017011366-appb-I000153
Figure PCTKR2017011366-appb-I000153
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 715.915.4 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] +: 715.91
[[ 합성예Synthesis Example 85] Mat 200의 합성 85] Synthesis of Mat 200
Figure PCTKR2017011366-appb-I000154
Figure PCTKR2017011366-appb-I000154
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 790.006.5 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] +: 790.00
[[ 합성예Synthesis Example 86] Mat 202의 합성 86] Synthesis of Mat 202
Figure PCTKR2017011366-appb-I000155
Figure PCTKR2017011366-appb-I000155
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 639.824.8 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] +: 639.82
[[ 합성예Synthesis Example 87] Mat 203의 합성 87] Synthesis of Mat 203
Figure PCTKR2017011366-appb-I000156
Figure PCTKR2017011366-appb-I000156
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 729.905.9 g of the title compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 729.90
[[ 합성예Synthesis Example 88] Mat 208의 합성 88] Synthesis of Mat 208
Figure PCTKR2017011366-appb-I000157
Figure PCTKR2017011366-appb-I000157
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 729.905.2 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 10] was used as a reactant. HRMS [M] +: 729.90
[[ 합성예Synthesis Example 89] Mat 215의 합성 89] Synthesis of Mat 215
Figure PCTKR2017011366-appb-I000158
Figure PCTKR2017011366-appb-I000158
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다.; HRMS [M]+: 794.984.3 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] +: 794.98
[[ 합성예Synthesis Example 90] Mat 216의 합성 90] Synthesis of Mat 216
Figure PCTKR2017011366-appb-I000159
Figure PCTKR2017011366-appb-I000159
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 871.075.0 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] +: 871.07
[[ 합성예Synthesis Example 91] Mat 218의 합성 91] Synthesis of Mat 218
Figure PCTKR2017011366-appb-I000160
Figure PCTKR2017011366-appb-I000160
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 870.094.7 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] +: 870.09
[[ 합성예Synthesis Example 92] Mat 219의 합성 92] Synthesis of Mat 219
Figure PCTKR2017011366-appb-I000161
Figure PCTKR2017011366-appb-I000161
반응물로 [준비예 10]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 767.955.6 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] +: 767.95
[[ 합성예Synthesis Example 93] Mat 221의 합성 93] Synthesis of Mat 221
Figure PCTKR2017011366-appb-I000162
Figure PCTKR2017011366-appb-I000162
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 774.975.1 g 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] +: 774.97
[[ 합성예Synthesis Example 94] Mat 222의 합성 94] Synthesis of Mat 222
Figure PCTKR2017011366-appb-I000163
Figure PCTKR2017011366-appb-I000163
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 774.975.0 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation 11] was used as a reactant. HRMS [M] +: 774.97
[[ 합성예Synthesis Example 95] Mat 225의 합성 95] Synthesis of Mat 225
Figure PCTKR2017011366-appb-I000164
Figure PCTKR2017011366-appb-I000164
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 849.056.8 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] +: 849.05
[[ 합성예Synthesis Example 96] Mat 227의 합성 96] Synthesis of Mat 227
Figure PCTKR2017011366-appb-I000165
Figure PCTKR2017011366-appb-I000165
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 698.874.5 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation 11] was used as a reactant. HRMS [M] +: 698.87
[[ 합성예Synthesis Example 97] Mat 228의 합성 97] Synthesis of Mat 228
Figure PCTKR2017011366-appb-I000166
Figure PCTKR2017011366-appb-I000166
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 788.954.7 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] +: 788.95
[[ 합성예Synthesis Example 98] Mat 233의 합성 98] Synthesis of Mat 233
Figure PCTKR2017011366-appb-I000167
Figure PCTKR2017011366-appb-I000167
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 788.956.6 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 11] was used as a reactant. HRMS [M] +: 788.95
[[ 합성예Synthesis Example 99] Mat 240의 합성 99] Synthesis of Mat 240
Figure PCTKR2017011366-appb-I000168
Figure PCTKR2017011366-appb-I000168
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 854.035.8 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] +: 854.03
[[ 합성예Synthesis Example 100] Mat 241의 합성 100] Synthesis of Mat 241
Figure PCTKR2017011366-appb-I000169
Figure PCTKR2017011366-appb-I000169
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 930.135.9 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 11] was used as a reactant. HRMS [M] +: 930.13
[[ 합성예Synthesis Example 101] Mat 243의 합성 101] Synthesis of Mat 243
Figure PCTKR2017011366-appb-I000170
Figure PCTKR2017011366-appb-I000170
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다.; HRMS [M]+: 929.144.3 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] +: 929.14
[[ 합성예Synthesis Example 102] Mat 244의 합성 102] Synthesis of Mat 244
Figure PCTKR2017011366-appb-I000171
Figure PCTKR2017011366-appb-I000171
반응물로 [준비예 11]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 827.004.8 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 11] was used as a reactant. HRMS [M] +: 827.00
[합성예 103] Mat 246의 합성Synthesis Example 103 Synthesis of Mat 246
Figure PCTKR2017011366-appb-I000172
Figure PCTKR2017011366-appb-I000172
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 774.975.6 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 774.97
[합성예 104] Mat 247의 합성Synthesis Example 104 Synthesis of Mat 247
Figure PCTKR2017011366-appb-I000173
Figure PCTKR2017011366-appb-I000173
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 774.975.1 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] +: 774.97
[합성예 105] Mat 250의 합성Synthesis Example 105 Synthesis of Mat 250
Figure PCTKR2017011366-appb-I000174
Figure PCTKR2017011366-appb-I000174
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 849.056.9 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] +: 849.05
[합성예 106] Mat 252의 합성Synthesis Example 106 Synthesis of Mat 252
Figure PCTKR2017011366-appb-I000175
Figure PCTKR2017011366-appb-I000175
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 698.874.8 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] +: 698.87
[합성예 107] Mat 253의 합성Synthesis Example 107 Synthesis of Mat 253
Figure PCTKR2017011366-appb-I000176
Figure PCTKR2017011366-appb-I000176
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 788.955.1 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 788.95
[합성예 108] Mat 258의 합성Synthesis Example 108 Synthesis of Mat 258
Figure PCTKR2017011366-appb-I000177
Figure PCTKR2017011366-appb-I000177
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 788.955.4 g 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] +: 788.95
[[ 합성예Synthesis Example 109] Mat 265의 합성 109] Synthesis of Mat 265
Figure PCTKR2017011366-appb-I000178
Figure PCTKR2017011366-appb-I000178
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 854.034.5 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] +: 854.03
[[ 합성예Synthesis Example 110] Mat 266의 합성 110] Synthesis of Mat 266
Figure PCTKR2017011366-appb-I000179
Figure PCTKR2017011366-appb-I000179
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 930.135.4 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 930.13
[합성예 111] Mat 268의 합성Synthesis Example 111 Synthesis of Mat 268
Figure PCTKR2017011366-appb-I000180
Figure PCTKR2017011366-appb-I000180
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 929.145.9 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] +: 929.14
[합성예 112] Mat 269의 합성Synthesis Example 112 Synthesis of Mat 269
Figure PCTKR2017011366-appb-I000181
Figure PCTKR2017011366-appb-I000181
반응물로 [준비예 12]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 827.005.6 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 12] was used as a reactant. HRMS [M] +: 827.00
[합성예 113] Mat 271의 합성Synthesis Example 113 Synthesis of Mat 271
Figure PCTKR2017011366-appb-I000182
Figure PCTKR2017011366-appb-I000182
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 699.855.7 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 699.85
[합성예 114] Mat 172의 합성Synthesis Example 114 Synthesis of Mat 172
Figure PCTKR2017011366-appb-I000183
Figure PCTKR2017011366-appb-I000183
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 699.855.8 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] +: 699.85
[합성예 115] Mat 175의 합성Synthesis Example 115 Synthesis of Mat 175
Figure PCTKR2017011366-appb-I000184
Figure PCTKR2017011366-appb-I000184
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 773.944.7 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] +: 773.94
[합성예 116] Mat 177의 합성Synthesis Example 116 Synthesis of Mat 177
Figure PCTKR2017011366-appb-I000185
Figure PCTKR2017011366-appb-I000185
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 629.765.2 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] +: 629.76
[합성예 117] Mat 178의 합성Synthesis Example 117 Synthesis of Mat 178
Figure PCTKR2017011366-appb-I000186
Figure PCTKR2017011366-appb-I000186
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 713.845.4 g 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] +: 713.84
[합성예 118] Mat 183의 합성Synthesis Example 118 Synthesis of Mat 183
Figure PCTKR2017011366-appb-I000187
Figure PCTKR2017011366-appb-I000187
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 713.844.8 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] +: 713.84
[합성예 119] Mat 190의 합성Synthesis Example 119 Synthesis of Mat 190
Figure PCTKR2017011366-appb-I000188
Figure PCTKR2017011366-appb-I000188
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 778.925.4 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] +: 778.92
[합성예 120] Mat 191의 합성Synthesis Example 120 Synthesis of Mat 191
Figure PCTKR2017011366-appb-I000189
Figure PCTKR2017011366-appb-I000189
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 855.015.8 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] +: 855.01
[[ 합성예Synthesis Example 121] Mat 193의 합성 121] Synthesis of Mat 193
Figure PCTKR2017011366-appb-I000190
Figure PCTKR2017011366-appb-I000190
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 854.035.5 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 854.03
[[ 합성예Synthesis Example 122] Mat 194의 합성 122] Synthesis of Mat 194
Figure PCTKR2017011366-appb-I000191
Figure PCTKR2017011366-appb-I000191
반응물로 [준비예 13]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 751.895.9 g of the title compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 13] was used as a reactant. HRMS [M] +: 751.89
[[ 합성예Synthesis Example 123] Mat 196의 합성 123] Synthesis of Mat 196
Figure PCTKR2017011366-appb-I000192
Figure PCTKR2017011366-appb-I000192
반응물로 [준비예 14] 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 699.855.6 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] +: 699.85
[[ 합성예Synthesis Example 124] Mat 197의 합성 124] Synthesis of Mat 197
Figure PCTKR2017011366-appb-I000193
Figure PCTKR2017011366-appb-I000193
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다.; HRMS [M]+: 699.854.3 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] +: 699.85
[[ 합성예Synthesis Example 125] Mat 300의 합성 125] Synthesis of Mat 300
Figure PCTKR2017011366-appb-I000194
Figure PCTKR2017011366-appb-I000194
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 773.944.7 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] +: 773.94
[[ 합성예Synthesis Example 126] Mat 302의 합성 126] Synthesis of Mat 302
Figure PCTKR2017011366-appb-I000195
Figure PCTKR2017011366-appb-I000195
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 623.766.1 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] +: 623.76
[[ 합성예Synthesis Example 127] Mat 303의 합성 127] Synthesis of Mat 303
Figure PCTKR2017011366-appb-I000196
Figure PCTKR2017011366-appb-I000196
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 713.845.4 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] +: 713.84
[[ 합성예Synthesis Example 128] Mat 308의 합성 128] Synthesis of Mat 308
Figure PCTKR2017011366-appb-I000197
Figure PCTKR2017011366-appb-I000197
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다.; HRMS [M]+: 713.846.0 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] +: 713.84
[[ 합성예Synthesis Example 129] Mat 315의 합성 129] Synthesis of Mat 315
Figure PCTKR2017011366-appb-I000198
Figure PCTKR2017011366-appb-I000198
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 778.924.5 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] +: 778.92
[[ 합성예Synthesis Example 130] Mat 316의 합성 130] Synthesis of Mat 316
Figure PCTKR2017011366-appb-I000199
Figure PCTKR2017011366-appb-I000199
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 855.014.2 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] +: 855.01
[합성예 131] Mat 318의 합성Synthesis Example 131 Synthesis of Mat 318
Figure PCTKR2017011366-appb-I000200
Figure PCTKR2017011366-appb-I000200
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 854.034.8 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] +: 854.03
[합성예 132] Mat 319의 합성Synthesis Example 132 Synthesis of Mat 319
Figure PCTKR2017011366-appb-I000201
Figure PCTKR2017011366-appb-I000201
반응물로 [준비예 14]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.2g을 얻었다.; HRMS [M]+: 751.896.2 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] +: 751.89
[합성예 133] Mat 321의 합성Synthesis Example 133 Synthesis of Mat 321
Figure PCTKR2017011366-appb-I000202
Figure PCTKR2017011366-appb-I000202
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 715.915.3 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 715.91
[합성예 134] Mat 322의 합성Synthesis Example 134 Synthesis of Mat 322
Figure PCTKR2017011366-appb-I000203
Figure PCTKR2017011366-appb-I000203
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 715.915.4 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 715.91
[합성예 135] Mat 325의 합성Synthesis Example 135 Synthesis of Mat 325
Figure PCTKR2017011366-appb-I000204
Figure PCTKR2017011366-appb-I000204
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 790.005.1 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 790.00
[합성예 136] Mat 327의 합성Synthesis Example 136 Synthesis of Mat 327
Figure PCTKR2017011366-appb-I000205
Figure PCTKR2017011366-appb-I000205
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 639.824.9 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 639.82
[합성예 137] Mat 328의 합성Synthesis Example 137 Synthesis of Mat 328
Figure PCTKR2017011366-appb-I000206
Figure PCTKR2017011366-appb-I000206
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 729.904.5 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 729.90
[합성예 138] Mat 333의 합성Synthesis Example 138 Synthesis of Mat 333
Figure PCTKR2017011366-appb-I000207
Figure PCTKR2017011366-appb-I000207
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.0g을 얻었다.; HRMS [M]+: 729.906.0 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 729.90
[합성예 139] Mat 340의 합성Synthesis Example 139 Synthesis of Mat 340
Figure PCTKR2017011366-appb-I000208
Figure PCTKR2017011366-appb-I000208
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 794.984.1 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 794.98
[합성예 140] Mat 341의 합성Synthesis Example 140 Synthesis of Mat 341
Figure PCTKR2017011366-appb-I000209
Figure PCTKR2017011366-appb-I000209
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 871.075.7 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 871.07
[[ 합성예Synthesis Example 141] Mat 343의 합성 141] Synthesis of Mat 343
Figure PCTKR2017011366-appb-I000210
Figure PCTKR2017011366-appb-I000210
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 합물 5.1g을 얻었다.; HRMS [M]+: 870.095.1 g of the target compound was obtained in the same manner as in [Synthesis Example 9], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 870.09
[[ 합성예Synthesis Example 142] Mat 344의 합성 142] Synthesis of Mat 344
Figure PCTKR2017011366-appb-I000211
Figure PCTKR2017011366-appb-I000211
반응물로 [준비예 15]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 767.955.7 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 15] was used as a reactant. HRMS [M] +: 767.95
[[ 합성예Synthesis Example 143] Mat 346의 합성 143] Synthesis of Mat 346
Figure PCTKR2017011366-appb-I000212
Figure PCTKR2017011366-appb-I000212
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 715.914.9 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 715.91
[[ 합성예Synthesis Example 144] Mat 347의 합성 144] Synthesis of Mat 347
Figure PCTKR2017011366-appb-I000213
Figure PCTKR2017011366-appb-I000213
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 715.915.5 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 715.91
[[ 합성예Synthesis Example 145] Mat 350의 합성 145] Synthesis of Mat 350
Figure PCTKR2017011366-appb-I000214
Figure PCTKR2017011366-appb-I000214
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 790.005.5 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 790.00
[[ 합성예Synthesis Example 146] Mat 352의 합성 146] Synthesis of Mat 352
Figure PCTKR2017011366-appb-I000215
Figure PCTKR2017011366-appb-I000215
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 639.825.8 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 639.82
[[ 합성예Synthesis Example 147] Mat 353의 합성 147] Synthesis of Mat 353
Figure PCTKR2017011366-appb-I000216
Figure PCTKR2017011366-appb-I000216
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 729.904.9 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 729.90
[[ 합성예Synthesis Example 148] Mat 358의 합성 148] Synthesis of Mat 358
Figure PCTKR2017011366-appb-I000217
Figure PCTKR2017011366-appb-I000217
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 729.905.6 g of the title compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 729.90
[[ 합성예Synthesis Example 149] Mat 365의 합성 149] Synthesis of Mat 365
Figure PCTKR2017011366-appb-I000218
Figure PCTKR2017011366-appb-I000218
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 794.984.8 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 794.98
[[ 합성예Synthesis Example 150] Mat 366의 합성 150] Synthesis of Mat 366
Figure PCTKR2017011366-appb-I000219
Figure PCTKR2017011366-appb-I000219
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 871.074.2 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 871.07
[합성예 151] Mat 368의 합성Synthesis Example 151 Synthesis of Mat 368
Figure PCTKR2017011366-appb-I000220
Figure PCTKR2017011366-appb-I000220
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 870.095.7 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 870.09
[합성예 152] Mat 369의 합성Synthesis Example 152 Synthesis of Mat 369
Figure PCTKR2017011366-appb-I000221
Figure PCTKR2017011366-appb-I000221
반응물로 [준비예 16]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 767.955.6 g of the title compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 16] was used as a reactant. HRMS [M] +: 767.95
[합성예 153] Mat 371의 합성Synthesis Example 153 Synthesis of Mat 371
Figure PCTKR2017011366-appb-I000222
Figure PCTKR2017011366-appb-I000222
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 774.976.1 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 774.97
[합성예 154] Mat 372의 합성Synthesis Example 154 Synthesis of Mat 372
Figure PCTKR2017011366-appb-I000223
Figure PCTKR2017011366-appb-I000223
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 4.3g을 얻었다.; HRMS [M]+: 774.974.3 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 774.97
[합성예 155] Mat 375의 합성Synthesis Example 155 Synthesis of Mat 375
Figure PCTKR2017011366-appb-I000224
Figure PCTKR2017011366-appb-I000224
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 849.055.8 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 849.05
[합성예 156] Mat 377의 합성Synthesis Example 156 Synthesis of Mat 377
Figure PCTKR2017011366-appb-I000225
Figure PCTKR2017011366-appb-I000225
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 698.875.5 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 698.87
[합성예 157] Mat 378의 합성Synthesis Example 157 Synthesis of Mat 378
Figure PCTKR2017011366-appb-I000226
Figure PCTKR2017011366-appb-I000226
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 788.955.7 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 788.95
[합성예 158] Mat 383의 합성Synthesis Example 158 Synthesis of Mat 383
Figure PCTKR2017011366-appb-I000227
Figure PCTKR2017011366-appb-I000227
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 788.956.4 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 788.95
[합성예 159] Mat 390의 합성Synthesis Example 159 Synthesis of Mat 390
Figure PCTKR2017011366-appb-I000228
Figure PCTKR2017011366-appb-I000228
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 854.035.2 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 854.03
[합성예 160] Mat 391의 합성Synthesis Example 160 Synthesis of Mat 391
Figure PCTKR2017011366-appb-I000229
Figure PCTKR2017011366-appb-I000229
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 930.135.4 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 930.13
[[ 합성예Synthesis Example 161] Mat 393의 합성 161] Synthesis of Mat 393
Figure PCTKR2017011366-appb-I000230
Figure PCTKR2017011366-appb-I000230
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 929.144.8 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 929.14
[[ 합성예Synthesis Example 162] Mat 394의 합성 162] Synthesis of Mat 394
Figure PCTKR2017011366-appb-I000231
Figure PCTKR2017011366-appb-I000231
반응물로 [준비예 17]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 827.005.8 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 17] was used as a reactant. HRMS [M] +: 827.00
[[ 합성예Synthesis Example 163] Mat 396의 합성 163] Synthesis of Mat 396
Figure PCTKR2017011366-appb-I000232
Figure PCTKR2017011366-appb-I000232
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 774.976.6 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 774.97
[[ 합성예Synthesis Example 164] Mat 397의 합성 164] Synthesis of Mat 397
Figure PCTKR2017011366-appb-I000233
Figure PCTKR2017011366-appb-I000233
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물6.1g을 얻었다.; HRMS [M]+: 774.97Except for using [Preparation Example 18] as a reactant to the same procedure as in [Synthesis Example 2] to give the target compound 6.1g; HRMS [M] +: 774.97
[[ 합성예Synthesis Example 165] Mat 400의 합성 165] Synthesis of Mat 400
Figure PCTKR2017011366-appb-I000234
Figure PCTKR2017011366-appb-I000234
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 849.055.9 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 849.05
[[ 합성예Synthesis Example 166] Mat 402의 합성 166] Synthesis of Mat 402
Figure PCTKR2017011366-appb-I000235
Figure PCTKR2017011366-appb-I000235
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 698.875.8 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 698.87
[[ 합성예Synthesis Example 167] Mat 403의 합성 167] Synthesis of Mat 403
Figure PCTKR2017011366-appb-I000236
Figure PCTKR2017011366-appb-I000236
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 788.955.6 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 788.95
[[ 합성예Synthesis Example 168] Mat 408의 합성 168] Synthesis of Mat 408
Figure PCTKR2017011366-appb-I000237
Figure PCTKR2017011366-appb-I000237
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 788.955.1 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 788.95
[[ 합성예Synthesis Example 169] Mat 415의 합성 169] Synthesis of Mat 415
Figure PCTKR2017011366-appb-I000238
Figure PCTKR2017011366-appb-I000238
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 854.035.5 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 854.03
[[ 합성예Synthesis Example 170] Mat 416의 합성 170] Synthesis of Mat 416
Figure PCTKR2017011366-appb-I000239
Figure PCTKR2017011366-appb-I000239
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 930.134.4 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 930.13
[[ 합성예Synthesis Example 171] Mat 418의 합성 171] Synthesis of Mat 418
Figure PCTKR2017011366-appb-I000240
Figure PCTKR2017011366-appb-I000240
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.9g을 얻었다.; HRMS [M]+: 929.144.9 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 929.14
[[ 합성예Synthesis Example 172] Mat 419의 합성 172] Synthesis of Mat 419
Figure PCTKR2017011366-appb-I000241
Figure PCTKR2017011366-appb-I000241
반응물로 [준비예 18]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.2g을 얻었다.; HRMS [M]+: 827.006.2 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 18] was used as a reactant. HRMS [M] +: 827.00
[[ 합성예Synthesis Example 173] Mat 421의 합성 173] Synthesis of Mat 421
Figure PCTKR2017011366-appb-I000242
Figure PCTKR2017011366-appb-I000242
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 749.916.7 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 749.91
[[ 합성예Synthesis Example 174] Mat 422의 합성 174] Synthesis of Mat 422
Figure PCTKR2017011366-appb-I000243
Figure PCTKR2017011366-appb-I000243
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 749.915.8 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 749.91
[[ 합성예Synthesis Example 175] Mat 425의 합성 175] Synthesis of Mat 425
Figure PCTKR2017011366-appb-I000244
Figure PCTKR2017011366-appb-I000244
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.7g을 얻었다.; HRMS [M]+: 824.006.7 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 824.00
[[ 합성예Synthesis Example 176] Mat 427의 합성 176] Synthesis of Mat 427
Figure PCTKR2017011366-appb-I000245
Figure PCTKR2017011366-appb-I000245
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 6.2g을 얻었다.; HRMS [M]+: 673.826.2 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 673.82
[[ 합성예Synthesis Example 177] Mat 428의 합성 177] Synthesis of Mat 428
Figure PCTKR2017011366-appb-I000246
Figure PCTKR2017011366-appb-I000246
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 763.906.4 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 763.90
[[ 합성예Synthesis Example 178] Mat 433의 합성 178] Synthesis of Mat 433
Figure PCTKR2017011366-appb-I000247
Figure PCTKR2017011366-appb-I000247
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 763.905.8 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 763.90
[[ 합성예Synthesis Example 179] Mat 440의 합성 179] Synthesis of Mat 440
Figure PCTKR2017011366-appb-I000248
Figure PCTKR2017011366-appb-I000248
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 828.984.4 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 828.98
[[ 합성예Synthesis Example 180] Mat 441의 합성 180] Synthesis of Mat 441
Figure PCTKR2017011366-appb-I000249
Figure PCTKR2017011366-appb-I000249
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 905.074.8 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 905.07
[[ 합성예Synthesis Example 181] Mat 443의 합성 181] Synthesis of Mat 443
Figure PCTKR2017011366-appb-I000250
Figure PCTKR2017011366-appb-I000250
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 904.095.5 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 904.09
[[ 합성예Synthesis Example 182] Mat 444의 합성 182] Synthesis of Mat 444
Figure PCTKR2017011366-appb-I000251
Figure PCTKR2017011366-appb-I000251
반응물로 [준비예 19]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 801.956.9 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 19] was used as a reactant. HRMS [M] +: 801.95
[[ 합성예Synthesis Example 183] Mat 446의 합성 183] Synthesis of Mat 446
Figure PCTKR2017011366-appb-I000252
Figure PCTKR2017011366-appb-I000252
반응물로 [준비예 20] 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.6g을 얻었다.; HRMS [M]+: 749.915.6 g of the title compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 749.91
[[ 합성예Synthesis Example 184] Mat 447의 합성 184] Synthesis of Mat 447
Figure PCTKR2017011366-appb-I000253
Figure PCTKR2017011366-appb-I000253
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 749.915.3 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 749.91
[[ 합성예Synthesis Example 185] Mat 450의 합성 185] Synthesis of Mat 450
Figure PCTKR2017011366-appb-I000254
Figure PCTKR2017011366-appb-I000254
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 5.7g을 얻었다.; HRMS [M]+: 824.005.7 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 824.00
[[ 합성예Synthesis Example 186] Mat 452의 합성 186] Synthesis of Mat 452
Figure PCTKR2017011366-appb-I000255
Figure PCTKR2017011366-appb-I000255
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 673.825.1 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 673.82
[[ 합성예Synthesis Example 187] Mat 453의 합성 187] Synthesis of Mat 453
Figure PCTKR2017011366-appb-I000256
Figure PCTKR2017011366-appb-I000256
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 763.905.4 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 20] was used as the reactant. HRMS [M] +: 763.90
[[ 합성예Synthesis Example 188] Mat 458의 합성 188] Synthesis of Mat 458
Figure PCTKR2017011366-appb-I000257
Figure PCTKR2017011366-appb-I000257
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 763.905.0 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 763.90
[[ 합성예Synthesis Example 189] Mat 465의 합성 189] Synthesis of Mat 465
Figure PCTKR2017011366-appb-I000258
Figure PCTKR2017011366-appb-I000258
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 828.985.5 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 828.98
[[ 합성예Synthesis Example 190] Mat 466의 합성 190] Synthesis of Mat 466
Figure PCTKR2017011366-appb-I000259
Figure PCTKR2017011366-appb-I000259
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 905.075.2 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 905.07
[[ 합성예Synthesis Example 191] Mat 468의 합성 191] Synthesis of Mat 468
Figure PCTKR2017011366-appb-I000260
Figure PCTKR2017011366-appb-I000260
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 904.905.8 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 904.90
[[ 합성예Synthesis Example 192] Mat 469의 합성 192] Synthesis of Mat 469
Figure PCTKR2017011366-appb-I000261
Figure PCTKR2017011366-appb-I000261
반응물로 [준비예 20]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 801.955.2 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 20] was used as a reactant. HRMS [M] +: 801.95
[[ 합성예Synthesis Example 193] Mat 471의 합성 193] Synthesis of Mat 471
Figure PCTKR2017011366-appb-I000262
Figure PCTKR2017011366-appb-I000262
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 765.975.3 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 21] was used as a reactant. HRMS [M] +: 765.97
[[ 합성예Synthesis Example 194] Mat 472의 합성 194] Synthesis of Mat 472
Figure PCTKR2017011366-appb-I000263
Figure PCTKR2017011366-appb-I000263
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 6.4g을 얻었다.; HRMS [M]+: 765.976.4 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 21] was used as a reactant. HRMS [M] +: 765.97
[[ 합성예Synthesis Example 195] Mat 475의 합성 195] Synthesis of Mat 475
Figure PCTKR2017011366-appb-I000264
Figure PCTKR2017011366-appb-I000264
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 4.1g을 얻었다.; HRMS [M]+: 840.064.1 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 21] was used as a reactant. HRMS [M] +: 840.06
[[ 합성예Synthesis Example 196] Mat 477의 합성 196] Synthesis of Mat 477
Figure PCTKR2017011366-appb-I000265
Figure PCTKR2017011366-appb-I000265
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 689.885.9 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 21] was used as a reactant. HRMS [M] +: 689.88
[[ 합성예Synthesis Example 197] Mat 478의 합성 197] Synthesis of Mat 478
Figure PCTKR2017011366-appb-I000266
Figure PCTKR2017011366-appb-I000266
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.5g을 얻었다.; HRMS [M]+: 779.965.5 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation 21] was used as a reactant. HRMS [M] +: 779.96
[[ 합성예Synthesis Example 198] Mat 483의 합성 198] Synthesis of Mat 483
Figure PCTKR2017011366-appb-I000267
Figure PCTKR2017011366-appb-I000267
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.0g을 얻었다.; HRMS [M]+: 779.96Except for using [Preparation Example 21] as a reactant to the same procedure as in [Synthesis Example 6] to give the target compound 5.0g; HRMS [M] +: 779.96
[[ 합성예Synthesis Example 199] Mat 490의 합성 199] Synthesis of Mat 490
Figure PCTKR2017011366-appb-I000268
Figure PCTKR2017011366-appb-I000268
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 845.045.1 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 21] was used as a reactant. HRMS [M] +: 845.04
[[ 합성예Synthesis Example 200] Mat 491의 합성 200] Synthesis of Mat 491
Figure PCTKR2017011366-appb-I000269
Figure PCTKR2017011366-appb-I000269
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 921.134.7 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 21] was used as a reactant. HRMS [M] +: 921.13
[[ 합성예Synthesis Example 201] Mat 493의 합성 201] Synthesis of Mat 493
Figure PCTKR2017011366-appb-I000270
Figure PCTKR2017011366-appb-I000270
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 합물 6.1g을 얻었다.; HRMS [M]+: 920.156.1 g of the target compound was obtained in the same manner as in Synthesis Example 9, except that [Preparation Example 21] was used as the reactant. HRMS [M] +: 920.15
[[ 합성예Synthesis Example 202] Mat 494의 합성 202] Synthesis of Mat 494
Figure PCTKR2017011366-appb-I000271
Figure PCTKR2017011366-appb-I000271
반응물로 [준비예 21]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 818.014.7 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 21] was used as a reactant. HRMS [M] +: 818.01
[[ 합성예Synthesis Example 203] Mat 496의 합성 203] Synthesis of Mat 496
Figure PCTKR2017011366-appb-I000272
Figure PCTKR2017011366-appb-I000272
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 765.975.9 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 765.97
[[ 합성예Synthesis Example 204] Mat 497의 합성 204] Synthesis of Mat 497
*
Figure PCTKR2017011366-appb-I000273
*
Figure PCTKR2017011366-appb-I000273
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 765.976.5 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 765.97
[[ 합성예Synthesis Example 205] Mat 500의 합성 205] Synthesis of Mat 500
Figure PCTKR2017011366-appb-I000274
Figure PCTKR2017011366-appb-I000274
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 740.064.5 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 740.06
[[ 합성예Synthesis Example 206] Mat 502의 합성 206] Synthesis of Mat 502
Figure PCTKR2017011366-appb-I000275
Figure PCTKR2017011366-appb-I000275
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 689.884.8 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 689.88
[[ 합성예Synthesis Example 207] Mat 503의 합성 207] Synthesis of Mat 503
Figure PCTKR2017011366-appb-I000276
Figure PCTKR2017011366-appb-I000276
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 779.965.9 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 779.96
[[ 합성예Synthesis Example 208] Mat 508의 합성 208] Synthesis of Mat 508
Figure PCTKR2017011366-appb-I000277
Figure PCTKR2017011366-appb-I000277
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 4.6g을 얻었다.; HRMS [M]+: 779.964.6 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 779.96
[[ 합성예Synthesis Example 209] Mat 515의 합성 209] Synthesis of Mat 515
Figure PCTKR2017011366-appb-I000278
Figure PCTKR2017011366-appb-I000278
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 845.045.8 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 845.04
[[ 합성예Synthesis Example 210] Mat 516의 합성 210] Synthesis of Mat 516
Figure PCTKR2017011366-appb-I000279
Figure PCTKR2017011366-appb-I000279
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.2g을 얻었다.; HRMS [M]+: 921.135.2 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 921.13
[[ 합성예Synthesis Example 211] Mat 518의 합성 211] Synthesis of Mat 518
Figure PCTKR2017011366-appb-I000280
Figure PCTKR2017011366-appb-I000280
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 920.154.7 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 920.15
[[ 합성예Synthesis Example 212] Mat 519의 합성 212] Synthesis of Mat 519
Figure PCTKR2017011366-appb-I000281
Figure PCTKR2017011366-appb-I000281
반응물로 [준비예 22]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 818.016.6 g of the target compound was obtained in the same manner as the [Synthesis Example 10] except that [Preparation Example 22] was used as a reactant. HRMS [M] +: 818.01
[[ 합성예Synthesis Example 213] Mat 521의 합성 213] Synthesis of Mat 521
Figure PCTKR2017011366-appb-I000282
Figure PCTKR2017011366-appb-I000282
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.1g을 얻었다.; HRMS [M]+: 825.035.1 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation 23] was used as a reactant. HRMS [M] +: 825.03
[[ 합성예Synthesis Example 214] Mat 522의 합성 214] Synthesis of Mat 522
Figure PCTKR2017011366-appb-I000283
Figure PCTKR2017011366-appb-I000283
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 5.3g을 얻었다.; HRMS [M]+: 825.035.3 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation 23] was used as a reactant. HRMS [M] +: 825.03
[[ 합성예Synthesis Example 215] Mat 525의 합성 215] Synthesis of Mat 525
Figure PCTKR2017011366-appb-I000284
Figure PCTKR2017011366-appb-I000284
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 4.8g을 얻었다.; HRMS [M]+: 899.114.8 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation 23] was used as a reactant. HRMS [M] +: 899.11
[[ 합성예Synthesis Example 216] Mat 527의 합성 216] Synthesis of Mat 527
Figure PCTKR2017011366-appb-I000285
Figure PCTKR2017011366-appb-I000285
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 4.5g을 얻었다.; HRMS [M]+: 748.934.5 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 23] was used as a reactant. HRMS [M] +: 748.93
[[ 합성예Synthesis Example 217] Mat 528의 합성 217] Synthesis of Mat 528
Figure PCTKR2017011366-appb-I000286
Figure PCTKR2017011366-appb-I000286
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 4.7g을 얻었다.; HRMS [M]+: 839.014.7 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation 23] was used as a reactant. HRMS [M] +: 839.01
[[ 합성예Synthesis Example 218] Mat 533의 합성 218] Synthesis of Mat 533
Figure PCTKR2017011366-appb-I000287
Figure PCTKR2017011366-appb-I000287
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 839.015.4 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation 23] was used as a reactant. HRMS [M] +: 839.01
[[ 합성예Synthesis Example 219] Mat 540의 합성 219] Synthesis of Mat 540
Figure PCTKR2017011366-appb-I000288
Figure PCTKR2017011366-appb-I000288
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 4.2g을 얻었다.; HRMS [M]+: 904.094.2 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation 23] was used as a reactant. HRMS [M] +: 904.09
[[ 합성예Synthesis Example 220] Mat 541의 합성 220] Synthesis of Mat 541
Figure PCTKR2017011366-appb-I000289
Figure PCTKR2017011366-appb-I000289
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 4.4g을 얻었다.; HRMS [M]+: 980.194.4 g of the target compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 23] was used as a reactant. HRMS [M] +: 980.19
[[ 합성예Synthesis Example 221] Mat 543의 합성 221] Synthesis of Mat 543
Figure PCTKR2017011366-appb-I000290
Figure PCTKR2017011366-appb-I000290
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.8g을 얻었다.; HRMS [M]+: 979.205.8 g of the target compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation 23] was used as a reactant. HRMS [M] +: 979.20
[[ 합성예Synthesis Example 222] Mat 544의 합성 222] Synthesis of Mat 544
Figure PCTKR2017011366-appb-I000291
Figure PCTKR2017011366-appb-I000291
반응물로 [준비예 23]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 877.066.8 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation 23] was used as a reactant. HRMS [M] +: 877.06
[[ 합성예Synthesis Example 223] Mat 546의 합성 223] Synthesis of Mat 546
Figure PCTKR2017011366-appb-I000292
Figure PCTKR2017011366-appb-I000292
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 825.036.6 g of the target compound was obtained in the same manner as the [Synthesis Example 1], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 825.03
[[ 합성예Synthesis Example 224] Mat 547의 합성 224] Synthesis of Mat 547
Figure PCTKR2017011366-appb-I000293
Figure PCTKR2017011366-appb-I000293
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 7.1g을 얻었다.; HRMS [M]+: 825.037.1 g of the target compound was obtained in the same manner as the [Synthesis Example 2], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 825.03
[[ 합성예Synthesis Example 225] Mat 550의 합성 225] Synthesis of Mat 550
Figure PCTKR2017011366-appb-I000294
Figure PCTKR2017011366-appb-I000294
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 6.9g을 얻었다.; HRMS [M]+: 899.116.9 g of the target compound was obtained in the same manner as the [Synthesis Example 3], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 899.11
[[ 합성예Synthesis Example 226] Mat 552의 합성 226] Synthesis of Mat 552
Figure PCTKR2017011366-appb-I000295
Figure PCTKR2017011366-appb-I000295
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 6.8g을 얻었다.; HRMS [M]+: 748.936.8 g of the target compound was obtained in the same manner as the [Synthesis Example 4], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 748.93
[[ 합성예Synthesis Example 227] Mat 553의 합성 227] Synthesis of Mat 553
Figure PCTKR2017011366-appb-I000296
Figure PCTKR2017011366-appb-I000296
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 6.6g을 얻었다.; HRMS [M]+: 839.016.6 g of the target compound was obtained in the same manner as the [Synthesis Example 5], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 839.01
[[ 합성예Synthesis Example 228] Mat 558의 합성 228] Synthesis of Mat 558
Figure PCTKR2017011366-appb-I000297
Figure PCTKR2017011366-appb-I000297
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 6.1g을 얻었다.; HRMS [M]+: 839.016.1 g of the target compound was obtained in the same manner as the [Synthesis Example 6], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 839.01
[[ 합성예Synthesis Example 229] Mat 565의 합성 229] Synthesis of Mat 565
Figure PCTKR2017011366-appb-I000298
Figure PCTKR2017011366-appb-I000298
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 6.5g을 얻었다.; HRMS [M]+: 904.096.5 g of the target compound was obtained in the same manner as the [Synthesis Example 7], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 904.09
[[ 합성예Synthesis Example 230] Mat 566의 합성 230] Synthesis of Mat 566
Figure PCTKR2017011366-appb-I000299
Figure PCTKR2017011366-appb-I000299
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 5.4g을 얻었다.; HRMS [M]+: 980.195.4 g of the title compound was obtained in the same manner as the [Synthesis Example 8], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 980.19
[[ 합성예Synthesis Example 231] Mat 568의 합성 231] Synthesis of Mat 568
Figure PCTKR2017011366-appb-I000300
Figure PCTKR2017011366-appb-I000300
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 5.9g을 얻었다.; HRMS [M]+: 979.205.9 g of the title compound was obtained in the same manner as the [Synthesis Example 9], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 979.20
[[ 합성예Synthesis Example 232] Mat 569의 합성 232] Synthesis of Mat 569
Figure PCTKR2017011366-appb-I000301
Figure PCTKR2017011366-appb-I000301
반응물로 [준비예 24]을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 6.2g을 얻었다.; HRMS [M]+: 877.066.2 g of the target compound was obtained in the same manner as the [Synthesis Example 10], except that [Preparation Example 24] was used as a reactant. HRMS [M] +: 877.06
[실시예 1 ~ 24] 녹색 유기 전계 발광 소자의 제작Examples 1 to 24 Fabrication of Green Organic Electroluminescent Devices
합성예 1~52에서 합성한 화합물 Mat 1 ~ Mat 129를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.Compounds 1 to 52 synthesized in Synthesis Examples 1 to 52 after high-purity sublimation purification by a commonly known method to produce a green organic electroluminescent device 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 129의 각각의 화합물 + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 EL 소자를 제작하였다. M-MTDATA (60 nm) / TCTA (80 nm) / Mat 1 to Mat 129 + 10% Ir (ppy) 3 (30nm) / BCP (10 nm) / Alq 3 ( An organic EL device was fabricated by stacking in the order of 30 nm) / LiF (1 nm) / Al (200 nm).
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 PCTKR2017011366-appb-I000302
Figure PCTKR2017011366-appb-I000302
Figure PCTKR2017011366-appb-I000303
Figure PCTKR2017011366-appb-I000303
[비교예 1] 녹색 유기 전계 발광 소자의 제작Comparative 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 ~ 35 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 35 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 7Mat 7 5.895.89 516516 4242
실시예 5Example 5 Mat 8Mat 8 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 21Mat 21 5.865.86 517517 3939
실시예 9Example 9 Mat 23Mat 23 5.875.87 516516 4040
실시예 10Example 10 Mat 26Mat 26 6.46.4 516516 4141
실시예 11Example 11 Mat 30Mat 30 5.85.8 516516 4242
실시예 12Example 12 Mat 32Mat 32 6.26.2 516516 4444
실시예 13Example 13 Mat 38Mat 38 5.95.9 516516 4343
실시예 14Example 14 Mat 45Mat 45 5.915.91 516516 4040
실시예 15Example 15 Mat 48Mat 48 6.06.0 516516 39.839.8
실시예 16Example 16 Mat 52Mat 52 5.95.9 516516 4141
실시예 17Example 17 Mat 55Mat 55 6.86.8 516516 3838
실시예 18Example 18 Mat 58Mat 58 6.26.2 516516 4343
실시예 19Example 19 Mat 63Mat 63 5.85.8 516516 4040
실시예 20Example 20 Mat 70Mat 70 6.66.6 517517 4141
실시예 21Example 21 Mat 73Mat 73 5.95.9 516516 4242
실시예 22Example 22 Mat 76Mat 76 6.46.4 516516 4444
실시예 23Example 23 Mat 80Mat 80 6.56.5 516516 4343
실시예 24Example 24 Mat 83Mat 83 5.895.89 516516 4040
실시예 25Example 25 Mat 88Mat 88 5.85.8 516516 39.839.8
실시예 26Example 26 Mat 95Mat 95 6.06.0 516516 4141
실시예 27Example 27 Mat 98Mat 98 5.95.9 516516 4242
실시예 28Example 28 Mat 101Mat 101 6.86.8 516516 4444
실시예 29Example 29 Mat 105Mat 105 6.26.2 516516 4343
실시예 30Example 30 Mat 107Mat 107 5.85.8 516516 4040
실시예 31Example 31 Mat 113Mat 113 6.66.6 516516 39.839.8
실시예 32Example 32 Mat 116Mat 116 5.95.9 517517 4141
실시예 33Example 33 Mat 120Mat 120 6.46.4 516516 3838
실시예 34Example 34 Mat 122Mat 122 6.56.5 516516 4343
실시예 35Example 35 Mat 128Mat 128 6.06.0 516516 4141
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 129)을 녹색 유기 전계 발광 소자의 발광층으로 사용하였을 경우(실시예 1~35) 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 129) according to the present invention were used as the light emitting layer of the green organic electroluminescent device (Examples 1 to 35), 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 36 ~ 57] 적색 유기 전계 발광 소자의 제조Examples 36 to 57 Fabrication of Red Organic Electroluminescent 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.
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 24 ~ Mat 569의 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 24 ~ Mat 569 + 10% (piq) 2 Ir (acac) (30 nm) / BCP (10 nm) / Alq 3 on the thus 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 24의 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 24 as a light emitting host material when forming the light emitting layer.
상기 실시예 36 ~ 57 및 비교예2 에서 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 36 to 57 and Comparative Example 2 are as follows.
Figure PCTKR2017011366-appb-I000304
Figure PCTKR2017011366-appb-I000304
[평가예 2][Evaluation Example 2]
실시예 36 ~ 57 및 비교예2 에서 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 36 to 57 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 36Example 36 Mat 24Mat 24 5.15.1 8.98.9
실시예 37Example 37 Mat 45Mat 45 5.05.0 8.38.3
실시예 38Example 38 Mat 49Mat 49 4.84.8 9.19.1
실시예 39Example 39 Mat 74Mat 74 4.84.8 9.09.0
실시예 40Example 40 Mat 99Mat 99 4.784.78 8.68.6
실시예 41Example 41 Mat 149Mat 149 3.83.8 10.810.8
실시예 42Example 42 Mat 174Mat 174 4.14.1 10.810.8
실시예 43Example 43 Mat 194Mat 194 4.04.0 11.611.6
실시예 44Example 44 Mat 219Mat 219 4.14.1 10.610.6
실시예 45Example 45 Mat 244Mat 244 4.34.3 11.511.5
실시예 46Example 46 Mat 269Mat 269 4.24.2 10.1210.12
실시예 47Example 47 Mat 294Mat 294 3.93.9 10.610.6
실시예 48Example 48 Mat 319Mat 319 3.93.9 10.610.6
실시예 49Example 49 Mat 369Mat 369 3.93.9 11.011.0
실시예 50Example 50 Mat 394Mat 394 4.24.2 10.5610.56
실시예 51Example 51 Mat 419Mat 419 4.04.0 10.510.5
실시예 52Example 52 Mat 444Mat 444 3.83.8 10.6210.62
실시예 53Example 53 Mat 469Mat 469 3.83.8 10.610.6
실시예 54Example 54 Mat 494Mat 494 4.04.0 10.610.6
실시예 55Example 55 Mat 519Mat 519 3.83.8 11.011.0
실시예 56Example 56 Mat 544Mat 544 3.83.8 11.5611.56
실시예 57Example 57 Mat 569Mat 569 4.24.2 11.511.5
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 36~57) 종래 CBP를 발광층의 재료로 사용한 적색 유기 전계 발광 소자(비교예2)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.
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 (14)

  1. 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2017011366-appb-I000305
    Figure PCTKR2017011366-appb-I000305
    상기 화학식 1에서, In Chemical Formula 1,
    X는 O, S, Se, N(Ar2), C(Ar3)(Ar4) 및 Si(Ar5)(Ar6)로 구성된 군으로부터 선택되고;X is selected from the group consisting of O, S, Se, N (Ar 2 ), C (Ar 3 ) (Ar 4 ) and Si (Ar 5 ) (Ar 6 );
    환 A 및 B는 각각 독립적으로 각각 독립적으로 C6~C30의 아렌 및 핵원자수 5 내지 30개의 헤테로아렌으로 이루어진 군에서 선택되며;Rings A and B are each independently selected from the group consisting of C 6 ~ C 30 arene and 5 to 30 heteroarenes of nuclear atoms;
    L1은 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되고;L 1 is 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 o는 각각 독립적으로 0 내지 4의 정수이며;l and o are each independently an integer from 0 to 4;
    m 및 n은 각각 독립적으로 0 내지 2의 정수이며;m and n are each independently an integer from 0 to 2;
    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 Ar6는 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 6 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 의 아릴렌기 및 헤테로아릴렌기와, 상기 Ar1 내지 Ar6 및 R1 내지 R4의 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 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group and cycloalkyl group of Ar 1 to Ar 6 and R 1 to R 4 , 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 An aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 to C 40 cycloalkyl group, nuclear atoms 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group, C 1 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono- or dia rilpo of If blood group and a C 6 ~ substituted by one or more substituents selected from the group consisting of C 60 or silyl aryl is unsubstituted, substituted by a plurality of substituents, they may be the same or different from each other.
  2. 제1항에 있어서,The method of claim 1,
    상기 환 A 및 B는 각각 독립적으로 하기 화학식 2 내지 4 중 어느 하나로 표시되는, 화합물:Rings A and B are each independently represented by any one of Formulas 2 to 4, Compound:
    [화학식 2][Formula 2]
    Figure PCTKR2017011366-appb-I000306
    Figure PCTKR2017011366-appb-I000306
    [화학식 3][Formula 3]
    Figure PCTKR2017011366-appb-I000307
    Figure PCTKR2017011366-appb-I000307
    [화학식 4][Formula 4]
    Figure PCTKR2017011366-appb-I000308
    Figure PCTKR2017011366-appb-I000308
    상기 화학식 2 내지 4에서,In Chemical Formulas 2 to 4,
    점선은 축합이 이루어지는 부분을 의미한다.The dotted line means the part where condensation takes place.
  3. 제2항에 있어서,The method of claim 2,
    상기 환 A 및 B 중 적어도 하나는 상기 화학식 3 또는 4로 표시되는, 화합물.At least one of the ring A and B is represented by the formula (3) or (4).
  4. 제1항에 있어서,The method of claim 1,
    상기 화합물은 하기 화학식 5 내지 12 중 어느 하나로 표시되는, 화합물:The compound is represented by any one of Formulas 5 to 12, Compound:
    [화학식 5][Formula 5]
    Figure PCTKR2017011366-appb-I000309
    Figure PCTKR2017011366-appb-I000309
    [화학식 6][Formula 6]
    Figure PCTKR2017011366-appb-I000310
    Figure PCTKR2017011366-appb-I000310
    [화학식 7][Formula 7]
    Figure PCTKR2017011366-appb-I000311
    Figure PCTKR2017011366-appb-I000311
    [화학식 8][Formula 8]
    Figure PCTKR2017011366-appb-I000312
    Figure PCTKR2017011366-appb-I000312
    [화학식 9][Formula 9]
    Figure PCTKR2017011366-appb-I000313
    Figure PCTKR2017011366-appb-I000313
    [화학식 10][Formula 10]
    Figure PCTKR2017011366-appb-I000314
    Figure PCTKR2017011366-appb-I000314
    [화학식 11][Formula 11]
    Figure PCTKR2017011366-appb-I000315
    Figure PCTKR2017011366-appb-I000315
    [화학식 12][Formula 12]
    Figure PCTKR2017011366-appb-I000316
    Figure PCTKR2017011366-appb-I000316
    상기 화학식 5 내지 12에서, In Chemical Formulas 5 to 12,
    X, Ar1, L1, R1, R4, l 및 o 각각은 제1항에서 정의된 바와 같다. X, Ar 1 , L 1 , R 1 , R 4 , l and o are each as defined in claim 1.
  5. 제4항에 있어서,The method of claim 4, wherein
    상기 화합물은 상기 화학식 7 내지 12 중 어느 하나로 표시되는, 화합물.The compound is represented by any one of Formulas 7 to 12, Compound.
  6. 제1항에 있어서,The method of claim 1,
    상기 L1은 단일결합이거나, 하기 화학식 A-1 내지 화학식 A-3 중 어느 하나로 표시되는 링커인, 화합물:Wherein L 1 is a single bond or a linker represented by one of Formulas A-1 to A-3:
    Figure PCTKR2017011366-appb-I000317
    Figure PCTKR2017011366-appb-I000317
    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.
  7. 제1항에 있어서,The method of claim 1,
    상기 Ar1은 하기 화학식 13으로 표시되는 치환기인, 화합물:Ar 1 is a substituent represented by Formula 13 below:
    [화학식 13][Formula 13]
    Figure PCTKR2017011366-appb-I000318
    Figure PCTKR2017011366-appb-I000318
    상기 화학식 13에서,In Chemical Formula 13,
    *은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    Z1 내지 Z5는 각각 독립적으로 N 또는 C(R5)이며;Z 1 to Z 5 are each independently N or C (R 5 );
    R5는 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 R5가 복수 개인 경우 이들은 서로 동일하거나 상이하며; R 5 is 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, nuclear atom 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C An alkylsilyl group of 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkyl boron group of C 1 to C 40, an aryl boron group of C 6 to C 60 , an arylphosphanyl group of C 6 to C 60 , C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylamine group selected from the group consisting of, or combine with adjacent groups to form a condensed ring, when there are a plurality of R 5 They are the same as each other Or different;
    상기 R5의 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 상이하다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R 5 , heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group and 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, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, 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, C 6 ~ C 60 the arylboronic group, one member selected from the group consisting of C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine of blood group and a C 6 ~ C 60 aryl group in the silyl Substituted with a substituent being unsubstituted or, if substituted by a plurality of substituents, they are same as or different from each other.
  8. 제7항에 있어서,The method of claim 7, wherein
    상기 화학식 13으로 표시되는 치환기는 하기 화학식 14로 표시되는 치환기인, 화합물:The substituent represented by Formula 13 is a substituent represented by the following Formula 14, the compound:
    [화학식 14][Formula 14]
    Figure PCTKR2017011366-appb-I000319
    Figure PCTKR2017011366-appb-I000319
    상기 화학식 14에서,In Chemical Formula 14,
    *은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    R6 및 R7은 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 6 and R 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 R6 및 R7의 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;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 R 6 and R 7 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 blood group and a C 6 ~ C 60 aryl silyl group selected from the group consisting of 1 When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other;
    Z1, Z3 및 Z5 각각은 제7항에서 정의된 바와 같다. Z 1 , Z 3 and Z 5 are each as defined in claim 7.
  9. 제1항에 있어서,The method of claim 1,
    상기 Ar1은 하기 화학식 15로 표시되는 치환기인, 화합물:Ar 1 is a substituent represented by Formula 15:
    [화학식 15][Formula 15]
    Figure PCTKR2017011366-appb-I000320
    Figure PCTKR2017011366-appb-I000320
    상기 화학식 15에서, In Chemical Formula 15,
    *은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    R8 및 R9는 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 8 and R 9 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 R8 및 R9의 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 상이하다.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 R 8 and R 9 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 blood group and a C 6 ~ C 60 aryl silyl group selected from the group consisting of 1 When substituted or unsubstituted with at least one substituent, and substituted with a plurality of substituents, they are the same as or different from each other.
  10. 제1항에 있어서,The method of claim 1,
    상기 Ar1은 하기 화학식 B-1 내지 B-8 중 어느 하나로 표시되는 치환기인, 화합물:Ar 1 is a substituent represented by any one of the following Formulas B-1 to B-8:
    Figure PCTKR2017011366-appb-I000321
    Figure PCTKR2017011366-appb-I000321
    상기 화학식 B-1 내지 B-8에서, In Chemical Formulas B-1 to B-8,
    *은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    Z5 내지 Z12는 각각 독립적으로 N 또는 C(R12)이며;Z 5 to Z 12 are each independently N or C (R 12 );
    상기 화학식 B-1에서 L1에 결합되는 Z5 내지 Z8 중 어느 하나는 C(R12)이고, 이때 상기 R12는 부재이며;Any one of Z 5 to Z 8 bonded to L 1 in Formula B-1 is C (R 12 ), wherein R 12 is absent;
    T1 및 T2는 각각 독립적으로 단일결합, C(R13)(R14), N(R15), 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 13 ) (R 14 ), N (R 15 ), O and S, but not both T 1 and T 2 are single bonds;
    q 및 r은 각각 독립적으로 0 내지 4의 정수이며;q and r are each independently integers of 0 to 4;
    R10 및 R11은 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 R10 및 R11 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 10 and R 11 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 there are a plurality of each of 10 and R 11 , they are the same as or different from each other;
    R12 내지 R15는 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 R12 내지 R15 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 12 to R 15 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 12 to R 15 is plural, they are the same as or different from each other;
    상기 R10 내지 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 상이하다.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 10 to R 15 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 When unsubstituted or substituted with one or more substituents, and substituted with a plurality of substituents, they are the same as or different from each other.
  11. 제1항에 있어서,The method of claim 1,
    상기 Ar1은 하기 화학식 C-1 내지 C-14 중 어느 하나로 표시되는 치환기인, 화합물:Ar 1 is a substituent represented by any one of Formulas C-1 to C-14:
    Figure PCTKR2017011366-appb-I000322
    Figure PCTKR2017011366-appb-I000322
    상기 화학식 C-1 내지 C-14에서, In Chemical Formulas C-1 to C-14,
    *은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
    q, r 및 s는 각각 독립적으로 0 내지 4의 정수이며;q, r and s are each independently integers of 0 to 4;
    R10, R11 및 R16은 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 R10, R11 및 R18 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 10 , R 11 and R 16 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 When R 10 , R 11 and R 18 are each plural, they are the same as or different from each other;
    R12 내지 R15는 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 12 to R 15 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 R10 내지 R16의 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 상이하다.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 10 to R 16 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 When unsubstituted or substituted with one or more substituents, and substituted with a plurality of substituents, they are the same as or different from each other.
  12. 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 PCTKR2017011366-appb-I000323
    Figure PCTKR2017011366-appb-I000323
    Figure PCTKR2017011366-appb-I000324
    Figure PCTKR2017011366-appb-I000324
    Figure PCTKR2017011366-appb-I000325
    Figure PCTKR2017011366-appb-I000325
    Figure PCTKR2017011366-appb-I000326
    Figure PCTKR2017011366-appb-I000326
    Figure PCTKR2017011366-appb-I000327
    Figure PCTKR2017011366-appb-I000327
    Figure PCTKR2017011366-appb-I000328
    Figure PCTKR2017011366-appb-I000328
    Figure PCTKR2017011366-appb-I000329
    Figure PCTKR2017011366-appb-I000329
    Figure PCTKR2017011366-appb-I000330
    Figure PCTKR2017011366-appb-I000330
    Figure PCTKR2017011366-appb-I000331
    Figure PCTKR2017011366-appb-I000331
    Figure PCTKR2017011366-appb-I000332
    Figure PCTKR2017011366-appb-I000332
    Figure PCTKR2017011366-appb-I000333
    Figure PCTKR2017011366-appb-I000333
    Figure PCTKR2017011366-appb-I000334
    Figure PCTKR2017011366-appb-I000334
    Figure PCTKR2017011366-appb-I000335
    Figure PCTKR2017011366-appb-I000335
    Figure PCTKR2017011366-appb-I000336
    Figure PCTKR2017011366-appb-I000336
    Figure PCTKR2017011366-appb-I000337
    Figure PCTKR2017011366-appb-I000337
    Figure PCTKR2017011366-appb-I000338
    Figure PCTKR2017011366-appb-I000338
    Figure PCTKR2017011366-appb-I000339
    Figure PCTKR2017011366-appb-I000339
    Figure PCTKR2017011366-appb-I000340
    Figure PCTKR2017011366-appb-I000340
    Figure PCTKR2017011366-appb-I000341
    Figure PCTKR2017011366-appb-I000341
    Figure PCTKR2017011366-appb-I000342
    Figure PCTKR2017011366-appb-I000342
    Figure PCTKR2017011366-appb-I000343
    Figure PCTKR2017011366-appb-I000343
    Figure PCTKR2017011366-appb-I000344
    Figure PCTKR2017011366-appb-I000344
    Figure PCTKR2017011366-appb-I000345
    Figure PCTKR2017011366-appb-I000345
    Figure PCTKR2017011366-appb-I000346
    Figure PCTKR2017011366-appb-I000346
  13. (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.
  14. 제13항에 있어서,The method of claim 13,
    상기 유기물층은 정공 주입층, 정공 수송층, 정공 수송 보조층, 전자 수송층, 전자 수송 보조층 및 발광층으로 이루어진 군에서 선택되는 하나 이상의 층을 포함하는, 유기 전계 발광 소자.The organic material layer includes an organic electroluminescent device comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer and a light emitting layer.
PCT/KR2017/011366 2016-10-27 2017-10-16 Organic compound and organic electroluminescent device comprising same WO2018080066A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2016-0141054 2016-10-27
KR1020160141054A KR102633650B1 (en) 2016-10-27 2016-10-27 Organic compounds and organic electro luminescence device comprising the same

Publications (1)

Publication Number Publication Date
WO2018080066A1 true WO2018080066A1 (en) 2018-05-03

Family

ID=62025155

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2017/011366 WO2018080066A1 (en) 2016-10-27 2017-10-16 Organic compound and organic electroluminescent device comprising same

Country Status (2)

Country Link
KR (1) KR102633650B1 (en)
WO (1) WO2018080066A1 (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111328329A (en) * 2018-10-16 2020-06-23 株式会社Lg化学 Novel heterocyclic compound and organic light emitting device using the same
US20200262825A1 (en) * 2017-06-29 2020-08-20 Lg Chem, Ltd. Novel heterocyclic compound and organic light emitting device comprising the same
CN113130799A (en) * 2019-12-31 2021-07-16 乐金显示有限公司 Organic electronic element, display panel including the same, and display device including the same
JP2021530518A (en) * 2019-01-30 2021-11-11 ソリュース先端素材株式会社Solus Advanced Materials Co., Ltd. Organic luminescent compounds and organic electroluminescent devices using them
CN114249713A (en) * 2020-09-22 2022-03-29 江苏三月科技股份有限公司 Organic compound containing xanthone or thioxanthone structure and application thereof
CN113130799B (en) * 2019-12-31 2024-07-05 乐金显示有限公司 Organic electronic element, display panel including the same, and display device including the same

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019004796A1 (en) * 2017-06-30 2019-01-03 주식회사 엘지화학 Novel heterocyclic compound and organic light-emitting device using same
KR102139859B1 (en) 2017-08-02 2020-07-30 주식회사 엘지화학 Hetero-cyclic compound and organic light emitting device comprising the same
WO2019027263A1 (en) * 2017-08-02 2019-02-07 주식회사 엘지화학 Heterocyclic compound and organic light-emitting element including same
KR102258617B1 (en) * 2018-10-19 2021-05-28 주식회사 엘지화학 Novel hetero-cyclic compound and organic light emitting device comprising the same
KR20200077949A (en) 2018-12-21 2020-07-01 두산솔루스 주식회사 Organic light-emitting compound and organic electroluminescent device using the same
WO2020162703A1 (en) * 2019-02-08 2020-08-13 주식회사 엘지화학 Novel heterocyclic compound and organic light emitting device using same
KR20210081967A (en) 2019-12-24 2021-07-02 솔루스첨단소재 주식회사 Organic compounds and organic electro luminescence device comprising the same
CN111004201B (en) * 2019-12-27 2023-04-07 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound, preparation method thereof and organic electroluminescent device

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140045266A (en) * 2012-10-08 2014-04-16 제일모직주식회사 Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode
CN104726087A (en) * 2013-12-24 2015-06-24 海洋王照明科技股份有限公司 Carbazole-unit-containing blue-light phosphorescence host material, and preparation method and organic electroluminescent device thereof
KR20160034832A (en) * 2014-09-22 2016-03-30 주식회사 엘지화학 Heterocyclic compound including nitrogen and organic light emitting device using the same
KR20160123453A (en) * 2015-04-15 2016-10-26 (주)위델소재 Phosphine oxide derivative compound and organic electroluminescent device using the same

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101440082A (en) * 2008-12-12 2009-05-27 南京邮电大学 Spirofluorene xanthene material, and preparation and use thereof
KR101231931B1 (en) * 2009-11-13 2013-02-08 주식회사 엘지화학 New fused cyclic compound and organic electronic device
KR101698640B1 (en) * 2013-09-26 2017-01-20 주식회사 엘지화학 Heterocyclic compound and organic light emitting device comprising the same
KR101993129B1 (en) * 2013-12-12 2019-06-26 메르크 파텐트 게엠베하 Materials for electronic devices
TWI629271B (en) * 2015-09-30 2018-07-11 Ｌｇ化學股份有限公司 Spiro structure having spiro structure, organic light emitting device compri sing the same , display device and lighting device

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140045266A (en) * 2012-10-08 2014-04-16 제일모직주식회사 Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode
CN104726087A (en) * 2013-12-24 2015-06-24 海洋王照明科技股份有限公司 Carbazole-unit-containing blue-light phosphorescence host material, and preparation method and organic electroluminescent device thereof
KR20160034832A (en) * 2014-09-22 2016-03-30 주식회사 엘지화학 Heterocyclic compound including nitrogen and organic light emitting device using the same
KR20160123453A (en) * 2015-04-15 2016-10-26 (주)위델소재 Phosphine oxide derivative compound and organic electroluminescent device using the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LIU, X.-Y. ET AL.: "The Study on Two Kinds of Spiro Systems for Improving th e Performance of Host Materials in Blue Phosphorescent Organic Light-emitting Diodes", JOURNAL OF MATERIALS CHEMISTRY C, vol. 3, 10 August 2015 (2015-08-10), pages 9053 - 9056, XP055482855 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20200262825A1 (en) * 2017-06-29 2020-08-20 Lg Chem, Ltd. Novel heterocyclic compound and organic light emitting device comprising the same
US11542258B2 (en) * 2017-06-29 2023-01-03 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
CN111328329A (en) * 2018-10-16 2020-06-23 株式会社Lg化学 Novel heterocyclic compound and organic light emitting device using the same
CN111328329B (en) * 2018-10-16 2023-05-02 株式会社Lg化学 Novel heterocyclic compound and organic light-emitting device using same
JP2021530518A (en) * 2019-01-30 2021-11-11 ソリュース先端素材株式会社Solus Advanced Materials Co., Ltd. Organic luminescent compounds and organic electroluminescent devices using them
JP7119204B2 (en) 2019-01-30 2022-08-16 ソリュース先端素材株式会社 Organic light-emitting compound and organic electroluminescent device using the same
US11917909B2 (en) 2019-01-30 2024-02-27 Solus Advanced Materials Co., Ltd. Organic compound and organic electroluminescence device using the same
CN113130799A (en) * 2019-12-31 2021-07-16 乐金显示有限公司 Organic electronic element, display panel including the same, and display device including the same
CN113130799B (en) * 2019-12-31 2024-07-05 乐金显示有限公司 Organic electronic element, display panel including the same, and display device including the same
CN114249713A (en) * 2020-09-22 2022-03-29 江苏三月科技股份有限公司 Organic compound containing xanthone or thioxanthone structure and application thereof
CN114249713B (en) * 2020-09-22 2024-05-03 江苏三月科技股份有限公司 Organic compound containing xanthone or thioxanthone structure and application thereof

Also Published As

Publication number Publication date
KR102633650B1 (en) 2024-02-06
KR20180046150A (en) 2018-05-08

Similar Documents

Publication Publication Date Title
WO2018080066A1 (en) Organic compound and organic electroluminescent device comprising same
WO2018093107A1 (en) Organic compound and organic electroluminescent element comprising same
WO2017179809A1 (en) Organic light-emitting compound and organic electroluminescent element using same
WO2018038401A1 (en) Organic compound and organic electroluminescence device including same
WO2020009467A1 (en) Polycyclic compound and organic light emitting diode comprising same
WO2018110958A1 (en) Organic light-emitting compound and organic electroluminescent element using same
WO2018080067A1 (en) Organic compound and organic electroluminescent device including same
WO2018216921A2 (en) Organic compound and organic electroluminescent element comprising same
WO2020209679A1 (en) Organic compound and organic electroluminescent element comprising same
WO2018038400A1 (en) Organic compound and organic electroluminescence device including same
WO2020130724A1 (en) Organic light-emitting compound and organic electroluminescent device using same
WO2014065498A1 (en) Organic electroluminescent device
WO2021020929A1 (en) Compound and organic light emitting device comprising same
WO2014142488A1 (en) Organic compound and organic electroluminescent element including same
WO2014025209A1 (en) Novel compound and organic electroluminescence device comprising same
WO2017023125A1 (en) Organic light-emitting compound and organic electroluminescent device using same
WO2014092354A1 (en) Organic compound and organic electroluminescent element comprising same
WO2016105054A2 (en) Organic light emitting compound and organic electroluminescent element using same
WO2015111943A1 (en) Organic compound, and organic electroluminescent device containing same
WO2014027822A1 (en) Novel compound and organic electroluminescent device comprising same
WO2017023126A1 (en) Organic light-emitting compound and organic electroluminescent device using same
WO2014046392A1 (en) Organic compound and electroluminescent element having same
WO2020027463A1 (en) Organic compound and organic electroluminescent device using same
WO2015020399A1 (en) Organic compound and organic electroluminescent light emitting diode comprising same
WO2013133575A1 (en) Novel compound and organic electroluminescence element including same

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17863588

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205 DATED 28/08/2019)

122 Ep: pct application non-entry in european phase

Ref document number: 17863588

Country of ref document: EP

Kind code of ref document: A1